3,4-Difluorocinnamoyl chloride

Base Information

• Chemical Name: 3,4-Difluorocinnamoyl chloride
• CAS No.: 376608-66-1
• Molecular Formula: C9H5ClF2O
• Molecular Weight: 202.588
• Mol file: 376608-66-1.mol

Synonyms:3,4-difluorocinnamoyl chloride;1043546-64-0;SCHEMBL248732;SCHEMBL248733;HLVDWMSYSIMRNI-DUXPYHPUSA-N;(E)-3-(3,4-difluorophenyl)-2-propenoyl chloride

Chemical Property of 3,4-Difluorocinnamoyl chloride

Chemical Property:

• PSA: 17.07000
• LogP: 2.74340
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 201.9996988
• Heavy Atom Count: 13
• Complexity: 218

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)Cl)F)F
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)Cl)F)F

Technology Process of 3,4-Difluorocinnamoyl chloride

There total 3 articles about 3,4-Difluorocinnamoyl 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: 100.0%

(E)-3-(3,4-difluorophenyl)acrylic acid (112897-97-9) → (E)-3-(3,4-difluorophenyl)acryloyl chloride (376608-66-1)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; Reflux; Inert atmosphere;

DOI:10.1016/j.bmc.2017.08.047

Reference yield:

3,4 difluorobenzaldehyde (34036-07-2) → (E)-3-(3,4-difluorophenyl)acryloyl chloride (376608-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine; pyridine / 90 °C / Inert atmosphere

2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / Reflux; Inert atmosphere

With piperidine; pyridine; thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; 1: |Knoevenagel Condensation;

DOI:10.1016/j.bmc.2017.08.047

Reference yield:

→ (E)-3-(3,4-difluorophenyl)acryloyl chloride (376608-66-1)

Guidance literature:

upstream raw materials:

(E)-3-(3,4-difluorophenyl)acrylic acid

3,4 difluorobenzaldehyde

Downstream raw materials:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylate

(E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-(3,4-difluorophenyl)acrylate

Refernces

• 1、 -. "Cinnamyl-containing rupestonic acid methyl ester derivative as well as preparation method and application of rupestonic acid methyl ester derivative". Paragraph 0077-0078; 0081. . Retrieved 2021/06/02.
• 2、 Qian, Jianchang,Chen, Xianxin,Shu, Sheng,Zhang, Wenxin,Fang, Bo,Chen, Xiaojing,Zhao, Yunjie,Liu, Zhiguo,Liang, Guang. "Design and synthesis novel di-carbonyl analogs of curcumin (DACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI)". . p. 414 - 425. Retrieved 2019/02/19.