Ethyl 3-(acetoxy)isocrotonate

Base Information

• Chemical Name: Ethyl 3-(acetoxy)isocrotonate
• CAS No.: 29214-62-8
• Molecular Formula: C8H12 O4
• Molecular Weight: 172.181
• European Community (EC) Number: 249-519-6,248-635-4,248-011-1
• DSSTox Substance ID: DTXSID401226669
• Nikkaji Number: J250.585A
• Mol file: 29214-62-8.mol

Synonyms:Ethyl 3-(acetoxy)isocrotonate;ethyl 3-acetoxybut-2-enoate;Ethyl 3-acetoxy-2-butenoate;27750-19-2;2-Butenoic acid, 3-(acetyloxy)-, ethyl ester;EINECS 248-011-1;EINECS 248-635-4;EINECS 249-519-6;29214-62-8;2-Butenoic acid, 3-(acetyloxy)-, ethyl ester, (E)-;2-Butenoic acid, 3-(acetyloxy)-, ethyl ester, (Z)-;VSCUAMOPAHJJTA-AATRIKPKSA-N;DTXSID401226669;NSC 167587;(E)-3-Acetoxy-2-butenoic acid ethyl ester

Chemical Property of Ethyl 3-(acetoxy)isocrotonate

Chemical Property:

• Vapor Pressure: 0.148mmHg at 25°C
• Boiling Point: 215.4°Cat760mmHg
• Flash Point: 98.6°C
• PSA: 52.60000
• Density: 1.069g/cm³
• LogP: 1.01640
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 205

Purity/Quality:

99.0% Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)OC(=O)C
• Isomeric SMILES: CCOC(=O)/C=C(\C)/OC(=O)C

Technology Process of Ethyl 3-(acetoxy)isocrotonate

There total 15 articles about Ethyl 3-(acetoxy)isocrotonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.6%

ethyl acetoacetate (141-97-9) + acetyl chloride (75-36-5) → 3-acetoxy-crotonic acid ethyl ester (29214-62-8)

Guidance literature:

With pyridine; at 120 ℃; for 0.25h;

DOI:10.1007/BF01430645

Reference yield: 85.0%

ethyl bromoacetate (105-36-2) + acetyl chloride (75-36-5) → 3-acetoxy-crotonic acid ethyl ester (29214-62-8)

Guidance literature:

With zinc; In 1,4-dioxane; diethyl ether; for 0.166667h; Heating;

Reference yield: 81.0%

ethyl 3-trimethylsiloxy-2-butenoate (13257-83-5) + acetyl chloride (75-36-5) → 3-acetoxy-crotonic acid ethyl ester (29214-62-8)

Guidance literature:

With zinc dibromide; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4020(01)88581-1

upstream raw materials:

Ketene

ethyl acetoacetate

Isopropenyl acetate

acetyl chloride

Downstream raw materials:

ethyl 3-oxo-2-benzoylbutanoate

ethyl 2-acetylacetoacetate

ethyl 3-acetoxybutanoate

butanoic acid ethyl ester

Refernces

• 1、 Spence,Degering. "-". . p. 1624. Retrieved 1944.
• 2、 Kislyi,Kurykin,Grinberg,Kagramanov,Semenov. "Anodic perfluoroalkylation of the enol acetate of ethyl acetoacetate". . p. 2800 - 2803. Retrieved 1996.
• 3、 Fotin,Shchepin,Fotin,Vakhrin. "Reactions of α-Bromo esters with zinc and acyl chlorides in the presence of dioxane". . p. 1278 - 1281. Retrieved 2007/10/03.