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399337

Sigma-Aldrich

Benzamide

purified by sublimation, ≥99.5%

Synonym(s):

Benzoic acid amide

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About This Item

Linear Formula:
C6H5CONH2
CAS Number:
55-21-0
Molecular Weight:
121.14
Beilstein/REAXYS Number:
385876
EC Number:
200-227-7
MDL number:
MFCD00007968
UNSPSC Code:
12352100
PubChem Substance ID:
24864807
NACRES:
NA.22

Quality Level

100

assay

≥99.5%

form

powder

purified by

sublimation

mp

125-128 °C (lit.)

solubility

ethanol: soluble 50 mg/mL, clear to slightly hazy, colorless to light yellow

functional group

amide
phenyl

SMILES string

NC(=O)c1ccccc1

InChI

1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)

InChI key

KXDAEFPNCMNJSK-UHFFFAOYSA-N

Gene Information

human ... PARP1(142)

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General description

Benzamide (Benzoic acid amide, BA) is an amide of benzoic acid. BA on crystallization in benzene (solvent) affords crystals suitable for X-ray analysis. Crystal structure studies suggest that its crystals are monoclinic having space group P21/c. Kinetics and mechanism of its reaction with hydrogen peroxide have been proposed.

Application

Benzamide was used to study the mechanism of photocatalytic decomposition of aqueous solution of acetic acid, acetamide and acetonitrile in the presence of semiconductors. Benzamide was used to develop a robust screening method to study biotransformations using (+)-γ-lactamase enzyme.

Biochem/physiol Actions

Inhibits poly(ADP-ribose) polymerase (PARP).

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

hcodes

H302,H341

Hazard Classifications

Acute Tox. 4 Oral - Muta. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

356.0 °F - closed cup

flash_point_c

180 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000179466
MKCC0318
MKBR3448V
MKBL3327V

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The mechanisms of hydrogen peroxide reactions. I. The conversion of benzonitrile to benzamide.
Wiberg KB.
Journal of the American Chemical Society, 75(16), 3961-3964 (1953)
The crystal and molecular structure of benzamide.
Penfold BR and White JCB.
Acta Crystallographica, 12(2), 130-135 (1959)
Photocatalytic Decompositions of Carboxylic Acid Derivatives by Semiconductors.
Park KH and Kim JH.
Bull. Korean Chem. Soc., 12(4), 439-439 (1991)
Anne Marie Hickey et al.
Biotechnology journal, 4(4), 510-516 (2009-03-18)
A (+)-gamma-lactamase was precipitated, cross-linked and the resulting solid crushed prior to immobilisation within a capillary column microreactor. The microreactor was subsequently used to study enzyme stability, activity, kinetics and substrate specificity. The thermophilic (+)-gamma-lactamase retained 100% of its initial
Walter Mier et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 55(1), 9-14 (2013-11-28)
The performance of cytotoxic drugs is defined by their selectivity of uptake and action in tumor tissue. Recent clinical responses achieved by treating metastatic malignant melanoma with therapeutic modalities based on gene expression profiling showed that malignant melanoma is amenable
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