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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:
385876
EC Number:
200-227-7
MDL number:
MFCD00007968
UNSPSC Code:
12352100
PubChem Substance ID:
24864807
NACRES:
NA.22

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

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

Signal Word

Warning

Hazard Statements

H302,H341

Hazard Classifications

Acute Tox. 4 Oral - Muta. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

356.0 °F - closed cup

Flash Point(C)

180 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
The crystal and molecular structure of benzamide.
Penfold BR and White JCB.
Acta Crystallographica, 12(2), 130-135 (1959)
Jamin D Steffen et al.
Journal of medicinal chemistry, 54(15), 5403-5413 (2011-06-23)
The metabolism of poly(ADP-ribose) (PAR) in response to DNA strand breaks, which involves the concerted activities of poly(ADP-ribose) polymerases (PARPs) and poly(ADP-ribose) glycohydrolase (PARG), modulates cell recovery or cell death depending upon the level of DNA damage. While PARP inhibitors
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
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