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Merck
CN

687855

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
UNSPSC Code:
12352116
PubChem Substance ID:
329761163
MDL number:
MFCD09800525
Assay:
97%
Form:
solid

Key Documents

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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

SMILES string

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

InChI key

SBNYNTYNEJTMQO-UHFFFAOYSA-N

assay

97%

form

solid

reaction suitability

reagent type: reductant

mp

131-135 °C

functional group

amine, hydrazide, nitro

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
06129HH

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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)
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.

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