Benzamide

Benzamide is an organic compound with the chemical formula of C₇H₇NO. It is the simplest amide derivative of benzoic acid. In powdered form, it appears as a white solid, while in crystalline form, it appears as colourless crystals. It is slightly soluble in water, and soluble in many organic solvents. It is a natural alkaloid found in the herbs of Berberis pruinosa.

Benzamide

Names
Preferred IUPAC name Benzamide
Systematic IUPAC name Benzenecarboxamide
Other names Benzoic acid amide Phenyl carboxamide Benzoylamide
Identifiers
CAS Number	55-21-0^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	385876
ChEBI	CHEBI:28179^Y
ChEMBL	ChEMBL267373^Y
ChemSpider	2241^Y
ECHA InfoCard	100.000.207
EC Number	200-227-7
KEGG	C09815^Y
PubChem CID	2331
RTECS number	CU8700000
UNII	6X80438640^Y
CompTox Dashboard (EPA)	DTXSID0021709
InChI InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)^Y Key: KXDAEFPNCMNJSK-UHFFFAOYSA-N^Y InChI=1/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9) Key: KXDAEFPNCMNJSK-UHFFFAOYAA
SMILES O=C(N)c1ccccc1 c1ccc(cc1)C(=O)N
Properties
Chemical formula	C7H7NO
Molar mass	121.139 g·mol^−1
Appearance	Off-white solid
Density	1.341 g/cm^3
Melting point	127 to 130 °C (261 to 266 °F; 400 to 403 K)
Boiling point	288 °C (550 °F; 561 K)
Solubility in water	13.5 g/L (at 25°C)
Acidity (pKa)	approx. 13 (in H2O) 23.3 (in DMSO)
Magnetic susceptibility (χ)	−72.3·10^−6 cm^3/mol
Pharmacology
ATC code	N05AL (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H341
Precautionary statements	P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, P501
NFPA 704 (fire diamond)	1 1 0
Flash point	180 °C (356 °F; 453 K)
Autoignition temperature	> 500 °C (932 °F; 773 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical derivatives

A number of substituted benzamides are commercial drugs, including:

Analgesics

• Ethenzamide
• Salicylamide

Antidepressants

• Moclobemide

Antiemetics/Prokinetics

• Alizapride
• Batanopride
• Bromopride
• Cinitapride
• Cisapride
• Clebopride
• Dazopride
• Itopride
• Metoclopramide
• Mosapride
• Prucalopride
• Renzapride
• Trimethobenzamide
• Veralipride
• Zacopride

Antipsychotics

• Azapride
• Amisulpride
• Levosulpiride
• Nemonapride
• Remoxipride
• Sulpiride
• Sultopride
• Tiapride

Opioids

• AH-7921
• Bromadoline
• U-47700
• U-77891

Others

• 3-Aminobenzamide
• Alpiropride
• Aminohippuric acid
• Chidamide
• Entinostat
• Eticlopride
• Imatinib
• Mocetinostat
• Procarbazine
• Raclopride
• Sunifiram

See also

• ATC code N05AL Benzamides – Pharmaceutical drug classification