tert-Butyl (3-(trifluoromethyl)phenyl)carbamate

Base Information

• Chemical Name: tert-Butyl (3-(trifluoromethyl)phenyl)carbamate
• CAS No.: 109134-07-8
• Molecular Formula: C12H14 F3 N O2
• Molecular Weight: 261.244
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID80446927
• Nikkaji Number: J2.132.244J
• Mol file: 109134-07-8.mol

Synonyms:109134-07-8;3-(N-BOC-Amino)benzotrifluoride;tert-Butyl (3-(trifluoromethyl)phenyl)carbamate;N-Boc-3-(trifluoromethyl)aniline;Tert-butyl N-[3-(trifluoromethyl)phenyl]carbamate;MFCD11040633;tert-Butyl [3-(trifluoromethyl)phenyl]carbamate;(3-TRIFLUOROMETHYLPHENYL)-CARBAMIC ACID TERT-BUTYL ESTER;SCHEMBL1013325;DTXSID80446927;PLLZDOLFXQKWQG-UHFFFAOYSA-N;AC2876;BBL101802;STL555599;AKOS008901086;BS-25705;SY130798;CS-0211981;FT-0684503;t-butyl (3-(trifluoromethyl)phenyl)carbamate;tert-butyl 3-(trifluoromethyl)phenylcarbamate;tert-Butyl(3-(trifluoromethyl)phenyl)carbamate;A925977;AU-004/43508030;1-(tert-Butoxycarbonylamino)-3-(trifluoromethyl)benzene

Chemical Property of tert-Butyl (3-(trifluoromethyl)phenyl)carbamate

Chemical Property:

• PSA: 38.33000
• LogP: 4.12540
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 261.09766318
• Heavy Atom Count: 18
• Complexity: 297

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

3-(N-Boc-Amino)benzotrifluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=CC=CC(=C1)C(F)(F)F
• Uses: 3-(N-Boc-Amino)benzotrifluoride is a reactant used in the preparation of transthyretin amyloidosis inhibitors containing carborane pharmacophores. It is also used in the design and synthesis of peripherally restricted transient receptor potential vanilloid 1 (TRPV1) antagonists.

Technology Process of tert-Butyl (3-(trifluoromethyl)phenyl)carbamate

There total 2 articles about tert-Butyl (3-(trifluoromethyl)phenyl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-trifluoromethylaniline (98-16-8) → t-butyl<3-(trifluoromethyl)phenyl>-carbamate (109134-07-8)

Guidance literature:

In toluene; Reflux;

DOI:10.1016/j.bmcl.2008.07.112

Reference yield: 81.0%

dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate (1895006-01-5) + tert-butyl (3-bromophenyl)carbamate (25216-74-4) → t-butyl<3-(trifluoromethyl)phenyl>-carbamate (109134-07-8)

Guidance literature:

With dilithium tetrabromocuprate; 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-trisilanol; [Ir(2-(2,4-difluorophenyl)-5-(methyl)pyridinyl)₂(4,4′-bis(tert-butyl)bipyridine)]*PF₆; sodium carbonate; In acetone; at 35 ℃; Irradiation;

DOI:10.1126/science.aat4133

Reference yield: 93.0%

2-chloro-3-aminopyridine (6298-19-7) + t-butyl<3-(trifluoromethyl)phenyl>-carbamate (109134-07-8) → 1-(2-chloropyridin-3-yl)-3-(3-(trifluoromethyl)phenyl)urea

Guidance literature:

With bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct; In tetrahydrofuran-d8; for 0.166667h; Microwave irradiation;

DOI:10.14233/ajchem.2019.21447

upstream raw materials:

di-tert-butyl dicarbonate

3-trifluoromethylaniline

dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate

tert-butyl (3-bromophenyl)carbamate

Downstream raw materials:

[2-(Hydroxy-phenyl-methyl)-5-trifluoromethyl-phenyl]-carbamic acid tert-butyl ester

(2-tert-Butoxycarbonylamino-4-trifluoromethyl-phenyl)-oxo-acetic acid ethyl ester

2-amino-4-(trifluoromethyl)benzaldehyde

[2-amino-4-(trifluoromethyl)phenyl]methan-1-ol

Refernces

• 1、 Le, Chip,Chen, Tiffany Q.,Liang, Tao,Zhang, Patricia,MacMillan, David W. C.. "A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes". . p. 1010 - 1014. Retrieved 2018/06/12.
• 2、 Stec, Markian M.,Bo, Yunxin,Chakrabarti, Partha P.,Liao, Lillian,Ncube, Mqhele,Tamayo, Nuria,Tamir, Rami,Gavva, Narender R.,Treanor, James J.S.,Norman, Mark H.. "Substituted aryl pyrimidines as potent and soluble TRPV1 antagonists". scheme or table. p. 5118 - 5122. Retrieved 2009/05/07.