374539

Dimethyl chloromalonate

94%

• Synonym(s): 1,3-Dimethyl 2-chloropropanedioate, 2-Chloro-malonic acid dimethyl ester, Chloropropanedioic acid dimethyl ester, Dimethyl α-chloromalonate, Dimethyl 2-chloromalonate, Dimethyl 2-chloropropanedioate
• Linear Formula: ClCH(COOCH₃)₂
• CAS Number: 28868-76-0
• Molecular Weight: 166.56
• Beilstein: 1768415
• EC Number: 249-275-0
• MDL number: MFCD00042837
• UNSPSC Code: 12352100
• PubChem Substance ID: 24863315
• NACRES: NA.22

Properties

• Quality Level: 200
• Assay: 94%
• form: liquid
• impurities: 4-5% dimethyl dichloromalonate
• refractive index: n20/D 1.437 (lit.)
• bp: 105-106 °C/19 mmHg (lit.)
• density: 1.305 g/mL at 25 °C (lit.)
• functional group: chloro; ester
• SMILES string: COC(=O)C(Cl)C(=O)OC
• InChI: 1S/C5H7ClO4/c1-9-4(7)3(6)5(8)10-2/h3H,1-2H3
• InChI key: LNBQBURECUEBKZ-UHFFFAOYSA-N

Description

General description

Dimethyl chloromalonate (dimethyl 2-chloromalonate) is a dialkyl 2-substituted malonate. Carbanions of dimethyl chloromalonate are reported to react with naphthoquinone derivatives, via vicarious nucleophilic substitution or oxidative nucleophilic substitution of hydrogen processes. Dimethyl chloromalonate is reported to react with hydroquinone and monosubstituted hydroquinones to afford 2-oxido-benzo[b]furan derivatives. Synthesis of dimethyl 2-chloromalonate, via chlorination of dimethyl malonate has been reported.

Application

Dimethyl chloromalonate is suitable for use in the synthesis of 4,5,6-trichloropyrimidine. It may be used in the stereoselective synthesis of highly functionalized nitrocyclopropanes. It may be used in one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes.

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): 224.6 °F - closed cup
• Flash Point(C): 107 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves