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Cas Database

187164-20-1

187164-20-1

Identification

  • Product Name:(S)-2-bromo-1-(2,4-dichlorophenyl)ethanol

  • CAS Number: 187164-20-1

  • EINECS:

  • Molecular Weight:269.953

  • Molecular Formula: C8H7BrCl2O

  • HS Code:

  • Mol File:187164-20-1.mol

Synonyms:

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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

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Relevant articles and documentsAll total 4 Articles be found

COMPOUNDS OF R-(-)-(E)-[4-(2,4-DICHLOROPHENYL)-1,3-DITHIOLAN-2-YLIDENE]-1 -IMIDAZOLYLACETONITRILE-HA (LULICONAZOLE-HA) AS ANTIFUNGALS

-

Page/Page column 36, (2017/08/01)

The present invention refers to compound R-(-)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolylacetonitrile HA, wherein HA is an acid; and to a process for their preparation. The present invention also refers to the use of compound R-(-)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolylacetonitrile HA for the manufacturing of luliconazole and pharmaceutically acceptable salts or co-crystals thereof in high yield and purity. The present invention further is directed to this compound R-(-)-(E)-[4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolylacetonitrile HA in the treatment of fungal infections.

Asymmetric chemoenzymatic synthesis of miconazole and econazole enantiomers. the importance of chirality in their biological evaluation

Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Malpartida, Francisco,Gotor, Vicente

experimental part, p. 2115 - 2122 (2011/05/19)

A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei, while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.

A switch in enantiomer preference between mitochondrial F1F 0-ATPase chemotypes

Bisaha, Sharon N.,Malley, Mary F.,Pudzianowski, Andrew,Monshizadegan, Hossain,Wang, Paulina,Madsen, Cort S.,Gougoutas, Jack Z.,Stein, Philip D.

, p. 2749 - 2751 (2007/10/03)

The preferred absolute configuration of two series of F1F 0-ATP synthase inhibitors was determined. Although the configuration of the active enantiomer in each series is different, each series presents the same 'triaryl' pharmacophor

Method for treating mycosis using imidazolylacetonitrile derivatives

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, (2008/06/13)

R-(+)-(E)-?4-(2-Chlorophenyl)-1,3-dithiolan-2-ylidene!-1-imidazolylacetonitrile, R-(-)-(E)-?4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene!-1-imidazolylacetonitrile, and pharmaceutically acceptable salts thereof which can be used as a pharmaceutical agent are disclosed. A process for producing them and a method for treating mycoses using them are also disclosed.

Process route upstream and downstream products

Process route

2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol
187164-20-1

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol

Conditions
Conditions Yield
With B-chlorodiisopinocampheylborane; In tetrahydrofuran; at -25 ℃; for 16h;
98%
2,4-dichlorophenacyl bromide; With borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 20 - 30 ℃; for 1h;
With methanol; In tetrahydrofuran; toluene; Cooling;
72%
borane-THF

borane-THF

2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol
187164-20-1

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol

Conditions
Conditions Yield
In tetrahydrofuran; methanol;
2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol
187164-20-1

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol

(R)-2-bromo-1-(2,4-dichlorophenyl)ethanol
860439-01-6

(R)-2-bromo-1-(2,4-dichlorophenyl)ethanol

Conditions
Conditions Yield
With alcohol dehydrogenase PR2; isopropyl alcohol; NADPH; at 30 ℃; for 24h; pH=7.5; optical yield given as %ee; TRIS-HBr-HCl buffer; Enzymatic reaction;
37 %Chromat.
2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol
187164-20-1

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol

Conditions
Conditions Yield
With B-chlorodiisopinocampheylborane; In tetrahydrofuran; at -25 ℃; for 16h;
98%
2,4-dichlorophenacyl bromide; With borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 20 - 30 ℃; for 1h;
With methanol; In tetrahydrofuran; toluene; Cooling;
72%
borane-THF

borane-THF

2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol
187164-20-1

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol

Conditions
Conditions Yield
In tetrahydrofuran; methanol;
2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol
187164-20-1

(S)-2-bromo-1-(2,4-dichlorophenyl)ethan-1-ol

(R)-2-bromo-1-(2,4-dichlorophenyl)ethanol
860439-01-6

(R)-2-bromo-1-(2,4-dichlorophenyl)ethanol

Conditions
Conditions Yield
With alcohol dehydrogenase PR2; isopropyl alcohol; NADPH; at 30 ℃; for 24h; pH=7.5; optical yield given as %ee; TRIS-HBr-HCl buffer; Enzymatic reaction;
37 %Chromat.

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