N-Phenyltrifluoromethanesulfonimide
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N-Phenyltrifluoromethanesulfonimide
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CAS No:
37595-74-7
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Formula:
C8H5F6NO4S2
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Chemical Name:
N-Phenyltrifluoromethanesulfonimide
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Synonyms:
Methanesulfonamide,1,1,1-trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]-;1,1,1-Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide;N,N-Bis(trifluoromethylsulfonyl)aniline;N,N-Bis(trifluoromethylsulfonyl)phenylamine;Phenyl triflimide;N-Phenyltriflimide;N,N-Bis(trifluoromethanesulfonyl)aniline;N-Phenyltrifluoromethanesulfonimide;N-Phenyltrifluoromethylsulfonimide;Phenyl bis((trifluoromethyl)sulfonyl)amine;Trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide;NSC 240874;N-Phenylbis(trifluoromethanesulfonimide);1,1,1-Trifluoro-N-phenyl-N-trifluoromethanesulfonylmethanesulfonamide;N-Phenyl-N-[(trifluoromethyl)sulfonyl]trifluoromethanesulfonamide;N-Phenylbis(trifluoromethanesulfonyl)imide;PhNTf2;N-Phenyl-N-(trifluoromethanesulfonyl)trifluoromethanesulfonamide;N,N′-Bis(trifluoromethanesulfonyl)aniline;N-Phenyl-bis(trifluoromethanesulfonimide);155262-60-5
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CAS No:
N-Phenyltrifluoromethanesulfonimide Basic Attributes
357.25
357.25
1269141
1592732-453-0
TIC0LRR43X
240874
DTXSID70191030
29242100
Characteristics
88.3
3.1
White or colorless Crystals or Crystalline Powder
1.8±0.1 g/cm3
95-96 °C
305.3°C at 760 mmHg
138.4±30.7 °C
1.488
soluble in methanol. Slightly soluble in chloroform and ethyl acetate.
N-Phenyltrifluoromethanesulfonimide Use and Manufacturing
To a 10 L found-bottomed flask was charged aniline (232.5 g, 2.5 mol), triethylamine (505 g, 5 mol) and dichloromethane (5 L).To a 10 L found-bottomed flask was charged aniline (232.5 g, 2.5 mol), triethylamine (505 g, 5 mol) and dichloromethane (5 L). The resulting mixture was cooled with an ice bath. Trifluoromethanesulfonic anhydride (1410 g, 5 mol) in dichlolormethane (1 L) was added dropwise. The reaction mixture was allowed to warm to RT and stirred overnight. The reaction was then added to crushed ice (4 kg) while stirring. The resulting biphasic mixture was separated. The organic layer was washed with brine (2 L x 2), dried over NaStep 1 : To a solution of aniline (1.0 g, 1.0 eq) and triethylamine (2.99 mL, 2.0 eq) in methylene chloride (100 mL) at -80 °C, under N
N-Phenylbis(trifluoromethanesulfonamide) is used in the enantioselective synthesis of β-amino acids via the Mannich reaction. Used in the synthesis of sphingosine 1-phosphate-1 receptor agonists useful in pharmaceutical application.
Computed Properties
Molecular Weight:357.3
XLogP3:3.1
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:3
Exact Mass:356.95641896
Monoisotopic Mass:356.95641896
Topological Polar Surface Area:88.3
Heavy Atom Count:21
Complexity:518
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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