54527-68-3

Basic information

• Product Name: 3-Oxobutyric acid 2-chloroethyl ester
• Synonyms: 3-Oxobutanoic acid 2-chloroethyl ester;3-Oxobutyric acid 2-chloroethyl ester;2-chloroethyl 3-oxobutanoate
• CAS NO: 54527-68-3
• Molecular Formula: C₆H₉ClO₃
• Molecular Weight: 164.5869
• Mol File: 54527-68-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 231.44°C (rough estimate)
• Flash Point: 103.4°C
• Appearance: /
• Density: 1.2055
• Vapor Pressure: 0.0432mmHg at 25°C
• Refractive Index: 1.4430 (estimate)
• Storage Temp.: 2-8°C
• PKA: 10.23±0.46(Predicted)
• CAS DataBase Reference: 3-Oxobutyric acid 2-chloroethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxobutyric acid 2-chloroethyl ester(54527-68-3)
• EPA Substance Registry System: 3-Oxobutyric acid 2-chloroethyl ester(54527-68-3)

Safety Data

• Hazardous Substances Data: 54527-68-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 233, 1996 DOI: 10.1016/0040-4039(95)02136-1

InChI:InChI=1/C6H9ClO3/c1-5(8)4-6(9)10-3-2-7/h2-4H2,1H3

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 96-24-2 3-monochloro-1,2-propanediol 
• 541-50-4 2-acetoacetic acid 
• 107-06-2 1,2-dichloro-ethane 
• 107-07-3 2-chloro-ethanol 
• 2911-21-9 2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine 
• 691-45-2 acetylketene 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 54851-30-8 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-chloroethyl ester 5-isopropyl ester 
• 54527-89-8 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester 
• 85396-59-4 4-(3-nitrophenyl)-2-hydroxymethyl-6-methyl-3-methoxycarbonyl-5-(β-chloroethoxy)carbonyl-1,4-dihydropyridine 
• 62760-02-5 2-chloroethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate 
• 58371-98-5 3, 5-dichloro-2-pentanone 
• 933782-12-8 2-cyclohexyl-4-ethoxycarbonyl-4-methyl-1,3-oxazole 
• 79851-62-0 ethyl 2-isopropyl-4-methyloxazole-5-carboxylate 
• 108337-97-9 6,2',6'-Trimethyl-1',4'-dihydro-[2,4']bipyridinyl-3',5'-dicarboxylic acid 5'-[2-(benzyl-methyl-amino)-ethyl] ester 3'-methyl ester 
• 75091-01-9 2-Cyano-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-{2-[(3,4-dichloro-benzyl)-methyl-amino]-ethyl} ester 3-ethyl ester 
• 75091-05-3 2-Cyano-6-methyl-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-{2-[(3,4-dichloro-benzyl)-methyl-amino]-ethyl} ester 3-ethyl ester 
• 75091-04-2 2-Cyano-6-methyl-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-{2-[(4-chloro-benzyl)-methyl-amino]-ethyl} ester 3-ethyl ester 
• 74655-11-1 2-Cyano-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-{2-[(4-chloro-benzyl)-methyl-amino]-ethyl} ester 3-ethyl ester 
• 75091-03-1 2-Cyano-4-(2-cyano-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-{2-[(3,4-dichloro-benzyl)-methyl-amino]-ethyl} ester 3-ethyl ester 
• 75530-93-7 2-Cyano-6-methyl-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-[2-(benzyl-methyl-amino)-ethyl] ester 3-ethyl ester 

Relevant articles and documents

A Novel Intramolecular Ester-Enolate Alkylation: Preparation of Acylketene Acetals

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Process for the transesterification of keto esters using solid acids as catalysts

A process for the transesterification of keto esters and alcohols in approximately stoichiometric amounts using a solid acid catalyst. Solid acid catalysts may be sulfated zirconia, sulfated tin oxide, sulfated titania, sulfated iron oxide, heteropoly acids, acidic clays, acidic zeolites, or any other solid acids with high acidity or super acidity, with or without dopants. One equivalent or more of keto ester, one equivalent or more of alcohol, the solid acid catalyst, and an appropriate solvent are mixed and heated to 70 to 120° C. at atmospheric or reduced pressure to furnish the keto transester in high yields.

Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay

Transesterification and transthiolesterification of β-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding β-keto esters in high yields. For the first time, transthiolesterification of β-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of β-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding β-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward β-keto esters is also described. Sterically hindered carbonyl groups as well as α,β-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.