(2R)-2-(4-fluorophenyl)-2-hydroxyacetic acid

Base Information

• Chemical Name: (2R)-2-(4-fluorophenyl)-2-hydroxyacetic acid
• CAS No.: 32222-45-0
• Molecular Formula: C₈H₇FO₃
• Molecular Weight: 170.14
• European Community (EC) Number: 662-945-0
• Nikkaji Number: J841.174C
• Mol file: 32222-45-0.mol

Synonyms:32222-45-0;(2R)-2-(4-fluorophenyl)-2-hydroxyacetic acid;(r)-4-fluoromandelic acid;(R)-2-(4-fluorophenyl)-2-hydroxyacetic acid;4-Fluoro-D-mandelic acid;SCHEMBL196920;RWCMOQXHIDWDDJ-SSDOTTSWSA-N;(R)-(-)-para-fluoromandelic acid;AKOS037649551;(R)-(4-fluorophenyl)hydroxyacetic acid;CS-11352;(2R)-(4-Fluorophenyl)(hydroxy)acetic acid;(R)-2-(4-fluorophenyl)-2-hydroxyaceticacid;CS-0343264;EN300-6754344;(R)-4-Fluoromandelic acid, ChiPros(R), produced by BASF, 98%

Chemical Property of (2R)-2-(4-fluorophenyl)-2-hydroxyacetic acid

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 170.03792224
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-2-(4-Fluorophenyl)-2-hydroxyaceticacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(=O)O)O)F
• Isomeric SMILES: C1=CC(=CC=C1[C@H](C(=O)O)O)F

Technology Process of (2R)-2-(4-fluorophenyl)-2-hydroxyacetic acid

There total 32 articles about (2R)-2-(4-fluorophenyl)-2-hydroxyacetic 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: 95.0%

(R)-2-(4-fluorophenyl)-2-hydroxyacetonitrile (149952-37-4,176485-58-8) → (R)-2-(4-fluorophenyl)-2-hydroxyacetic acid (32222-45-0)

Guidance literature:

With hydrogenchloride; water; at 20 ℃; for 21h; Reflux;

DOI:10.21608/ejchem.2017.3262

Reference yield: 90.0%

2-(4-fluorophenyl)-2-hydroxyacetonitrile (133721-87-6,176485-58-8) → 4-fluoromandelic acid (32222-45-0,52923-25-8,52950-15-9,395-33-5)

Guidance literature:

With hydrogenchloride; water; at 20 ℃; for 21h; Reflux;

DOI:10.21608/ejchem.2017.3262

Reference yield: 81.0%

2-(4-fluorophenyl)-2-hydroxyacetonitrile (133721-87-6,176485-58-8) → (R)-2-(4-fluorophenyl)-2-hydroxyacetic acid (32222-45-0)

Guidance literature:

With phosphate buffer; nitrilase I; In methanol; at 37 ℃; pH=8;

DOI:10.1021/ja0259842

upstream raw materials:

[2,2,2-Trichloro-1-(4-fluoro-phenyl)-ethyl]-carbamic acid methyl ester

chloro-trimethyl-silane

potassium cyanide

4-fluorobenzaldehyde

Downstream raw materials:

methyl 4-fluoro-α-hydroxyphenylacetate

2-(4-fluorophenyl)-2-oxoacetic acid

4-Fluorobenzoic acid

4-fluorobenzaldehyde

Refernces

• 1、 Xue, Ya-Ping,Wang, Chuang,Wang, Di-Chen,Liu, Zhi-Qiang,Zheng, Yu-Guo. "Highly Efficient Deracemization of Racemic 2-Hydroxy Acids in a Three-Enzyme Co-Expression System Using a Novel Ketoacid Reductase". . p. 1 - 13. Retrieved 2018/04/26.
• 2、 Guo, Huan,Li, Jing,Liu, Delong,Zhang, Wanbin. "The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation". . p. 3665 - 3673. Retrieved 2017/09/11.