28868-76-0

Basic information

• Product Name: Dimethyl chloromalonate
• Synonyms: 2-CHLORO-MALONIC ACID DIMETHYL ESTER;DIMETHYL CHLOROMALONATE;CL-DMM;AURORA KA-6079;Ethylsuccinyl monochloride;2-Chloropropanedioic acid dimethyl ester;Chloro-Methyl Malonate;ChlorotwoMethylMalonic acid
• CAS NO: 28868-76-0
• Molecular Formula: C5H7ClO4
• Molecular Weight: 166.56
• EINECS: 249-275-0
• Product Categories: Pharmaceutical Intermediates;TheMalonateRamificationProducts;C2 to C5;Carbonyl Compounds;Esters;ester series
• Mol File: 28868-76-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 105-106 °C19 mm Hg(lit.)
• Flash Point: 224 °F
• Appearance: /
• Density: 1.305 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.148mmHg at 25°C
• Refractive Index: n20/D 1.437(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.02±0.46(Predicted)
• BRN: 1768415
• CAS DataBase Reference: Dimethyl chloromalonate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl chloromalonate(28868-76-0)
• EPA Substance Registry System: Dimethyl chloromalonate(28868-76-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 28868-76-0(Hazardous Substances Data)

Usage

Uses

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.

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.

InChI:InChI=1/C5H7ClO4/c1-9-4(7)3(6)5(8)10-2/h3H,1-2H3

Upstream product

• 563-79-1 2,3-Dimethyl-2-butene 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 17911-97-6 2-Chlor-3,3-dimethoxy-acrylsaeure-methylester 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 72955-05-6 Dimethyl-p-methoxyphenoxymalonat 
• 53295-30-0 5-[2,2-bis(methoxycarbonyl)ethyl]tetrahydrofuran-2-one 
• 82437-42-1 dimethyl 2-(2-chloro-2-phenylethyl)malonate 
• 1228117-34-7 2-(4-bromophenoxy)malonic acid dimethyl ester 
• 4702-34-5 isochroman-1-one 

Relevant articles and documents

Halogenation of carbonyl compounds by an ionic liquid, [AcMIm]X, and Ceric Ammonium Nitrate (CAN)

An ionic liquid, acetylmethylimidazolium halide ([AcMIm]X), in combination with ceric ammonium nitrate promotes halogenations of a wide variety of ketones and 1,3-keto esters at the ?-position. The ionic liquid acts here as reagent as well as reaction medium, and thus the reaction does not require any organic solvent or conventional halogenating agent. The reaction is completely arrested when the radical quencher TEMPO is used. A plausible radical mechanism is also suggested. CSIRO 2007.