63921-06-2

Basic information

• Product Name: dimethyl methyloxosuccinate
• Synonyms: dimethyl methyloxosuccinate;2-Methyl-3-oxobutanedioic acid dimethyl ester
• CAS NO: 63921-06-2
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.1513
• EINECS: 264-564-1
• Mol File: 63921-06-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 229°Cat760mmHg
• Flash Point: 93.4°C
• Appearance: /
• Density: 1.172g/cm³
• Vapor Pressure: 0.0713mmHg at 25°C
• Refractive Index: 1.425
• PKA: 9.20±0.46(Predicted)
• CAS DataBase Reference: dimethyl methyloxosuccinate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl methyloxosuccinate(63921-06-2)
• EPA Substance Registry System: dimethyl methyloxosuccinate(63921-06-2)

Safety Data

• Hazardous Substances Data: 63921-06-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H10O5/c1-4(6(9)11-2)5(8)7(10)12-3/h4H,1-3H3

Upstream product

• 553-90-2 Dimethyl oxalate 
• 554-12-1 propanoic acid methyl ester 
• 328-42-7 Oxalacetic acid 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 98268-20-3 methyl 2,4-dioxo-3-diazopentanoate 

Downstream Products

• 85199-56-0 2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 89497-03-0 (2R,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 85199-56-0 (2S,3S)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 50460-80-5 dimethyl 2-hydroxy-3-methylbutane-1,4-dioate 
• 50460-80-5 dimethyl 2-hydroxy-3-methylbutane-1,4-dioate 
• 50460-80-5 dimethyl (2R,3RS)-2-hydroxy-3-methylsuccinate 
• 608-41-3 erythro-2-hydroxy-3-methylbutane-1,4-dioic acid 
• 609-02-9 methyl-malonic acid dimethylester 
• 6065-52-7 2-Methylpropanedioic Acid Ethyl Methyl Ester 
• 609-08-5 Diethyl methylmalonate 

Relevant articles and documents

Evidence for Ketene Intermediates in the Reactions of 2-Oxobutanedioic Acid Diesters with Alcohols and Water

The reactions of diethyl ester (1a) and dimethyl ester (1b) of 3-methyl-2-oxobutanedioic acid with excess ethanol, methanol, or water in a sealed tube at approximately 125 deg C were studied.With methanol, 1a yielded mainly 3-methyl-2-oxobutanedioic acid 1-ethyl 4-methyl diester, 2a; with ethanol, 1b yielded mainly the 4-ethyl 1-methyl diester, 2b, while reaction of 1a with water yielded carbon dioxide, 2-oxobutanoic acid ethyl ester, 6, and 2-methyl-3-oxopropanoic acid ethyl ester, 7.These results suggested that the ketene intermediates 3-methyl-2,4-dioxo-3-butenoic acid ethyl or methyl ester, 4a and 4b, respectively, are implicated.The similarity of these reactions to those exhibited by ethyl acetoacetate, such as alkoxy group exchange, and formation of dehydroacetic acid, now thought to proceed by way of acetyl ketene, was demonstrated.

Photolysis of Methyl 3-Diazo-2-oxopropionate Wolff Migration of the Carbomethoxy Group

-

The Use of Microorganisms in Organic Synthesis. II. Microbiological Asymmetric Reduction of 2-Methyl-3-oxosuccinates

In order to synthesize four optically active methyl 2-methylmalates (10-13), microbiological asymmetric reduction of the corresponding dimethyl 2-methyl-3-oxosuccinate (9) was carried out.The β-keto diester 9 was found to be reduced by fermenting baker's yeast (Saccharomyces cerevisiae) and Candida albicans to afford a mixture of the (2R,3R)-isomer 10 and the (2S,3R)-isomer 11.Although the optical purity of 10 produced by Candida albicans was reasonably high (95percent e.e.), optical yields of other products were unexpectedly low.However, identification of the four possible isomers 14-17 was found to be easily carried out by means of nuclear magnetic resonance spectroscopy.Keywords - α-methyl-β-keto ester; methylmalate; asymmetric reduction; microbiological reduction; yeast; methyl 2-methylmalate