(S)-2-Chloro-1-(3-chloro-phenyl)-ethanol

Base Information

• Chemical Name: (S)-2-Chloro-1-(3-chloro-phenyl)-ethanol
• CAS No.: 174699-78-6
• Molecular Formula: C8H8Cl2O
• Molecular Weight: 191.057
• DSSTox Substance ID: DTXSID40431455
• Nikkaji Number: J1.189.185C
• Wikidata: Q82245339
• Mol file: 174699-78-6.mol

Synonyms:174699-78-6;(S)-2-Chloro-1-(3-chloro-phenyl)-ethanol;(S)-2-chloro-1-(3-chlorophenyl)ethanol;(1S)-2-CHLORO-1-(3-CHLOROPHENYL)ETHANOL;(S)-2-CHLORO-1-(3-CHLOROPHENYL)ETHAN-1-OL;(1S)-2-chloro-1-(3-chlorophenyl)ethan-1-ol;SCHEMBL3917396;DTXSID40431455;LBSKQOSGSUKVDG-MRVPVSSYSA-N;AKOS017405540;(S)-2-chloro-1-(m-chlorophenyl)ethanol;(S)-1-(3-Chlorophenyl)-2-chloroethanol;CS-0003904

Chemical Property of (S)-2-Chloro-1-(3-chloro-phenyl)-ethanol

Chemical Property:

• PSA: 20.23000
• LogP: 2.61220
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 189.9952203
• Heavy Atom Count: 11
• Complexity: 119

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-Chloro-1-(3-chlorophenyl)ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)Cl)C(CCl)O
• Isomeric SMILES: C1=CC(=CC(=C1)Cl)[C@@H](CCl)O
• Uses: (S)-2-Chloro-1-(3-chlorophenyl)ethanol is used in the synthetic preparation of benzimidazolyl pyridinones as IGF kinase inhibitors.

Technology Process of (S)-2-Chloro-1-(3-chloro-phenyl)-ethanol

There total 9 articles about (S)-2-Chloro-1-(3-chloro-phenyl)-ethanol 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: 100.0%

3-chlorophenacyl chloride (21886-56-6) → (S)-2-chloro-1-(3-chlorophenyl)-ethanol (174699-78-6)

Guidance literature:

With borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; for 1h;

DOI:10.1021/jm050392q

Reference yield: 99.2%

3-chlorophenacyl chloride (21886-56-6) → (S)-2-chloro-1-(3-chlorophenyl)-ethanol (174699-78-6) + (R)-1-(3-chlorophenyl)-2-chloro-1-hydroxyethane (106262-93-5,142763-10-8)

Guidance literature:

With D-glucose; nicotinamide adenine dinucleotide phosphate; In dimethyl sulfoxide; at 40 ℃;

DOI:10.1016/j.procbio.2019.09.037

Reference yield: 39.5%

(+)-2-chloro-1-(3-chlorophenyl)ethanol (106262-93-5) → (S)-2-chloro-1-(3-chlorophenyl)-ethanol (174699-78-6) + (S)-(+)-1-(3-chlorophenyl)-1,2-ethanediol (152008-72-5) + (R)-(-)-1-(3-chlorophenyl)-1,2-ethanediol (80051-04-3)

Guidance literature:

With epoxide hydrolase from Agrobacterium radiobacter AD₁; halohydrin dehalogenase from Agrobacterium radiobacter AD₁; Tris-SO₄ buffer; In water; at 30 ℃; pH=7.5;

DOI:10.1016/S0957-4166(99)00308-0

upstream raw materials:

3-chlorophenacyl chloride

(+)-2-chloro-1-(3-chlorophenyl)ethanol

3-chlorostyrene oxide

3'-Chloroacetophenone

Downstream raw materials:

(S)-4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one

(S)-3-chlorostyrene oxide

(S)-2-amino-1-(3-chlorophenyl)ethanol hydrochloride

Refernces

• 1、 Hanson, Ronald L.,Goldberg, Steven,Goswami, Animesh,Tully, Thomas P.,Patel, Ramesh N.. "Purification and cloning of a ketoreductase used for the preparation of chiral alcohols". . p. 1073 - 1080. Retrieved 2005.
• 2、 Hu, Die,Wen, Zheng,Li, Chuang,Hu, Bochun,Zhang, Ting,Li, Jianfang,Wu, Minchen. "Characterization of a robust glucose 1-dehydrogenase, SyGDH, and its application in NADPH regeneration for the asymmetric reduction of haloketone by a carbonyl reductase in organic solvent/buffer system". . p. 55 - 62. Retrieved 2019/11/26.
• 3、 Xia, Shi Wen,Lin, Hui,Chen, Yong Zheng. "Preparation of (R)-2-chloro-1-(m-chlorophenyl)ethanol by Lipozyme TL IM-catalyzed second resolution". experimental part. p. 289 - 292. Retrieved 2012/05/05.