Phenoxyacetyl chloride Chemical Properties

Melting point:

100-100.5 °C

Boiling point:

225-226 °C (lit.)

Density 

1.235 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.534(lit.)

Flash point:

227 °F

storage temp. 

Store at RT.

form 

Liquid

color 

Clear slightly yellow to brown

Water Solubility 

Reacts with water.

Sensitive 

Moisture Sensitive

BRN 

607585

CAS DataBase Reference

701-99-5(CAS DataBase Reference)

NIST Chemistry Reference

Acetyl chloride, phenoxy-(701-99-5)

EPA Substance Registry System

Acetyl chloride, phenoxy- (701-99-5)

Safety Information

Hazard Codes 

C

Risk Statements 

14-34-36/37

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-19

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29189090

MSDS

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Phenoxyacetyl chloride Usage And Synthesis

Chemical Properties

Colorless to brown liquid

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.

Uses

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

Purification Methods

If it has no OH band in the IR then distil it in a vacuum, taking precautions for the moisture-sensitive compound. If it contains free acid (due to hydrolysis, OH bands in the IR), then add an equal volume of redistilled SOCl2, reflux for 2-3hours, evaporate and distil the residue in a vacuum as before. The amide has m 101o. [McElvain & Carney J Am Chem Soc 68 2592 1946, Beilstein 6 III 613.]

Phenoxyacetyl chloride(701-99-5)Related Product Information

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• 2-PHENOXYPROPIONYL CHLORIDE