170432-54-9

Basic information

• Product Name: 2,3-Difluoro-N-methyl-6-nitroaniline
• Synonyms: 2,3-Difluoro-N-methyl-6-nitroaniline
• CAS NO: 170432-54-9
• Molecular Formula: C₇H₆F₂N₂O₂
• Molecular Weight: 188.1315464
• Mol File: 170432-54-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-Difluoro-N-methyl-6-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Difluoro-N-methyl-6-nitroaniline(170432-54-9)
• EPA Substance Registry System: 2,3-Difluoro-N-methyl-6-nitroaniline(170432-54-9)

Safety Data

• Hazardous Substances Data: 170432-54-9(Hazardous Substances Data)

Upstream product

• 211693-73-1 2-amino-3,4-difluoronitro-benzene 
• 77-78-1 dimethyl sulfate 
• 771-69-7 2,3,4-trifluoronitrobenzene 
• 593-51-1 methylamine hydrochloride 

Downstream Products

• 1357192-56-3 N¹-(diphenylmethyl)-2-fluoro-N³-methyl-4-nitrobenzene-1,3-diamine 
• 1357192-57-4 N-(diphenylmethyl)-7-fluoro-1,2-dimethyl-1H-benzimidazol-6-amine 

Relevant articles and documents

Di- and Trifluorinated 2-Azidobenzimidazole Derivatives: Synthesis, Photooxygenation, and 19F NMR Prediction

The photoreactivity of a series of hitherto unknown, multiply fluorinated 2-azidobenzimidazole derivatives was investigated. The synthesis of the starting material includes regioselective p-defluorination of nitrobenzene derivatives employing Ogoshi's conditions. If the 6-position was unsubstituted, irradiation in the presence of N-protected amino acids at 300 nm (Rayonet) led to the formation of arylesters by oxygenation of the 6-position in good to excellent yields and perfect regioselectivity. We did not observe any displacement of fluoride. If the 6-position itself was fluorinated, alternative positions of the benzene portion were attacked. Mechanistically, the reaction proceeds through ring opening of the singlet nitrene to the cyanodiimine or via the iminobenzimidazolium ion. The availability of a set of fluorinated photo-adducts prompted the quantum chemical calculation of their 19F NMR chemical shifts. Even with the most suitable method investigated (ωB97XD/TApr-cc-pVDZ), deviations of up to 5 ppm from the experimental values were observed, underlining the importance of experimental measurements.

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