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Acetone hydrazone

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Acetone hydrazone
Names
IUPAC name Propan-2-ylidenehydrazine
Other names Isopropylidenehydrazine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 226-110-0
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H8N2/c1-3(2)5-4/h4H2,1-2H3Key: JIQXKYSNGXUDJU-UHFFFAOYSA-N
SMILES
  • CC(=NN)C
Properties
Chemical formula C3H8N2
Molar mass 72.111 g·mol
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word 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 , 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].

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. Likewise, it is susceptible to disproportionation to revert to acetone azine and hydrazine, especially in the presence of water.

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

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. ^ 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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