Methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate

Base Information

• Chemical Name: Methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate
• CAS No.: 935534-18-2
• Molecular Formula: C₉H₈F₃NO₄
• Molecular Weight: 251.162
• DSSTox Substance ID: DTXSID50702885
• Wikidata: Q82634905
• Mol file: 935534-18-2.mol

Synonyms:935534-18-2;methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate;DTXSID50702885

Chemical Property of Methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate

Chemical Property:

• PSA: 81.78000
• LogP: 2.24080
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 251.04054222
• Heavy Atom Count: 17
• Complexity: 284

Purity/Quality:

2-HYDROXY-3-AMINO-5-TRIFLUOROMETHOXY-BENZOIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C(=CC(=C1)OC(F)(F)F)N)O

Technology Process of Methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate

There total 3 articles about Methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate 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:

methyl 2-hydroxy-3-nitro-5-(trifluoromethoxy)benzoate (935534-17-1) → methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate (935534-18-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃; for 16h; under 760.051 Torr;

DOI:10.1021/acs.jmedchem.9b01411

Reference yield:

methyl 2-hydroxy-5-(trifluoromethoxy)benzoate (175204-89-4) → methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate (935534-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; nitric acid / dichloromethane / 0 °C

2: 5%-palladium/activated carbon; hydrogen / methanol / 16 h / 20 °C / 760.05 Torr

With sulfuric acid; 5%-palladium/activated carbon; hydrogen; nitric acid; In methanol; dichloromethane;

DOI:10.1021/acs.jmedchem.9b01411

Reference yield:

TFMSA (129644-57-1) → methyl 3-amino-2-hydroxy-5-(trifluoromethoxy)benzoate (935534-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 °C

2: sulfuric acid; nitric acid / dichloromethane / 0 °C

3: 5%-palladium/activated carbon; hydrogen / methanol / 16 h / 20 °C / 760.05 Torr

With dmap; sulfuric acid; 5%-palladium/activated carbon; hydrogen; nitric acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane;

DOI:10.1021/acs.jmedchem.9b01411

upstream raw materials:

methyl 2-hydroxy-5-(trifluoromethoxy)benzoate

methyl 2-hydroxy-3-nitro-5-(trifluoromethoxy)benzoate

TFMSA