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

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

Uses

Used in Pharmaceutical Industry:
Methyl 2-chloroacetoacetate is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its ability to participate in one-pot synthesis makes it a valuable component in the creation of complex molecules with potential therapeutic applications.
Used in Chemical Synthesis:
Methyl 2-chloroacetoacetate is used as a reagent in the synthesis of 2-arylimidazole-4-carboxylic acids and 3,5-disubstituted 1,2,4-triazoles. These compounds have a wide range of applications, including their use as building blocks for pharmaceuticals, agrochemicals, and other specialty chemicals.

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

• 109002-50-8 C₁₁H₈BrClN₂O₅ 
• 109002-49-5 C₁₁H₇BrClN₂O₅^(1-)*Na⁽¹⁺⁾ 
• 70736-27-5 C₉H₈N₂O₂ClCH₃O 
• 125240-30-4 C₁₁H₁₃ClN₂O₂ 
• 505-29-3 1,4-Dithiane 
• 3643-97-8 5,6-dihydro-2-methyl-1,4-oxathiine 
• 130538-48-6 (2-Acetoxy-ethylsulfanyl)-acetic acid methyl ester 
• 102437-87-6 5,6-dihydro-2-methyl-1,4-oxathiine-3-carboxylic acid methyl ester 
• 3829-80-9 2-amino-4-methylthiazole-5-carboxylic acid methyl ester 
• 5805-84-5 1-allyl-2-methyl-1H-benzo[d]imidazole 
• 181861-57-4 C₁₈H₁₈ClN₃O₂ 
• 181861-60-9 C₁₉H₂₀ClN₃O₂ 
• 181861-76-7 C₁₈H₁₆ClN₃O₂ 
• 184226-56-0 C₂₁H₂₀ClN₃O₃ 

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.

Simple and efficient methods for selective preparation of α-mono or α,α-dichloro ketones and β-ketoesters by using DCDMH

New processes that can selectively prepare α-mono or α,α-dichloro ketones and β-ketoesters using 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) are reported. Using silica gel as the catalyst and methanol as the solvent and heating for 1 h under reflux, α-monochlorinated products were selectively obtained in 86-98% yield. However using a deep eutectic solvent (choline chloride: p-TsOH = 1:1) as the solvent and stirring for 45 min at room temperature, α,α- dichlorinated products were selectively obtained in 86-95% yield.

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.

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.

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.