6655-27-2

Basic information

• Product Name: N-ISOPROPYLIDENE-N'-2-NITROBENZENESULFO&
• Synonyms: N-ISOPROPYLIDENE-N'-2-NITROBENZENESULFO&;2-NITRO-N'-(PROPAN-2-YLIDENE)BENZENESULFONOHYDRAZIDE ;IPNBSH, Isopropylidenehydrazide o-nitro-benzenesulfonic acid;N-Isopropylidene-Nμ-2-nitrobenzenesulfonyl hydrazine;N'-Isopropylidene-2-nitrobenzenesulfonohydrazide;N-Isopropylidene-N-2-Nitrobenzenesulfonohydrazide;IPNBSH;2-(1-Methylethylidene)hydrazide-2-nitrobenzenesulfonic acid
• CAS NO: 6655-27-2
• Molecular Formula: C₉H₁₁N₃O₄S
• Molecular Weight: 257.26634
• Mol File: 6655-27-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 131-135 °C
• Boiling Point: 421.267 °C at 760 mmHg
• Flash Point: 208.575 °C
• Appearance: /
• Density: 1.411 g/cm³
• Storage Temp.: <0°C
• PKA: 9.11±0.40(Predicted)
• CAS DataBase Reference: N-ISOPROPYLIDENE-N'-2-NITROBENZENESULFO&(CAS DataBase Reference)
• NIST Chemistry Reference: N-ISOPROPYLIDENE-N'-2-NITROBENZENESULFO&(6655-27-2)
• EPA Substance Registry System: N-ISOPROPYLIDENE-N'-2-NITROBENZENESULFO&(6655-27-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6655-27-2(Hazardous Substances Data)

Usage

Uses

IPNBSH A Reagent for the Simple Reduction of AlcoholsReactant for synthesis of: (-)-Acylfulvene and (-)-irofulven for use as antitumor agentsBicycloundecadienones and bicyclodecadienones via carbonylative cycloadditionMonoalkyldiazenes for allylic reductionReacts with di-Me phosphonate

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 5906-99-0 2-nitrobenzenesulfonyl hydrazide 
• 67-64-1 acetone 

Downstream Products

• 930599-20-5 N-isopropylidene-N'-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl)-N'-2-nitrobenzenesulfonyl hydrazide 
• 92098-15-2 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 2959-75-3 isopropyl-diphenyl-phosphine oxide 
• 54552-77-1 Dimethyl isopropylphosphonate 

Relevant articles and documents

Chemoenzymatic Formal Total Synthesis of Pancratistatin from Narciclasine-Type Compounds via Myers Transposition: Model Study for a Short Conversion of Narciclasine to Pancratistatin

A formal total synthesis of pancratistatin was accomplished by conversion of advanced intermediates, used in the synthesis of narciclasine, to pancratistatin precursors via Myers' reductive transposition as the key strategic step. The synthesis began with the whole cell fermentation of m -dibromobenzene with JM109(pDTG601a), a recombinant strain that over-expresses toluene dioxygenase, which provided the corresponding cis -dihydrodiol 16 as a single isomer with complete optical purity. The key reductive transposition of the allylic alcohol 8a to olefin 9a allowed for further installation of the C-1/C-2 trans -diol, required for the pancratistatin scaffold, through the introduction of a cyclic sulfate and its subsequent opening. The formal synthesis of pancratistatin was accomplished in 14 steps (12 operations) from commercially available m -dibromobenzene. Experimental and spectral data are provided for all new compounds.

A stereospecific palladium-catalyzed route to monoalkyl diazenes for mild allylic reduction

(Chemical Equation Presented) One step beyond: The first single-step stereospecific transition-metal-catalyzed conversion of allylic electrophiles into monoalkyl diazenes is described. This synthesis of allylic monoalkyl diazenes offers a new strategy for asymmetric synthesis by the reduction of optically active substrates or the use of chiral catalyst systems. Sensitive substrates are reduced in a highly selective manner. Ar = 2-NO2C 6H2.

Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven

(Chemical Equation Presented) Antitumor agents (-)-acylfulvene and (-)-irofulven are prepared in an approach that employs the powerful enyne ring-closing metathesis reaction to secure the spiro-bicyclic AB rings. Other key features of this synthesis include an efficient aldol-based introduction of the stereocenter at C2, a diazene-mediated reductive allylic transposition, and a ring-closing metathesis/oxidation sequence.