229334-55-8

Basic information

• Product Name: (S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol
• Synonyms: (S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol;(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate;(S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol methanesulfonate;(S)-(2,4-Dichlorophenyl)(chloromethyl)methyl methanesulfonate
• CAS NO: 229334-55-8
• Molecular Formula: C8H7Cl3O
• Molecular Weight: 225.49958
• EINECS: -0
• Mol File: 229334-55-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 439.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.501±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol(229334-55-8)
• EPA Substance Registry System: (S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol(229334-55-8)

Safety Data

• Hazardous Substances Data: 229334-55-8(Hazardous Substances Data)

Usage

General Description

(S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol is a chemical compound with the molecular formula C8H7Cl3O. It is commonly used as a chiral intermediate in the synthesis of various pharmaceutical compounds and agrochemicals. (S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol is derived from the parent compound benzene and contains two chlorine atoms and a chloromethyl group attached to the benzene ring. Its chiral nature makes it a valuable building block in the creation of complex molecules with specific biological and chemical properties. This chemical is utilized in the production of a wide range of pharmaceuticals and agrochemicals, making it an important component in the synthesis of many commercial products.

Upstream product

• 53066-16-3 rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate 
• 13692-14-3 α-(chloromethyl)-2,4-dichlorobenzyl alcohol 
• 124-63-0 methanesulfonyl chloride 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 541-73-1 1,3-Dichlorobenzene 
• 114446-57-0 (S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol 

Downstream Products

• 187164-19-8 [(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile 
• 187164-19-8 luliconazole 
• 187164-19-8 (Z/E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF LULICONAZOLE

The present invention provides a process for the preparation E-isomer of Luliconazole (I) with substantially free of Z-isomer and unwanted salts.

Synthesis of Conformationally Locked and C-Linked Analogues of Imidazole-Based Ketene Dithioacetal Fungicides

First examples with the unknown tricyclic 4,8 b -dihydro-3 aH -indeno[1,2- d ][1,3]dithiole ring system have been prepared. Also, imidazoles linked in ring position 5 to a ketene dithioacetal and 1,3-dithiane derivatives with an exocyclic cyano- and imidazole-substituted C-C double bond are completely new. All these compounds are either conformationally locked, C-linked or six-ring analogues of the antifungal agent luliconazole. Synthesis and fungicidal activity of these sterol biosynthesis inhibitors are reported.

Chemoenzymatic Synthesis of Luliconazole Mediated by Lipases

A straightforward chemoenzymatic synthesis of luliconazole has been developed. The key step involved the preparation of the enantiomerically pure β-halohydrin (1S)-2-chloro-1-(2,4-dichlorophenyl)-1-ethanol through kinetic resolution of the corresponding racemic acetate. This was achieved by a hydrolytic approach, mediated by the lipase from Thermomyces lanuginosus or Novozym 435. The latter enzyme proved to be a robust biocatalyst for the kinetic resolution, and the (S)-β-halohydrin was obtained with high selectivity (ee > 99 %, E > 200) after just 15 min, at 45 °C. It could be reused five times with maintenance of high values of both conversion and enantioselectivity. Subsequently, the (S)-β-halohydrin was subjected to a mesylation reaction; the mesylated derivative reacted with 1-cyanomethylimidazole in the presence of CS2 to give luliconazole in 43 % yield with >99 % ee.