Compound: oxalic acid
SMILES: O=C(O)C(=O)O
InChIKey: MUBZPKHOEPUJKR-UHFFFAOYSA-N
Synonyms: oxalic acid, ethanedioic acid, 144-62-7, Aktisal, Aquisal, Oxiric acid, Oxaalzuur, Oxalsaeure, Kyselina stavelova, Acidum oxalicum, Acide oxalique, Acido ossalico, Ethanedionic acid, NCI-C55209, Ethane-1,2-dioic acid, NSC-62774, DTXSID0025816, Oxalic acid, anhydrous, 9E7R5L6H31, DTXCID805816, CHEBI:16995, Acid, Oxalic, hydron;oxalate, 2-oxo-2-oxonioacetate, Oxalic acid (aqueous), Oxalate, Ferric, Oxalate, Sodium, Oxalate, Iron, Oxalate, Aluminum, Oxalate, Chromium, Oxalate, Disodium, Oxalate, Dilithium, Oxalate, Magnesium, Oxalate, Potassium, Oxalate, Diammonium, Oxalate, Monosodium, Oxalate, Dipotassium, Oxalate, Monoammonium, Oxalate, Monopotassium, RefChem:6477, Oxalate, Potassium Chromium, Oxalate, Monohydrogen Monopotassium, 205-634-3, Caswell No. 625, Oxaalzuur [Dutch], Oxalsaeure [German], Oxalic acid anhydrous, Acide oxalique [French], C2H2O4, Acido ossalico [Italian], Kyselina stavelova [Czech], NSC 62774, CCRIS 1454, EPA Pesticide Chemical Code 009601, HSDB 1100, AI3-26463, BRN 0385686, HOOCCOOH, Ultraplast Activate S 52, Oxalic acid /Ethanedioic acid, Oxalicacid, bis(5-azaspiro[2.5]octan-8-ol), bis((2R)-azetidine-2-carbonitrile), MFCD00002573, bis(1-(3-methyloxetan-3-yl)ethan-1-amine), C00209, Oxalic acid alpha polymorph, Oxalic acid diammonium salt, CAS-144-62-7, OXD, NSC115893, EINECS 205-634-3, Ethandisaeure, Ethanedionate, Ascorbic Acid EP Impurity E, Oxagel, DeerClean, UNII-9E7R5L6H31, 2dua, 2hwg, H2ox, Oxalic Acid Dianion, Anhydrous oxalic acid, Ethane-1,2-dioate, Oxalic acid, 98%, Oxalic acid (8CI), oxalic acid 2 hydrate, Oxalic acid 2-Hydrate, 1o4n, 1t5a, Oxalic acid 10 microg/mL in Acetonitrile, WLN: QVVQ, Ethanedioic acid (9CI), OXALIC ACID [MI], Oxalic acid dihydrate ACS, SCHEMBL776, bmse000106, EC 205-634-3, OXALIC ACID [HSDB], NCIOpen2_000770, NCIOpen2_001022, NCIOpen2_001042, NCIOpen2_001202, NCIOpen2_008831, OXALIC ACID [VANDF], OXALIC ACID, 99%, 4-02-00-01819 (Beilstein Handbook Reference), OXALIC ACID [WHO-DD], SCHEMBL812380, Oxalic acid, AR, >=99%, Oxalic acid, LR, >=98%, CHEMBL146755, orb1304742, orb3025233, Oxalic acid, 99% (Standard), Oxalic acid, analytical standard, SCHEMBL10471058, BDBM14674, HY-Y0262R, MeSH ID: D019815, HMS5086K21, HY-Y0262, NSC62774, STR01359, Tox21_202122, Tox21_303346, BBL003000, EBC-04354, NSC 76990, s9354, STK379550, AKOS005449445, CCG-266020, DB03902, FO26604, NSC 132055, NSC 151956, SB40938, SB40959, SB40985, Oxalic acid, ReagentPlus(R), >=99%, MSK000232-1000W, NCGC00249170-01, NCGC00257376-01, NCGC00259671-01, BP-21133, Oxalic acid Solution in Water, 1000ug/mL, Oxalic acid, SAJ first grade, >=97.0%, CS-0013716, NS00077150, Oxalic Acid(Discontinued,See C4X-177924), Oxalic acid, Vetec(TM) reagent grade, 98%, OXALIPLATIN IMPURITY A [EP IMPURITY], EN300-16428, USP Solution Oxalic Acid TS Conforms to USP, G73503, Oxalic acid, purum, anhydrous, >=97.0% (RT), F600888, Q184832, Calcium ascorbate dihydrate Impurity E [EP Impurity], F1B1B2D7-C290-4CE6-8550-F25B202AFADE, F2191-0257, Oxalic acid, puriss. p.a., anhydrous, >=99.0% (RT), Oxalic acid, purified grade, 99.999% trace metals basis, InChI=1/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6, Oxalate standard for IC, 1.000 g/L in H2O, analytical standard, Reagecon Oxalic Acid 0.05M according to Chinese Pharmacopoeia (ChP), bis(tert-butyl 4-[3-(methanesulfonyloxy)propyl]piperazine-1-carboxylate), 48J, Ribavirin Impurity U;Ascorbic Acid EP Impurity E;Sodium Ascorbate EP Impurity E;Oxaliplatin EP Impurity A
Theoretical properties:
molecular_formula: C2H2O4
molecular_weight: 90.03 g/mol
exact_mass: 89.99530854 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 6
topological_polar_surface_area: 74.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: ANHYDROUS OXALIC ACID, CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBIC, CRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA
color: ANHYDROUS OXALIC ACID, CRYSTALLIZED FROM GLACIAL ACETIC ACID IS ORTHORHOMBIC, CRYSTALS BEING PYRAMIDAL OR ELONGATED OCTAHEDRA
odor: Odorless.
boiling_point: Sublimes (NIOSH, 2024)
melting_point: 372 °F (Decomposes) (NTP, 1992)
density: 1.9 at 59 °F (USCG, 1999) - Denser than water; will sink
solubility: 50 to 100 mg/mL at 75 °F (NTP, 1992)
vapor_pressure: 0.001 mmHg at 68 °F (NTP, 1992)
Descriptions:
pubchem: Oxalic acid is an alpha,-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2. It has a role as a plant metabolite, a human metabolite and an algal metabolite. It is a conjugate acid of an oxalate and an oxalate(1-).
chebi: An α,ω-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.
chembl: OXALIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.
wikipedia: Oxalic acid is an organic acid with the systematic name ethanedioic acid and chemical formula HO−C(=O)−C(=O)−OH, also written as (COOH)2 or (CO2H)2 or H2C2O4. It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name is derived from early investigators who isolated oxalic acid from flowering plants of the genus Oxalis, commonly known as wood-sorrels. It occurs naturally in many foods.  It can be toxic when eaten in significant quantities, and contact with concentrated forms can cause chemical burns.
Oxalic acid is a much stronger acid than acetic acid. It is a reducing agent and its conjugate bases hydrogenoxalate (HC2O−4) and oxalate (C2O2−4) are chelating agents for metal cations. It is used as a cleaning agent, especially for the removal of rust, because it forms a water-soluble ferric iron complex, the ferrioxalate ion. Oxalic acid typically occurs as the dihydrate with the formula H2C2O4·2H2O.