Benzamide
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Names | |
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Preferred IUPAC name Benzamide[1] | |
Systematic IUPAC name Benzenecarboxamide | |
Other names Benzoic acid amide Phenyl carboxamide Benzoylamide | |
Identifiers | |
3D model (JSmol) | |
3DMet | |
385876 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.207 |
EC Number |
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KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C7H7NO | |
Molar mass | 121.139 g·mol−1 |
Appearance | Off-white solid |
Density | 1.341 g/cm3 |
Melting point | 127 to 130 °C (261 to 266 °F; 400 to 403 K) |
Boiling point | 288 °C (550 °F; 561 K) |
13.5 g/L (at 25°C)[2] | |
Acidity (pKa) | |
-72.3·10−6 cm3/mol | |
Pharmacology | |
N05AL (WHO) | |
Hazards | |
GHS labelling: | |
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Warning | |
H302, H341 | |
P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 180 °C (356 °F; 453 K) |
> 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). |
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.[5] It is slightly soluble in water,[2] and soluble in many organic solvents.[6] It is a natural alkaloid found in the herbs of Berberis pruinosa.[6]
Chemical derivatives
[edit]A number of substituted benzamides are commercial drugs, including:
- Analgesics
- Antidepressants
- Antiemetics/Prokinetics
- Alizapride
- Batanopride
- Bromopride
- Cinitapride
- Cisapride
- Clebopride
- Dazopride
- Itopride
- Metoclopramide
- Mosapride
- Prucalopride
- Renzapride
- Trimethobenzamide
- veralipride
- Zacopride
- Antipsychotics
- Opioids
- Others
- 3-Aminobenzamide
- aminohippuric acid
- Chidamide
- Denipride
- Entinostat
- Eticlopride
- imatinib
- Mocetinostat
- Procarbazine
- Pyramide (pyridinyl ethylbenzimide)[7]
- Raclopride
- Sunifiram
See also
[edit]- ATC code N05AL Benzamides – Pharmaceutical drug classification
References
[edit]- ^ 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.
- ^ a b "Benzamide | 55-21-0 supplier and manufacturer". BuyersGuideChem. Archived from the original on July 29, 2017. Retrieved October 11, 2022.
- ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–89 [sic]. 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
- ^ 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.
- ^ CID 2331 from PubChem
- ^ a b "benzamide, CAS number 55-21-0". The Good Scents Company. Retrieved October 11, 2022.
- ^ Kent, James A.; Singh, K. N.; Merchant, Kavita (2012). "The Agrochemical Industry, Annex 17.1". In Kent, James A. (ed.). Handbook of Industrial Chemistry and Biotechnology. New York: Springer Verlag. pp. 643–698. doi:10.1007/978-1-4614-4259-2_17. ISBN 9781461442592. OCLC 1097100876. Archived from the original on 2022-10-11. Retrieved 2022-10-11.