Phenoxyacetyl chloride

Base Information

• Chemical Name: Phenoxyacetyl chloride
• CAS No.: 701-99-5
• Deprecated CAS: 343594-49-0
• Molecular Formula: C8H7ClO2
• Molecular Weight: 170.595
• Hs Code.: 29189090
• European Community (EC) Number: 211-862-4
• NSC Number: 9808
• UNII: NS65CKB849
• DSSTox Substance ID: DTXSID1061029
• Nikkaji Number: J62.847F
• Wikidata: Q63398649
• Mol file: 701-99-5.mol

Synonyms:Phenoxyacetyl chloride;701-99-5;2-phenoxyacetyl chloride;Acetyl chloride, phenoxy-;Phenyloxyacetyl chloride;phenoxyacetic acid chloride;Acetyl chloride, 2-phenoxy-;NSC 9808;NSC-9808;EINECS 211-862-4;Phenoxyacetic acid chloride;Phenoxyethanoyl chloride;phenoxylacetylchloride;MFCD00000726;2-phenoxyacetylchloride;phenoxy acetyl chloride;phenoxy-acetyl chloride;(phenyloxy)acetyl chloride;SCHEMBL6013;Phenoxyacetyl chloride, 98%;NS65CKB849;DTXSID1061029;NSC9808;STR07065;AKOS000104374;R(+)-SKF-38393HYDROCHLORIDE;AMY202100119;FT-0632844;P0113;EN300-20022;E78941;Q63398649;F2190-0093

Chemical Property of Phenoxyacetyl chloride

Chemical Property:

• Appearance/Colour: Colorless to brown liquid
• Vapor Pressure: 0.0823mmHg at 25°C
• Melting Point: 100-100.5 °C
• Refractive Index: n20/D 1.534(lit.)
• Boiling Point: 225-226 ºC
• Flash Point: 108 ºC
• PSA: 26.30000
• Density: 1.235
• LogP: 1.83080
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 170.0134572
• Heavy Atom Count: 11
• Complexity: 130

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phenoxyacetyl Chloride >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OCC(=O)Cl
• Uses: Acylation of D- and DL-WV with phenoxyacetyl chloride, followed by cleavage of the t-butyl ester,afforded the penultimate penicilloic acids. Phenoxyacetyl chloride was used in the synthesis of series of macrocyclic bis-β-lactams, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester, N-protected guanosine derivatives, useful in RNA synthesis, phenyloxyketene, for cycloaddition to imines leading to β-lactams. Treatment of iminophosphoranes with phenoxyacetyl chloride afforded respectively the trans- and cis-3-(acylamino)-p-lactams. By the oxidative addition of stannous fluoride to allyliodide, with 1, 2-O-isopropylidene-D-glyceraldehyde and phenoxyacetyl chloride results in the predominant formation of erythro homoallylester, which is in turn converted into 2-deoxy-D-ribose. The 4-disubstituted P-lactams (4a-c and 6a-b) were prepared through the reaction of N,N-diphenylhydrazones and N-methyl-N-phenylhydrazones of ketones with phenoxyacetyl chloride/Et3N in dichloromethane. Phenoxyacetyl chloride was used in the synthesis of:series of macrocyclic bis-β-lactams5-phenyl-6-epiphenoxymethylpenicillin benzyl esterN-protected guanosine derivatives, useful in RNA synthesisphenyloxyketene, for cycloaddition to imines leading to β-lactams

Technology Process of Phenoxyacetyl chloride

There total 12 articles about Phenoxyacetyl 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: 92.6%

→ Phenoxyacetyl chloride (701-99-5)

Guidance literature:

With thionyl chloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 50 ℃; for 5h;

Reference yield: 90.0%

2-phenoxyacetic acid (122-59-8) → Phenoxyacetyl chloride (701-99-5)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; for 5h; Reflux;

DOI:10.1002/jhet.2737

Reference yield:

chloroacetic acid (79-11-8) + phenol (108-95-2,27073-41-2) → Phenoxyacetyl chloride (701-99-5)

Guidance literature:

chloroacetic acid; phenol; With sodium hydroxide; In water;

With thionyl chloride; In benzene; at 20 ℃;

DOI:10.2174/1570180812999150812164251

upstream raw materials:

2-phenoxyacetic acid

phosphorus pentachloride

phenol

sodium phenoxide

Downstream raw materials:

methyl 3-phenoxypropanoate

phenoxy-acetic acid-(1,1-dimethyl-3-piperidino-butyl ester); hydrochloride

phenoxy-acetic acid-(4-amino-2-methyl-[6]quinolylamide)

phenoxy-acetic acid-[methyl-(2-oxo-indolin-3-ylidene)-hydrazide]

Refernces

• 1、 Chen, Yong-Jia,Liu, Hua,Zhang, Shao-Yong,Li, Hu,Ma, Kun-Yuan,Liu, Ying-Qian,Yin, Xiao-Dan,Zhou, Rui,Yan, Yin-Fang,Wang, Ren-Xuan,He, Ying-Hui,Chu, Qing-Ru,Tang, Chen. "Design, Synthesis, and Antifungal Evaluation of Cryptolepine Derivatives against Phytopathogenic Fungi". . p. 1259 - 1271. Retrieved 2021/02/16.
• 2、 Xin, Weixiang,Li, Zezhong,Wang, Qing,Du, Jin,Zhu, Mingyan,Zhou, Huchen. "Design and synthesis of α-phenoxy-N-sulfonylphenyl acetamides as Trypanosoma brucei Leucyl-tRNA synthetase inhibitors". . . Retrieved 2019/11/26.