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

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

Uses

Used in Pharmaceutical Industry:
(S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol is used as a chiral intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and chiral properties enable the creation of complex molecules with specific biological activities, making it an essential component in the development of many commercial pharmaceutical products.
Used in Agrochemical Industry:
(S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol is also utilized as a chiral intermediate in the synthesis of agrochemicals. Its ability to form complex molecules with specific chemical properties allows for the development of effective and targeted agrochemicals, contributing to improved crop protection and yield.

Upstream product

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

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.

Preparation method of azole antifungal drug

The invention discloses a preparation method of an azole antifungal drug, which comprises the following steps: (a) reacting (S)-2-chloro-1-(2,4-dichlorophenyl)ethanol with methanesulfonyl chloride, and crystallizing the reaction product to obtain a compound crystal as shown in a formula (III); (b) reacting imidazole with chloroacetonitrile, and crystallizing the reaction product to obtain 1-(cyanomethyl)imidazole crystals; (c) reacting the 1-(cyanomethyl)imidazole with carbon disulfide under an alkaline condition to obtain a compound as shown in a formula (VIII); (d) reacting the compound as shown in the formula (III) with a compound as shown in a formula (VIII) under an alkaline condition to obtain luliconazole oil; and (e) dissolving the luliconazole oil into acetonitrile, dropwise adding water into the solution, separating out crystals, and filtering the mixture while hot to obtain a luliconazole pure product. According to the method, industrially common and cheap raw materials areselected, the luliconazole pure product conforming to the medicine is efficiently prepared, so that the invention solves the technical problems that the luliconazole purification yield is low, 1- (cyanomethyl) imidazole is prone to water absorption and deliquescence, and (S)-2-chloro-1-(2,4-dichlorophenyl) ethyl methanesulfonate is unstable and easy to decompose at the normal temperature.

Development of an Enzymatic Process for the Synthesis of (S)-2-Chloro-1-(2,4-dichlorophenyl) Ethanol

(S)-2-Chloro-1-(2,4-dichlorophenyl) ethanol (3) is a chiral intermediate in the synthesis of luliconazole ((R)-E-1). Here, we report a novel biopreparation of 3 by bioreduction of 2-chloro-1-(2,4-dichlorophenyl) ethanone (2) using recombinant Escherichia

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.

PROCESS FOR PREPARATION OF LULICONAZOLE

A process for the preparation of luliconazole and salts thereof is disclosed.

Method for synthesizing Luliconazole

The invention relates to a method for synthesizing Luliconazole. The method comprises the steps of subjecting m-dichlorobenzene to Friedel-Crafts acylation with chloroacetyl chloride, catalytic chiral reduction with (S)-2-methyl-CBS-oxazaborolidine and esterification with methylsulfonyl chloride so as to obtain (S)-2,2',4'-ethyl trichlorobenzene methanesulfonate, and finally, subjecting (S)-2,2',4'-ethyl trichlorobenzene methanesulfonate to a reaction with carbon disulfide and imidazolyl acetonitrile, thereby obtaining Luliconazole. According to the method, the total yield is about 30%.

NOVEL MICROBIOCIDES

Compounds of formula (I), wherein the other substituents X, Y, Z, A, Q, R1, R2, R3, R4, R6 and R7 are as defined in claim 1, and their use in compositions and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.