(E)-Ethyl 4-chloro-4-oxobut-2-enoate

Base Information

• Chemical Name: (E)-Ethyl 4-chloro-4-oxobut-2-enoate
• CAS No.: 26367-48-6
• Molecular Formula: C6H7ClO3
• Molecular Weight: 162.573
• Hs Code.: 2918300090
• European Community (EC) Number: 628-424-7,823-822-9
• Nikkaji Number: J1.103.768B,J2.312.308H
• Wikidata: Q76416639
• Mol file: 26367-48-6.mol

Synonyms:26367-48-6;(E)-Ethyl 4-chloro-4-oxobut-2-enoate;Ethyl fumaroyl chloride;3-CHLOROCARBONYLACRYLIC ACID ETHYL ESTER;Ethyl 4-chloro-4-oxobut-2-enoate;ethyl (E)-4-chloro-4-oxobut-2-enoate;(E)-3-(Chloroformyl)-acrylic acid ethyl ester;ethyl (2E)-4-chloro-4-oxobut-2-enoate;Ethyl fumaryl chloride;66130-92-5;2-Butenoic acid, 4-chloro-4-oxo-, ethyl ester, (2E)-;SCHEMBL1418555;(Fumaric acid 1-ethyl) chloride;YYLWXDIGYFPUSK-ONEGZZNKSA-N;ethyl (E)-3-chlorocarbonylacrylate;BBA36748;Ethyl fumaroyl chloride, >=97.0%;ethyl trans-3-(chloroformyl)acrylate;MFCD03002066;AKOS015902225;(E)-Ethyl4-chloro-4-oxobut-2-enoate;AS-77194;4-Chloro-4-oxo-2-butenoic acid ethyl ester;(E)-3-chlorocarbonyl acrylic acid ethyl ester;E78218;EN300-262026;EN300-1721902;J-016397

Chemical Property of (E)-Ethyl 4-chloro-4-oxobut-2-enoate

Chemical Property:

• Vapor Pressure: 0.131mmHg at 25°C
• Melting Point: 16 °C
• Refractive Index: 1.461
• Boiling Point: 217.704 °C at 760 mmHg
• Flash Point: 92.72 °C
• PSA: 43.37000
• Density: 1.221 g/cm³
• LogP: 0.87110
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 162.0083718
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

Ethyl(E)-4-Chloro-4-oxobut-2-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 22-34-43
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC(=O)Cl
• Isomeric SMILES: CCOC(=O)/C=C/C(=O)Cl

Technology Process of (E)-Ethyl 4-chloro-4-oxobut-2-enoate

There total 7 articles about (E)-Ethyl 4-chloro-4-oxobut-2-enoate 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: 97.0%

(E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4) → fumaric acid ethyl ester mono chloride (26367-48-6)

Guidance literature:

With thionyl chloride; at 20 ℃; for 24h;

DOI:10.3390/molecules24152812

Reference yield:

malonic acid monoethyl ester (2459-05-4,3249-53-4,3990-03-2) → fumaric acid ethyl ester mono chloride (26367-48-6)

Guidance literature:

With thionyl chloride; In toluene; at 100 ℃; for 2h; Yield given; Heating;

DOI:10.1021/jm00160a013

Reference yield:

oxalyl dichloride (79-37-8) + (E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4) → fumaric acid ethyl ester mono chloride (26367-48-6)

Guidance literature:

DOI:10.1021/jo015501x

upstream raw materials:

ethanol

fumaryl dichloride

(E)-4-ethoxy-4-oxobut-2-enoic acid

maleic anhydride

Downstream raw materials:

exo-6-(Chlorcarbonyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-en-endo-5-carbonsaeure-ethylester

endo-5-(Chlorcarbonyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-en-exo-6-carbonsaeure-ethylester

(7-Chloro-1-isopropyl-2-oxo-5,5-diphenyl-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl)-acetic acid ethyl ester

(1-Benzyl-2-oxo-5,5-diphenyl-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl)-acetic acid ethyl ester

Refernces

• 1、 Beus, Maja,Fallarero, Adyary,Patel, Jayendra Z.,Savijoki, Kirsi,Yli-Kauhaluoma, Jari,Zorc, Branka. "Chloroquine fumardiamides as novel quorum sensing inhibitors". . . Retrieved 2020.
• 2、 Sterk, Markus,Bannwarth, Willi. "Modulation of reactivities of dienophiles for diels-alder reactions via complexation of α,β-unsaturated chelating amides". . p. 287 - 307. Retrieved 2015.
• 3、 Verma, Vishal A.,Wang, Lan,Labadie, Sharada S.,Liang, Jun,Sellers, Benjamin D.,Wang, Jian,Dong, Liting,Wang, Qiuyue,Zhang, Shuang,Xu, Zhongya,Zhang, Yexia,Niu, Yanan,Wang, Xinxin,Wai, John,Koehler, Michael F. T.,Hu, Huiyong,Alexander, Mary Kate,Nishiyama, Mireille,Miu, Anh,Xu, Yiming,Pang, Jodie,Katakam, Anand K.,Reichelt, Michael,Austin, Cary D.,Ho, Hoangdung,Payandeh, Jian,Koth, Christopher M.. "Discovery of Inhibitors of the Lipopolysaccharide Transporter MsbA: From a Screening Hit to Potent Wild-Type Gram-Negative Activity". supporting information. p. 4085 - 4120. Retrieved 2022/03/02.
• 4、 Kagawa, Natsuko,Otsuka, Jyo,Takabatake, Tetsuhiko,Toyota, Masahiro,Yoneda, Takumi. "Artificial intelligence-designed stereoselective one-pot synthesis of trans-β-lactams and its application to cholesterol absorption inhibitor SCH 47949 synthesis". . p. 60 - 84. Retrieved 2020/01/28.