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

• 141-97-9 ethyl acetoacetate 
• 107-07-3 2-chloro-ethanol 
• 2911-21-9 2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine 
• 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 
• 674-82-8 4-methyleneoxetan-2-one 
• 691-45-2 acetylketene 

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 
• 62760-10-5 2-chloroethyl 2-(3-nitrobenzyliden)acetoacetate 
• 54527-89-8 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester 
• 130370-24-0 2-[1-(2,3-Dichloro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid 2-chloro-ethyl ester 
• 62760-01-4 2-[1-(2-Nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid 2-chloro-ethyl 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 
• 79851-62-0 ethyl 2-isopropyl-4-methyloxazole-5-carboxylate 
• 58371-98-5 3, 5-dichloro-2-pentanone 
• 933782-12-8 2-cyclohexyl-4-ethoxycarbonyl-4-methyl-1,3-oxazole 
• 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 
• 100427-03-0 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-(2-propoxy-ethyl) ester 
• 91040-32-3 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-isobutyl ester 
• 54585-92-1 2-chloroethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-ethoxy-carbonyl-1,4-dihydropyridine-3-carboxylate 

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.

Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6- dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity

A series of asymmetric 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates characterized by the presence of a 3,3-diphenylpropylamino moiety in one of the ester groups were synthesized. They exhibited remarkable antihypertensive activity in spontaneously hypertensive rats as well as affinity for the 1,4- dihydropyridines binding site labelled by 3H-nitrendipine in the calcium channel. Introduction of this bulky and lipophilic amine confers to the whole series an elevated level of antihypertensive activity and a long duration of action, a structure-dependent modulation of the activity being found only in the subset characterized by the presence of a branched propylene bridge between the ester and the amino groups. The presence of the amino group is essential for oral activity. Out of this series, compound 9u (Rec 15/2375- lercanidipine) was selected for clinical development and obtained marketing authorization as an antihypertensive in several countries.