4-Pentenoyl chloride

Base Information

• Chemical Name: 4-Pentenoyl chloride
• CAS No.: 39716-58-0
• Molecular Formula: C5H7ClO
• Molecular Weight: 118.563
• Hs Code.: 2916190090
• European Community (EC) Number: 700-100-0
• DSSTox Substance ID: DTXSID50401043
• Nikkaji Number: J1.188.424E
• Wikidata: Q72500064
• Mol file: 39716-58-0.mol

Synonyms:4-Pentenoyl chloride;39716-58-0;Pent-4-enoyl Chloride;MFCD00799572;pent-4-enoylchloride;4-PENTENOYLCHLORIDE;Allylacetylchlorid;Pent-4-enoylchlorde;allyl acetyl chloride;EC 700-100-0;SCHEMBL38207;4-Pentenoyl chloride, 98%;AMY808;DTXSID50401043;JDKQTIKEGOOXTJ-UHFFFAOYSA-N;STR06478;GEO-04116;AKOS005146131;SY302319;FT-0647592;F16765;A824704;J-523876

Chemical Property of 4-Pentenoyl chloride

Chemical Property:

• Vapor Pressure: 12.4mmHg at 25°C
• Refractive Index: 1.433
• Boiling Point: 125.124 °C at 760 mmHg
• Flash Point: 35.885 °C
• PSA: 17.07000
• Density: 1.034 g/cm³
• LogP: 1.71800
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 118.0185425
• Heavy Atom Count: 7
• Complexity: 78.1

Purity/Quality:

99.9% ^*data from raw suppliers

4-Pentenoyl chloride ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCCC(=O)Cl
• Uses: 4-Pentenoyl chloride may be used in the preparation of:D-pro-L-derived cyclic peptides4-pentenoylcobalt tricarbonylN-4-pentenoyl-L-cysteine methyl ester

Technology Process of 4-Pentenoyl chloride

There total 7 articles about 4-Pentenoyl 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: 99.0%

pent-4-enoic acid (591-80-0) → pent-4-enoyl chloride (39716-58-0)

Guidance literature:

With oxalyl dichloride; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/S0040-4020(00)00429-4

Reference yield:

N-methoxy-N-methyl-4-pentenamide (95091-90-0) → pent-4-enoyl chloride (39716-58-0)

Guidance literature:

With Chloroiodomethane; methyllithium; In diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1002/anie.200454007

Reference yield:

oxalyl dichloride (79-37-8) + pent-4-enoic acid (591-80-0) → pent-4-enoyl chloride (39716-58-0)

Guidance literature:

In hexane; at 20 - 45 ℃; for 17.1667h; Inert atmosphere;

DOI:10.1002/ejoc.201300084

upstream raw materials:

pent-4-enoic acid

N-methoxy-N-methyl-4-pentenamide

(2-propenyl)propanedioic acid diethyl ester

2-acetyl-pent-4-enoic acid ethyl ester

Downstream raw materials:

5-hexenoic acid

pent-4-enoic acid-(2-cyclohexyl-4,6-dinitro-phenyl ester)

hept-6-en-3-one

cyclopent-2-enone

Refernces

• 1、 Tong, Chao-Lai,Xu, Xiu-Hua,Qing, Feng-Ling. "Oxidative Hydro-, Bromo-, and Chloroheptafluoroisopropylation of Unactivated Alkenes with Heptafluoroisopropyl Silver". . p. 9532 - 9535. Retrieved 2019.
• 2、 Fournial, Anais,Ranaivondrambola, Tsiresy,Mathe-Allainmat, Monique,Robins, Richard J.,Lebreton, Jacques. "A short and efficient synthesis of bridgehead mono-and dideuteriated tropinones". . p. 152 - 156. Retrieved 2010.
• 3、 Das, Kanad,Nakade, Hiroshi,Penelle, Jacques,Rotello, Vincent M.. "Synthesis and recognition properties of polymers containing embedded binding sites". . p. 310 - 314. Retrieved 2004.
• 4、 Kennington, Stuart C. D.,Teloxa, Saul F.,Mellado-Hidalgo, Miguel,Galeote, Oriol,Puddu, Sabrina,Bellido, Marina,Romea, Pedro,Urpí, Fèlix,Aullón, Gabriel,Font-Bardia, Mercè. "Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes". supporting information. p. 15307 - 15312. Retrieved 2021/06/11.
• 5、 Wei, Dian,Liu, Tu-Ming,Zhou, Bo,Han, Bing. "Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids". supporting information. p. 234 - 238. Retrieved 2020/01/02.