4755-81-1

Basic information

• Product Name: Methyl 2-chloroacetoacetate
• Synonyms: 2-chloro-3-oxo-butanoicacimethylester;Methyl 2-chloro-3-oxobutanoate;METHYL 2-CHLORO-3-OXOBUTANATE;METHYL 2-CHLOROACETOACETATE;2-CHLOROACETOACETIC ACID METHYL ESTER;2-chloro-3-oxobutanoic acid, methyl ester;Chloroacetoaceticacidmethylester;Butanoic acid, 2-chloro-3-oxo-, methyl ester
• CAS NO: 4755-81-1
• Molecular Formula: C₅H₇ClO₃
• Molecular Weight: 150.56
• EINECS: 225-286-6
• Product Categories: C2 to C5;Carbonyl Compounds;Esters;Building Blocks;C2 to C5;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 4755-81-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: −33-−32.7 °C(lit.)
• Boiling Point: 137 °C(lit.)
• Flash Point: 161 °F
• Appearance: Clear yellow/Liquid
• Density: 1.236 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.19mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.89±0.46(Predicted)
• Water Solubility: 50 g/L (20 ºC)
• CAS DataBase Reference: Methyl 2-chloroacetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-chloroacetoacetate(4755-81-1)
• EPA Substance Registry System: Methyl 2-chloroacetoacetate(4755-81-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-27-28-36/37/39-37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4755-81-1(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW LIQUID

Uses

Methyl 2-chloroacetoacetate was used in one-pot synthesis of 2-arylimidazole-4-carboxylic acids. It was also used in synthesis of 3,5-disubstituted 1,2,4-triazoles.

Synthesis Reference(s)

Synthesis, p. 188, 1987 DOI: 10.1055/s-1987-27886

InChI:InChI=1/C5H7ClO3/c1-3(7)4(6)5(8)9-2/h4H,1-2H3/t4-/m0/s1

Upstream product

• 6134-69-6 methyl 2,2-dichloro-3-oxobutanoate 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 91565-70-7 3-[methoxy-(4-nitro-phenoxy)-phosphoryloxy]-crotonic acid methyl ester 
• 58131-64-9 methyl 2-chloro-2-(2-phenylhydrazono)acetate 
• 7786-34-7 phosdrin 
• 96722-54-2 C₁₂H₁₅ClN₂O₃ 
• 75998-58-2 Methyl-2-chlor-2-<2-(4-<2,4-dichlorphenoxy>phenyl)hydrazono>acetat 
• 118429-10-0 C₉H₈BrClN₂O₂ 
• 91075-68-2 C₉H₈N₂O₂ClNO₂ 
• 82417-84-3 methyl 2-chloro-2-(4-methylphenyl-hydrazono)acetate 
• 70736-27-5 C₉H₈N₂O₂ClCH₃O 
• 62465-90-1 methyl (N-(4-chlorophenyl)hydrazono)chloroacetate 
• 118010-84-7 p-fluorophenylchlorohydrazone 
• 35272-08-3 4-Iodphenylhydrazon-chloressigsaeuremethylester 
• 71987-90-1 methyl chloroglyoxylate (o-cis-β-methylstyryl)hydrazone 
• 71987-91-2 methyl chloroglyoxylate (o-trans-β-methylstyryl)hydrazone 

Relevant articles and documents

Synthesis and characterisation of novel N substituted 2-methylimidazo[1,2a] pyridine-3-carboxamides

A series of novel N substituted 2-methylimidazo[1,2a]pyridine-3- carboxamides has been synthesised in high yield by a convenient method and characterised by 1H NMR, MS, IR and elemental analysis.

Design, synthesis, and biological evaluation of antiviral agents targeting flavivirus envelope proteins

Flavivirus envelope proteins (E proteins) have been shown to play a pivotal role in virus assembly, morphogenesis, and infection of host cells. Inhibition of flavivirus infection of a host cell by means of a small molecule envelope protein antagonist is an attractive strategy for the development of antiviral agents. Virtual screening of the NCI chemical database using the dengue virus envelope protein structure revealed several hypothetical hit compounds. Bioassay results identified a class of thiazole compounds with antiviral potency in cell-based assays. Modification of these lead compounds led to a series of analogues with improved antiviral activity and decreased cytotoxicity. The most active compounds 11 and 36 were effective in the low micromolar concentration range in a cellular assay system.

A Convenient Synthesis of 1-Chloro-2-alkanones

1-Chloro-2-alkanones (α-chloromethylketones) were conveniently prepared by chlorination of methyl β-ketoesters and subsequent demethoxycarbonylation using 50percent sulfuric acid.