Acetone hydrazone

Acetone hydrazone
Names
IUPAC name
Propan-2-ylidenehydrazine
Other names
Isopropylidenehydrazine
Identifiers
CAS Number
  • 5281-20-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 71270
EC Number
  • 226-110-0
PubChem CID
  • 78937
CompTox Dashboard (EPA)
  • DTXSID10967276 Edit this at Wikidata
InChI
  • InChI=1S/C3H8N2/c1-3(2)5-4/h4H2,1-2H3
    Key: JIQXKYSNGXUDJU-UHFFFAOYSA-N
  • CC(=NN)C
Properties
Chemical formula
 C3H8N2
Molar mass 72.111 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
 GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
Hazard statements
 H226, H301, H311, H314, H331, H351, H411
Precautionary statements
 P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P318, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Acetone hydrazone (isopropylidenehydrazine) is the product of condensation of acetone and hydrazine, as typical for hydrazone formation. It is an intermediate in the synthesis of 2-diazopropane [fr].[2]

Acetone hydrazone can be produced on large scale by reaction of acetone azine with hydrazine, a more convenient reaction than direct reaction of acetone and hydrazine.[3] Likewise, it is susceptible to disproportionation to revert to acetone azine and hydrazine, especially in the presence of water.[3]

The chemical is one of the metabolic products of the antihypertensive pharmaceutical hydralazine, and itself also have antihypertensive effects.[4]

References

  1. ^ "Acetone hydrazone". pubchem.ncbi.nlm.nih.gov.
  2. ^ Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. (1970). "2-Diazopropane". Organic Syntheses: 27; Collected Volumes, vol. 6, 1988, p. 392.
  3. ^ a b Day, A. C.; Whiting, M. C. "Acetone Hydrazone". Organic Syntheses; Collected Volumes, vol. 6, p. 10.
  4. ^ Cohn JN, McInnes GT, Shepherd AM (2011). "Direct-acting vasodilators". Journal of Clinical Hypertension. 13 (9): 690–692. doi:10.1111/j.1751-7176.2011.00507.x. PMC 8108999. PMID 21896152.
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