| Identification | More | [Name]
alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol | [CAS]
24155-42-8 | [Synonyms]
1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANOL
1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol
1-(2,4-DICHLOROPHENYL)-2-IMIDAZOL-1-YL ETHANOL
1H-IMIDAZOLE-1-ETHANOL, ALPHA-(2,4-DICHLOROPHENYL)-
ALPHA-(2,4-DICHLOROPHENYL)-1H-IMIDAZOLE-1-ETHANOL
ALPHA-(2,4-DICHLOROPHENYL)-2-1H-IMIDAZOLE-1-ETHANOL
ALPHA-(2,4-DICHLORO PHENYL)-B-(IMIDAZOLE-YL)ETHANOL
-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol
2,4-dichloro-alpha-(1-imidazolylmethyl)-benzylalcoho
alpha-(2,4-dichlorophenyl)-imidazole-1-ethano
n-(beta-(2,4-dichlorophenyl)-beta-hydroxyethyl)imidazole
r14821
t824
1-(2,4-Dichlorphenyl)-2-1-Imidazolyl)-Ethanol
1-(2,4-Dichlorophenyl)-2-((1H)-imidazol-1-yl)-ethane
alpha-(2,4-Dichlorophenyl)-1H-
2-(2,4-dichlorobenzene)-imidazole-1-ethanol
ALPHA-(2,4-DICHLOROPHENYL)-1H-IMIDAZOLE-ETHANOL
IMIDAZOLE ETHANOL
Imidazole-1-ethanol alpha-(2,4-dichlorophenyl) | [EINECS(EC#)]
246-042-5 | [Molecular Formula]
C11H10Cl2N2O | [MDL Number]
MFCD00044708 | [Molecular Weight]
257.12 | [MOL File]
24155-42-8.mol |
| Chemical Properties | Back Directory | [Appearance]
cream-coloured to beige powder | [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) | [form ]
neat | [pka]
12.25±0.20(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [RTECS ]
NI5485000 | [HS Code ]
2933290000 |
| Hazard Information | Back Directory | [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. | [Application]
In the pharmaceutical field, alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol is an important precursor for the synthesis of various imidazole antifungal drugs (such as econazole and miconazole), which are widely used to treat fungal infections. Furthermore, it is an intermediate in the production of agricultural fungicides (such as imidazoles), which are used in agriculture to control various plant diseases, such as powdery mildew and black rot, thereby increasing crop yields. | [Flammability and Explosibility]
Notclassified | [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 |
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