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

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

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

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

Downstream Products

• 384793-21-9 (2-bromo-5-trifluoromethylphenyl)-carbamic acid tert-butyl ester 
• 659731-72-3 C₁₄H₁₉BF₃NO₄ 
• 114627-41-7 [2-(Hydroxy-phenyl-methyl)-5-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester 
• 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 

Relevant articles and documents

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A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

Transition metal–catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper’s capacity to broadly facilitate haloarene coupling protocols. Here, we demonstrate that this copper oxidative addition problem can be overcome with an aryl radical–capture mechanism, wherein the aryl radical is generated through a silyl radical halogen abstraction. This strategy was applied to a general trifluoromethylation of aryl bromides through dual copper-photoredox catalysis. Mechanistic studies support the formation of an open-shell aryl species.

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.

Substituted aryl pyrimidines as potent and soluble TRPV1 antagonists

Clinical candidate AMG 517 (1) is a potent antagonist toward multiple modes of activation of TRPV1; however, it suffers from poor solubility. Analogs with various substituents at the R region of 3 were prepared to improve the solubility while maintaining

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

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Regioselectively fluoro-, trifluoromethyl- and trifluoromethoxy-substituted 3-methyleneindolines have been prepared using a four-step procedure involving metalation/bromination of fluorinated Boc-protected anilines, N-propargylation of the resulting o-bro

Vanilloid receptor ligands and their use in treatments

Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

Vanilloid receptor ligands and their use in treatments

Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

Catalytic enantioselective fluorination of oxindoles

We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluor

Synthesis of regiospecifically substituted quinolines from anilines

A protocol for the synthesis of quinolines substituted on both pyridine and benzo-fused rings is reported. The method is based on the formylation of a substituted N-(tert-butoxycarbonyl)aniline followed by direct cyclisation and aromatisation of the inter