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Benzamide

From Wikipedia, the free encyclopedia
Benzamide
Skeletal formula
Skeletal formula
Ball-and-stick model
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)
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 checkYX markN ?)

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]

Properties

[edit]

Benzamide is slightly soluble in water and soluble in polar organic solvents, including ethanol, diethyl ether, and chloroform. It has a melting point of 127–130 °C and a boiling point of 288 °C. The molecule consists of a phenyl group attached to a carboxamide group. Resonance stabilization between the carbonyl oxygen, the nitrogen atom, and the aromatic ring influences its reactivity and dipole moment.

Applications

[edit]

Pharmaceuticals

[edit]

Substituted benzamides form a major class of pharmacological compounds, designated as benzamides. Derivatives of this structural pharmacophore exhibit varied biological activities:

  • Antipsychotics: Sulpiride, amisulpride, and tiapride act as dopamine receptor antagonists.
  • Gastroprokinetics and Antiemetics: Metoclopramide and domperidone are widely used to treat nausea and gastrointestinal disorders.
  • Oncology: Benzamide derivatives, such as olaparib and entinostat, function as PARP inhibitors and histone deacetylase (HDAC) inhibitors, respectively.

Chemical Synthesis

[edit]

Benzamide serves as a synthetic intermediate in industrial chemical manufacturing for dyes, agricultural chemicals, and specialty polymers.

List of Derivatives

[edit]
Analgesics
Antidepressants
Antiemetics/Prokinetics
Antipsychotics
Opioids
Pesticides
Others

Toxicity and Safety

[edit]

Benzamide is classified as harmful if swallowed (LD50 oral, mouse: ~1,160 mg/kg). It is listed as a Category 2 suspect germ cell mutagen based on in vitro assay data. Exposure to benzamide dust may cause mild physical irritation to the skin, eyes, and upper respiratory tract. Elevated temperatures or combustion generate toxic fumes, including nitrogen oxides and carbon monoxide.

References

[edit]
  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. 1 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. pp. 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. 1 2 "benzamide, CAS number 55-21-0". The Good Scents Company. Retrieved October 11, 2022.
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