[2-(Trifluoromethyl)phenyl]glycolic acid

Base Information

• Chemical Name: [2-(Trifluoromethyl)phenyl]glycolic acid
• CAS No.: 339-93-5
• Molecular Formula: C9H7 F3 O3
• Molecular Weight: 220.148
• Hs Code.: 2918199090
• European Community (EC) Number: 206-428-6
• DSSTox Substance ID: DTXSID70955492
• Nikkaji Number: J193.787A
• Mol file: 339-93-5.mol

Synonyms:339-93-5;[2-(Trifluoromethyl)phenyl]glycolic acid;2-hydroxy-2-[2-(trifluoromethyl)phenyl]acetic acid;2-trifluoromethylmandelic acid;2-Hydroxy-2-(2-(trifluoromethyl)phenyl)acetic acid;(2-(Trifluoromethyl)phenyl)glycolic acid;2-(Trifluoromethyl)mandelic acid;EINECS 206-428-6;hydroxy[2-(trifluoromethyl)phenyl]acetic acid;SCHEMBL736845;DTXSID70955492;MFCD00014338;AKOS005265722;SY199124;CS-0238814;EN300-200998;2-Hydroxy-2-(2-(trifluoromethyl)phenyl)aceticacid;Z788000804

Chemical Property of [2-(Trifluoromethyl)phenyl]glycolic acid

Chemical Property:

• Vapor Pressure: 0.000197mmHg at 25°C
• Boiling Point: 314.5°C at 760 mmHg
• PKA: 3.24±0.10(Predicted)
• Flash Point: 144°C
• PSA: 57.53000
• Density: 1.481g/cm³
• LogP: 1.82340
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 220.03472857
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

98%min ^*data from raw suppliers

2-Hydroxy-2-(2-(trifluoromethyl)phenyl)aceticacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of [2-(Trifluoromethyl)phenyl]glycolic acid

There total 7 articles about [2-(Trifluoromethyl)phenyl]glycolic 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: 83.0%

carbon dioxide (124-38-9,18923-20-1) + 2-Trifluoromethylbenzaldehyde (447-61-0) → 2-(trifluoromethyl)mandelic acid (339-93-5)

Guidance literature:

With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole; In acetonitrile; at 20 ℃; for 1h; Reagent/catalyst; Solvent; Catalytic behavior; Schlenk technique; Irradiation;

DOI:10.1021/acs.orglett.1c02592

Reference yield: 61.0%

carbon dioxide (124-38-9,18923-20-1) + 2-Trifluoromethylbenzaldehyde (447-61-0) → 1,2-Bis-(2-trifluoromethyl-phenyl)-ethane-1,2-diol + 2-(trifluoromethyl)mandelic acid (339-93-5)

Guidance literature:

With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole; In acetonitrile; at 20 ℃; for 1h; Reagent/catalyst; Schlenk technique; Irradiation;

DOI:10.1021/acs.orglett.1c02592

Reference yield:

Bromoform (75-25-2) + 2-Trifluoromethylbenzaldehyde (447-61-0) → 2-(trifluoromethyl)mandelic acid (339-93-5)

Guidance literature:

With potassium hydroxide; lithium chloride; In 1,4-dioxane; at 10 - 15 ℃;

DOI:10.1021/jm990378b

upstream raw materials:

Bromoform

2-Trifluoromethylbenzaldehyde

carbon dioxide

Downstream raw materials:

methyl (RS)-[5-(1,3-benzodioxol-5-ylmethoxy)-2-cyanophenoxy]-(2-trifluoromethylphenyl)acetate

methyl (RS)-[2-cyano-5-(thien-3-ylmethoxy)phenoxy]-(2-trifluoromethylphenyl)acetate

methyl 2-bromo-2-(2-(trifluoromethyl)phenyl)acetate

Refernces

• 1、 Coles,Ellis,Leung,Sarson,Threlfall,Tizzard. "Relationships between the racemic structures of substituted mandelic acids containing 8- and 10-membered hydrogen bonded dimer rings". . p. 10816 - 10823. Retrieved 2015/02/19.
• 2、 Astles, Peter C.,Brown, Thomas J.,Halley, Frank,Handscombe, Caroline M.,Harris, Neil V.,Majid, Tahir N.,McCarthy, Clive,McLay, Lain M.,Morley, Andrew,Porter, Barry,Roach, Alan G.,Sargent, Carol,Smith, Christopher,Walsh, Roger J. A.. "Selective ET(A) antagonists. 5. Discovery and structure-activity relationships of phenoxyphenylacetic acid derivatives". . p. 900 - 910. Retrieved 2007/10/03.