Compound: Dimethyl malonate
SMILES: O=C(OC)CC(=O)OC
InChIKey: BEPAFCGSDWSTEL-UHFFFAOYSA-N
Synonyms: Dimethyl malonate, 108-59-8, Dimethyl propanedioate, Methyl malonate, MALONIC ACID, DIMETHYL ESTER, DTXSID4029145, EM8Y79998C, DTXCID309145, RefChem:134253, 203-597-8, Malonic Acid Dimethyl Ester, Propanedioic acid, dimethyl ester, 1,3-dimethyl propanedioate, MFCD00008460, Dimethyl 1,3-propanedioate, CAS-108-59-8, CCRIS 8981, propanedioic acid dimethyl ester, EINECS 203-597-8, Malonic acid-dimethyl ester, UNII-EM8Y79998C, Dimethyl malonate, 98%, malonic acid dimethylester, CH2(COOMe)2, EC 203-597-8, SCHEMBL53913, METHYL MALONATE [MI], SCHEMBL167723, Dimethyl ester of malonic acid, CH2(CO2CH3)2, orb1301575, orb3025647, SCHEMBL2125856, SCHEMBL7279690, CHEMBL1986332, HY-Y1787, STR00450, Tox21_201608, Tox21_300375, BBL011438, MSK176913, NSC620046, STL146546, Dimethyl malonate, analytical standard, AKOS001426594, EBC-618125, NSC-620046, Propanedioic acid, 1,3-dimethyl ester, MSK176913-1000H, NCGC00248011-01, NCGC00248011-02, NCGC00254271-01, NCGC00259157-01, BP-31034, DA-52562, NCI60_005924, CS-0019394, Dimethyl malonate, purum, >=96.0% (GC), M0030, NS00006418, EN300-15469, D72530, Dimethyl malonate Solution in Hexane, 1000ug/mL, Dimethyl malonate, Vetec(TM) reagent grade, 98%, F996204, Q4263082, Z18909219, F0001-0174, InChI=1/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H, PROPANEDIOIC ACID,DIMETHYL ESTER  (MALONIC ACID,DIMETHYL ESTER), 75238-25-4
Theoretical properties:
molecular_formula: C5H8O4
molecular_weight: 132.11 g/mol
exact_mass: 132.04225873 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 4
heavy_atom_count: 9
topological_polar_surface_area: 52.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
vapor_pressure: 14.7 [mmHg]
Descriptions:
{"pubchem": null, "chebi": null, "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Dimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide.\n\n  \n    \n      \n        \n          \n            H\n            \n              2\n            \n          \n          C\n          (\n          O\n          C\n          \n            H\n            \n              3\n            \n          \n          \n            )\n            \n              2\n            \n          \n          +\n          2\n           \n          C\n          O\n          \u27f6\n          C\n          \n            H\n            \n              2\n            \n          \n          (\n          C\n          \n            O\n            \n              2\n            \n          \n          C\n          \n            H\n            \n              3\n            \n          \n          \n            )\n            \n              2\n            \n          \n        \n      \n    \n    {\\displaystyle \\mathrm {H_{2}C(OCH_{3})_{2}+2\\ CO\\longrightarrow CH_{2}(CO_{2}CH_{3})_{2}} }\n  \n\nDimethyl malonate is used extensively in the fragrance industry as a raw material in the synthesis of jasmonates. For example, methyl dihydrojasmonate is synthesized from cyclopentanone, pentanal and dimethyl malonate. Hedione is used in almost all fine fragrances and is found in Christian Dior's Eau Sauvage and \"Diorella\", Hermes' \"Voyage d'Hermes Parfum\", Calvin Klein's \"CKOne\", Chanel's \"Chanel No. 19\", and Mark Jacob's \"Blush\", among others. As of 2009, Hedione was Firmenich's top selling compound by volume.\nHebei Chengxin is the world's largest producer of dimethyl malonate by volume and uses a chloroacetic acid/sodium cyanide process developed in the 1940s."}