Benzoylhydrazine

Benzoylhydrazine
Names
Systematic IUPAC name
benzohydrazide
Identifiers
3D model (JSmol)
471797
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.423
EC Number
  • 210-363-9
68991
UNII
  • InChI=1S/C7H8N2O/c8-9-7(10)6-4-2-1-3-5-6/h1-5H,8H2,(H,9,10)
    Key: WARCRYXKINZHGQ-UHFFFAOYSA-N
  • C1=CC=C(C=C1)P
Properties
C7H8N2O
Molar mass 136.154 g·mol−1
Appearance white solid
Boiling point 267 °C (513 °F; 540 K)
soluble
Solubility soluble in alcohol
slightly soluble in ether, acetone, chloroform
Hazards
GHS labelling:[1]
Danger
H301, H315, H319, H335
P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Lethal dose or concentration (LD, LC):
122 mg/kg (mouse, subcutaneous/intraperitoneal) [2]
102 mg/kg (rabbit, subcutaneous) 100 mg/kg (rat, intraperitoneal) [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzoylhydrazine, also known as benzenecarbohydrazide, or benzoic hydrazide is an organic chemical compound, which is a hydrazide functionally linked to benzoic acid. It is typically used as a precursor in pharmaceutical and chemical synthesis, or used as a chemical intermediate for the production of hydrazine-based products.

Metabolism

During metabolism it forms metabolites including hydrazine, benzoic acid and hippuric acid.[1][2]

Safety

It is both neurotoxic and hepatoxic as well as an osteolathyrogen and carcinogen, and also a potential teratogen that affects the development of fetal abnormalities.[3][4][5][6][7][8][9][10]

The mechanism responsible for the development of osteolathyrism is identical to the reference osteolathyrogen β-aminopropionitrile.[8][7][9]

A violent reaction occurs with benzeneselenic acid. When heated to decomposition it emits toxic fumes of nitrogen oxides.[11][1]

References

  1. ^ a b PubChem. "Hazardous Substances Data Bank (HSDB) : 2737". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-26.
  2. ^ "The Biochemistry of Foreign Compounds". ScienceDirect. Retrieved 2026-02-27.
  3. ^ "Benzhydrazide - Hazardous Agents | Haz-Map". haz-map.com. Retrieved 2026-02-26.
  4. ^ Schreiber, Julian A.; Müller, Sebastian L.; Westphälinger, Stefanie E.; Schepmann, Dirk; Strutz-Seebohm, Nathalie; Seebohm, Guiscard; Wünsch, Bernhard (2018-10-05). "Systematic variation of the benzoylhydrazine moiety of the GluN2A selective NMDA receptor antagonist TCN-201". European Journal of Medicinal Chemistry. 158: 259–269. doi:10.1016/j.ejmech.2018.09.006. ISSN 1768-3254. PMID 30218911.
  5. ^ Ma, Huan-Yue; Zha, Zheng-Gen; Zhang, Zhen-Lei; Meng, Li; Wang, Zhi-Yong (2013-09-01). "Electrosynthesis of oxadiazoles from benzoylhydrazines". Chinese Chemical Letters. 24 (9): 780–782. doi:10.1016/j.cclet.2013.05.032. ISSN 1001-8417.
  6. ^ Dawson, D. A. (1993-07-28). "Joint action of benzoic hydrazide and beta-aminopropionitrile on Xenopus embryo development". Toxicology. 81 (2): 123–130. doi:10.1016/0300-483x(93)90004-c. ISSN 0300-483X. PMID 8378938.
  7. ^ a b Dawson, Douglas A. "Comparative joint actions of semicarbazide and thiosemicarbazide on induction of malformations and osteolathyrism in mixtures with benzoic hydrazide". Teratogenesis, Carcinogenesis, and Mutagenesis. 13 (1): 23–33. doi:10.1002/tcm.1770130104. ISSN 0270-3211.
  8. ^ a b Dawson, Douglas A. (1993-07-28). "Joint action of benzoic hydrazide and β-aminopropionitrile on Xenopus embryo development". Toxicology. 81 (2): 123–130. doi:10.1016/0300-483X(93)90004-C. ISSN 0300-483X.
  9. ^ a b Riggin, Geoffrey W.; Schultz, T. Wayne (1986). "Teratogenic Effects of Benzoyl Hydrazine on Frog Embryos". Transactions of the American Microscopical Society. 105 (3): 197–210. doi:10.2307/3226294. ISSN 0003-0023.
  10. ^ Dawson, Douglas A.; Schultz, T. Wayne; Baker, Leslie L. (1991-04-01). "Structure-activity relationships for osteolathyrism: IV. Para-substituted benzoic acid hydrazides and alkyl carbazates". Environmental Toxicology and Chemistry. 10 (4): 455–461. doi:10.1002/etc.5620100405. ISSN 0730-7268. Archived from the original on 2025-04-04.
  11. ^ Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. V2 376
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