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158623

Sigma-Aldrich

Phenoxyacetyl chloride

98%

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About This Item

Linear Formula:
C6H5OCH2COCl
CAS Number:
701-99-5
Molecular Weight:
170.59
Beilstein:
607585
EC Number:
211-862-4
MDL number:
MFCD00000726
UNSPSC Code:
12352100
PubChem Substance ID:
24849768
NACRES:
NA.22

Quality Level

100

Assay

98%

refractive index

n20/D 1.534 (lit.)

bp

225-226 °C (lit.)

density

1.235 g/mL at 25 °C (lit.)

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

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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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314 - H335

Hazard Classifications

Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Natarajan Arumugam et al.
Medicinal chemistry (Shariqah (United Arab Emirates)), 10(7), 730-737 (2014-02-27)
A series of macrocyclic bis-β-lactams has been synthesized in three good yielding steps using a Staudinger [2+2] cycloaddition reaction of ketene derived from phenoxyacetyl chloride as the key step. The reaction provided a diastereomeric mixture of cis-anti-cis (C2-symmetry) and cis-syn-cis
Tetrahedron, 63, 3380-3380 (2007)
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
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
Tetrahedron Letters, 48, 1657-1657 (2007)
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