109134-07-8

Basic information

• Product Name: (3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: (3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER;3-(N-BOC-Amino)benzotrifluoride
• CAS NO: 109134-07-8
• Molecular Formula: C₁₂H₁₄F₃NO₂
• Molecular Weight: 261.25
• Mol File: 109134-07-8.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER(109134-07-8)
• EPA Substance Registry System: (3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER(109134-07-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 109134-07-8(Hazardous Substances Data)

Usage

Description

(3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER, also known as 3-(N-Boc-Amino)benzotrifluoride, is a chemical compound with the molecular formula C11H14F3NO2. It is a white crystalline solid that is soluble in organic solvents. (3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER is characterized by the presence of a trifluoromethylphenyl group attached to a carbamic acid moiety, which is further protected by a tert-butyl ester group. The Boc (tert-butyloxycarbonyl) protection allows for selective deprotection under mild acidic conditions, making it a versatile intermediate in organic synthesis.

Uses

Used in Pharmaceutical Industry:
(3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER is used as a reactant in the preparation of transthyretin amyloidosis inhibitors containing carborane pharmacophores. Transthyretin amyloidosis is a rare genetic disorder characterized by the accumulation of amyloid fibrils in various tissues, leading to organ dysfunction. The carborane pharmacophore, a boron-containing cluster, has been shown to bind selectively to transthyretin, stabilizing its native tetrameric structure and preventing the formation of amyloid fibrils.
Additionally, (3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER is used in the design and synthesis of peripherally restricted transient receptor potential vanilloid 1 (TRPV1) antagonists. TRPV1 is a non-selective cation channel expressed in sensory neurons and is involved in the sensation of pain, inflammation, and heat. Antagonizing TRPV1 has been shown to provide analgesic and anti-inflammatory effects, making it a promising target for the development of novel pain relief medications.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 98-16-8 3-trifluoromethylaniline 
• 1895006-01-5 dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate 
• 25216-74-4 tert-butyl (3-bromophenyl)carbamate 

Downstream Products

• 159684-36-3 (2-tert-Butoxycarbonylamino-4-trifluoromethyl-phenyl)-oxo-acetic acid ethyl ester 
• 343-69-1 6-(Trifluoromethyl)-1H-indol-2,3-dione 
• 187523-36-0 (-)-BMS-204352 
• 879609-79-7 2-(tert-butoxycarbonylamino)-4-(trifluoromethyl)phenylboronic acid 
• 384793-21-9 (2-bromo-5-trifluoromethylphenyl)-carbamic acid tert-butyl ester 
• 659731-72-3 C₁₄H₁₉BF₃NO₄ 
• 5215-27-0 N-(3-fluorophenyl)-2-phenylacetamide 
• 18109-43-8 N-(3-chlorophenyl)-2-phenylacetamide 
• 1939-21-5 2-phenyl-N-(3-(trifluoromethyl)phenyl)acetamide 
• 13140-73-3 N-(3-bromophenyl)-2-phenylacetamide 
• 187523-35-9 (S)-(+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one 
• 183720-15-2 3-(5-Chloro-2-methoxyphenyl)-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2H-indol-2-one 
• 385764-29-4 (+)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one 
• 862907-27-5 3-tert-butoxycarbonyloxy-3-(5-chloro-2-methoxy-phenyl)-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Enantioselective synthesis of BMS-204352 (MaxiPost) using N-fluoroammonium salts of cinchona alkaloids (F-CA-BF4).

The enantioselective synthesis of a potent Maxi-K potassium channel opener (BMS-204352) mediated by N-fluoroammonium salts of cinchona alkaloids is described. Two synthetic pathways were evaluated. An ee as high as 88% was achieved (>99% after a single re

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles

Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.

Design and synthesis of peripherally restricted transient receptor potential vanilloid 1 (TRPV1) antagonists

Transient receptor potential vanilloid 1 (TRPV1) channel antagonists may have clinical utility for the treatment of chronic nociceptive and neuropathic pain. We recently advanced a TRPV1 antagonist, 3 (AMG 517), into clinical trials as a new therapy for t