39184-67-3

Basic information

• Product Name: 3-Chloro-3-(4-nitrophenyl)-3H-diazirine
• Synonyms: 3-Chloro-3-(4-nitrophenyl)-3H-diazirine
• CAS NO: 39184-67-3
• Molecular Formula: C₇H₄ClN₃O₂
• Molecular Weight: 197.57856
• Mol File: 39184-67-3.mol

Chemical Properties

• Appearance: /
• Density: 1.67±0.1 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: 3-Chloro-3-(4-nitrophenyl)-3H-diazirine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-3-(4-nitrophenyl)-3H-diazirine(39184-67-3)
• EPA Substance Registry System: 3-Chloro-3-(4-nitrophenyl)-3H-diazirine(39184-67-3)

Safety Data

• Hazardous Substances Data: 39184-67-3(Hazardous Substances Data)

Upstream product

• 15723-90-7 4-nitrobenzamidine hydrochloride 

Downstream Products

• 619-78-3 1-dichloromethyl-4-nitrobenzene 
• 83846-29-1 2-chloro-2-methyl-3-(p-nitrophenyl)-3-propanone 
• 60644-67-9 2-methyl-3-(p-nitrophenyl)-1-propene-3-one 
• 115107-32-9 2,2-Dimethyl-4-(4-nitro-phenyl)-5-p-tolyl-[1,3]dioxole 
• 115107-31-8 4-(4-Chloro-phenyl)-2,2-dimethyl-5-(4-nitro-phenyl)-[1,3]dioxole 
• 108604-19-9 (1S,2S)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 135004-83-0 2-Ethoxy-1-(4-nitro-phenyl)-propenone 
• 555-16-8 4-nitrobenzaldehdye 
• 108438-41-1 2-Hydroxy-5,5-dimethyl-2-(4-nitro-phenyl)-2,5-dihydro-furan-3,4-dicarboxylic acid dimethyl ester 
• 108647-84-3 (1S,2R,3R)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 108647-83-2 (1R,2S,3S)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 628-34-2 2-chloroethyl ethyl ether 
• 2403-53-4 2-(4-nitrophenyl)-1,3-dioxolane 
• 25412-75-3 4-nitrobenzamidine 

Relevant articles and documents

Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines

Herein, we report a reaction that selectively generates 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores, respectively. By employing α-chlorodiazirines as thermal precursors to the corresponding chlorocarbenes, the traditional haloform-based protocol central to the parent Ciamician-Dennstedt rearrangement can be modified to directly afford 3-(hetero)arylpyridines and quinolines. Chlorodiazirines are conveniently prepared in a single step by oxidation of commercially available amidinium salts. Selectivity as a function of pyrrole substitution pattern was examined, and a predictive model based on steric effects is put forward, with DFT calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is further demonstrated through the preparation of quinolinophanes and the skeletal editing of pharmaceutically relevant pyrroles.

Hammett analysis of a family of carbene-carbene complex equilibria

p-X-substituted phenylchlorocarbenes (X = NO2, CF3, Cl, H, Me, and MeO) form π-type complexes with trimethoxybenzene in pentane. The carbenes and complexes are in equilibrium, and logarithms of the measured equilibrium constants are well correlated by Hammett σp constants with ρ = 2.48. The carbene complexes are characterized by UV-vis spectroscopy, and computational analysis is afforded by DFT calculations.(Figure Presented)