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Merck
CN

158623

Phenoxyacetyl chloride

98%

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About This Item

Linear Formula:
C6H5OCH2COCl
CAS Number:
Molecular Weight:
170.59
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
211-862-4
Beilstein/REAXYS Number:
607585
MDL number:
Assay:
98%
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Quality Level

assay

98%

refractive index

n20/D 1.534 (lit.)

bp

225-226 °C (lit.)

density

1.235 g/mL at 25 °C (lit.)

functional group

acyl chloride, phenoxy

SMILES string

ClC(=O)COc1ccccc1

InChI

1S/C8H7ClO2/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2

InChI key

PKUPAJQAJXVUEK-UHFFFAOYSA-N

Application

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


pictograms

CorrosionExclamation mark

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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H Vanderhaeghe et al.
Journal of medicinal chemistry, 18(5), 486-490 (1975-05-01)
Cycloaddition of azidoacetyl chloride to benzyl D-5,5-dimethyl-5-phenyl-2-thiazoline-4-carboxylate (1a) gave 5-phenyl-6alpha-azidopenicillanate (2a). By catalytic reduction of 2a and reaction with phenoxyacetyl chloride, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester (4a) was obtained. Oxidation of 4a gave the sulfoxide 6, which was isomerized in the presence
Tetrahedron Letters, 48, 1657-1657 (2007)
Yupeng Fan et al.
Organic letters, 6(15), 2555-2557 (2004-07-17)
[reaction: see text] The formation of a guanosine derivative silylated at both the O6 and amino groups was identified by (15)N NMR. This intermediate allows facile reaction with acetyl chloride or phenoxyacetyl chloride to give in high yield the corresponding



Global Trade Item Number

SKUGTIN
158623-10G04061838346285
158623-250G04061838744098
158623-50G04061838744104