Wikipedia

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.[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]

Benzamide
Skeletal formula
Ball-and-stick model
Names
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 Edit this at Wikidata
EC Number
  • 200-227-7
KEGG
RTECS number
  • CU8700000
UNII
  • InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9) checkY
    Key: KXDAEFPNCMNJSK-UHFFFAOYSA-N checkY
  • InChI=1/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)
    Key: KXDAEFPNCMNJSK-UHFFFAOYAA
  • O=C(N)c1ccccc1
  • c1ccc(cc1)C(=O)N
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)
  • approx. 13 (in H2O)[3]
  • 23.3 (in DMSO)[4]
-72.3·10−6 cm3/mol
Pharmacology
N05AL (WHO)
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H302, H341
P201, P202, P264, P270, P281, P301 P312, P308 P313, P330, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
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).
checkY verify (what is checkY☒N ?)

Chemical derivatives

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A number of substituted benzamides are commercial drugs, including:

Analgesics
Antidepressants
Antiemetics/Prokinetics
Antipsychotics
Opioids
Others

See also

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References

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  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. ^ a b "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 [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
  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. ^ a b "benzamide, CAS number 55-21-0". The Good Scents Company. Retrieved October 11, 2022.
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