alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol Chemical Properties

Melting point:

134-138 °C

Boiling point:

468.5±45.0 °C(Predicted)

Density 

1.4133 (rough estimate)

vapor pressure 

0Pa at 20℃

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

12.25±0.20(Predicted)

form 

solid

color 

White to Pale Yellow

Water Solubility 

1300 g/L (20 ºC)

InChIKey

UKVLTPAGJIYSGN-UHFFFAOYSA-N

LogP

2.31 at 20℃

CAS DataBase Reference

24155-42-8(CAS DataBase Reference)

EPA Substance Registry System

1H-Imidazole-1-ethanol, ?-(2,4-dichlorophenyl)- (24155-42-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

38-28B-36-26

WGK Germany 

3

RTECS 

NI5485000

HS Code 

2933290000

MSDS

• Language:English Provider:alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol
• Language:English Provider:ACROS

alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol Usage And Synthesis

Chemical Properties

cream-coloured to beige powder

Uses

Intermediate in the preparation of Miconazole. An impurity in the synthesis of Fenticonazole. An impurity in the synthesis of Ketoconazole.

Uses

Intermediate in the preparation of Miconazole.An impurity in the synthesis of Fenticonazole.An impurity in the synthesis of Ketoconazole.Econazole EP Impurity A.

Flammability and Explosibility

Not classified

Synthesis

General procedure for the synthesis of alpha-(2,4-dichlorophenyl)-1H-imidazole-1-ethanol from 2'-(1H-imidazol-1-yl)-2,4-dichloroacetophenone: In a 1000 mL three-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, add 102 g of 2'-(1H-imidazol-1-yl)-2,4-dichloroacetophenone (0.4 mol) and 300 mL of methanol. Potassium borohydride was added in batches and slowly heated to reflux. After completion of the reaction, stirring was continued for 1 h and the progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent was ethyl acetate: methanol = 10:1, v/v). At the end of the reaction, methanol was recovered by distillation under reduced pressure. The concentrate was adjusted to pH 4-5 with 5% hydrochloric acid solution and subsequently diafiltrated. The filtrate was adjusted pH to 7-8 with 5% sodium bicarbonate solution, when a white solid precipitated. The solid was collected by filtration, washed with water, dried and recrystallized to give 93.1 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol in 90.5% yield with a melting point of 134-135 °C.

References

[1] Patent: CN102180835, 2016, B. Location in patent: Paragraph 0015; 0016
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1665 - 1674
[3] Polyhedron, 2013, vol. 52, p. 106 - 114
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 23, p. 4288 - 4294
[5] Medicinal Chemistry Research, 1999, vol. 9, # 3, p. 162 - 175

alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol(24155-42-8)Related Product Information

• Monoethanolamine
• Imidazole
• Diethanolamine
• Dichlorodiphenylsilane
• Ethanol
• Levamisole
• Econazole
• Isoconazole
• Dichloroethane
• Ethyl acetate
• Diethylstilbestrol
• Dichloromethylphenylsilane
• 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOLE-1-YL) ETHANONE
• ALPHA-(CHLOROMETHYL)-2,4-DICHLOROBENZYL ALCOHOL
• Miconazole nitrate
• 2,4-Dichloro-β-[(2,6-dichlorophenyl)methoxy]benzeneethanamine
• Miconazole Impurity
• Miconazole IMpurity I