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Sigma-Aldrich

N-Isopropylidene-N′-2-nitrobenzenesulfonyl hydrazine

97%

Synonym(s):

2-(1-Methylethylidene)hydrazide-2-nitrobenzenesulfonic acid, Acetone 2-nitrobenzenesulfonylhydrazone, IPNBSH, Isopropylidenehydrazide o-nitro-benzenesulfonic acid

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About This Item

Empirical Formula (Hill Notation):
C9H11N3O4S
CAS Number:
6655-27-2
Molecular Weight:
257.27
MDL number:
MFCD09800525
UNSPSC Code:
12352116
PubChem Substance ID:
329761163

assay

97%

form

solid

reaction suitability

reagent type: reductant

mp

131-135 °C

SMILES string

C\C(C)=N\NS(=O)(=O)c1ccccc1[N+]([O-])=O

InChI

1S/C9H11N3O4S/c1-7(2)10-11-17(15,16)9-6-4-3-5-8(9)12(13)14/h3-6,11H,1-2H3

InChI key

SBNYNTYNEJTMQO-UHFFFAOYSA-N

Application

IPNBSH A Reagent for the Simple Reduction of Alcohols

Reactant for synthesis of:
  • (-)-Acylfulvene and (-)-irofulven for use as antitumor agents
  • Bicycloundecadienones and bicyclodecadienones via carbonylative cycloaddition
  • Monoalkyldiazenes for allylic reduction

Reacts with di-Me phosphonate
Reagent for allylic transposition and reduction of alcohols, as well as mild and stereoselective reduction of allylic carbonates and vinyl epoxides.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Mohammad Movassaghi et al.
The Journal of organic chemistry, 72(5), 1838-1841 (2007-02-06)
The reagent N-isopropylidene-N'-2-nitrobenzenesulfonyl hydrazine (IPNBSH) is used in the reduction of alcohols via the loss of dinitrogen from transiently formed monoalkyl diazene intermediates accessed by sequential Mitsunobu displacement, hydrolysis, and fragmentation under mild reaction conditions.
A stereospecific palladium-catalyzed route to monoalkyl diazenes for mild allylic reduction.
Mohammad Movassaghi et al.
Angewandte Chemie (International ed. in English), 47(46), 8909-8912 (2008-10-17)

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