(R)-(-)-3-CHLOROMANDELIC ACID

Base Information

• Chemical Name: (R)-(-)-3-CHLOROMANDELIC ACID
• CAS No.: 61008-98-8
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.595
• Mol file: 61008-98-8.mol

Synonyms:Benzeneaceticacid, 3-chloro-a-hydroxy-,(R)-;(R)-(3-Chlorophenyl)hydroxyacetic acid;(R)-2-(3-Chlorophenyl)-2-hydroxyethanoic acid;(R)-3-Chloromandelic acid;(R)-m-Chloromandelic acid;

Chemical Property of (R)-(-)-3-CHLOROMANDELIC ACID

Chemical Property:

• Vapor Pressure: 1.92E-05mmHg at 25°C
• Melting Point: 100-104 °C(lit.)
• Refractive Index: 1.605
• Boiling Point: 348.2 °C at 760 mmHg
• PKA: 3.24±0.10(Predicted)
• Flash Point: 164.4 °C
• PSA: 57.53000
• Density: 1.468 g/cm³
• LogP: 1.45800
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly), Water (Spar

Purity/Quality:

99%, ^*data from raw suppliers

(R)-(?)-3-Chloromandelic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-(-)-3-Chloromandelic Acid is a reagent used in asymmetric syntheses due to its chirality. Used in the synthesis of a fluorescent analog of phenytoin as an inhibitor of neuropathic pain.

Technology Process of (R)-(-)-3-CHLOROMANDELIC ACID

There total 48 articles about (R)-(-)-3-CHLOROMANDELIC 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: 89.0%

3'-Chloroacetophenone (99-02-5) → 3-chloromandelic acid (16273-37-3,32222-43-8,52950-16-0,61008-98-8)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; water; at 90 ℃; for 24h;

DOI:10.3184/174751912X13551435784584

Reference yield: 70.0%

2-(3-chlorophenyl)-2-hydroxyacetonitrile (97070-75-2,122047-10-3,137766-66-6,53313-92-1) → (R)-3-chloromandelic acid (16273-37-3,32222-43-8,52950-16-0,61008-98-8)

Guidance literature:

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

DOI:10.1021/ja0259842

Reference yield: 21.0%

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + m-Chlorobenzaldehyde (587-04-2) → 3-chloromandelic acid (16273-37-3,32222-43-8,52950-16-0,61008-98-8)

Guidance literature:

With sodium hydroxide; In chloroform; water; at 56 ℃; for 1h;

upstream raw materials:

(S)-(-)-2-hydroxy-2-(3-chlorophenyl)acetonitrile

3-chloromandelic acid

m-Chlorobenzaldehyde

(R)-3-chloromandelic acid

Downstream raw materials:

m-Chlorobenzaldehyde

(S)-(-)-methyl 2-(3-chlorophenyl)-2-hydroxyacetate

(S)-2-(3-chlorophenyl)-2-hydroxyacetic acid

(R)-3-chloromandelic acid

Refernces

• 1、 Wang, Jie,Ao, Qiong,Peng, Yangfeng,Feng, Cai. "Diastereomeric resolution of 3-chloromandelic acid with threo-(1S,2S)-2-amino-l-p-nitrophenyl-1,3-propanediol". . p. 824 - 839. Retrieved 2021/09/13.
• 2、 Liu, Yidong,Liu, Song,Li, Dongmei,Zhang, Nan,Peng, Lei,Ao, Jun,Song, Choong Eui,Lan, Yu,Yan, Hailong. "Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides: A Combination of Experimental and Theoretical Studies". supporting information. p. 1150 - 1159. Retrieved 2019/01/11.