Butenoyl chloride

Base Information

• Chemical Name: Butenoyl chloride
• CAS No.: 10487-71-5
• Molecular Formula: C4H5ClO
• Molecular Weight: 104.536
• Hs Code.: 2916 19 95
• DSSTox Substance ID: DTXSID2065096
• Mol file: 10487-71-5.mol

Synonyms:Butenoyl chloride;2-Butenoyl chloride;but-2-enoyl chloride;methylacrylchloride;methylacryl chloride;rac-Crotonoyl Chloride;3-methylacryloyl chloride;3-methyl-acryloyl chloride;DTXSID2065096;AKOS028108515;FT-0603173;FT-0624105;FT-0624106

Chemical Property of Butenoyl chloride

Chemical Property:

• Appearance/Colour: clear to light yellow liquid
• Vapor Pressure: 12.707mmHg at 25°C
• Melting Point: 116 - 124 °C
• Refractive Index: n20/D 1.459(lit.)
• Boiling Point: 124.499 °C at 760 mmHg
• Flash Point: 35 °C
• PSA: 17.07000
• Density: 1.081 g/cm³
• LogP: 1.32790
• Storage Temp.: Store below +30°C.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 104.0028925
• Heavy Atom Count: 6
• Complexity: 75.6

Purity/Quality:

99% ^*data from raw suppliers

rac-CrotonoylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 10-34-36/37
• Safety Statements: 16-26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)Cl

Technology Process of Butenoyl chloride

There total 20 articles about Butenoyl chloride 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: 93.0%

2-butenoic acid (3724-65-0) → crotonyl chloride (10487-71-5)

Guidance literature:

With thionyl chloride; at 80 ℃; for 3h;

DOI:10.1039/c5cc00072f

Reference yield: 89.0%

2-butenoic acid (3724-65-0) → trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5)

Guidance literature:

With thionyl chloride; at 20 - 80 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol400381q

Reference yield: 82.0%

(E)-but-2-enoic acid (107-93-7) → trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5)

Guidance literature:

With thionyl chloride; at 80 ℃;

DOI:10.1016/0022-328X(87)85001-5

upstream raw materials:

2-butenoic acid

2-hydroxy-3-butene

butene-2

(E/Z)-2-buten-1-ol

Downstream raw materials:

trans-crotonic acid-(3,4-dimethyl-phenyl ester)

p-tolyl crotonate

1-(3,4-dimethyl-phenyl)-buten-(2t)-one-⁽¹⁾

(E)-5-isopropyl-2-methylphenyl but-2-enoate

Refernces

• 1、 Chen, Xia,Lu, Yuling,Guan, Zhenhua,Gu, Lianghu,Chen, Chunmei,Zhu, Hucheng,Luo, Zengwei,Zhang, Yonghui. "Synthesis of Succinimides via Intramolecular Alder-Ene Reaction of 1,6-Enynes". . p. 3173 - 3178. Retrieved 2021.
• 2、 Movsisyan, Marine,Heugebaert, Thomas S. A.,Dams, Rudy,Stevens, Christian V.. "Safe, selective, and high-yielding synthesis of acryloyl chloride in a continuous-flow system". . p. 1945 - 1952. Retrieved 2016.
• 3、 Pyser, Joshua B.,Baker Dockrey, Summer A.,Benítez, Attabey Rodríguez,Joyce, Leo A.,Wiscons, Ren A.,Smith, Janet L.,Narayan, Alison R. H.. "Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products". . p. 18551 - 18559. Retrieved 2019.
• 4、 Nandakumar, Natarajan,Muthuraman, Subramani,Gopinath, Pushparathinam,Nithya, Pattusamy,Gopas, Jacob,Kumar, Rajendran Saravana. "Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity". . p. 1076 - 1087. Retrieved 2017.
• 5、 Turbitt,Watts. "-". . p. 109,113. Retrieved 1972.
• 6、 Cummins, Ian,Landrum, Marie,Steel, Patrick G.,Edwards, Robert. "Structure activity studies with xenobiotic substrates using carboxylesterases isolated from Arabidopsis thaliana". . p. 811 - 818. Retrieved 2007.
• 7、 Ando, Yuki,Kamatsuka, Takuto,Shinokubo, Hiroshi,Miyake, Yoshihiro. "Selective α-arylation of α,β-unsaturated imides mediated by a visible light photoredox catalyst". . p. 9136 - 9138. Retrieved 2017.
• 8、 Logeswaran, Ravichandran,Jeganmohan, Masilamani. "Effect of Transition Metals on Chemodivergent Cross-Coupling of Acrylamides with Vinyl Acetate via C-H Activation". supporting information. p. 5679 - 5683. Retrieved 2021/08/03.