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| | Phenoxyacetyl chloride Basic information |
| | Phenoxyacetyl chloride Chemical Properties |
| 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 |
| | 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 Preparation Products And Raw materials |
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