29214-62-8

Basic information

• Product Name: ethyl 3-acetoxy-2-butenoate
• Synonyms: ethyl 3-acetoxy-2-butenoate;3-Acetoxy-2-butenoic acid ethyl ester;3-Acetyloxy-2-butenoic acid ethyl ester
• CAS NO: 29214-62-8
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.17848
• EINECS: 249-519-6
• Mol File: 29214-62-8.mol

Chemical Properties

• Boiling Point: 215.4°Cat760mmHg
• Flash Point: 98.6°C
• Appearance: /
• Density: 1.069g/cm³
• Vapor Pressure: 0.148mmHg at 25°C
• Refractive Index: 1.441
• CAS DataBase Reference: ethyl 3-acetoxy-2-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-acetoxy-2-butenoate(29214-62-8)
• EPA Substance Registry System: ethyl 3-acetoxy-2-butenoate(29214-62-8)

Safety Data

• Hazardous Substances Data: 29214-62-8(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
Ethyl 3-acetoxy-2-butenoate is used as a flavoring agent for its fruity and sweet aroma, enhancing the taste and smell of various food and drink products.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care industry, ethyl 3-acetoxy-2-butenoate serves as a fragrance, adding pleasant scents to products and improving the overall sensory experience for consumers.
Storage and Safety:
Due to its potential reactivity with strong oxidizing agents, ethyl 3-acetoxy-2-butenoate should be stored in a cool, dry place away from heat and open flames to ensure its stability and safety during handling and transportation.

InChI:InChI=1/C8H12O4/c1-4-11-8(10)5-6(2)12-7(3)9/h5H,4H2,1-3H3

Upstream product

• 463-51-4 Ketene 
• 141-97-9 ethyl acetoacetate 
• 108-22-5 Isopropenyl acetate 
• 75-36-5 acetyl chloride 
• 2678-54-8 ketene diethyl acetal 
• 60-29-7 diethyl ether 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 5177-66-2 1-ethoxyvinyl acetate 
• 108-24-7 acetic anhydride 
• 105-36-2 ethyl bromoacetate 
• 13257-83-5 ethyl 3-trimethylsiloxy-2-butenoate 
• 7664-93-9 sulfuric acid 

Downstream Products

• 3977-29-5 2-amino-6-methyl-3H-pyrimidin-4-one 
• 141-97-9 ethyl acetoacetate 
• 141-78-6 ethyl acetate 
• 520-45-6 Dehydracetic acid 
• 603-69-0 ethyl 2-acetylacetoacetate 
• 569-37-9 ethyl 3-oxo-2-benzoylbutanoate 
• 27846-49-7 ethyl 3-acetoxybutanoate 
• 105-54-4 butanoic acid ethyl ester 
• 15802-69-4 2-(4-nitrophenylmethylene)acetoacetic acid ethyl ester 
• 15725-26-5 (Z)-1-(4-Methoxyphenyl)-2-ethoxycarbonyl-1-buten-3-one 

Relevant articles and documents

Anodic perfluoroalkylation of the enol acetate of ethyl acetoacetate

Electrochemical perfluoroalkylation of the enol acetate of ethyl acetoacetate was studied in the conditions of the Kolbe reaction. The yields of alkylation products depend on the competing adsorption of the enol acetate, the solvent, and perfluorocarboxylates on the surface of a platinum electrode.

Enzyme Promiscuity as a Remedy for the Common Problems with Knoevenagel Condensation

A new protocol based on lipase-catalyzed tandem reaction toward α,β-enones/enoesters is presented. For the synthesis of the desired products the tandem process based on enzyme-catalyzed hydrolysis and Knoevenagel reaction starting from enol acetates and aldehyde is developed. The relevant impact of the reaction conditions including organic solvent, enzyme type, and temperature on the course of the reaction was revealed. It was shown that controllable release of the active methylene compound from the corresponding enol carboxylate ensured by enzymatic reaction diminishes significantly the formation of the unwanted co-products. Furthermore, this protocol was extended by including a second tandem chemoenzymatic transformation engaging various aldehyde precursors. After a careful optimization of the reaction conditions, the target products were obtained with yields up to 86 % and with excellent E/Z-selectivity.

Reactions of α-Bromo esters with zinc and acyl chlorides in the presence of dioxane

Organozinc intermediates (Reformatsky reagents) derived from α-bromocarboxylic acid esters react with acyl chlorides in the presence of dioxane to afford both C- and O-acylation products, 3-oxoalkanoic (3-acyloxy-2-alkenoic) acid esters and 1-acyloxy-1-alkoxyalkenes. The latter are formed as the only reaction products when the organozinc intermediate contains an alkyl group at the nucleophilic C2 center and when the acyl chloride possesses a bulky radical on the carbonyl group.