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Cas Database

13692-14-3

13692-14-3

Identification

Synonyms:Benzylalcohol, 2,4-dichloro-α-(chloromethyl)- (8CI);2,4-Dichloro-α-(chloromethyl)benzyl alcohol;2-Chloro-1-(2,4-dichlorophenyl)ethanol;α-(2,4-Dichlorophenyl)-β-chloroethanol;α-(Chloromethyl)-2,4-dichlorobenzylalcohol;

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H319 Causes serious eye irritation

  • 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:TRC
  • Product Description:α-(Chloromethyl)-2,4-dichlorobenzylAlcohol
  • Packaging:1g
  • Price:$ 110
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:2-Chloro-1-(2,4-dichlorophenyl)ethanol 95+%
  • Packaging:10g
  • Price:$ 419
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  • Manufacture/Brand:Chemenu
  • Product Description:2-Chloro-1-(2,4-dichlorophenyl)ethanol 95%
  • Packaging:10g
  • Price:$ 396
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:2,4-Dichloro-alpha-(chloromethyl)benzyl alcohol
  • Packaging:25 g
  • Price:$ 600
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:2,4-Dichloro-alpha-(chloromethyl)benzyl alcohol
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:2,4-Dichloro-alpha-(chloromethyl)benzyl alcohol
  • Packaging:5 g
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:2,4-Dichloro-alpha-(chloromethyl)benzyl alcohol
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:2,4-Dichloro-alpha-(chloromethyl)benzyl alcohol
  • Packaging:1 g
  • Price:$ 65
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:ALPHA-(CHLOROMETHYL)-2,4-DICHLOROBENZYL ALCOHOL 95.00%
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  • Price:$ 9586.5
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:ALPHA-(CHLOROMETHYL)-2,4-DICHLOROBENZYL ALCOHOL 95.00%
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Relevant articles and documentsAll total 11 Articles be found

Lipase mediated enzymatic kinetic resolution of phenylethyl halohydrins acetates: A case of study and rationalization

Fonseca, Thiago de Sousa,Vega, Kimberly Benedetti,da Silva, Marcos Reinaldo,de Oliveira, Maria da Concei??o Ferreira,de Lemos, Telma Leda Gomes,Contente, Martina Letizia,Molinari, Francesco,Cespugli, Marco,Fortuna, Sara,Gardossi, Lucia,de Mattos, Marcos Carlos

, (2020/02/18)

Racemic phenylethyl halohydrins acetates containing several groups attached to the aromatic ring were resolved via hydrolysis reaction in the presence of lipase B from Candida antarctica (Novozym 435). In all cases, the kinetic resolution was highly selective (E > 200) leading to the corresponding (S)-β-halohydrin with ee > 99 %. However, the time required for an ideal 50 % conversion ranged from 15 min for 2,4-dichlorophenyl chlorohydrin acetate to 216 h for 2-chlorophenyl bromohydrin acetate. Six chlorohydrins and five bromohydrins were evaluated, the latter being less reactive. For the β-brominated substrates, steric hindrance on the aromatic ring played a crucial role, which was not observed for the β-chlorinated derivatives. To shed light on the different reaction rates, docking studies were carried out with all the substrates using MD simulations. The computational data obtained for the β-brominated substrates, based on the parameters analysed such as NAC (near attack conformation), distance between Ser-O and carbonyl-C and oxyanion site stabilization were in agreement with the experimental results. On the other hand, the data obtained for β-chlorinated substrates suggested that physical aspects such as high hydrophobicity or induced change in the conformation of the enzymatic active site are more relevant aspects when compared to steric hindrance effects.

Use of miconazole and derivatives thereof as TGR5 agonists (by machine translation)

-

Paragraph 0031-0034, (2020/05/02)

The invention belongs to the technical field of medicines, and relates to novel application TGR5 of miconazole and derivatives thereof in treatment, of diseases and conditions of a biological pathologic process involved in treatment, and. The miconazole and the analogues thereof can activate TGR5 active, for use TGR5 in the treatment or prevention of diseases associated with, activity modulation. (by machine translation)

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

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

supporting information, 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.

Enantioselective Reduction of α,β-Unsaturated Ketones and Aryl Ketones by Perakine Reductase

Cai, Sheng,Shao, Nana,Chen, Yuanyuan,Li, Anbang,Pan, Jie,Zhu, Huajian,Zou, Hongbin,Zeng, Su,Sun, Lianli,Zhao, Jinhao

supporting information, p. 4411 - 4414 (2019/05/22)

This report describes the enantioselective reduction of structurally diverse α,β-unsaturated ketones and aryl ketones by perakine reductase (PR) from Rauvolfia. This enzymatic reduction produces α-chiral allylic and aryl alcohols with excellent enantioselectivity and most of the products in satisfactory yields. Furthermore, the work demonstrates 1 mmol scale reactions for product delivery without any detrimental effect on yield and enantioselectivity. The catalytic mechanism, determined by 3D-structure-based modeling of PR and ligand complexes, is also described.

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

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

2,2',4'-trichloroacetophenone

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

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

Conditions
Conditions Yield
With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h; Inert atmosphere;
98%
With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 0.666667h;
90%
With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 0.666667h;
90%
With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 6h;
90.1%
2,2',4'-trichloroacetophenone; With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 1.5h; Inert atmosphere;
With water; In methanol;
89%
With sodium tetrahydroborate; In isopropyl alcohol; at 3 - 20 ℃; for 2h;
73%
With sodium tetrahydroborate; In methanol; at 20 ℃;
With sodium tetrahydroborate; In methanol; Inert atmosphere;
With methanol; sodium tetrahydroborate; at 0 ℃; for 0.25h;
1.99 g
With aluminum isopropoxide; In isopropyl alcohol; at 65 ℃; for 5h; Green chemistry; Industrial scale;
With methanol; sodium tetrahydroborate; Inert atmosphere;
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
1H-imidazole
288-32-4

1H-imidazole

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

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

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol
24155-42-8

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

Conditions
Conditions Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; alumina-supported potassium hydroxide; at 45 ℃; for 3.5h;
90%
With potassium carbonate; sodium iodide; In water; butanone;
78.7%
With sodium; In N-methyl-acetamide; methanol; water;
tetra-n-butylammonium imidazolate
67035-78-3

tetra-n-butylammonium imidazolate

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

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

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol
24155-42-8

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

Conditions
Conditions Yield
In acetonitrile; Reflux;
68%
α-(chloromethyl)-2,4-dichlorobenzyl alcohol
13692-14-3,114446-57-0

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

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: acetonitrile / Reflux
2.1: sodium hydride / 1,4-dioxane; mineral oil / 1 h / 20 °C / Inert atmosphere; Reflux
2.2: Inert atmosphere; Reflux
3.1: nitric acid / acetone / 12 h
With nitric acid; sodium hydride; In 1,4-dioxane; acetone; acetonitrile; mineral oil;
α-(chloromethyl)-2,4-dichlorobenzyl alcohol
13692-14-3,114446-57-0

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

acetic anhydride
108-24-7

acetic anhydride

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

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

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; for 3h; Inert atmosphere;
96%
With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;
91%
With dmap; In dichloromethane; at 20 ℃; for 2h;
91%
1,2,4-Triazole
288-88-0

1,2,4-Triazole

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

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

1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-1-ethanol
58905-18-3

1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-1-ethanol

Conditions
Conditions Yield
With potassium hydroxide; In N,N-dimethyl-formamide; at 60 ℃; for 6h;
78.1%
α-(chloromethyl)-2,4-dichlorobenzyl alcohol
13692-14-3,114446-57-0

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

2-azido-1-(2,4-dichlorophenyl)ethan-1-ol
1301629-37-7

2-azido-1-(2,4-dichlorophenyl)ethan-1-ol

Conditions
Conditions Yield
With sodium azide; tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; for 12h; Reflux;
69%
1,2,3-triazole
288-36-8

1,2,3-triazole

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

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

1-(2,4-dichlorophenyl)-2-(1H-1,2,3-triazol-1-yl)ethanol
1301629-00-4

1-(2,4-dichlorophenyl)-2-(1H-1,2,3-triazol-1-yl)ethanol

1-(2,4-dichlorophenyl)-2-(2H-1,2,3-triazol-2-yl)ethanol
1301629-01-5

1-(2,4-dichlorophenyl)-2-(2H-1,2,3-triazol-2-yl)ethanol

Conditions
Conditions Yield
With potassium carbonate; In acetonitrile; at 80 ℃; for 0.833333h; Microwave irradiation;
43%
14%

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