phenylacetyl chloride

Base Information

• Chemical Name: phenylacetyl chloride
• CAS No.: 103-80-0
• Molecular Formula: C8H7ClO
• Molecular Weight: 154.596
• Hs Code.: 2916.39
• European Community (EC) Number: 203-146-5
• UN Number: 2577
• UNII: T30899DRND
• DSSTox Substance ID: DTXSID6059281
• Nikkaji Number: J5.021K
• Wikidata: Q27289593
• Mol file: 103-80-0.mol

Synonyms:Benzeneacetyl chloride;Acetylchloride, phenyl- (6CI,7CI,8CI);2-Phenylacetyl chloride;2-Phenylethanoylchloride;Phenacetyl chloride;Phenylacetic acid chloride;Phenylaceticchloride;a-Phenylacetyl chloride;

Chemical Property of phenylacetyl chloride

Chemical Property:

• Appearance/Colour: Colourless liquid
• Vapor Pressure: 0.124mmHg at 25°C
• Melting Point: 91oC
• Refractive Index: 1.5325
• Boiling Point: 218.7 °C at 760 mmHg
• Flash Point: 90 °C
• PSA: 17.07000
• Density: 1.16 g/cm³
• LogP: 1.99450
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with alcohol and ether.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 154.0185425
• Heavy Atom Count: 10
• Complexity: 116
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Benzeneacetyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37-14
• Safety Statements: 26-36/37/39-45-25-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C1=CC=C(C=C1)CC(=O)Cl
• Uses: Phenylacetyl chloride is used in the preparation of 1,2-diphenyl-ethanone by reaction with iodobenzene using tetrabutylammonium tetrafluoroborate as a phase transfer catalyst. It is widely used in the chemical industry for manufacturing dyes and pharmaceutical products. It plays an important role in the preparation of penicillin. Further, it is used to prepare esters for flavorings. Phenylacetyl chloride is used as a key precursor in the total synthesis of vialinin B. It is employed as a linker to prepare dendrimers and also used in the synthesis of various conjugated aromatic small molecules.

Technology Process of phenylacetyl chloride

There total 22 articles about phenylacetyl 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: 37.0%

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (383865-57-4) → N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-2-phenyl-acetamide + phenylacetyl chloride (103-80-0)

Guidance literature:

Reference yield: 34.0%

benzeneacetic acid methyl ester (101-41-7) → phenylacetyl chloride (103-80-0)

Guidance literature:

With iodine; phosphorus trichloride; at 160 ℃; for 48h; Schlenk technique; Sealed tube;

DOI:10.1002/ejoc.202100630

Reference yield:

4-chloro-1,3,4-triphenyl-butan-2-one (937611-56-8) → stilbene (588-59-0) + phenylacetyl chloride (103-80-0)

Guidance literature:

upstream raw materials:

phenylacetic acid

oxalyl dichloride

sodium phenylacetate

4-chloro-1,3,4-triphenyl-butan-2-one

Downstream raw materials:

(E)-2,3-diphenylpropenoic acid

(Z)-2,3-diphenylprop-2-enoic acid

1,2-diphenyl-benzo[f]chromen-3-one

1-(4-methyl-phenacyl)-3-phenylacetyl-benzene

Refernces

• 1、 Arpaci, Ozlem Temiz,Oren, Ilkay,Altanlar, Nurten. "Synthesis and antimicrobial activity of some novel 2-(p-substituted-phenyl)-5-substituted-carbonylaminobenzoxazoles.". . p. 175 - 181. Retrieved 2002.
• 2、 Song, Qiu-Yan,Nan, Zhi-Biao,Gao, Kun,Song, Hui,Tian, Pei,Zhang, Xing-Xu,Li, Chun-Jie,Xu, Wen-Bo,Li, Xiu-Zhang. "Antifungal, Phytotoxic, and Cytotoxic Activities of Metabolites from Epichlo bromicola, a Fungus Obtained from Elymus tangutorum Grass". . p. 8787 - 8792. Retrieved 2015.
• 3、 Lee. "-". . p. 3440. Retrieved 1966.
• 4、 Baures, Paul W.,Beatty, Alicia M.,Dhanasekaran, Muthu,Helfrich, Brian A.,Perez-Segarra, Waleska,Desper, John. "Solution and solid-state models of peptide CH...O hydrogen bonds". . p. 11315 - 11323. Retrieved 2002.
• 5、 Stille,Regan. "-". . p. 1508,1513. Retrieved 1974.
• 6、 Ward,Rhee. "A simple method for the microscale preparation of Mosher's acid chloride". . p. 7165 - 7166. Retrieved 1991.
• 7、 Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul. "Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates". supporting information. p. 5022 - 5037. Retrieved 2021/05/04.
• 8、 Cailotto, Simone,Negrato, Matteo,Daniele, Salvatore,Luque, Rafael,Selva, Maurizio,Amadio, Emanuele,Perosa, Alvise. "Carbon dots as photocatalysts for organic synthesis: Metal-free methylene-oxygen-bond photocleavage". supporting information. p. 1145 - 1149. Retrieved 2020/03/11.