4-Chloromandelic acid

Base Information

• Chemical Name: 4-Chloromandelic acid
• CAS No.: 492-86-4
• Deprecated CAS: 7138-34-3
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.595
• Hs Code.: 29181990
• European Community (EC) Number: 207-764-6,679-590-2
• NSC Number: 31400,8112
• DSSTox Substance ID: DTXSID30883404
• Nikkaji Number: J182.241A
• ChEMBL ID: CHEMBL3247382
• Mol file: 492-86-4.mol

Synonyms:Mandelicacid, p-chloro- (6CI,7CI,8CI);(4-Chlorophenyl)(hydroxy)acetic acid;(p-Chlorophenyl)hydroxyacetic acid;2-(4-Chlorophenyl)-2-(hydroxy)acetic acid;2-Hydroxy-2-(4-chlorophenyl)aceticacid;4-Chloro-DL-mandelic acid;DL-4-Chloromandelicacid;DL-p-Chloromandelic acid;NSC 31400;NSC 8112;p-Chloromandelic acid;7138-34-3;

Chemical Property of 4-Chloromandelic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 7.43E-06mmHg at 25°C
• Melting Point: 114-118 °C
• Refractive Index: 1.5250 (estimate)
• Boiling Point: 361.4 °C at 760 mmHg
• PKA: 3.14±0.10(Predicted)
• Flash Point: 172.4 °C
• PSA: 57.53000
• Density: 1.468 g/cm³
• LogP: 1.45800
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.0083718
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

4-Chloromandelic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-36-26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(=O)O)O)Cl
• Uses: 4-?Chloromandelic acid has been used as a catalyst for Michael Addition of 2-?(1-?Ethylpropoxy)?acetaldehyde to N-?[(1Z)?-?2-?Nitroethenyl]?acetamide. As well, it has been used as a nucleation inhibitor for dutch resolution for diastereomers of racemic 3-?methoxyphenylethylamine with chiral mandelic acid.

Technology Process of 4-Chloromandelic acid

There total 56 articles about 4-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: 97.0%

para-chloroacetophenone (99-91-2) → p-chloromandelic acid (7138-34-3,32189-36-9,76496-63-4,492-86-4)

Guidance literature:

With selenium(IV) oxide; ytterbium(III) triflate; In 1,4-dioxane; water; at 90 ℃; for 18h;

DOI:10.1021/ol050125e

Reference yield: 95.0%

4-chloromandelonitrile (13312-83-9) → p-chloromandelic acid (7138-34-3,32189-36-9,76496-63-4,492-86-4)

Guidance literature:

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

Reference yield: 92.0%

phosphoric acid (4-chloro-phenyl)-dicyano-methyl ester diethyl ester → p-chloromandelic acid (7138-34-3,32189-36-9,76496-63-4,492-86-4)

Guidance literature:

With hydrogenchloride; for 10h; Heating;

DOI:10.1016/S0040-4039(98)02099-1

upstream raw materials:

2,2-dibromo-1-(4-chlorophenyl)ethanone

4-chloromandelonitrile

dichloroacethyl chloride

chlorobenzene

Downstream raw materials:

ethoxy-(4-chloro-phenyl)-acetic acid ethyl ester

bis(4'-chlorophenyl)acetic acid

α-(4-chlorophenyl)phenylacetic acid

(R)-4-chloro-α-hydroxy-benzeneacetic acid

Refernces

• 1、 Peng, Yangfeng,Wang, Jie. "Resolution of halogenated mandelic acids through enantiospecific co-crystallization with levetiracetam". . . Retrieved 2021/09/18.
• 2、 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.