4-ethynylbenzoyl Chloride

Base Information

• Chemical Name: 4-ethynylbenzoyl Chloride
• CAS No.: 62480-31-3
• Molecular Formula: C9H5ClO
• Molecular Weight: 164.591
• DSSTox Substance ID: DTXSID80448729
• Nikkaji Number: J514.158C
• Wikidata: Q72477723
• Mol file: 62480-31-3.mol

Synonyms:4-ethynylbenzoyl Chloride;62480-31-3;Benzoyl chloride, 4-ethynyl- (9CI);4-ethynylbenzoic acid chloride;SCHEMBL107623;DTXSID80448729;XGVGIJULTHHKJM-UHFFFAOYSA-N

Chemical Property of 4-ethynylbenzoyl Chloride

Chemical Property:

• PSA: 17.07000
• LogP: 2.04690
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 164.0028925
• Heavy Atom Count: 11
• Complexity: 193

Purity/Quality:

98% ^*data from raw suppliers

4-Ethynylbenzoylchloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CC=C(C=C1)C(=O)Cl

Technology Process of 4-ethynylbenzoyl Chloride

There total 11 articles about 4-ethynylbenzoyl 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%

p-Ethynylbenzoic acid potassium salt (144693-66-3) → 4-ethynylbenzoyl chloride (62480-31-3)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In chloroform; for 5h; Ambient temperature;

DOI:10.1021/jo00051a063

Reference yield: 82.2%

4-Ethynyl-benzoic acid (10602-00-3) → 4-ethynylbenzoyl chloride (62480-31-3)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/ma0344543

Reference yield:

methyl 4-(3-hydroxy-3-methylbut-1-ynyl)benzoate (33577-98-9) → 4-ethynylbenzoyl chloride (62480-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / isopropyl alcohol / 4 h / 20 °C

2: thionyl chloride; N,N-dimethyl-formamide / chloroform / 0 - 20 °C / Inert atmosphere

With thionyl chloride; N,N-dimethyl-formamide; potassium hydroxide; In chloroform; isopropyl alcohol;

DOI:10.1002/pola.24442

upstream raw materials:

p-Ethynylbenzoic acid potassium salt

4-Ethynyl-benzoic acid

4-Bromobenzoic acid

4-methoxycarbonylphenyl bromide

Downstream raw materials:

2-diethylaminoethyl p-ethynyl benzoate hydrochloride

N-(3-(triethoxysilyl)propyl)-4-ethynylbenzamide

pentafluorophenyl 4-ethynylbenzoate

ethyl 4-ethynylbenzoate

Refernces

• 1、 Yashima,Maeda,Sato. "Switching of a macromolecular helicity for visual distinction of molecular recognition events [22]". . p. 8159 - 8160. Retrieved 2001.
• 2、 Matsuura, Kazunori,Furuno, Shin-Ichi,Kobayashi, Kazukiyo. "Helical stereoregular artificial glycoconjugate polymers based on poly(phenylacetylene) backbone: Synthesis and molecular recognition with lectin". . p. 847 - 848. Retrieved 1998.
• 3、 Masubuchi, Kana,Maehata, Masakiyo,Suzuki, Chieko,Matsuoka, Ryoji,Sekiguchi, Maki,Chigira, Naoto,Amano, Yoshitsugu,Inokuchi, Mayu,Li, Qintong,Hasegawa, Teruaki. "Synthesis and conformational analysis of poly(phenylacetylene)s with serinol-tethered carbohydrate appendages". . p. 23 - 30. Retrieved 2019/06/20.
• 4、 Václavík, Ji?í,Zschoche, Reinhard,Klimánková, Iveta,Matou?ek, Václav,Beier, Petr,Hilvert, Donald,Togni, Antonio. "Irreversible Cysteine-Selective Protein Labeling Employing Modular Electrophilic Tetrafluoroethylation Reagents". supporting information. p. 6490 - 6494. Retrieved 2017/05/15.