115127-52-1

Basic information

• Product Name: 3-Chloro-3-[4-(trifluoromethyl)phenyl]-3H-diazirine
• Synonyms: 3-Chloro-3-[4-(trifluoromethyl)phenyl]-3H-diazirine
• CAS NO: 115127-52-1
• Molecular Formula: C₈H₄ClF₃N₂
• Molecular Weight: 220.5789696
• Mol File: 115127-52-1.mol

Chemical Properties

• Boiling Point: 212.6±50.0℃ (760 Torr)
• Flash Point: 82.4±30.1℃
• Appearance: /
• Density: 1.54±0.1 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: 3-Chloro-3-[4-(trifluoromethyl)phenyl]-3H-diazirine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-3-[4-(trifluoromethyl)phenyl]-3H-diazirine(115127-52-1)
• EPA Substance Registry System: 3-Chloro-3-[4-(trifluoromethyl)phenyl]-3H-diazirine(115127-52-1)

Safety Data

• Hazardous Substances Data: 115127-52-1(Hazardous Substances Data)

Upstream product

• 38980-96-0 4-(trifluoromethyl)benzimidamide hydrochloride 

Downstream Products

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 134346-90-0 2-methyl-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 
• 86295-95-6 para-trifluoromethylphenylchlorocarbene 
• 455-18-5 4-CF₃C₆H₄CN 
• 882-33-7 diphenyldisulfane 
• 131472-28-1 4-trifluoromethylbenzamidine 
• 116377-08-3 C₁₆H₈Cl₂F₆ 
• 116377-09-4 C₁₆H₈Cl₂F₆N₂ 

Relevant articles and documents

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)

SRN1 Reactions of Arylhalodiazirines with Azide Ion

(m-(Trifluoromethyl)phenyl)bromodiazirine, 10, reacts with 15N terminally labeled sodium azide in dimethyl sulfoxide to give m-(trifluoromethyl)benzonitrile which, in all cases, contains 15N incorporation.The largest amount of label incorporation (42 percent) and the fastest rate, is observed when the reaction is carried out in room light.The smallest amount of label incorporation (11 percent), and the slowest reaction, is observed when the reaction is carried out in the dark and a trace of the free radical, galvinoxyl, is added.The reaction in the light is proposed to occur mainly via the SRN1 chain process.The intermediate C-azidodiazirine substitution product is not observed, but presumably rapidly loses 2 mol of nitrogen to give the nitrile product. (p-Nitrophenyl)bromodiazirine, 20, can also react with azide ion via an analogous SRN1 process, and the reaction is more facile than that of 10.Label incorporation from 15N-labeled sodium azide is substantial (47.3 percent) and is in agreement with the proposed SRN1 process.A variety of arylchlorodiazirines, substituted with electron-deficient aromatic groups, also react with azide ion in room light, to give nitriles via C-azidodiazirines, which lose molecular nitrogen.Evidence for the proposed SRN1 process includes initiation of the reaction by exposure to room light, initiation by the addition of the sodium salt of 2-nitropropane or sodium thiophenoxide, and inhibition of the reaction by the addition of galvinoxyl.In the case of these arylchlorodiazirines, reaction with 15N terminally labeled sodium azide led to 15N label incorporation approaching the maximum amount possible for a reaction proceeding exclusively via C-azidodiazirines.These studies show the propensity for arylhalodiazirines to undergo reaction initiated by electron-transfer processes.