359890

Dimethyl bromomalonate

technical grade, 90%

• Linear Formula: BrCH(COOCH₃)₂
• CAS Number: 868-26-8
• Molecular Weight: 211.01
• Beilstein: 971135
• EC Number: 212-775-4
• MDL number: MFCD00025865
• UNSPSC Code: 12352100
• PubChem Substance ID: 24862117
• NACRES: NA.22

Properties

• grade: technical grade
• Quality Level: 100
• Assay: 90%
• form: liquid
• refractive index: n20/D 1.460 (lit.)
• bp: 105-108 °C/11 mmHg (lit.)
• density: 1.601 g/mL at 25 °C (lit.)
• SMILES string: COC(=O)C(Br)C(=O)OC
• InChI: 1S/C5H7BrO4/c1-9-4(7)3(6)5(8)10-2/h3H,1-2H3
• InChI key: NEMOJKROKMMQBQ-UHFFFAOYSA-N

Description

General description

Dimethyl bromomalonate undergoes manganese(III)-promoted free-radical chain addition reaction with olefins, to yield dimethyl 2-bromoalkylmalonates. Organocatalyzed Michael addition of dimethyl bromomalonate to nitrostyrenes to yield synthetically useful nitrocyclopropanes has been reported. Dimethyl bromomalonate reacts readily with arylnitroso compounds to yield the corresponding N-aryl-C,C-dimethoxycarbonylnitrones.

Application

Dimethyl bromomalonate may be used in the enantioselective synthesis of nitrocyclopropanes.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• Hazard Classifications: Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): 230.0 °F - closed cup
• Flash Point(C): 110 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves