Methyl 2-oxoacetate Chemical Properties

Melting point:

40-42°C

Boiling point:

102.98°C (rough estimate)

Density 

1.2076 (rough estimate)

refractive index 

1.3720 (estimate)

solubility 

sol H2O; sol most organic solvents, e.g. ether, CH2Cl2, THF, acetone, etc.

CAS DataBase Reference

922-68-9(CAS DataBase Reference)

NIST Chemistry Reference

Methyl glyoxylate(922-68-9)

EPA Substance Registry System

Acetic acid, oxo-, methyl ester (922-68-9)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Methyl 2-oxoacetate Usage And Synthesis

Uses

Methyl Glyoxylate is a useful compound for preparation of pyridine and quinoline derivatives.

Preparation

Preparative Methods of Methyl 2-oxoacetate: efficient methods include oxidative cleavage of tartrate diesters, ozonolysis of maleate/fumarate derivatives, exchange reaction between appropriate dialkoxyacetate and glyoxylic acid, and NaOAc-catalyzed elimination of nitrite ion from nitrate esters.^[1]

General Description

Methyl Glyoxylate is a two-carbon synthon utilized in electrocyclic processes (Diels-Alder reaction, ene reactions), various condensations (Mannich, aldol, Wittig, Prins, acyloin), carbinolamine formation, and Friedel-Crafts reactions.

storage

Methyl 2-oxoacetate stores under N2 in a refrigerator due to their tendency to form a monohydrate and/or polymerize.

References

1. (a) Wolf, F. J.; Weijland, J. OSC 1963, 4, 124. (b) Jung, M. E.; Shishido, K.; Davis, L. H. JOC 1982, 47, 891. (c) Blake, J.; Tretter, J. R.; Juhasz, G. J.; Bonthrone, W.; Rappoport, H. JACS 1966, 88, 4061. (d) Haggerty, J. G.; Kelly, T. R.; Schmidt, T. E. S 1972, 544. Hook, J. M. SC 1984, 14, 83. (e) Kornblum, N.; Frazier, H. W. JACS 1966, 88, 865.

Methyl 2-oxoacetate(922-68-9)Related Product Information

• Methyl salicylate
• Methanol
• Methyl acrylate
• FATTY ACID METHYL ESTER MIX C8-C22
• Methyl methacrylate
• Glyoxylic acid
• Paraquat dichloride
• Methyl benzoate
• Basic Violet 1
• Methyl acetate
• Ethyl glyoxalate
• Methyl formate
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• Acetonitrile
• Carbonic acid, ethyl 2-methylpropyl ester
• Methyl
• Glyoxylic acid monohydrate