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Cas Database

229334-55-8

229334-55-8

Identification

  • Product Name:(S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol

  • CAS Number: 229334-55-8

  • EINECS:-0

  • Molecular Weight:303.59

  • Molecular Formula: C9H9Cl3O3S

  • HS Code:

  • Mol File:229334-55-8.mol

Synonyms:(S)-2,4-dichloro-a-(chloromethyl)-benzenemethanol;(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

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Relevant articles and documentsAll total 8 Articles be found

PROCESS FOR THE PREPARATION OF LULICONAZOLE

-

Page/Page column 12, (2021/02/05)

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

-

Paragraph 0075-0079, (2020/11/26)

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

Wei, Teng-Yun,Tang, Jia-Wei,Ni, Guo-Wei,Wang, Hong-Yi,Yi, Dong,Zhang, Fu-Li,Chen, Shao-Xin

, p. 1822 - 1828 (2019/09/30)

(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

Gagnepain, Julien,Jeanmart, Stephane,Bonvalot, Damien,Jacob, Olivier,Lamberth, Clemens

, p. 59 - 62 (2019/01/04)

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

Fonseca, Thiago de S.,Lima, Lara D.,de Oliveira, Maria da C. F.,de Lemos, Telma L. G.,Zampieri, Davila,Molinari, Francesco,de Mattos, Marcos C.

, p. 2110 - 2116 (2018/05/31)

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 route upstream and downstream products

Process route

α-(chloromethyl)-2,4-dichlorobenzyl alcohol
13692-14-3,114446-57-0

α-(chloromethyl)-2,4-dichlorobenzyl alcohol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

[2-chloro-1-(2,4-dichlorophenyl)ethyl] methanesulfonate
53984-39-7,229334-55-8

[2-chloro-1-(2,4-dichlorophenyl)ethyl] methanesulfonate

Conditions
Conditions Yield
With triethylamine; In ethyl acetate; at 0 ℃; for 0.5h; Inert atmosphere;
98%
With triethylamine; In ethyl acetate; at 0 ℃; for 0.166667h;
673 mg
2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

[2-chloro-1-(2,4-dichlorophenyl)ethyl] methanesulfonate
53984-39-7,229334-55-8

[2-chloro-1-(2,4-dichlorophenyl)ethyl] methanesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: methanol; sodium tetrahydroborate / 0.25 h / 0 °C
2: triethylamine / ethyl acetate / 0.17 h / 0 °C
With methanol; sodium tetrahydroborate; triethylamine; In ethyl acetate;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere
2: triethylamine / ethyl acetate / 0.5 h / 0 °C / Inert atmosphere
With sodium tetrahydroborate; triethylamine; In methanol; ethyl acetate;
[2-chloro-1-(2,4-dichlorophenyl)ethyl] methanesulfonate
53984-39-7,229334-55-8

[2-chloro-1-(2,4-dichlorophenyl)ethyl] methanesulfonate

Conditions
Conditions Yield
aus Methansulfonylchlorid, 2,4-Dichlor-α-(chlormethyl)benzylalkohol und Pyridin;
(S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol
114446-57-0

(S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

Conditions
Conditions Yield
With triethylamine; In dichloromethane; at 10 ℃; for 3h;
97%
With triethylamine; In toluene; at 5 ℃;
97%
With triethylamine; In dichloromethane; at 0 - 20 ℃; for 7h;
93.6%
With triethylamine; In dichloromethane; at 0 - 5 ℃; for 0.333333h; Large scale;
93%
With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 7h;
89%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

Conditions
Conditions Yield
2,2',4'-trichloroacetophenone; With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; toluene;
methanesulfonyl chloride; With triethylamine; In dichloromethane; toluene; at 10 - 15 ℃; Solvent;
2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene; tert-butyl methyl ether / 2.5 h / 0 °C
2: triethylamine / dichloromethane / 3 h / 10 °C
With borane Ν,Ν-diethylaniline complex; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; tert-butyl methyl ether; toluene;
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C
2: dmap; triethylamine / dichloromethane / 2 h / 20 °C
3: candida antarctica lipase type B immobilized on acrylic resin / aq. phosphate buffer / 0.25 h / 45 °C / pH 7 / Resolution of racemate; Enzymatic reaction
4: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
With dmap; sodium tetrahydroborate; candida antarctica lipase type B immobilized on acrylic resin; triethylamine; In methanol; aq. phosphate buffer; dichloromethane;
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C
2: dmap; triethylamine / dichloromethane / 2 h / 20 °C
3: thermomyces lanuginosus lipase immobilized on immobead-150 / aq. phosphate buffer / 0.25 h / 45 °C / pH 7 / Resolution of racemate; Enzymatic reaction
4: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
With dmap; sodium tetrahydroborate; thermomyces lanuginosus lipase immobilized on immobead-150; triethylamine; In methanol; aq. phosphate buffer; dichloromethane;
Multi-step reaction with 2 steps
1: NADP / isopropyl alcohol; aq. phosphate buffer / 1.5 h / 25 °C / pH 7 / Enzymatic reaction
2: triethylamine / dichloromethane / 7 h / 0 - 20 °C
With NADP; triethylamine; In aq. phosphate buffer; dichloromethane; isopropyl alcohol;
Multi-step reaction with 2 steps
1: NADP / isopropyl alcohol; aq. phosphate buffer / 30 h / 35 °C / pH 6 / Enzymatic reaction
2: triethylamine / dichloromethane / 7 h / 0 - 20 °C
With NADP; triethylamine; In aq. phosphate buffer; dichloromethane; isopropyl alcohol;
α-(chloromethyl)-2,4-dichlorobenzyl alcohol
13692-14-3,114446-57-0

α-(chloromethyl)-2,4-dichlorobenzyl alcohol

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: dmap; triethylamine / dichloromethane / 2 h / 20 °C
2: candida antarctica lipase type B immobilized on acrylic resin / aq. phosphate buffer / 0.25 h / 45 °C / pH 7 / Resolution of racemate; Enzymatic reaction
3: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
With dmap; candida antarctica lipase type B immobilized on acrylic resin; triethylamine; In aq. phosphate buffer; dichloromethane;
Multi-step reaction with 3 steps
1: dmap; triethylamine / dichloromethane / 2 h / 20 °C
2: thermomyces lanuginosus lipase immobilized on immobead-150 / aq. phosphate buffer / 0.25 h / 45 °C / pH 7 / Resolution of racemate; Enzymatic reaction
3: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
With dmap; thermomyces lanuginosus lipase immobilized on immobead-150; triethylamine; In aq. phosphate buffer; dichloromethane;
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: aluminum (III) chloride / dichloromethane / 3 h / Reflux
2: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene; tert-butyl methyl ether / 2.5 h / 0 °C
3: triethylamine / dichloromethane / 3 h / 10 °C
With aluminum (III) chloride; borane Ν,Ν-diethylaniline complex; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; tert-butyl methyl ether; toluene;
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 8 h
2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / dichloromethane; toluene
2.2: 10 - 15 °C
With aluminum (III) chloride; dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; toluene;
rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: candida antarctica lipase type B immobilized on acrylic resin / aq. phosphate buffer / 0.25 h / 45 °C / pH 7 / Resolution of racemate; Enzymatic reaction
2: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
With dmap; candida antarctica lipase type B immobilized on acrylic resin; triethylamine; In aq. phosphate buffer; dichloromethane;
α-(chloromethyl)-2,4-dichlorobenzyl alcohol
13692-14-3,114446-57-0

α-(chloromethyl)-2,4-dichlorobenzyl alcohol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

[2-chloro-1-(2,4-dichlorophenyl)ethyl] methanesulfonate
53984-39-7,229334-55-8

[2-chloro-1-(2,4-dichlorophenyl)ethyl] methanesulfonate

Conditions
Conditions Yield
With triethylamine; In ethyl acetate; at 0 ℃; for 0.5h; Inert atmosphere;
98%
With triethylamine; In ethyl acetate; at 0 ℃; for 0.166667h;
673 mg

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