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187164-19-8

187164-19-8

Identification

  • Product Name:Luliconazole

  • CAS Number: 187164-19-8

  • EINECS:247-960-9

  • Molecular Weight:354.284

  • Molecular Formula: C14H9Cl2N3S2

  • HS Code:

  • Mol File:187164-19-8.mol

Synonyms:1H-Imidazole-1-acetonitrile,a-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-,[R-(E)]-;Lulicon;NND 502;1H-Imidazole-1-acetonitrile,a-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-,(aE)-;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:Luliconazole
  • Packaging:500mg
  • Price:$ 319
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Luliconazole
  • Packaging:250mg
  • Price:$ 105
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Luliconazole >98.0%(HPLC)(N)
  • Packaging:250mg
  • Price:$ 49
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Luliconazole >98.0%(HPLC)(N)
  • Packaging:1g
  • Price:$ 133
  • Delivery:In stock
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Luliconazole
  • Packaging:250 mg
  • Price:$ 585
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  • Manufacture/Brand:Labseeker
  • Product Description:Luliconazole 98
  • Packaging:50g
  • Price:$ 538
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Luliconazole >98%
  • Packaging:250 mg
  • Price:$ 500
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  • Manufacture/Brand:Crysdot
  • Product Description:Luliconazole 98+%
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  • Price:$ 162
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  • Manufacture/Brand:ChemScene
  • Product Description:Luliconazole 99.99%
  • Packaging:50mg
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  • Manufacture/Brand:ChemScene
  • Product Description:Luliconazole 99.99%
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Relevant articles and documentsAll total 12 Articles be found

PROCESS FOR THE PREPARATION OF LULICONAZOLE

-

, (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.

Production methods of luliconazole and hydrochloride thereof

-

Paragraph 0118-0119; 0124-0160, (2021/10/27)

The invention discloses production methods of luliconazole and hydrochloride thereof. The production method of the luliconazole hydrochloride comprises the following step of: i, with or without inert gas protection, reacting a luliconazole product with hydrogen chloride in a mixed solvent of an ether solvent and an ester solvent to obtain the luliconazole hydrochloride. The production method of the luliconazole comprises the following step of: a, with or without inert gas protection, reacting the luliconazole hydrochloride with an alkaline substance in a mixed solvent of water and an ester solvent to obtain luliconazole. According to the methods disclosed by the invention, the luliconazole hydrochloride and the alkaline substance react to produce luliconazole, the target product is convenient to separate and purify, a luliconazole product with high purity and high e.e. value can be conveniently obtained, and a brand new process route is provided for the production of luliconazole.

Preparation method of azole antifungal drug

-

, (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

A PROCESS FOR PREPARATION OF LULICONAZOLE

-

Page/Page column 15-18, (2019/08/26)

The present invention discloses an improved process for preparation of Luliconazole in high yield and purity involving a novel intermediate i.e., (S)- 2,4-Dichloro-alpha-(chloro methyl)benzene methanol 4-chlorosulfonyl chloride.

Process route upstream and downstream products

Process route

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

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

C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>S<sub>2</sub><sup>(2-)</sup>*2K<sup>(1+)</sup>

C6H3N3S2(2-)*2K(1+)

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
With potassium hydroxide; In acetonitrile; at -10 - 10 ℃; for 1h; Large scale;
91%
(E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hydrobromide

(E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hydrobromide

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
With water; sodium carbonate; at 20 ℃;
90%
(E)-(4S)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hemifumarate

(E)-(4S)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile hemifumarate

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
With water; sodium hydroxide; at 40 ℃; for 0.333333h;
92%
(E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile toluenesulfonate

(E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile toluenesulfonate

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
With water; sodium hydroxide; at 40 ℃; for 0.333333h;
91%
2-cyanomethyl-imidazole
23184-45-4

2-cyanomethyl-imidazole

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

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

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile
256424-63-2,187164-19-8

(-)-(E)-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolane-2-ylidene]-1H-imidazol-1-acetonitrile

Conditions
Conditions Yield
2-cyanomethyl-imidazole; With carbon disulfide; sodium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 5h;
(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate; In dimethyl sulfoxide; at 20 ℃;
40%
(R)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1-imidazolyl)acetonitrile hydrochloride

(R)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1-imidazolyl)acetonitrile hydrochloride

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
With sodium hydrogencarbonate; In water; ethyl acetate; Concentration;
80%
(Z/E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile
187164-19-8

(Z/E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
(Z/E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile; With hydrogen bromide; In water; at 60 - 65 ℃;
With ammonium hydroxide; In water; ethyl acetate; pH=8-9; Solvent; Reagent/catalyst; Temperature;
98 g
(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

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

C<sub>6</sub>H<sub>4</sub>N<sub>3</sub>S<sub>2</sub><sup>(1-)</sup>*K<sup>(1+)</sup>

C6H4N3S2(1-)*K(1+)

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
In acetonitrile; at -5 - 0 ℃; for 20h; Large scale;
51.97%
carbon disulfide
75-15-0,12122-00-8

carbon disulfide

(1S)-1-(2,4-dichlorophenyl)ethyl 1,2-bismethanesulfonate

(1S)-1-(2,4-dichlorophenyl)ethyl 1,2-bismethanesulfonate

1-cyanomethylimidazole
98873-55-3

1-cyanomethylimidazole

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
carbon disulfide; 1-cyanomethylimidazole; With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 1h; Cooling with ice;
(1S)-1-(2,4-dichlorophenyl)ethyl 1,2-bismethanesulfonate; In dimethyl sulfoxide; at 20 ℃; for 2h;
5.1 g
lithium 2-cyano-2-(1H-imidazol-1-yl)ethene-1,1-bis(thiolate)

lithium 2-cyano-2-(1H-imidazol-1-yl)ethene-1,1-bis(thiolate)

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

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

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

[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
With lithium tert-butoxide; In tetrahydrofuran; at 0 - 30 ℃; for 1h;
1.05 g
0.72 g

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  • Amadis Chemical Co., Ltd.
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