Isobutanol - wikipedia Isobutanol Isobutanol Names Preferred IUPAC name 2 - Methylpropan - 1 - ol Other names Isobutyl alcohol IBA 2 - Methyl - 1 - propanol 2 - Methylpropyl alcohol Isopropylcarbinol Identifiers CAS Number 78 - 83 - 1 3D model ( JSmol ) Interactive image ChEBI CHEBI : 46645 ChEMBL ChEMBL269630 ChemSpider 6312 ECHA InfoCard 100.001. 044 EC Number 201 - 148 - 0 KEGG C14710 PubChem CID 6560 RTECS number NP9625000 UNII 56F9Z98TEM InChI InChI = 1S / C4H10O / c1 - 4 ( 2 ) 3 - 5 / h4 - 5H, 3H2, 1 - 2H3 Key : ZXEKIIBDNHEJCQ - UHFFFAOYSA - N InChI = 1 / C4H10O / c1 - 4 ( 2 ) 3 - 5 / h4 - 5H, 3H2, 1 - 2H3 SMILES CC ( C ) CO Properties Chemical formula C H O Molar mass 74.122 g / mol Appearance Colorless liquid Odor sweet, musty Density 0.802 g / cm, liquid Melting point − 108 ° C ( − 162 ° F ; 165 K ) Boiling point 107.89 ° C ( 226.20 ° F ; 381.04 K ) Solubility in water 8.7 mL / 100 mL log P 0.8 Vapor pressure 9 mmHg ( 20 ° C ) Refractive index ( n ) 1.3959 Viscosity 3.95 cP at 20 ° C Hazards Safety data sheet ICSC 0113 EU classification ( DSD ) ( outdated ) Irritant ( Xi ) R - phrases ( outdated ) R10 R37 / 38 R41, R67 S - phrases ( outdated ) ( S2 ) S7 / 9 S13 S26 S37 / 39 S46 NFPA 704 0 Flash point 28 ° C ( 82 ° F ; 301 K ) Autoignition temperature 415 ° C ( 779 ° F ; 688 K ) Explosive limits 1.7 -- 10.9 % Lethal dose or concentration ( LD, LC ) : LD ( lowest published ) 3750 mg / kg ( rabbit, oral ) 2460 mg / kg ( rat, oral ) US health exposure limits ( NIOSH ) : PEL ( Permissible ) TWA 100 ppm ( 300 mg / m ) REL ( Recommended ) TWA 50 ppm ( 150 mg / m ) IDLH ( Immediate danger ) 1600 ppm Related compounds Related butanols n - Butanol sec - Butanol tert - Butanol Related compounds Isobutyraldehyde Isobutyric acid Except where otherwise noted, data are given for materials in their standard state ( at 25 ° C ( 77 ° F ), 100 kPa ). Y verify ( what is ? ) Infobox references Isobutanol ( IUPAC nomenclature : 2 - methylpropan - 1 - ol ) is an organic compound with the formula ( CH ) CHCH OH ( sometimes represented as i - BuOH ). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent. Its isomers, the other butanols, include n - butanol, 2 - butanol, and tert - butanol, all of which are important industrially. Contents 1 Production 1.1 Biosynthesis of Isobutanol 1.1. 1 Cyanobacteria 1.1. 2 Bacillus subtilis 1.1. 3 Saccharomyces cerevisiae 1.1. 4 Ralstonia eutropha 2 Applications 2.1 Second - generation biofuel 3 Safety and regulation 4 See also 5 References 6 External links Production Isobutanol is produced by the carbonylation of propylene. Two methods are practiced industrially, hydroformylation is more common and generates a mixture of isobutyraldehydes, which are hydrogenated to the alcohols and then separated. Reppe carbonylation is also practiced. Biosynthesis of isobutanol Higher - chain alcohols have energy densities close to gasoline, are not as volatile or corrosive as ethanol, and do not readily absorb water. Furthermore, branched - chain alcohols, such as isobutanol, have higher - octane numbers, resulting in less knocking in engines. Although produced naturally during the fermentation of carbohydrates and may also be a byproduct of the decay process of organic matter, Isobutanol or C5 alcohols have never been produced from a renewable source with yields high enough to make them viable as a gasoline substitute before the 2008 Nature article that produced over 20g / L isobutanol from glucose in E. coli. To modify an organism to produce these compounds usually results in toxicity in the cell. This difficulty was bypassed by leveraging the native metabolic networks in E. coli but altered its intracellular chemistry using genetic engineering to produce these alcohols. Key pathways in E. coli were modified to produce several higher - chain alcohols from glucose, including isobutanol, 1 - butanol, 2 - methyl - 1 - butanol, 3 - methyl - 1 - butanol, and 2 - phenylethanol. This strategy exploits the E. coli host 's highly active amino acid biosynthetic pathway by shifting part of it to alcohol production. It is proposed that these unusual alcohols can be produced as efficiently as the biosynthesis of ethanol. Escherichia coli Escherichia coli, or E. coli, is a Gram - negative, rod - shaped bacteria. E. coli is the microorganism most likely to move on to commercial production of isobutanol. In its engineered form E. coli produces the highest yields of isobutanol of any microorganism. Methods such as elementary mode analysis have been used to improve the metabolic efficiency of E. coli so that larger quantities of isobutanol may be produced. E. coli is an ideal isobutanol bio-synthesizer for several reasons : E. coli is an organism for which several tools of genetic manipulation exist, and it is an organism for which an extensive body of scientific literature exists. This wealth of knowledge allows E. coli to be easily modified by scientists. E. coli has the capacity to use lignocellulose ( waste plant matter left over from agriculture ) in the synthesis of isobutanol. The use of lignocellulose prevents E. coli from using plant matter meant for human consumption, and prevents any food - fuel price relationship which would occur from the biosynthesis of isobutanol by E. coli. Genetic modification has been used to broaden the scope of lignocellulose which can be used by E. coli. This has made E. coli a useful and diverse isobutanol bio-synthesizer. The primary drawback of E. coli is that it is susceptible to bacteriophages when being grown. This susceptibility could potentially shut down entire bioreactors. Clostridium While cellulosic biomass like corn stover and switchgrass is abundant and cheap, it is much more difficult to utilize than corn and sugar cane. This is due in large part because of recalcitrance, or a plant 's natural defenses to being chemically dismantled. Adding to the complexity is the fact biofuel production that involves several steps -- pretreatment, enzyme treatment and fermentation -- is more costly than a method that combines biomass utilization and the fermentation of sugars to biofuel into a single process. To make the conversion possible, researchers had to develop a strain of Clostridium cellulolyticum, a native cellulose - degrading microbe, that could synthesize isobutanol directly from cellulose. This proof of concept research sets the stage for studies that will likely involve genetic manipulation of other consolidated bioprocessing microorganisms. Cyanobacteria Cyanobacteria, are a phylum of photosynthetic bacteria. Cyanobacteria are suited for isobutanol biosynthesis when genetically engineered to produce isobutanol and its corresponding aldehydes. Isobutanol producing species of cyanobacteria offer several advantages as biofuel synthesizers : Cyanobacteria grow faster than plants and also absorb sunlight more efficiently than plants. This means they can be replenished at a faster rate than the plant matter used for other biofuel biosynthesizers. Cyanobacteria can be grown on non-arable land ( land not used for farming ). This prevents competition between food sources and fuel sources. The supplements necessary for the growth of Cyanobacteria are CO, H O, and sunlight. This presents two advantages : Because CO is derived from the atmosphere, Cyanobacteria do not need plant matter to synthesize isobutanol ( in other organisms which synthesize isobutanol, plant matter is the source of the carbon necessary to synthetically assemble isobutanol ). Since plant matter is not used by this method of isobutanol production, the necessity to source plant matter from food sources and create a food - fuel price relationship is avoided. Because CO is absorbed from the atmosphere by Cyanobacteria, the possibility of bioremediation ( in the form of Cyanobacteria removing excess CO from the atmosphere ) exists. The primary drawbacks of Cyanobacteria are : Cyanobacteria are sensitive to environmental conditions when being grown. Cyanobacteria suffer greatly from sunlight of inappropriate wavelength and intensity, CO of inappropriate concentration, or H O of inappropriate salinity though a wealth of cyanobacteria are able to grow in brackish and marine waters. These factors are generally hard to control, and present a major obstacle in cyanbacterial production of isobutanol. Cyanobacteria bioreactors require high energy to operate. Cultures require constant mixing, and the harvesting of biosynthetic products is energy intensive. This reduces the efficiency of isobutanol production via Cyanobacteria. Bacillus subtilis Bacillus subtilis is a gram - positive rod - shaped bacteria. Bacillus subtilis offers many of the same advantages and disadvantages of E. coli, but it is less prominently used and does not produce isobutanol in quantities as large as E. coli. Similar to E. coli, Bacillus subtilis is capable of producing isobutanol from lignocellulose, and is easily manipulated by common genetic techniques. Elementary mode analysis has also been used to improve the isobutanol - synthesis metabolic pathway used by Bacillus subtilis, leading to higher yields of isobutanol being produced. Saccharomyces cerevisiae Saccharomyces cerevisiae, or S. cerevisiae is a species of yeast. S. cerevisiae naturally produces isobutanol in small quantities via its valine biosynthetic pathway. S. cerevisiae is an ideal candidate for isobutanol biofuel production for several reasons : S. cerevisiae can be grown at low pH levels, helping prevent contamination during growth in industrial bioreactors. S. cerevisiae can not be affected by bacteriophages because it is a eukaryote. Extensive scientific knowledge about S. cerevisiae and its biology already exists. Overexpression of the enzymes in the valine biosynthetic pathway of S. cerevisiae has been used to improve isobutanol yields. S. cerevisiae, however, has proved difficult to work with because of its inherent biology : As a eukaryote, S. cerevisiaeis genetically more complex than E. coli or B. subtilis, and is harder to genetically manipulate as a result. S. cerevisiae has the natural ability to produce ethanol. This natural ability can `` overpower '' and consequently inhibit isobutanol production by S. cerevisiae. S. cerevisiae can not use five carbon sugars to produce isobutanol. The inability to use five - carbon sugars restricts S. cerevisiae from using lignocellulose, and means S. cerevisiae must use plant matter intended for human consumption to produce isobutanol. This results in an unfavorable food / fuel price relationship when isobutanol is produced by S. cerevisiae. Ralstonia eutropha Ralstonia eutropha is a gram - negative soil bacterium of the betaproteobacteria class. Ralstonia eutropha is capable of converting electrical energy into isobutanol. This conversion is completed in several steps : Anodes are placed in a mixture of H O and CO. An electric current is run through the anodes, and through an electrochemical process H O and CO are combined to synthesize formic acid. A culture of Ralstonia eutropha ( composed of a strain tolerant to electricity ) is kept within the H O and CO mixture. The culture of Ralstonia eutropha then converts formic acid from the mixture into isobutanol. The biosynthesized isobutanol is then separated from the mixture, and can be used as a biofuel. This method of isobutanol production offers a way to chemically store energy produced from sustainable sources. Applications Isobutanol has a variety of technical and industrial applications : feedstock in the manufacture of isobutyl acetate, which is used in the production of lacquer and similar coatings, and in the food industry as a flavoring agent precursor of derivative esters -- isobutyl esters such as diisobutyl phthalate ( DIBP ) are used as plasticizers in plastics, rubbers, and other dispersions precursor of p - xylene, a building block for plastic bottles, textiles and clothing. paint solvent varnish remover ink ingredient paint additive, to reduce viscosity, improve brush flow, and retard formation of oil residues ( blush ) on painted surfaces gasoline additive, to reduce carburetor icing automotive polish additive automotive paint cleaner additive chemical extractant in production of organic compounds mobile phase in thin layer chromatography. potential gasoline alternative Second - generation biofuel Isobutanol can be used as a biofuel substitute for gasoline in the current petroleum infrastructure. Isobutanol has not yet been put into mainstream use as a biofuel and would serve as a replacement for ethanol. Ethanol is a first - generation biofuel, and is used primarily as a gasoline additive in the petroleum infrastructure. Isobutanol is a second - generation biofuel with several qualities that resolve issues presented by ethanol. Isobutanol 's properties make it an attractive biofuel : relatively high energy density, 98 % of that of gasoline. does not readily absorb water from air, preventing the corrosion of engines and pipelines. can be mixed at any proportion with gasoline, meaning the fuel can `` drop into '' the existing petroleum infrastructure as a replacement fuel or major additive. can be produced from plant matter not connected to food supplies, preventing a fuel - price / food - price relationship. Safety and regulation Isobutanol is one of the least toxic of the butanols with an LD of 2460 mg / kg ( rat, oral ). In March 2009, the Canadian government announced a ban on isobutanol use in cosmetics. See also Alcohol to jet fuel References ^ Jump up to : `` NIOSH Pocket Guide to Chemical Hazards # 0352 ''. National Institute for Occupational Safety and Health ( NIOSH ). Jump up ^ `` Iso - butanol ''. ChemicalLand21. ^ Jump up to : Isobutanol, International Chemical Safety Card 0113, Geneva : International Programme on Chemical Safety, April 2005. Jump up ^ `` Isobutyl alcohol ''. Immediately Dangerous to Life and Health Concentrations ( IDLH ). National Institute for Occupational Safety and Health ( NIOSH ). Jump up ^ Hahn, Heinz - Dieter ; Dämbkes, Georg ; Rupprich, Norbert ( 2005 ), `` Butanols '', Ullmann 's Encyclopedia of Industrial Chemistry, Weinheim : Wiley - VCH, doi : 10.1002 / 14356007. a04_463. ^ Jump up to : Atsumi, Shota ; Hanai, Taizo ; Liao, James C. ( January 2008 ). `` Non-fermentative pathways for synthesis of branched - chain higher alcohols as biofuels ''. Nature. 451 ( 7174 ) : 86 -- 89. doi : 10.1038 / nature06450. PMID 18172501. ^ Jump up to : Peralta - Yahya, Pamela P. ; Zhang, Fuzhong ; del Cardayre, Stephen B. ; Keasling, Jay D. ; Del Cardayre, Stephen B. ; Keasling, Jay D. ( 15 August 2012 ). `` Microbial engineering for the production of advanced biofuels ''. Nature. 488 ( 7411 ) : 320 -- 328. Bibcode : 2012Natur. 488... 320P. doi : 10.1038 / nature11478. PMID 22895337. CS1 maint : Multiple names : authors list ( link ) ^ Jump up to : Trinh, Cong T. ( 9 June 2012 ). `` Elucidating and reprogramming Escherichia coli metabolisms for obligate anaerobic n - butanol and isobutanol production ''. Applied Microbiology and Biotechnology. 95 ( 4 ) : 1083 -- 1094. doi : 10.1007 / s00253 - 012 - 4197 - 7. PMID 22678028. ^ Jump up to : Nakashima, Nobutaka ; Tamura, Tomohiro ( 1 July 2012 ). `` A new carbon catabolite repression mutation of Escherichia coli, mlc ∗, and its use for producing isobutanol ''. Journal of Bioscience and Bioengineering. 114 ( 1 ) : 38 -- 44. doi : 10.1016 / j. jbiosc. 2012.02. 029. PMID 22561880. Jump up ^ Higashide, Wendy ; Li, Yongchao ; Yang, Yunfeng ; Liao, James C. ( 2011 - 04 - 15 ). `` Metabolic Engineering of Clostridium cellulolyticum for Production of Isobutanol from Cellulose ''. Applied and Environmental Microbiology. 77 ( 8 ) : 2727 -- 2733. doi : 10.1128 / AEM. 02454 - 10. ISSN 0099 - 2240. PMC 3126361. PMID 21378054. Jump up ^ Cyanobacteria Jump up ^ Atsumi, Shota ; Higashide, Wendy ; Liao, James C ( December 2009 ). `` Direct photosynthetic recycling of carbon dioxide to isobutyraldehyde ''. Nature Biotechnology. 27 ( 12 ) : 1177 -- 1180. doi : 10.1038 / nbt. 1586. PMID 19915552. ^ Jump up to : Machado, Iara M.P. ; Atsumi, Shota ( 1 November 2012 ). `` Cyanobacterial biofuel production ''. Journal of Biotechnology. 162 ( 1 ) : 50 -- 56. doi : 10.1016 / j. jbiotec. 2012.03. 005. PMID 22446641. ^ Jump up to : Varman, A.M. ; Xiao, Y. ; Pakrasi, H.B. ; Tang, Y.J. ( 26 November 2012 ). `` Metabolic Engineering of Synechocystis sp. Strain PCC 6803 for Isobutanol Production ''. Applied and Environmental Microbiology. 79 ( 3 ) : 908 -- 914. doi : 10.1128 / AEM. 02827 - 12. PMC 3568544. PMID 23183979. ^ Jump up to : Singh, Nirbhay Kumar ; Dhar, Dolly Wattal ( 11 March 2011 ). `` Microalgae as second generation biofuel. A review ''. Agronomy for Sustainable Development. 31 ( 4 ) : 605 -- 629. doi : 10.1007 / s13593 - 011 - 0018 - 0. ^ Jump up to : Li, Shanshan ; Huang, Di ; Li, Yong ; Wen, Jianping ; Jia, Xiaoqiang ( 1 January 2012 ). `` Rational improvement of the engineered isobutanol - producing Bacillus subtilis by elementary mode analysis ''. Microbial Cell Factories. 11 ( 1 ) : 101. doi : 10.1186 / 1475 - 2859 - 11 - 101. ^ Jump up to : Kondo, Takashi ; Tezuka, Hironori ; Ishii, Jun ; Matsuda, Fumio ; Ogino, Chiaki ; Kondo, Akihiko ( 1 May 2012 ). `` Genetic engineering to enhance the Ehrlich pathway and alter carbon flux for increased isobutanol production from glucose by Saccharomyces cerevisiae ''. Journal of Biotechnology. 159 ( 1 -- 2 ) : 32 -- 37. doi : 10.1016 / j. jbiotec. 2012.01. 022. PMID 22342368. Jump up ^ MATSUDA, Fumio ; KONDO, Takashi ; IDA, Kengo ; TEZUKA, Hironori ; ISHII, Jun ; KONDO, Akihiko ( 1 January 2012 ). `` Construction of an Artificial Pathway for Isobutanol Biosynthesis in the Cytosol of Saccharomyces cerevisiae ''. Bioscience, Biotechnology, and Biochemistry. 76 ( 11 ) : 2139 -- 2141. doi : 10.1271 / bbb. 120420. Jump up ^ Lee, Won - Heong ; Seo, Seung - Oh ; Bae, Yi - Hyun ; Nan, Hong ; Jin, Yong - Su ; Seo, Jin - Ho ( 28 April 2012 ). `` Isobutanol production in engineered Saccharomyces cerevisiae by overexpression of 2 - ketoisovalerate decarboxylase and valine biosynthetic enzymes ''. Bioprocess and Biosystems Engineering. 35 ( 9 ) : 1467 -- 1475. doi : 10.1007 / s00449 - 012 - 0736 - y. PMID 22543927. Jump up ^ Li, H. ; Opgenorth, P.H. ; Wernick, D.G. ; Rogers, S. ; Wu, T. - Y. ; Higashide, W. ; Malati, P. ; Huo, Y. - X. ; Cho, K.M. ; Liao, J.C. ( 29 March 2012 ). `` Integrated Electromicrobial Conversion of CO2 to Higher Alcohols ''. Science. 335 ( 6076 ) : 1596 -- 1596. Bibcode : 2012Sci... 335.1596 L. doi : 10.1126 / science. 1217643. PMID 22461604. Jump up ^ Lu, Jingnan ; Brigham, Christopher J. ; Gai, Claudia S. ; Sinskey, Anthony J. ( 4 August 2012 ). `` Studies on the production of branched - chain alcohols in engineered Ralstonia eutropha ''. Applied Microbiology and Biotechnology. 96 ( 1 ) : 283 -- 297. doi : 10.1007 / s00253 - 012 - 4320 - 9. PMID 22864971. Jump up ^ Ting, Cindy Ng Wei ; Wu, Jinchuan ; Takahashi, Katsuyuki ; Endo, Ayako ; Zhao, Hua ( 8 September 2012 ). `` Screened Butanol - Tolerant Enterococcus faecium Capable of Butanol Production ''. Applied Biochemistry and Biotechnology. 168 ( 6 ) : 1672 -- 1680. doi : 10.1007 / s12010 - 012 - 9888 - 0. PMID 22961352. Jump up ^ `` Cosmetic Chemicals Banned in Canada '', Chem. Eng. News, 87 ( 11 ) : 38, 2009 - 03 - 16. External links Wikimedia Commons has media related to Isobutanol. International Chemical Safety Card 0113 `` NIOSH Pocket Guide to Chemical Hazards # 0352 ''. National Institute for Occupational Safety and Health ( NIOSH ). IPCS Environmental Health Criteria 65 : Butanols : four isomers IPCS Health and Safety Guide 9 : Isobutanol Alcohols Straight - chain primary alcohols ( 1 ° ) Methanol ( C ) Ethanol ( C ) 1 - Propanol ( C ) n - Butanol ( C ) 1 - Pentanol ( C ) 1 - Hexanol ( C ) 1 - Heptanol ( C ) 1 - Octanol ( C ) 1 - Nonanol ( C ) 1 - Decanol ( C ) Undecanol ( C ) Dodecanol ( C ) Tridecan - 1 - ol ( C ) 1 - Tetradecanol ( C ) Pentadecan - 1 - ol ( C ) Cetyl alcohol ( C ) Heptadecan - 1 - ol ( C ) Stearyl alcohol ( C ) Nonadecan - 1 - ol ( C ) Arachidyl alcohol ( C ) Heneicosan - 1 - ol ( C ) Docosanol ( C ) Tricosan - 1 - ol ( C ) 1 - Tetracosanol ( C ) Pentacosan - 1 - ol ( C ) 1 - Hexacosanol ( C ) 1 - Heptacosanol ( C ) 1 - Octacosanol ( C ) 1 - Nonacosanol ( C ) Triacontanol ( C ) Other primary alcohols Isobutanol ( C ) Isoamyl alcohol ( C ) 2 - Methyl - 1 - butanol ( C ) Phenethyl alcohol ( C ) Tryptophol ( C ) Secondary alcohols ( 2 ° ) Isopropanol ( C ) 2 - Butanol ( C ) 2 - Pentanol ( C ) 2 - Hexanol ( C ) 2 - Heptanol ( C ) Cyclohexanol ( C ) 2 - Octanol ( C ) Tertiary alcohols ( 3 ° ) tert - Butyl alcohol ( C ) tert - Amyl alcohol ( C ) 2 - Methyl - 2 - pentanol ( C ) 2 - Methylhexan - 2 - ol ( C ) 2 - Methylheptan - 2 - ol ( C ) 3 - Methyl - 3 - pentanol ( C ) 3 - Methyloctan - 3 - ol ( C ) Hypnotics / sedatives ( N05C ) GABA Alcohols 2M2B Chloralodol Ethanol ( alcohol ) Ethchlorvynol Methylpentynol Trichloroethanol Barbiturates Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital Benzodiazepines Brotizolam Cinolazepam Climazolam Doxefazepam Estazolam Flunitrazepam Flurazepam Flutoprazepam Lorazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitrazepam Phenazepam Quazepam Temazepam Triazolam Carbamates Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate Imidazoles Etomidate Metomidate Propoxate Monoureides Acecarbromal Apronal ( apronalide ) Bromisoval Capuride Carbromal Ectylurea Neuroactive steroids Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Hydroxydione Minaxolone Progesterone Nonbenzodiazepines Eszopiclone Indiplon Lirequinil Necopidem Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone Phenols Propofol Piperidinediones Glutethimide Methyprylon Pyrithyldione Piperidione Quinazolinones Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone Others Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol Kavalactones Loreclezole Paraldehyde Petrichloral Sulfonylalkanes Sulfonmethane ( sulfonal ) Tetronal Trional Triclofos Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid GABA 1, 4 - Butanediol 4 - Fluorophenibut Aceburic acid Baclofen GABOB GHB ( sodium oxybate ) GBL GVL Phenibut Tolibut Antihistamines Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine Antidepressants Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc. Antipsychotics Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc. α - Adrenergic Clonidine Detomidine Dexmedetomidine Lofexidine Medetomidine Romifidine Tizanidine Xylazine 5 - HT Antidepressants Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc. Antipsychotics Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc. Others Niaprazine Melatonin Agomelatine Melatonin Ramelteon Tasimelteon Orexin Almorexant Filorexant Suvorexant α δ VDCC Gabapentin Gabapentin enacarbil Mirogabalin Phenibut Pregabalin Others Cannabidiol Cannabis Chlorophenylalkyldiols Fenpentadiol Metaglycodol Phenaglycodol Diethylpropanediol Evoxine Fenadiazole Guaifenesin - related muscle relaxants Chlorphenesin Mephenesin Mephenoxalone Metaxalone Methocarbamol Opioids ( e.g., morphine ) Passion flower Scopolamine Trazodone UMB68 Valnoctamide GABA receptor positive modulators Alcohols Brometone Butanol Chloralodol Chlorobutanol ( cloretone ) Ethanol ( alcohol ) ( alcoholic drink ) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert - Butanol ( 2M2P ) tert - Pentanol ( 2M2B ) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol Barbiturates ( - ) - DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital / Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital Benzodiazepines 2 - Oxoquazepam 3 - Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP - 1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT - 201 FG - 8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N - Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH - II - 66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48 - 6791 Ro48 - 8684 SH - 053 - R - CH3 - 2 ′ F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam ( Ro5 - 2904 ) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam Carbamates Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate Flavonoids 6 - Methylapigenin Ampelopsin ( dihydromyricetin ) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc - OMe Skullcap constituents ( e.g., baicalin ) Wogonin Imidazoles Etomidate Metomidate Propoxate Kava constituents 10 - Methoxyyangonin 11 - Methoxyyangonin 11 - Hydroxyyangonin Desmethoxyyangonin 11 - Methoxy - 12 - hydroxydehydrokavain 7, 8 - Dihydroyangonin Kavain 5 - Hydroxykavain 5, 6 - Dihydroyangonin 7, 8 - Dihydrokavain 5, 6, 7, 8 - Tetrahydroyangonin 5, 6 - Dehydromethysticin Methysticin 7, 8 - Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal ( apronalide ) Bromisoval Carbromal Capuride Ectylurea Neuroactive steroids Acebrochol Allopregnanolone ( brexanolone ) Alfadolone Alfaxalone 3α - Androstanediol Androstenol Androsterone Certain anabolic - androgenic steroids Cholesterol DHDOC 3α - DHP 5α - DHP 5β - DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG - 20599 ORG - 21465 P1 - 185 Pregnanolone ( eltanolone ) Progesterone Renanolone SAGE - 105 SAGE - 217 SAGE - 324 SAGE - 516 SAGE - 689 SAGE - 872 Testosterone THDOC Nonbenzodiazepines β - Carbolines : Abecarnil Gedocarnil Harmane SL - 651,498 ZK - 93423 Cyclopyrrolones : Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines : Alpidem DS - 1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines : Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others : Adipiplon CGS - 8216 CGS - 9896 CGS - 13767 CGS - 20625 CL - 218,872 CP - 615,003 CTP - 354 ELB - 139 GBLD - 345 Imepitoin JM - 1232 L - 838,417 Lirequinil ( Ro41 - 3696 ) NS - 2664 NS - 2710 NS - 11394 Pipequaline ROD - 188 RWJ - 51204 SB - 205,384 SX - 3228 TGSC01AA TP - 003 TPA - 023 TP - 13 U-89843A U-90042 Viqualine Y - 23684 Phenols Fospropofol Propofol Thymol Piperidinediones Glutethimide Methyprylon Piperidione Pyrithyldione Pyrazolopyridines Cartazolate Etazolate ICI - 190,622 Tracazolate Quinazolinones Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL - 164 Volatiles / gases Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane ( methyl chloroform ) Trichloroethylene Vinyl ether Others / unsorted 3 - Hydroxybutanal α - EMTBL AA - 29504 Avermectins ( e.g., ivermectin ) Bromide compounds ( e.g., lithium bromide, potassium bromide, sodium bromide ) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines ( e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid ( dihydroergotoxine ) ) DS2 Efavirenz Etazepine Etifoxine Fenamates ( e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid ) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans ( e.g., 4 - O - methylhonokiol, honokiol, magnolol, obovatol ) Loreclezole Menthyl isovalerate ( validolum ) Monastrol Niacin Nicotinamide ( niacinamide ) Org 25,435 Phenytoin Propanidid Retigabine ( ezogabine ) Safranal Seproxetine Stiripentol Sulfonylalkanes ( e.g., sulfonmethane ( sulfonal ), tetronal, trional ) Terpenoids ( e.g., borneol ) Topiramate Valerian constituents ( e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol ) Unsorted benzodiazepine site positive modulators : α - Pinene MRK - 409 ( MK - 0343 ) TCS - 1105 TCS - 1205 See also : Receptor / signaling modulators GABA receptor modulators GABA metabolism / transport modulators Retrieved from `` https://en.wikipedia.org/w/index.php?title=Isobutanol&oldid=821499974 '' Categories : Alcohol solvents Primary alcohols GABAA receptor positive allosteric modulators Sedatives Hypnotics Alkanols Hidden categories : CS1 maint : Multiple names : authors list ECHA InfoCard ID from Wikidata Chembox having DSD data Articles containing unverified chemical infoboxes Chembox image size set Talk Contents About Wikipedia تۆرکجه Bosanski Čeština Deutsch Español Esperanto Euskara فارسی Français Italiano עברית Magyar Nederlands 日本 語 Norsk Português Română Русский Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska 中文 Edit links This page was last edited on 20 January 2018, at 21 : 35. 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Question: what is the iupac name for isobutyl alcohol
Answer: 2-methylpropan-1-ol