(2r)-(4-Chlorophenyl)[3-(Trifluoromethyl)phenoxy]ethanoic Acid

Base Information

• Chemical Name: (2r)-(4-Chlorophenyl)[3-(Trifluoromethyl)phenoxy]ethanoic Acid
• CAS No.: 23953-39-1
• Molecular Formula: C15H10ClF3O3
• Molecular Weight: 330.691
• European Community (EC) Number: 689-412-5
• UNII: EWR4G9V8JG
• ChEMBL ID: CHEMBL3341939
• DSSTox Substance ID: DTXSID90477247
• Wikidata: Q27463139
• Mol file: 23953-39-1.mol

Synonyms:MBX-102 acid;23953-39-1;(2r)-(4-Chlorophenyl)[3-(Trifluoromethyl)phenoxy]ethanoic Acid;CHEMBL3341939;(2R)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetic acid;Arhalofenic Acid;(-)-Halofenic acid;Mbx-102 acid form;EWR4G9V8JG;SCHEMBL12189837;DTXSID90477247;BDBM50525183;MBX-102 acid, >=98% (HPLC), powder;Q27463139;(alphaR)-4-Chloro-alpha-[3-(trifluoromethyl)phenoxy]benzeneacetic acid;Benzeneacetic acid, 4-chloro-alpha-[3-(trifluoromethyl)phenoxy]-, (alphaR)-;MGZ

Chemical Property of (2r)-(4-Chlorophenyl)[3-(Trifluoromethyl)phenoxy]ethanoic Acid

Chemical Property:

• PSA: 46.53000
• LogP: 4.56350
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 330.0270564
• Heavy Atom Count: 22
• Complexity: 381

Purity/Quality:

MBX-102 acid ≥98% (HPLC), powder ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)OC(C2=CC=C(C=C2)Cl)C(=O)O)C(F)(F)F
• Isomeric SMILES: C1=CC(=CC(=C1)O[C@H](C2=CC=C(C=C2)Cl)C(=O)O)C(F)(F)F

Technology Process of (2r)-(4-Chlorophenyl)[3-(Trifluoromethyl)phenoxy]ethanoic Acid

There total 12 articles about (2r)-(4-Chlorophenyl)[3-(Trifluoromethyl)phenoxy]ethanoic 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: 97.32%

R-4-chloro-α-(3-trifluoromethylphenoxy)phenylacetic acid cinchonidine salt → (2R)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetic acid (23953-39-1)

Guidance literature:

In water; pH=1; Acidic conditions;

Reference yield: 59.0%

halofenic acid (4687-08-5,23953-40-4) → (2R)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetic acid (23953-39-1)

Guidance literature:

halofenic acid; With (1S)-1-(2-naphthyl)ethylamine; potassium hydroxide; In ethanol; water; for 12h; Heating; Resolution of racemate;

With hydrogenchloride; In diethyl ether; water; Resolution of racemate;

DOI:10.1002/cmdc.201402462

Reference yield: 51.0%

(2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate (930779-79-6) + 3-Trifluoromethylphenol (98-17-9) → (2R)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetic acid (23953-39-1)

Guidance literature:

3-Trifluoromethylphenol; With lithium tert-butoxide; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;

(2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate; In tetrahydrofuran; at -5 ℃; for 4h;

With dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; water; at 0 - 5 ℃; for 1.5h; Temperature; Time; Concentration;

upstream raw materials:

(2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate

C₇H₄F₃O^(1-)*Li⁽¹⁺⁾

4-chlorophenylacetic Acid

4-chlorophenacetyl chloride

Downstream raw materials:

Arhalofenate

C₁₅H₉Cl₂F₃O₂

Refernces

• 1、 -. "Preparation method of optically-active R-4-chloro-alpha-(3-trifluoromethyl phenoxy)phenylacetic acid". Paragraph 0015; 0016. . Retrieved 2019/03/08.
• 2、 -. "COMPOSITIONS AND METHODS FOR THE TREATMENT OF METABOLIC SYNDROME". Paragraph 0099; 00100. . Retrieved 2013/12/03.