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301019

Sigma-Aldrich

Benzyloxyacetyl chloride

95%

Synonym(s):

α-(Benzyloxy)acetyl chloride, (Phenylmethoxy)acetyl chloride, 2-(Benzyloxy)acetyl chloride, 2-(Phenylmethoxy)acetyl chloride, 2-Phenylmethoxyacetyl chloride

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About This Item

Linear Formula:
C6H5CH2OCH2COCl
CAS Number:
19810-31-2
Molecular Weight:
184.62
Beilstein:
1947363
MDL number:
MFCD00010768
UNSPSC Code:
12352100
PubChem Substance ID:
24858157
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.523 (lit.)

bp

84-87 °C/0.4 mmHg (lit.)

density

1.17 g/mL at 25 °C (lit.)

functional group

acyl chloride
ether
phenyl

storage temp.

2-8°C

SMILES string

ClC(=O)COCc1ccccc1

InChI

1S/C9H9ClO2/c10-9(11)7-12-6-8-4-2-1-3-5-8/h1-5H,6-7H2

InChI key

QISAUDWTBBNJIR-UHFFFAOYSA-N

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Application

Benzyloxyacetyl chloride was used in preparation of:
  • (S)-3-(methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile, key intermediate in the preparation of fluoroquinolone antibiotic for respiratory tract infections
  • non-racemic helicene
  • β-lactams
  • substituted 2-azetidinones for further elaboration into annulated β-lactams

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBQ3192V
BCBN1723V
MKBQ3418V
MKBN9560V
1453045V

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The Journal of Organic Chemistry, 58, 1646-1646 (1993)
The Journal of Organic Chemistry, 59, 932-932 (1994)
Willem Van Brabandt et al.
The Journal of organic chemistry, 71(18), 7083-7086 (2006-08-26)
A high-yielding, asymmetric synthesis of novel 4-formyl-1-(2- and 3-haloalkyl)azetidin-2-ones was developed as valuable starting materials for the synthesis of different enantiomerically enriched bicyclic azetidin-2-ones, such as piperazine, morpholine, and 1,4-diazepane annulated beta-lactam derivatives. Especially the hydride reduction of 4-imidoyl-1-(2- and
Manjinder S Lall et al.
The Journal of organic chemistry, 77(10), 4732-4739 (2012-04-25)
(S)-3-(methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile (1) is a key intermediate in the preparation of PF-00951966, (1) a fluoroquinolone antibiotic for use against key pathogens causing community-acquired respiratory tract infections including multidrug resistant (MDR) organisms. The current work describes the development of a highly efficient
Synthesis, structure, and properties of a helical columnar liquid crystal.
Nuckolls C and Katz TJ.
Journal of the American Chemical Society, 120(37), 9541-9544 (1998)

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