3-Chloromandelic acid

Base Information

• Chemical Name: 3-Chloromandelic acid
• CAS No.: 16273-37-3
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.595
• Hs Code.: 2918199090
• European Community (EC) Number: 240-376-5
• NSC Number: 126599
• DSSTox Substance ID: DTXSID801314787
• Nikkaji Number: J286.857A
• Mol file: 16273-37-3.mol

Synonyms:3-chloromandelic acid

Chemical Property of 3-Chloromandelic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.92E-05mmHg at 25°C
• Melting Point: 111-113 °C
• Boiling Point: 348.211 °C at 760 mmHg
• PKA: pK1: 3.237 (25°C)
• Flash Point: 164.393 °C
• PSA: 57.53000
• Density: 1.468 g/cm³
• LogP: 1.45800
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.0083718
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

3-?ChloromandelicAcid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)Cl)C(C(=O)O)O
• Uses: 3-?Chloromandelic Acid is an organic reagent used in the synthesis of vinyl N-heterocycles. Also used in the preparation of aromatic amides.

Technology Process of 3-Chloromandelic acid

There total 48 articles about 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

3-chlorobenzoate

(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.