(1R)-3-Chloro-1-phenyl-propan-1-ol

Base Information

• Chemical Name: (1R)-3-Chloro-1-phenyl-propan-1-ol
• CAS No.: 100306-33-0
• Molecular Formula: C9H11ClO
• Molecular Weight: 170.639
• Hs Code.: 29062990
• Mol file: 100306-33-0.mol

Synonyms:Benzenemethanol,α-(2-chloroethyl)-, (R)-;(+)-3-Chloro-1-phenyl-1-propanol;(R)-(+)-3-Chloro-1-phenyl-1-propanol;(R)-3-Chloro-1-phenyl-1-propanol;(R)-3-Chloro-1-phenyl-propanol;(R)-3-Chloro-1-phenylpropanol;

Chemical Property of (1R)-3-Chloro-1-phenyl-propan-1-ol

Chemical Property:

• Appearance/Colour: off-white cryst
• Vapor Pressure: 0.000651mmHg at 25°C
• Melting Point: 58-61 °C
• Refractive Index: 1.543
• Boiling Point: 296.4°C at 760 mmHg
• PKA: 13.92±0.20(Predicted)
• Flash Point: 132°C
• PSA: 20.23000
• Density: 1.149 g/cm³
• LogP: 2.34890
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-3-Chloro-1-phenyl-1-propanol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of (S)-Norfluoxetine (R)-(+)-3-Chloro-1-phenyl-1-propanol may be used as a building block in the synthesis of antidepressants such as (R)- and (S)-tomoxetine, fluoxetine and nisoxetine. It may also be used in the synthesis of biologically active 2-substituted chromans such as tephrowatsin E.

Technology Process of (1R)-3-Chloro-1-phenyl-propan-1-ol

There total 20 articles about (1R)-3-Chloro-1-phenyl-propan-1-ol 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: 99.0%

3-chloropropiophenone (936-59-4) → (1R)-3-chloro-1-phenylpropanol (100306-33-0,125712-82-5)

Guidance literature:

With borane; S-oxaborolidine; In tetrahydrofuran; at 0 ℃; for 0.833333h;

DOI:10.1016/S0040-4039(01)93743-8

Reference yield: 75.0%

3-chloropropiophenone (936-59-4) → 3-chloro-1-phenylpropanol (100306-34-1,125712-82-5) + (1R)-3-chloro-1-phenylpropanol (100306-33-0,125712-82-5)

Guidance literature:

With dimethylsulfide borane complex; C₂₃H₂₂BNO₃; In tetrahydrofuran; at 20 ℃; for 2h; Reagent/catalyst;

Reference yield: 31.0%

Isopropenyl acetate (108-22-5) + 3-chloro-1-phenyl-propan-1-ol (18776-12-0,125712-82-5) → 3-chloro-1-phenylpropanol (100306-34-1,125712-82-5) + (1R)-3-chloro-1-phenylpropanol (100306-33-0,125712-82-5) + (R)-3-chloro-1-phenyl-1-propyl acetate

Guidance literature:

With Pseudomonas cepacia lipase immobilized on toyonite; potassium tert-butylate; sodium carbonate; [2,3,4,5-Ph4(η⁵-C4CNH(i-Pr))]Ru(CO)2Cl; In toluene; at 25 ℃; for 168h;

DOI:10.1021/jo0355799

upstream raw materials:

3-chloropropiophenone

1-Phenyl-3-chlor-propyl-monochloracetat

3-Cloro-1-phenylpropyl butanoate

3-chloro-1-phenyl-propan-1-ol

Downstream raw materials:

(S)-(-)-1-chloro-3-(4-iodo-2-methylphenoxy)-3-phenylpropane

-(-)-1-chloro-3-phenyl-3-(2-methoxyphenoxy)propane

(R)-(+)-2-Phenyloxetane

(S)-2,4-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene

Refernces

• 1、 Zhou, Ji-Ning,Fang, Qiang,Hu, Yi-Hu,Yang, Li-Yao,Wu, Fei-Fei,Xie, Lin-Jie,Wu, Jing,Li, Shijun. "Copper(ii)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: Asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine". . p. 1009 - 1017. Retrieved 2014.
• 2、 Chen, Xu,Lu, Zhan. "Iminophenyl Oxazolinylphenylamine for Enantioselective Cobalt-Catalyzed Hydrosilylation of Aryl Ketones". . p. 4658 - 4661. Retrieved 2016.
• 3、 ?wiklińska, Marta,Krzemiński, Marek P.,Tafelska-Kaczmarek, Agnieszka. "Chiral terpene auxiliaries III: Spiroborate esters from (1R,2S,3R,5R)-3-amino-apopinan-2-ol as highly effective catalysts for asymmetric reduction of ketones with borane". . p. 1453 - 1458. Retrieved 2015.
• 4、 Shang, Yue-Peng,Chen, Qi,Kong, Xu-Dong,Zhang, Yu-Jun,Xu, Jian-He,Yu, Hui-Lei. "Efficient Synthesis of (R)-2-Chloro-1-(2,4-dichlorophenyl)ethanol with a Ketoreductase from Scheffersomyces stipitis CBS 6045". . p. 426 - 431. Retrieved 2017.
• 5、 Janeczko, Tomasz,Kostrzewa-Suslow, Edyta. "Enantioselective reduction of propiophenone formed from 3-chloropropiophenone and stereoinversion of the resulting alcohols in selected yeast cultures". . p. 1264 - 1269. Retrieved 2014.
• 6、 Stepanenko, Viatcheslav,Jesús, Melvin De,Correa, Wildeliz,Guzmán, Irisbel,Vázquez, Cindybeth,de la Cruz, Wilanet,Ortiz-Marciales, Margarita,Barnes, Charles L.. "Enantioselective reduction of prochiral ketones using spiroborate esters as catalysts". . p. 5799 - 5802. Retrieved 2007.
• 7、 Corey, E. J.,Reichard, Gregory A.. "ENANTIOSELECTIVE AND PRACTICAL SYNTHESES OF R- AND S-FLUOXETINES". . p. 5207 - 5210. Retrieved 1989.
• 8、 Mahale, Rajendra D.,Chaskar, Sudhir P.,Patil, Kiran E.,Maikap, Golak C.,Gurjar, Mukund K.. "Corey-itsuno reduction of ketones: A development of safe and inexpensive process for synthesis of some API intermediates". . p. 710 - 713. Retrieved 2012.
• 9、 Li, Min,Li, Bin,Xia, Hong-Feng,Ye, Danru,Wu, Jing,Shi, Yifeng. "Mesoporous silica KIT-6 supported superparamagnetic CuFe2O 4 nanoparticles for catalytic asymmetric hydrosilylation of ketones in air". . p. 2680 - 2688. Retrieved 2014.
• 10、 Jiang, Biao,Feng, Yan,Hang, Jian-Feng. "Catalytic enantioselective synthesis of secondary alcohols using C2-symmetric diamino diol ligands". . p. 2323 - 2329. Retrieved 2001.