Tert-Butylhydrazine

tert-Butylhydrazine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.190.618 Edit this at Wikidata
EC Number
  • 664-395-7
  • InChI=1S/C4H12N2/c1-4(2,3)6-5/h6H,5H2,1-3H3
    Key: MUQNAPSBHXFMHT-UHFFFAOYSA-N
  • CC(C)(C)NN
Properties
C4H12N2
Molar mass 88.154 g·mol−1
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
Danger
H225, H301, H311, H314, H331, H351
P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, 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, 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).

tert-Butylhydrazine is a chemical compound belonging to the class of hydrazines.

Synthesis

tert-Butylhydrazine can be obtained by the hydrolysis of benzophenone tert-butylhydrazone, which in turn can be prepared by reacting diphenyldiazomethane with tert-butylmagnesium chloride.

Reactions

tert-Butylhydrazine reacts with suitable carbonyl groups to form pyrazoles.

Uses

tert-Butylhydrazine is used in the synthesis of insecticides. Active ingredients of the dibenzoylhydrazine class—methoxyfenozide, tebufenozide, halofenozide, chromafenozide, and fufenozide—contain a tert-butylhydrazine moiety as a central structural element essential for their activity. These insecticides, used particularly against the larvae of butterflies (Lepidoptera), act as agonists of the ecdysone receptor and kill pests by inducing premature molting. In the synthesis of these active ingredients, tert-butylhydrazine undergoes acylation with various carboxylic acid chlorides.

tert-Butylhydrazine is a reducing agent. Because it can reduce neptunium and plutonium present in high oxidation states, it is being investigated—along with many other compounds—as a reagent for reprocessing.

References

  1. ↑ "tert-Butylhydrazine". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-10-10.
  2. ↑ Peter A. S. Smith, John M. Clegg, Julian Lakritz (November 1958), "Preparation of Alkyl Azides from Hydrazine Derivatives 1", The Journal of Organic Chemistry, vol. 23, no. 11, pp. 1595–1599, doi:10.1021/jo01105a001{{citation}}: CS1 maint: multiple names: authors list (link)
  3. ↑ Clarissa P. Frizzo, Mara R.B. Marzari, Lilian Buriol, Dayse N. Moreira, Fernanda A. Rosa, Pâmela S. Vargas, Nilo Zanatta, Helio G. Bonacorso, Marcos A.P. Martins (September 2009), "Ionic liquid effects on the reaction of β-enaminones and tert-butylhydrazine and applications for the synthesis of pyrazoles", Catalysis Communications, vol. 10, no. 15, pp. 1967–1970, doi:10.1016/j.catcom.2009.07.005{{citation}}: CS1 maint: multiple names: authors list (link)
  4. ↑ Fernanda Rosa, Pablo Machado, Pâmela Vargas, Helio Bonacorso, Nilo Zanatta, Marcos Martins (2008-06-11), "Straightforward and Regiospecific Synthesis of Pyrazole-5-carboxylates from Unsymmetrical Enaminodiketones", Synlett, vol. 2008, no. 11, pp. 1673–1678, doi:10.1055/s-2008-1078482{{citation}}: CS1 maint: multiple names: authors list (link)
  5. ↑ Clemens Lamberth, Jürgen Dinges (2016-05-17), Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals, John Wiley & Sons, pp. 467–472, ISBN 978-3-527-69396-2
  6. ↑ V. I. Marchenko, V. N. Alekseenko, K. N. Dvoeglazov (July 2015), "Organic reductants of Pu and Np ions in wet technology for spent nuclear fuel reprocessing", Radiochemistry, vol. 57, no. 4, pp. 366–377, Bibcode:2015Radch..57..366M, doi:10.1134/S1066362215040050{{citation}}: CS1 maint: multiple names: authors list (link)