2-Chloromandelic acid

Base Information

• Chemical Name: 2-Chloromandelic acid
• CAS No.: 10421-85-9
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.595
• Hs Code.: 29181990
• European Community (EC) Number: 233-900-9
• NSC Number: 31401
• DSSTox Substance ID: DTXSID101314879
• Nikkaji Number: J212.385A
• Wikidata: Q106902652
• ChEMBL ID: CHEMBL1253488
• Mol file: 10421-85-9.mol

Synonyms:2-chloromandelic acid;o-chloromandelic acid

Chemical Property of 2-Chloromandelic acid

Chemical Property:

• Appearance/Colour: White to pale cream crystalline powder
• Vapor Pressure: 1.66E-05mmHg at 25°C
• Melting Point: 90-93 °C(lit.)
• Refractive Index: 1.5250 (estimate)
• Boiling Point: 350.3 °C at 760 mmHg
• PKA: 3.30±0.10(Predicted)
• Flash Point: 165.7 °C
• PSA: 57.53000
• Density: 1.468 g/cm³
• LogP: 1.45800
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• Water Solubility.: Very soluble in water.
• 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

2-Chloromandelic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C(=C1)C(C(=O)O)O)Cl
• Uses: 2-Chloromandelic acid, is used as a pharmaceutical intermediate as well as in the medicine industry. It is used as a intermediate of clopidrogrel.

Technology Process of 2-Chloromandelic acid

There total 67 articles about 2-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: 93.2%

(R)-2-chloromandelonitrile (121986-01-4) → (R)-2-chloromandelic acid (10421-85-9,52923-23-6,52950-19-3,52950-18-2)

Guidance literature:

(R)-2-chloromandelonitrile; With hydrogenchloride; In water; at 60 ℃; for 7h;

With sodium hydroxide; In toluene; at 10 ℃; for 4h;

Reference yield: 92.0%

2-chloromandelonitrile (13312-84-0) → (R)-2-chloromandelic acid (10421-85-9,52923-23-6,52950-19-3,52950-18-2)

Guidance literature:

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

DOI:10.1021/ja0259842

Reference yield: 90.0%

1-(2-chlorophenyl)ethanone (2142-68-9) → 2-chloromandelic acid (10421-85-9,52923-23-6,52950-18-2,52950-19-3)

Guidance literature:

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

DOI:10.3184/174751912X13551435784584

upstream raw materials:

2-chloromandelonitrile

chloroform

2-chloro-benzaldehyde

2-(2-chloro-phenyl)-5-imino-2,5-dihydro-furan-3,4-diol

Downstream raw materials:

(R)-2-chloromandelic acid

N-(2-phenylethyl)-2-chloromandelamide

methyl (R)-2-chloromandelate

(S)-2-chloromandelic acid

Refernces

• 1、 Szeleczky, Zsolt,Bagi, Péter,Pálovics, Emese,Fogassy, Elemér. "The effect of SDE on the separation of diastereomeric salts: A case study for the resolution of mandelic acid derivatives with Pregabalin". . p. 1095 - 1099. Retrieved 2014.
• 2、 Ding, Jiawei,Zhang, Ming,Dai, Huixue,Lin, Chunmian. "Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography". . p. 1245 - 1256. Retrieved 2018.
• 3、 Wang, Hualei,Sun, Huihui,Gao, Wenyuan,Wei, Dongzhi. "Efficient production of (R)-o-chloromandelic acid by recombinant escherichia coli cells harboring nitrilase from burkholderia cenocepacia J2315". . p. 767 - 773. Retrieved 2014.
• 4、 Hu, Yu,Wu, Chang,Wu, Xue-Ying,Li, Shao-Lei,Sun, Xiao-Xia,Tang, Ze-Biao. "Efficient preparation of (R)-2-chloromandelic acid via a recycle process of resolution". . p. 281 - 285. Retrieved 2015.
• 5、 Xue, Ya-Ping,Shi, Cheng-Ci,Xu, Zhe,Jiao, Biao,Liu, Zhi-Qiang,Huang, Jian-Feng,Zheng, Yu-Guo,Shen, Yin-Chu. "Design of nitrilases with superior activity and enantioselectivity towards sterically hindered nitrile by protein engineering". . p. 1741 - 1750. Retrieved 2015.
• 6、 Van Langen, Luuk M.,Van Rantwijk, Fred,Sheldon, Roger A.. "Enzymatic Hydrocyanation of a Sterically Hindered Aldehyde. Optimization of a Chemoenzymatic Procedure for (R)-2-Chloromandelic Acid". . p. 828 - 831. Retrieved 2003.
• 7、 Mizuno, Masanori,Shioiri, Takayuki. "Reaction of carboxylic acids with diethyl phosphorocyanidate; a novel synthesis of homologated α-hydroxycarboxylic acids from carboxylic acids". . p. 9209 - 9210. Retrieved 1998.
• 8、 Peng, Yangfeng,Wang, Jie. "Resolution of halogenated mandelic acids through enantiospecific co-crystallization with levetiracetam". . . Retrieved 2021/09/18.