164071-56-1

Basic information

• Product Name: 3-CHLORO-1-(2-THIENYL)-1-PROPANOL
• Synonyms: 3-CHLORO-1-(2-THIENYL)-1-PROPANOL;S-(-)-3-chloro-1-(2-thienyl)-1-propanol;(S)-3-Chloro-1-(thiophen-2-yl)propan-1-ol
• CAS NO: 164071-56-1
• Molecular Formula: C₇H₉ClOS
• Molecular Weight: 176.66
• Mol File: 164071-56-1.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-CHLORO-1-(2-THIENYL)-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-1-(2-THIENYL)-1-PROPANOL(164071-56-1)
• EPA Substance Registry System: 3-CHLORO-1-(2-THIENYL)-1-PROPANOL(164071-56-1)

Safety Data

• Hazardous Substances Data: 164071-56-1(Hazardous Substances Data)

Usage

General Description

3-Chloro-1-(2-thienyl)-1-propanol is a chemical compound with the molecular formula C7H9ClOS. It is an organochlorine compound with a thiol group, and it is commonly used in pharmaceutical and chemical research. 3-CHLORO-1-(2-THIENYL)-1-PROPANOL is a colorless liquid with a slightly sweet odor, and it is soluble in water and ethanol. It is primarily used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. The presence of the thiol group in its structure gives it reactive properties and makes it useful in a variety of chemical reactions. Additionally, it has been studied for its potential pharmacological applications and biological activity.

Upstream product

• 40570-64-7 3-chloro-1-(2-thienyl)propan-1-one 

Downstream Products

• 164071-58-3 S-(-)-3-iodo-1-(2-thienyl)-1-propanol 
• 116539-58-3 Duloxetine 
• 116539-55-0 (S)-3-methylamino-1-(2-thienyl)-1-propanol 
• 357405-45-9 4-Chloro-2-[[(1R)-3-chloro-1-(2-thienyl)propyl]oxy]benzonitrile 
• 357404-46-7 2-[(1R)-3-Chloro-1-(2,5-dichlorophenoxy)propyl]thiophene 
• 132335-44-5 (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol 

Relevant articles and documents

Bioreductive production of enantiopure (S)-duloxetine intermediates catalyzed with ketoreductase ChKRED15

The blockbuster antidepressant drug duloxetine contains one stereo-center derived from chiral alcohol intermediates. The stereoselective bioreductive production of five of such intermediates could be achieved using the recombinant ketoreductase ChKRED15, yielding the enantiopure (S)-alcohols with >99% ee. Sequence alignment indicated that ChKRED15 lacks the conserved G-rich motif, which was then amended by a single mutation of S12G. The resulting S12G mutant displayed significantly improved catalytic activity and protein stability. When coupled with a cofactor recycling system, the S12G mutant was able to catalyze the complete conversion of ethyl 3-oxo-3-(thiophen-2-yl)propanoate within 6 h and N-methyl-3-oxo-3-(thiophen-2-yl)propanamide within 24 h at substrate concentrations of 10 and 50 g/l, respectively, without the compromise of enantioselectivity.

Chemoenzymatic synthesis of (S)-duloxetine using carbonyl reductase from Rhodosporidium toruloides

A chemoenzymatic strategy was developed for (S)-duloxetine production employing carbonyl reductases from newly isolated Rhodosporidium toruloides into the enantiodetermining step. Amongst the ten most permissive enzymes identified, cloned, and overexpressed in Escherichia coli, RtSCR9 exhibited excellent activity and enantioselectivity. Using co-expressed E. coli harboring both RtSCR9 and glucose dehydrogenase, (S)-3-(dimethylamino)-1-(2-thienyl)-1-propanol 3a was fabricated with so far the highest substrate loading (1000 mM) in a space-time yield per gram of biomass (DCW) of 22.9 mmol L-1 h-1 g DCW-1 at a 200-g scale. The subsequent synthetic steps from RtSCR9-catalyzed (S)-3a were further performed, affording (S)-duloxetine with 60.2% overall yield from 2-acethylthiophene in >98.5% ee.

Copper(ii)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: Asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine

A set of reaction conditions has been established to facilitate the non-precious copper-catalyzed enantioselective hydrosilylation of a number of structurally diverse β-, γ- or ε-halo-substituted alkyl aryl ketones and α-, β- or γ-halo-substituted alkyl heteroaryl ketones under air to afford a broad spectrum of halo alcohols in high yields and good to excellent enantioselectivities (up to 99% ee). The developed procedure has been successfully applied to the asymmetric synthesis of antidepressant drugs (R)-fluoxetine and (S)-duloxetine, which highlighted its synthetic utility.