Acetone hydrazone

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

Names
IUPAC name Propan-2-ylidenehydrazine
Other names Isopropylidenehydrazine
Identifiers
CAS Number	5281-20-9 Y
3D model (JSmol)	Interactive image
ChemSpider	71270
EC Number	226-110-0
PubChem CID	78937
CompTox Dashboard (EPA)	DTXSID10967276
InChI InChI=1S/C3H8N2/c1-3(2)5-4/h4H2,1-2H3 Key: JIQXKYSNGXUDJU-UHFFFAOYSA-N
SMILES CC(=NN)C
Properties
Chemical formula	C3H8N2
Molar mass	72.111 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
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 [77 °F], 100 kPa). Infobox references

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. 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.