| Identification | More | [Name]
Phenoxyacetyl chloride | [CAS]
701-99-5 | [Synonyms]
AKOS BBS-00003927
LABOTEST-BB LT00643586
PHENOXYACETYL CHLORIDE
phenoxy-acetylchlorid
Phenyloxyacetyl chloride
Acyl chloride kind
Acetylchloride,phenoxy-
Phenoxyacetic acid chloride | [EINECS(EC#)]
211-862-4 | [Molecular Formula]
C8H7ClO2 | [MDL Number]
MFCD00000726 | [Molecular Weight]
170.59 | [MOL File]
701-99-5.mol |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R14:Reacts violently with water.
R34:Causes burns.
R36/37:Irritating to eyes and respiratory system . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [F ]
10-19 | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29189090 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to brown liquid | [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
| [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. | [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.] |
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