N,N-bis(trifluoromethylsulfonyl)aniline (CAS 37595-74-7) User Guide
1. Product Information
Chemical Name: N,N-bis(trifluoromethylsulfonyl)aniline
CAS Number: 37595-74-7
Molecular Formula: C₈H₅F₆NO₄S₂
Molecular Weight: 369.25 g/mol
Appearance: White to off-white crystalline powder
Purity: ≥98% (HPLC)
Storage: Store in a cool, dry place at 2-8°C under inert atmosphere.
2. Applications
N,N-bis(trifluoromethylsulfonyl)aniline is a high-performance electrophilic trifluoromethylation reagent widely used in:
- Organic synthesis for introducing trifluoromethyl groups into aromatic and heteroaromatic compounds.
- Pharmaceutical intermediates for drug discovery and development.
- Agrochemical production to enhance compound stability and bioactivity.
- Advanced material science for fluorinated polymer research.
3. Usage Guidelines
Safety Precautions
- Wear PPE: gloves, goggles, and lab coat.
- Handle under nitrogen/argon in a fume hood.
Typical Reaction Setup
- Dissolve substrate (1 equiv) in anhydrous dichloromethane (DCM).
- Add N,N-bis(trifluoromethylsulfonyl)aniline (1.2 equiv) at 0°C.
- Stir at room temperature for 6-12 hours.
- Quench with ice water and extract with DCM.
- Purify via column chromatography (hexane:ethyl acetate = 4:1).
4. Case Studies
Case 1: Trifluoromethylation of Indole Derivatives
Reaction: Indole + N,N-bis(trifluoromethylsulfonyl)aniline → 3-Trifluoromethylindole
Conditions: DCM, 25°C, 8 hours
Yield: 82%
Key Advantage: Superior regioselectivity compared to Umemoto's reagent.
Case 2: Pharmaceutical Intermediate Synthesis
Used in final-step trifluoromethylation of a COX-2 inhibitor precursor, achieving 78% yield with 99.5% HPLC purity.
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