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B12695

Sigma-Aldrich

Benzoyl chloride

ReagentPlus®, ≥99%

Synonym(s):

Benzoic acid chloride, alpha-chlorobenzaldehyde

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About This Item

Linear Formula:
C6H5COCl
CAS Number:
98-88-4
Molecular Weight:
140.57
Beilstein:
471389
EC Number:
202-710-8
MDL number:
MFCD00000653
UNSPSC Code:
12352100
PubChem Substance ID:
24891577
NACRES:
NA.21

vapor density

4.88 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 32 °C)

product line

ReagentPlus®

Assay

≥99%

form

liquid

autoignition temp.

1056 °F

expl. lim.

4.9 %

refractive index

n20/D 1.553 (lit.)

bp

198 °C (lit.)

mp

−1 °C (lit.)

density

1.211 g/mL at 25 °C (lit.)

functional group

acyl chloride
phenyl

SMILES string

ClC(=O)c1ccccc1

InChI

1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H

InChI key

PASDCCFISLVPSO-UHFFFAOYSA-N

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General description

Benzoyl chloride, an acid chloride, is a commonly used benzoylating agent. The arylation of 1,1- and 1,2-disubstituted activated alkenes using benzoyl chloride in the presence of palladium catalyst has been investigated.

Application

Benzoyl chloride may be used to synthesize:
  • 4-Methoxybenzophenone via acylation of anisole in the presence of cesium-substituted dodecatungstophosphoric acid (Cs2.5H0.5PW12O40) supported on K-10 clay.
  • Benzoylamino acids via acylation of amino acids in the presence of diisopropylethylamine.
  • p-, o-, m-Methylbenzophenones via benzoylation of toluene in the presence of Al-promoted sulfated zirconia catalysts.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

161.6 °F - closed cup

Flash Point(C)

72 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2585
STBL0603
SDBB1932
STBL3610
SDBB0398

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Stereochemical course of the palladium-catalysed arylation of disubstituted activated alkenes with benzoyl chloride.
Spencer A.
Journal of Organometallic Chemistry, 240(2), 209-216 (1982)
Benzoylation of anisole over borate zirconia solid acid catalyst.
Patil PT, et al.
Catalysis Communications, 3(9), 411-416 (2002)
Benzoylation of toluene with benzoyl chloride on Al-promoted sulfated solid superacids.
Xia Y, et al.
Catalysis Letters, 55(2), 105-112 (1998)
Nils C Gassen et al.
Nature communications, 12(1), 3818-3818 (2021-06-23)
Viruses manipulate cellular metabolism and macromolecule recycling processes like autophagy. Dysregulated metabolism might lead to excessive inflammatory and autoimmune responses as observed in severe and long COVID-19 patients. Here we show that SARS-CoV-2 modulates cellular metabolism and reduces autophagy. Accordingly
Cesium-substituted dodecatungstophosphoric acid on K-10 clay for benzoylation of anisole with benzoyl chloride.
Yadav GD, et al.
J. Catal., 217(1), 88-99 (2003)
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