Product Name

  • Name

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

  • EINECS 246-042-5
  • CAS No. 24155-42-8
  • Article Data27
  • CAS DataBase
  • Density 1.39 g/cm3
  • Solubility water: 1300 g/L (20 °C )
  • Melting Point 134-138 °C
  • Formula C11H10Cl2N2O
  • Boiling Point 468.5 °C at 760 mmHg
  • Molecular Weight 257.119
  • Flash Point 237.1 °C
  • Transport Information
  • Appearance White to light pink crystal
  • Safety 38-28B-36-26
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 24155-42-8 (alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms Imidazole-1-ethanol,a-(2,4-dichlorophenyl)- (8CI);1-(2,4-Dichlorophenyl)-2-(1-imidazolyl)ethanol;FI 7001;R 14821;T 824;UK11147;a-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol;Alpha-(2,4-dichlorophenyl)-1H-imidazole-1-ethanol;
  • PSA 38.05000
  • LogP 2.92350

Synthetic route

1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone
46503-52-0

1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone

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
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 12h;98%
With potassium borohydride In methanol for 1h; Reflux;90.5%
With sodium tetrahydroborate In methanol for 2h; Reflux;88%
1H-imidazole
288-32-4

1H-imidazole

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

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
ConditionsYield
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; butanone78.7%
With sodium In N-methyl-acetamide; methanol; water
1H-imidazole
288-32-4

1H-imidazole

2-(2,4-dichlorophenyl)oxirane
13692-15-4

2-(2,4-dichlorophenyl)oxirane

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
ConditionsYield
With pyridine In ethanol for 12h; Ring cleavage; Heating;63%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
Stage #2: 2-(2,4-dichlorophenyl)oxirane In N,N-dimethyl-formamide at 60℃; Inert atmosphere;		57%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide Inert atmosphere;
Stage #2: 2-(2,4-dichlorophenyl)oxirane In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
tetra-n-butylammonium imidazolate
67035-78-3

tetra-n-butylammonium imidazolate

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

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
ConditionsYield
In acetonitrile Reflux;68%
1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone nitrate

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone nitrate

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
ConditionsYield
With sodium tetrahydroborate In methanol for 2h;95%
tetra-n-butylammonium imidazolate
67035-78-3

tetra-n-butylammonium imidazolate

2-bromo-1-(2,4-dichlorophenyl)ethanol
53066-15-2

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

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
ConditionsYield
In acetonitrile Reflux;40%
2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

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
ConditionsYield
Multi-step reaction with 2 steps
1: 28 percent / CH2Cl2 / 2 h / 40 °C
2: sodium borohydride
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / isopropyl alcohol / 2 h / 3 - 20 °C
2: acetonitrile / Reflux
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane
2: potassium borohydride / methanol / 1 h / Reflux
View Scheme
2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

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
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / isopropyl alcohol / 2 h / 3 - 20 °C
2: acetonitrile / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide; water / 20 °C
2: sodium tetrahydroborate / methanol / 2 h / 5 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / 20 °C
2: sodium tetrahydroborate / methanol / 2 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / tetrahydrofuran / 3 h / 20 °C
2: sodium tetrahydroborate / methanol / 3 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 20 °C
2: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux
View Scheme
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

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
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / 3 h / 30 °C
2.1: triethylamine / methanol / 20 °C
2.2: 4 h / 65 °C
3.1: sodium tetrahydroborate / ethanol / 12 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: aluminum (III) chloride
2: triethylamine / methanol / 65 °C
3: sodium tetrahydroborate / ethanol / 20 °C
View Scheme
1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

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
ConditionsYield
Multi-step reaction with 3 steps
1: bromine / chloroform / 1.5 h / 0 - 20 °C
2: potassium carbonate / 20 °C
3: sodium tetrahydroborate / methanol / 2 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: bromine / chloroform / 1 h / 0 - 20 °C
2: potassium carbonate / tetrahydrofuran / 3 h / 20 °C
3: sodium tetrahydroborate / methanol / 3 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 3 steps
1: bromine / chloroform / 1 h / 0 - 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 20 °C
3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux
View Scheme
2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

A

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

B

n-butyl halide

n-butyl halide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile
2: NaBH4 / ethanol
View Scheme
2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

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
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium hydroxide / acetonitrile; water / 3 h / 60 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2.2: 60 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: potassium hydroxide / acetonitrile / 60 - 65 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere
2.2: 20 °C / Inert atmosphere
View Scheme
2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

A

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

B

n-butyl halide

n-butyl halide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CHCl3 / 0 °C
2: sodium borohydride / ethanol / 4 h / Heating
View Scheme
2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

A

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

B

3,4-Cl2-C6H3-SO2CH2-X, (X=Cl or Br)

3,4-Cl2-C6H3-SO2CH2-X, (X=Cl or Br)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / aq. KOH / acetonitrile / 3 h / 60 °C
2: 63 percent / pyridine / ethanol / 12 h / Heating
View Scheme
Hexanoyl chloride
142-61-0

Hexanoyl chloride

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

1-[2,4-dichloro-β-(n-pentylcarbonyloxy)phenethyl]imidazole

1-[2,4-dichloro-β-(n-pentylcarbonyloxy)phenethyl]imidazole

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;97%
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

2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
16977-78-9, 85193-55-1, 86651-32-3, 86651-40-3

2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide

1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide

Conditions
ConditionsYield
In acetonitrile at 110℃;96%
In acetonitrile at 110℃; for 24h;90%
3-Bromomethyl-7-chlorobenzothiophene
17512-61-7

3-Bromomethyl-7-chlorobenzothiophene

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

sertaconazole nitrate
99592-39-9

sertaconazole nitrate

Conditions
ConditionsYield
Stage #1: 3-Bromomethyl-7-chlorobenzothiophene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutyl-ammonium chloride; sodium hydroxide In water; toluene at 80℃; for 4h;
Stage #2: With nitric acid		95.7%
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

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole
35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 1h;
Stage #2: 3-chloroprop-1-ene In water; dimethyl sulfoxide at 30℃; for 3h; Solvent; Temperature;		95.6%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With potassium hydroxide In water; dimethyl sulfoxide at 20 - 35℃; for 1h;
Stage #2: 3-chloroprop-1-ene In water; dimethyl sulfoxide at 35 - 40℃; Reagent/catalyst;		68%
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

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-1-octanoyloxy-ethane
68571-21-1

1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-1-octanoyloxy-ethane

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;95%
n-decanoyl chloride
112-13-0

n-decanoyl chloride

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

1-[2,4-dichloro-β-(n-nonylcarbonyloxy)phenethyl]imidazole

1-[2,4-dichloro-β-(n-nonylcarbonyloxy)phenethyl]imidazole

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;91%
acetic anhydride
108-24-7

acetic anhydride

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

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl acetate
61258-54-6

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl acetate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 1.5h; Inert atmosphere;91%
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

(±)-1-(2-azido-2-(2, 4-dichlorophenyl)ethyl)-1H-imidazole
94038-18-3

(±)-1-(2-azido-2-(2, 4-dichlorophenyl)ethyl)-1H-imidazole

Conditions
ConditionsYield
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0 - 20℃; for 3.25h; Inert atmosphere;87%
With diazabicycloundecane; diphenyl phosphoryl azide In tetrahydrofuran
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide
3-(bromomethyl)benzothiophene
1196-19-6

3-(bromomethyl)benzothiophene

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

1-(2-(benzo[b]thiophen-3-ylmethoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
99592-24-2

1-(2-(benzo[b]thiophen-3-ylmethoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h;
Stage #2: 3-(bromomethyl)benzothiophene In toluene for 3h; Heating;		86%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h;
Stage #2: 3-(bromomethyl)benzothiophene In toluene for 3h; Heating;		86%
With sodium hydride 1.) HMPT, RT; 2.) HMPT, 50 deg C, 1 h, 3.) HMPT, 0 deg C, 5 h;; Multistep reaction;
1-phenylthio-4-chloromethyl-benzene
1208-87-3

1-phenylthio-4-chloromethyl-benzene

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

α-(2,4-dichlorophenyl)-β,N-imidazolylethyl 4-phenylthiobezyl ether nitrate

α-(2,4-dichlorophenyl)-β,N-imidazolylethyl 4-phenylthiobezyl ether nitrate

Conditions
ConditionsYield
Stage #1: 1-phenylthio-4-chloromethyl-benzene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 58 - 60℃; for 13.5h;
Stage #2: With nitric acid In ethyl acetate; toluene at 25℃; for 3h;		85.1%
Stage #1: 1-phenylthio-4-chloromethyl-benzene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydroxide In tetrahydrofuran; water for 4.5h;
Stage #2: With nitric acid In water		82.1%
Stage #1: 1-phenylthio-4-chloromethyl-benzene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 58℃; for 13.5h;
Stage #2: With nitric acid In ethyl acetate; toluene at 25℃; for 3h;		74.7%
Stage #1: 1-phenylthio-4-chloromethyl-benzene; 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 58 - 60℃; for 13.5h;
Stage #2: With nitric acid In ethyl acetate at 25℃; for 3h;		71.4%
Nonanoyl chloride
764-85-2

Nonanoyl chloride

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

1-[2,4-dichloro-β-(n-octylcarbonyloxy)phenethyl]imidazole

1-[2,4-dichloro-β-(n-octylcarbonyloxy)phenethyl]imidazole

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;84%
propionyl chloride
79-03-8

propionyl chloride

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

Propionic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Propionic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;83%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

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

1-(2,4-dichloro-phenyl)-1-dodecanoyloxy-2-imidazol-1-yl-ethane
68571-23-3

1-(2,4-dichloro-phenyl)-1-dodecanoyloxy-2-imidazol-1-yl-ethane

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;82%
undecanoyl chloride
17746-05-3

undecanoyl chloride

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

Undecanoic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Undecanoic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;82%
trans-geranyl bromide
6138-90-5

trans-geranyl bromide

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

1-[2-(2,4-dichlorophenyl)-2-((E)-3,7-dimethylocta-2,6-dienyloxy)ethyl]-1H-imidazole

1-[2-(2,4-dichlorophenyl)-2-((E)-3,7-dimethylocta-2,6-dienyloxy)ethyl]-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide at 40℃; for 0.5h; deprotonation;
Stage #2: trans-geranyl bromide In N,N-dimethyl-formamide at 20℃; for 0.5h; Etherification;		82%
In N-methyl-acetamide
7-chloro-3-(chloromethyl)benzo[b]thiophene

7-chloro-3-(chloromethyl)benzo[b]thiophene

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

sertaconazole
99592-32-2

sertaconazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetra-(n-butyl)ammonium iodide; sodium hydroxide In water; toluene at 50℃; for 0.25h; Inert atmosphere;
Stage #2: 7-chloro-3-(chloromethyl)benzo[b]thiophene In water; toluene at 50℃; for 4h; Inert atmosphere;		82%
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

2-(bromomethyl)naphthalene
3163-27-7

2-(bromomethyl)naphthalene

1-(2-(2,4-dichlorophenyl)-2-(naphthalen-1-ylmethoxy)ethyl)-1H-imidazole

1-(2-(2,4-dichlorophenyl)-2-(naphthalen-1-ylmethoxy)ethyl)-1H-imidazole

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; tetra-(n-butyl)ammonium iodide; sodium hydride at 0℃;80%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h;
Stage #2: 2-(bromomethyl)naphthalene In toluene for 3h; Heating;		72%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h;
Stage #2: 2-(bromomethyl)naphthalene In toluene for 3h; Heating;		72%
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

2-bromomethylnaphthyl bromide
939-26-4

2-bromomethylnaphthyl bromide

1-(2-(2,4-dichlorophenyl)-2-(naphthalen-2-ylmethoxy)ethyl)-1H-imidazole

1-(2-(2,4-dichlorophenyl)-2-(naphthalen-2-ylmethoxy)ethyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h;
Stage #2: 2-bromomethylnaphthyl bromide In toluene for 3h; Heating;		76%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h;
Stage #2: 2-bromomethylnaphthyl bromide In toluene for 3h; Heating;		76%
With sodium hydride 1.) HMPA, 20 degC - 25 degC, 1 h; 50 degC - 60 degC, 2 h; 2.) 50 degC, 20 h; Yield given. Multistep reaction;
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

1-chloro-1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethane
46503-49-5

1-chloro-1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethane

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 12h;74.3%
With thionyl chloride In dichloromethane
With thionyl chloride at 20℃;
butyryl chloride
141-75-3

butyryl chloride

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

Butyric acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Butyric acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;74%
2,4-Dichlorobenzyl chloride
94-99-5

2,4-Dichlorobenzyl chloride

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

miconazole
22916-47-8

miconazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Substitution;
Stage #2: 2,4-Dichlorobenzyl chloride In tetrahydrofuran at 45℃; for 16h; Substitution;		73%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide Inert atmosphere;
Stage #2: 2,4-Dichlorobenzyl chloride In N,N-dimethyl-formamide at 20℃;
p-phenylbenzyl bromide
2567-29-5

p-phenylbenzyl bromide

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

1-[2-biphenyl-4-ylmethoxy-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole
73151-17-4

1-[2-biphenyl-4-ylmethoxy-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; tetra-(n-butyl)ammonium iodide; sodium hydride at 0℃;73%
n-valeryl chloride
638-29-9

n-valeryl chloride

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

Pentanoic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Pentanoic acid 1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane for 4h; Ambient temperature;71%
3-Bromomethylthiophene
34846-44-1

3-Bromomethylthiophene

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

1-(2-(2,4-dichlorophenyl)-2-(thiophen-3-ylmethoxy)ethyl)-1H-imidazole
119386-74-2

1-(2-(2,4-dichlorophenyl)-2-(thiophen-3-ylmethoxy)ethyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h;
Stage #2: 3-Bromomethylthiophene In toluene for 3h; Heating;		71%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With tetrabutylammomium bromide; sodium hydroxide In toluene at 85℃; for 0.5h;
Stage #2: 3-Bromomethylthiophene In toluene for 3h; Heating;		71%
1,3-Dichloro-2-chloromethyl-benzene
2014-83-7

1,3-Dichloro-2-chloromethyl-benzene

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

isoconazole

isoconazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 1h; Inert atmosphere; Reflux;
Stage #2: 1,3-Dichloro-2-chloromethyl-benzene In 1,4-dioxane; mineral oil Inert atmosphere; Reflux;		70%
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

4-bromobenzyl halide

4-bromobenzyl halide

1-(2-((4-bromobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

1-(2-((4-bromobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide at -5 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: 4-bromobenzyl halide In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;		68.4%

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

IUPAC Name: 1-(2,4-Dichlorophenyl)-2-imidazol-1-ylethanol
Synonyms of alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol (CAS NO.24155-42-8): Benzyl alcohol, 2,4-dichloro-alpha-(1-imidazolylmethyl)- ; N-(beta-(2,4-Dichlorophenyl)-beta-hydroxyethyl)imidazole ; 1H-Imidazole-1-ethanol, alpha-(2,4-dichlorophenyl)- (9CI) ; Imidazole-1-ethanol, alpha-(2,4-dichlorophenyl)-
CAS NO: 24155-42-8
Molecular Formula: C11H10Cl2N2O
Molecular Weight: 257.12
Molecular Structure:
EINECS: 246-042-5
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 27.05 Å2
Index of Refraction: 1.626
Molar Refractivity: 65.2 cm3
Molar Volume: 184 cm3
Surface Tension: 48.8 dyne/cm
Density: 1.39 g/cm3
Flash Point: 237.1 °C
Enthalpy of Vaporization: 76.98 kJ/mol
Boiling Point: 468.5 °C at 760 mmHg
Vapour Pressure: 1.41E-09 mmHg at 25°C
Melting Point: 134-138 °C
Water Solubility 1300 g/L (20 ºC)
Appearance: alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol (CAS NO.24155-42-8) is cream-coloured to beige powder.
SMILES: Clc1ccc(c(Cl)c1)C(O)Cn2ccnc2
InChI: InChI=1/C11H10Cl2N2O/c12-8-1-2-9(10(13)5-8)11(16)6-15-4-3-14-7-15/h1-5,7,11,16H,6H2
InChIKey: UKVLTPAGJIYSGN-UHFFFAOYAR
Std. InChI: InChI=1S/C11H10Cl2N2O/c12-8-1-2-9(10(13)5-8)11(16)6-15-4-3-14-7-15/h1-5,7,11,16H,6H2
Std. InChIKey: UKVLTPAGJIYSGN-UHFFFAOYSA-N
Product Categories: Imidazol&Benzimidazole;Imidazoles

alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 300mg/kg (300mg/kg) BEHAVIORAL: ANTICONVULSANT Journal of Medicinal Chemistry. Vol. 24, Pg. 727, 1981.

alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol Safety Profile

Hazard Codes: HarmfulXn,Xi
Risk Statements: 22-36/37/38
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 38-28-36-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S28: After contact with skin, wash immediately with plenty of soap-suds. 
S36: Wear suitable protective clothing. 
S38: In case of insufficient ventilation, wear suitable respiratory equipment.
RTECS: NI5485000

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

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol (CAS NO.24155-42-8) in a cool, dry place. Store in a tightly closed container.

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