2-[(tert-Butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid

Base Information

• Chemical Name: 2-[(tert-Butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid
• CAS No.: 561304-40-3
• Molecular Formula: C13H14F3NO5
• Molecular Weight: 321.253
• Hs Code.: 2924299090
• European Community (EC) Number: 800-218-3
• DSSTox Substance ID: DTXSID601150666
• Nikkaji Number: J1.917.922B
• Mol file: 561304-40-3.mol

Synonyms:561304-40-3;2-[(tert-Butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid;2-((tert-Butoxycarbonyl)amino)-3-(trifluoromethoxy)benzoic acid;2-{[(tert-butoxy)carbonyl]amino}-3-(trifluoromethoxy)benzoic acid;2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(trifluoromethoxy)benzoic Acid;SCHEMBL2061128;DTXSID601150666;MFCD09800581;AKOS016028557;SS-4551;CS-0358422;2-tert-butoxycarbonylamino-3-trifluoromethoxy-benzoic acid;2-((tert-Butoxycarbonyl)amino)-3-(trifluoromethoxy)benzoicacid;2-[(tert-Butyloxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid;2-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-(trifluoromethoxy)benzoic acid

Chemical Property of 2-[(tert-Butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid

Chemical Property:

• PSA: 84.86000
• LogP: 3.70340
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 321.08240703
• Heavy Atom Count: 22
• Complexity: 419

Purity/Quality:

99% ^*data from raw suppliers

2-{[(tert-Butoxy)carbonyl]amino}-3-(trifluoromethoxy)benzoic acid ^*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=C(C=CC=C1OC(F)(F)F)C(=O)O

Technology Process of 2-[(tert-Butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid

There total 4 articles about 2-[(tert-Butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid 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: 79.0%

carbon dioxide (124-38-9,18923-20-1) + tert-butyl N-[2-(trifluoromethoxy)phenyl]carbamate (561304-39-0) → 2-[(tert-butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid (561304-40-3)

Guidance literature:

tert-butyl N-[2-(trifluoromethoxy)phenyl]carbamate; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - -50 ℃; for 1h;

carbon dioxide; In tetrahydrofuran; pentane;

With hydrogenchloride; In water; pH=1;

Reference yield:

tert-butyl N-(4-trifluoromethoxyphenyl)carbamate (212696-37-2) → 2-[(tert-butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid (561304-40-3)

Guidance literature:

With hydrogenchloride; sec.-butyllithium; In tetrahydrofuran;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-[(tert-butoxycarbonyl)amino]-3-(trifluoromethoxy)benzoic acid (561304-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / toluene / 2 h / 100 °C

2.1: t-BuLi / pentane; tetrahydrofuran / 2 h / -50 °C

2.2: 78 percent / pentane; tetrahydrofuran / 25 °C

With tert.-butyl lithium; In tetrahydrofuran; toluene; pentane;

DOI:10.1021/jo0267798

upstream raw materials:

carbon dioxide

tert-butyl N-[2-(trifluoromethoxy)phenyl]carbamate

di-tert-butyl dicarbonate

2-trifluoromethoxy aniline

Downstream raw materials:

2-amino-3-(trifluoromethoxy)benzoic acid

Refernces

• 1、 Leroux, Frederic,Castagnetti, Eva,Schlosser, Manfred. "Trifluoromethoxy substituted anilines: Metalation as the key step for structural elaboration". . p. 4693 - 4699. Retrieved 2007/10/03.