5453-44-1

Basic information

• Product Name: 2-Butenoic acid, 2-propenyl ester, (E)-
• CAS NO: 5453-44-1
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Mol File: 5453-44-1.mol

Chemical Properties

• CAS DataBase Reference: 2-Butenoic acid, 2-propenyl ester, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenoic acid, 2-propenyl ester, (E)-(5453-44-1)
• EPA Substance Registry System: 2-Butenoic acid, 2-propenyl ester, (E)-(5453-44-1)

Safety Data

• Hazardous Substances Data: 5453-44-1(Hazardous Substances Data)

Upstream product

• 625-35-4 trans-chrotonyl chloride 
• 14593-43-2 benzyl allyl ether 
• 107-18-6 allyl alcohol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 497-23-4 2-buten-4-olide 
• 139449-92-6 2-Bromo-3-p-toluenesulphonylpropyl crotonate 
• 139449-93-7 2-Iodo-3-p-toluenesulphonylpropyl crotonate 
• 107-93-7 (E)-but-2-enoic acid 
• 106-98-9 1-butylene 
• 6308-15-2 2,3-Dibrompropylcrotonat 
• 5864-51-7 2-oxylanylmethyl crotonate 

Relevant articles and documents

Revisiting the Palladium-Catalyzed Carbonylation of Allyl Alcohol: Mechanistic Insight and Improved Catalytic Efficiency

Although crotonic acid (CA) is in high demand due to its use in various industrial applications, the preparation of CA currently requires a multi-step process from the petrochemical cracking of ethane with a very low overall yield and poor selectivity. An atom economical, one-step, carbonylation of readily accessible allyl alcohol to CA is one of the attractive approaches. In this study, the direct carbonylative transformation of allyl alcohol to CA was analyzed in detail to detect the reaction intermediates and propose a reaction mechanism. Following the reaction mechanism, the process was optimized to synthesize CA via the direct carbonylation of allyl alcohol with improved efficiency and productivity (TON = 420) under mild reaction conditions using Pd-based catalytic systems.

DBU-mediated Ireland-Claisen rearrangement of allyl alk-3-enoates: an efficient synthesis of 2-ethylidene-γ,δ-unsaturated carboxylic acids

Ireland-Claisen rearrangement, triggered by silyl enolization of allylic but-3-enoates 2, has been developed using DBU as the base in the presence of an excess amount of TMSCl under reflux in acetonitrile for a couple of hours. The procedure allows the synthesis of a range of 2-ethylidene-γ,δ-unsaturated carboxylic acids 5 in moderate to high yields. It is further revealed that the rearrangement proceeds equally well with allylic (E)-hexa-3,5-dienoates 10 derived from sorbic acid under similar conditions to provide 2-allyl substituted hexa-2,4-dienoic acids 13.

Cobalt(II)chloride catalysed cleavage of ethers with acyl halides: Scope and mechanism

Cobalt(II) chloride in acetonitrile catalyses the cleavage of a wide variety of ethers with acyl halides under mild conditions to give the corresponding esters in good yields. Acyclic aliphatic ethers are cleaved to the corresponding ester and chlorides whereas the cyclic aliphatic ethers give rise to the ω-chloroesters. The benzyl ethers can be converted to the corresponding esters along with the formation of benzyl chloride and benzyl acetamide. A comparative study for the cleavage of allyl and benzyl ether has revealed that benzyl ether can be selectively cleaved in presence of the allyl ethers. The oxiranes can be cleaved in highly regioselective manner to the corresponding-β-chloroesters. The vinyl ethers undergo sp2-hybridised carbon-oxygen bond cleavage under these conditions. Based on product analysis, a mechanism involving electron transfer followed by O-acylation and S(N)1 or S(N)2 attack by chloride-ion is discussed.

A VERSATILE ROUTE TO MIXED VINYLKETENE ACETALS : USE OF 1-t-BUTYLDIMETHYLSILOXY-1-ETHOXY BUTADIENE IN CYCLOHEXENONE SYNTHESIS

The successful entry to the diverse mixed vinylketene acetals 3 extends the participation of these intermediates in cyclohexenone synthesis.