178460-78-1

Basic information

• Product Name: (S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol
• Synonyms: (S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol
• CAS NO: 178460-78-1
• Molecular Weight: 191.057
• Mol File: 178460-78-1.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: (S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol(178460-78-1)
• EPA Substance Registry System: (S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol(178460-78-1)

Safety Data

• Hazardous Substances Data: 178460-78-1(Hazardous Substances Data)

Usage

Description

(S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol is an organochlorine compound that is a chiral molecule with a carbon center to which both a chlorine and a hydroxyl group are attached. It is significant as an intermediate in the synthesis of pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
(S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol is used as an intermediate for the synthesis of various pharmaceuticals due to its unique chemical structure and reactivity.
Used in Agrochemical Industry:
(S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol is used as an intermediate in the production of insecticides, contributing to its role in pest control and agriculture.
Used in Industrial Chemicals:
(S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol is also utilized in the creation of other industrial chemicals, highlighting its versatility in chemical synthesis.
Environmental and Health Considerations:
Due to its potentially harmful effects on the environment and human health, (S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol must be handled and disposed of properly according to regulatory guidelines to minimize its impact.

Upstream product

• 6378-66-1 2-chloro-1-(4-chlorophenyl)ethanol 
• 33491-02-0 1-chloro-4-(chloroethynyl)benzene 
• 99-91-2 para-chloroacetophenone 
• 4128-31-8 rac-octan-2-ol 
• 937-20-2 p-chlorophenacyl chloride 
• 152142-03-5 (1R)-1-(4-chlorophenyl)-1,2-ethanediol 
• 1073-67-2 4-vinylbenzyl chloride 
• 204581-98-6 (R)-4-(4-Chloro-phenyl)-[1,3,2]dioxathiolane 2-oxide 

Downstream Products

• 2788-86-5 (2S)-2-(4-chlorophenyl)oxirane 

Relevant articles and documents

Unmasking the Hidden Carbonyl Group Using Gold(I) Catalysts and Alcohol Dehydrogenases: Design of a Thermodynamically-Driven Cascade toward Optically Active Halohydrins

A concurrent cascade combining the use of a gold(I) N-heterocyclic carbene (NHC) and an alcohol dehydrogenase (ADH) is disclosed for the synthesis of highly valuable enantiopure halohydrins in an aqueous medium and under mild reaction conditions. The meth

Molecular switch manipulating Prelog priority of an alcohol dehydrogenase toward bulky-bulky ketones

Structure-guided rational design revealed the molecular switch manipulating the Prelog and anti-Prelog priorities of an NADPH-dependent alcohol dehydrogenase toward prochiral ketones with bulky and similar substituents. Synergistic effects of unconserved residues at 214 and 237 in small and large substrate binding pockets were proven to be vital in governing the stereoselectivity. The ee values of E214Y/S237A and E214C/S237 G toward (4-chlorophenyl)-(pyridin-2-yl)-methanone were 99.3% (R) and 78.8% (S) respectively. Substrate specificity analysis revealed that similar patterns were also found with (4’-chlorophenyl)-phenylmethanone, (4’-bromophenyl)-phenylmethanone and (4’-nitrophenyl)-phenylmethanone. This study provides valuable evidence for understanding the molecular mechanism on enantioselective recognition of prochiral ketones by alcohol dehydrogenase.

Deep Eutectic Solvents as Media in Alcohol Dehydrogenase-Catalyzed Reductions of Halogenated Ketones

The application of deep eutectic solvents (DESs) in biotechnological processes has gained an outstanding relevance, as they can be used as greener media to obtain higher productivities and selectivities. In the present contribution, an eutectic mixture composed of choline chloride (ChCl): glycerol (1 : 2 mol/mol) has been used as a reaction medium in combination with Tris?SO4 50 mM buffer pH 7.5, applied to the alcohol dehydrogenase (ADH)-catalyzed reduction of various carbonyl precursors of chiral halohydrins. These alcohols are key intermediates of biologically active compounds, and hence they are of industrial interest. In the presence of up to 50 % v/v of DES, these biotransformations were achieved up to 300–400 mM of the α-halogenated ketone substrate, getting access to the final compounds with excellent conversions (usually >90 %) and enantiomeric excess (ee >99 %). Among the different ADHs tested, two stereocomplementary enzymes (Lactobacillus brevis ADH and Rhodococcus ruber ADH) afforded the best results, so both alcohol enantiomers could be obtained in all the studied examples. Selected bioreductions were scaled up to 250 mg and 1 g, demonstrating the potential that DESs can offer as media in redox processes for substrates with low solubility in water.