36457-58-6

Basic information

• Product Name: N-BENZYLTRIFLUOROMETHANESULFONAMIDE
• Synonyms: Methanesulfonamide, 1,1,1-trifluoro-N-(phenylmethyl)-;LABOTEST-BB LT00454902;N-BENZYLTRIFLUOROMETHANESULFONAMIDE;N-BENZYLTRIFLUOROMETHANESULPHONAMIDE;N-benzyl-1,1,1-trifluoromethanesulphonamide;N-Benzyltriflamide;N-Benzyltrifluoromethanesulphonamide 97%;N-Benzyltrifluoromethanesulphonamide97%
• CAS NO: 36457-58-6
• Molecular Formula: C₈H₈F₃NO₂S
• Molecular Weight: 239.21
• EINECS: 253-050-2
• Mol File: 36457-58-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 44-46°C
• Boiling Point: 268.2°Cat760mmHg
• Flash Point: 116°C
• Appearance: /
• Density: 1.419g/cm³
• Vapor Pressure: 0.00779mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.15±0.40(Predicted)
• BRN: 2119124
• CAS DataBase Reference: N-BENZYLTRIFLUOROMETHANESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYLTRIFLUOROMETHANESULFONAMIDE(36457-58-6)
• EPA Substance Registry System: N-BENZYLTRIFLUOROMETHANESULFONAMIDE(36457-58-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• Hazardous Substances Data: 36457-58-6(Hazardous Substances Data)

Usage

General Description

N-Benzyltrifluoromethanesulfonamide is a chemical compound with the molecular formula C8H8F3NO2S. It is a sulfonamide derivative with a benzyl group attached to the nitrogen atom, and three trifluoromethyl groups attached to the sulfur atom. N-BENZYLTRIFLUOROMETHANESULFONAMIDE is commonly used as a reagent in organic synthesis, particularly in the field of medicinal and pharmaceutical chemistry. It is known for its ability to act as a nucleophilic catalyst in various reactions, and has also been studied for its potential antimicrobial and anti-inflammatory properties. Additionally, N-benzyltrifluoromethanesulfonamide is used as a building block in the preparation of other compounds and is considered to have potential applications in the development of new drug candidates.

InChI:InChI=1/C8H8F3NO2S/c9-8(10,11)15(13,14)12-6-7-4-2-1-3-5-7/h1-5,12H,6H2

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 100-46-9 benzylamine 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 121-44-8 triethylamine 
• 421-85-2 Trifluoromethanesulfonamide 
• 100-39-0 benzyl bromide 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 16191-72-3 N-Benzyl-β-tosylethylamine 
• 114532-98-8 N-benzyl-N-nitrosotrifluoromethanesulfonamide 
• 158612-50-1 N-Benzyl-C,C,C-trifluoro-N-[2-(toluene-4-sulfonyl)-ethyl]-methanesulfonamide 

Downstream Products

• 114532-98-8 N-benzyl-N-nitrosotrifluoromethanesulfonamide 
• 58044-89-6 N,N-dibenzyl-1,1,1-trifluoromethanesulfonamide 
• 205885-30-9 N-Benzyl-C,C,C-trifluoro-N-trimethylsilanylethynyl-methanesulfonamide 
• 210405-58-6 3-(N-benzyl-N-trifluoromethanesulfonamido)propan-1-ol 
• 412044-52-1 N-benzyl-C,C,C-trifluoro-N-(5-iodo-pent-4-enyl)-methanesulfonamide 
• 1082208-85-2 C₈H₆F₅NO₂S 
• 1159505-61-9 C₈H₇F₄NO₂S 
• 51029-14-2 N-benzyl-N-ethyl-1,1,1-trifluoromethanesulfonamide 
• 52322-83-5 N-benzyl-N-((trifluoromethyl)sulfonyl)benzamide 
• 58090-39-4 N-Benzyl-N-heptyltriflamid 

Relevant articles and documents

Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction

An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.

Sulfoxide ligand metal catalyzed oxidation of olefins

The enantioselective synthesis of isochroman motifs has been accomplished via Pd(II)-catalyzed allylic C—H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C—H oxidation reaction proceeds with the broadest scope and highest levels asymmetric induction reported to date (avg. 92% ee, 13 examples ≥90% ee). Additionally, C(sp3)-N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) catalyzed intermolecular allylic C—H amination is disclosed. A range of 52 allylic amines are furnished in good yields (avg. 76%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). For the first time, a variety of singly activated aromatic and aliphatic nitrogen nucleophiles, including ones with stereochemical elements, can be used in fragment coupling stiochiometries for intermolecular C—H amination reactions.

Triflamides: Highly Reactive, Electronically Activated N-Sulfonyl Amides in Catalytic N-C(O) Amide Cross-Coupling

The direct, highly chemoselective Suzuki-Miyaura cross-coupling of trifluoromethanesulfonamides (triflamides) by selective N-C(O) amide bond cleavage is reported. This operationally simple, mild, and user-friendly method accomplishes the direct synthesis of ketones from amides by a catalytic manifold as a powerful alternative to Weinreb amides. Mechanistic studies support rotational inversion and electronic activation, favoring selective insertion under mild conditions. Our data strongly suggest that triflamides should be routinely considered as precursors in amide bond cross-coupling.