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Benzamide

Names
Preferred IUPAC name Benzamide
Systematic IUPAC name Benzenecarboxamide
Other names Benzoic acid amide Phenyl carboxamide Benzoylamide
Identifiers
CAS Number	55-21-0
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	385876
ChEBI	CHEBI:28179
ChEMBL	ChEMBL267373
ChemSpider	2241
ECHA InfoCard	100.000.207
EC Number	200-227-7
KEGG	C09815
PubChem CID	2331
RTECS number	CU8700000
UNII	6X80438640
CompTox Dashboard (EPA)	DTXSID0021709
InChI InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)Key: KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
Appearance	Off-white solid
Density	1.341 g/cm
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 cm/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 , 100 kPa). Y verify (what is  ?) Infobox references

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.

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

References

1. Favre, Henri A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. p. 841. doi:10.1039/9781849733069-FP001. ISBN 9780854041824. OCLC 1077224056. Archived from the original on 2022-10-11. Retrieved 2022-10-11.
2. ^ "Benzamide | 55-21-0 supplier and manufacturer". BuyersGuideChem. Archived from the original on July 29, 2017. Retrieved October 11, 2022.
3. Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–89 . ISBN 9781498754286. OCLC 1012162798. Archived from the original on 2022-10-11. Retrieved 2022-10-11. page cited is 5-89, not 5 to 89
4. Bordwell, Frederick G.; Ji, Guo Zhen (October 1991). "Effects of structural changes on acidities and homolytic bond dissociation energies of the hydrogen-nitrogen bonds in amidines, carboxamides, and thiocarboxamides". Journal of the American Chemical Society. 113 (22): 8398–8401. doi:10.1021/ja00022a029. Archived from the original on 2020-12-11. Retrieved 2022-10-11.
5. CID 2331 from PubChem
6. ^ "benzamide, CAS number 55-21-0". The Good Scents Company. Retrieved October 11, 2022.

External links

• Physical characteristics
• Safety MSDS data

• Benzamides
• Phenyl compounds