140925-20-8

Basic information

• Product Name: Oxiranecarboxylic acid, 3-formyl-, ethyl ester, (2S-trans)- (9CI)
• Synonyms: Oxiranecarboxylic acid, 3-formyl-, ethyl ester, (2S-trans)- (9CI)
• CAS NO: 140925-20-8
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.12532
• Product Categories: CARBOXYLICESTER;ALDEHYDE
• Mol File: 140925-20-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Oxiranecarboxylic acid, 3-formyl-, ethyl ester, (2S-trans)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranecarboxylic acid, 3-formyl-, ethyl ester, (2S-trans)- (9CI)(140925-20-8)
• EPA Substance Registry System: Oxiranecarboxylic acid, 3-formyl-, ethyl ester, (2S-trans)- (9CI)(140925-20-8)

Safety Data

• Hazardous Substances Data: 140925-20-8(Hazardous Substances Data)

Upstream product

• 2960-66-9 4-oxo-but-2-enoic acid ethyl ester 
• 136171-94-3 (2S,3R)-2,3-epoxy-4-hydroxybutanoic acid ethyl ester 

Downstream Products

• 135693-13-9 3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid ethyl ester; compound with pyrrolidine 

Relevant articles and documents

On the mechanism of the organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes

Mechanistic studies on the organocatalytic epoxidation of α,β-unsaturated aldehydes explore the autoinductive behavior of the reaction and establish that the hydrate/peroxyhydrate of the product is acting as a phase-transfer catalyst. Based on these studies, an improved methodology that provides high selectivities and decreased catalyst loading, through the addition of chloral hydrate, is developed. Self-promotion: Mechanistic studies on the organocatalytic epoxidation of α,β-unsaturated aldehydes reveal the autoinductive behavior and establish that the hydrate/peroxyhydrate of the product is acting as a phase-transfer catalyst. Based on these results, an improved methodology that provides high selectivities and decreased catalyst loading, through the addition of chloral hydrate, has been developed (see scheme). Copyright

Amine-catalyzed asymmetric epoxidation of α,β-unsaturated aldehydes

The direct organocatalytic enantioselective epoxidation of α,β-unsaturated aldehydes with different peroxides is presented. Proline, chiral pyrrolidine derivatives, and amino acid-derived imidazolidinones catalyze the asymmetric epoxidation of α,β-unsatur

Asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes with hydrogen peroxide

The first asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes is presented. A chiral bisaryl-silyl-protected pyrrolidine acts as a very selective epoxidation organocatalyst using simple oxidation agents, such as hydrogen peroxide and tert-butyl hydroperoxide. The asymmetric epoxidation reactions proceed under environmental friendly reaction condition in, for example, water mixtures of alcohols, and the scope of the reaction is demonstrated by the formation of optically active α,β-epoxy aldehydes in high yields and enantioselectivities >94% ee. Furthermore, the direct synthesis of the sex pheromone from an acaric mite by asymmetric epoxidation of citral is presented. Copyright