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:
Molecular Weight:
257.27
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
Assay
97%
form
solid
reaction suitability
reagent type: reductant
mp
131-135 °C
functional group
amine
hydrazide
nitro
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:
Reacts with di-Me phosphonate
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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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