872-82-2

Basic information

• Product Name: Imidazolyl-4-ethanol
• Synonyms: 2-(3H-IMIDAZOL-4-YL)-ETHANOL;2-[1(3)H-IMIDAZOL]-4-YL-ETHANOL;2-(1H-IMIDAZOL-4-YL)-ETHANOL;2,2,2-Trifluoro-1-(2-methyl-3H-imidazol-4-yl)ethanol;4(5)-(Hydroxyethyl)imidazole;imidazolyl-4-ethanol;histaminol;1H-Imidazole-4-ethanol
• CAS NO: 872-82-2
• Molecular Formula: C₅H₈N₂O
• Molecular Weight: 112.13
• Product Categories: pharmacetical
• Mol File: 872-82-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 82 °C
• Boiling Point: 359.8ºC at 760 mmHg
• Flash Point: 171.4ºC
• Appearance: /
• Density: 1.228 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 14.11±0.10(Predicted)
• CAS DataBase Reference: Imidazolyl-4-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: Imidazolyl-4-ethanol(872-82-2)
• EPA Substance Registry System: Imidazolyl-4-ethanol(872-82-2)

Safety Data

• Hazardous Substances Data: 872-82-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 2382, 1983 DOI: 10.1021/ja00346a046

InChI:InChI=1/C5H8N2O/c8-2-1-5-3-6-4-7-5/h3-4,8H,1-2H2,(H,6,7)

Synthetic route

formaldehyd (50-00-0) + 1,4-dihydroxy-2-butanone (140-86-3) → 2-(1H-imidazol-4-yl)ethanol (872-82-2)

Conditions	Yield
With ammonium hydroxide; copper(II) sulfate
With ammonium hydroxide; copper(I) sulfate In water at 80℃; for 2h;	31.6 g

4-(2-hydroxy-ethyl)-1,3-dihydro-imidazole-2-thione (90773-75-4) → 2-(1H-imidazol-4-yl)ethanol (872-82-2)

Conditions	Yield
With nitric acid

histamine hydrochloride (55-36-7) → 2-(1H-imidazol-4-yl)ethanol (872-82-2)

Conditions	Yield
With ethanol; diamine oxidase from pea seedling; liver alcohol dehydrogenase; NAD; catalase at 37℃; for 48h; phosphate buffer (pH 7);	34 mg
With hydrogenchloride; sodium nitrite In water at 40℃; for 2h; Reagent/catalyst; Temperature;

4-<β-amino-ethyl>-1(3)H-imidazole hydrochloride → 2-(1H-imidazol-4-yl)ethanol (872-82-2)

Conditions	Yield
With barium nitrite; water

formaldehyd (50-00-0) + 1,4-dihydroxy-2-butanone (140-86-3) + ammonia (7664-41-7) + water (7732-18-5) + copper(II) sulfate (7758-99-8) → 2-(1H-imidazol-4-yl)ethanol (872-82-2)

Conditions	Yield
at 70 - 80℃;

methyl 2-(1H-imidazol-4-yl)acetate hydrochloride (51718-80-0) → 2-(1H-imidazol-4-yl)ethanol (872-82-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating / reflux;

4-(2′-methoxyethyl)imidazole (30290-08-5) → 2-(1H-imidazol-4-yl)ethanol (872-82-2)

Conditions	Yield
With hydrogen bromide for 1.5h; Reflux;	5.41 g

2-(1H-imidazol-4-yl)ethanol (872-82-2) + tert-butyl 2-chloro-4-iodobenzoate → C11H10ClN3O3*(x)ClH

Conditions	Yield
Stage #1: 2-(1H-imidazol-4-yl)ethanol; tert-butyl 2-chloro-4-iodobenzoate With potassium phosphate; copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane In dimethyl sulfoxide at 50℃; for 2h; Stage #2: With hydrogenchloride In 1,4-dioxane at 70℃; for 15h;	96%

copper(II) nitrate trihydrate + 2-(1H-imidazol-4-yl)ethanol (872-82-2) → C10H16CuN6O8

Conditions	Yield
In methanol for 1h; Heating;	58.8%

4-amino-6-chloropyrimidine (5305-59-9) + 2-(1H-imidazol-4-yl)ethanol (872-82-2) → 2-(1-(6-aminopyrimidin-4-yl)-1H-imidazole-4-yl)ethan-1-ol

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 140℃; for 12h;	58%
With caesium carbonate In N,N-dimethyl-formamide at 140℃; for 12h;	58%

copper(II) nitrate trihydrate + 2-(1H-imidazol-4-yl)ethanol (872-82-2) → C5H10CuN4O8

Conditions	Yield
In methanol; water for 1h; Heating;	55.4%

pyridine-2-thione (2637-34-5) + 2-(1H-imidazol-4-yl)ethanol (872-82-2) → 2-<<2-<4(5)-imidazolyl>ethyl>thio>pyridine hydrobromide hydrate

Conditions	Yield
With hydrogen bromide for 24h; Heating;	48%

2-(1H-imidazol-4-yl)ethanol (872-82-2) + trityl chloride (76-83-5) → 1-triphenylmethyl-4-(2-hydroxyethyl)-1H-imidazole (127607-62-9)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	40%

2-(1H-imidazol-4-yl)ethanol (872-82-2) + ethyl 7-fluoro-3-ethoxy-6-nitroquinoxaline-2-carboxylate (221164-86-9) → ethyl 3-ethoxy-7-[4-(2-hydroxyethyl)imidazol-1-yl]-6-nitroquinoxaline-2-carboxylate (221167-10-8)

Conditions	Yield
With triethylamine In N,N-dimethyl acetamide at 120℃; for 15h;	28%
With triethylamine In N,N-dimethyl acetamide at 120℃; for 15h;	28%
With triethylamine

copper(II) nitrate trihydrate + 2-(1H-imidazol-4-yl)ethanol (872-82-2) → C20H32CuN8O4(2+)*2NO3(1-)

Conditions	Yield
In methanol for 1h; Heating;	26.8%

2-(1H-imidazol-4-yl)ethanol (872-82-2) + phenyl isocyanate (103-71-9) → Phenyl-carbamic acid 2-(1H-imidazol-4-yl)-ethyl ester (74294-66-9)

Conditions	Yield
With pyridine at 80℃; for 0.5h;	803 mg

2-(1H-imidazol-4-yl)ethanol (872-82-2) + p-toluenesulfonyl chloride (98-59-9) → NO-bis-p-tolylsulphonylhistaminol (74294-60-3)

Conditions	Yield
With pyridine at -23℃; for 2h;	336 mg

2-(1H-imidazol-4-yl)ethanol (872-82-2) + water (7732-18-5) → 2-(1H-imidazol-4-yl)acetic acid (645-65-8)

Conditions	Yield
UV-Licht.Irradiation;

2-(1H-imidazol-4-yl)ethanol (872-82-2) + nitric acid (7697-37-2) → 5 (resp. 4)-nitro-imidazole-carboxylic acid-(4 resp. 5)

di-tert-butyl dicarbonate (24424-99-5) + 2-(1H-imidazol-4-yl)ethanol (872-82-2) → tert-butyl 4-(2-hydroxyethyl)imidazole-1-carboxylate (211503-47-8)

Conditions	Yield
With TEA In methanol at 20℃;

2-(1H-imidazol-4-yl)ethanol (872-82-2) → 4-(2-methanesulfonyloxy-ethyl)-imidazole-1-carboxylic acid tert-butyl ester (908015-61-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: TEA / methanol / 20 °C 2: TEA / CH2Cl2 / 1 h / 20 °C View Scheme

2-(1H-imidazol-4-yl)ethanol (872-82-2) → histamine dichloride (56-92-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 336 mg / pyridine / 2 h / -23 °C 2: 180 mg / lithium azide / dimethylformamide / 18 h / 21 °C 3: 90 mg / aq. hydrochloric acid, hydrogen / palladium-charcoal / ethanol / 8 h View Scheme

2-(1H-imidazol-4-yl)ethanol (872-82-2) → 4-(2-Azido-ethyl)-1-(toluene-4-sulfonyl)-1H-imidazole (74294-62-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 336 mg / pyridine / 2 h / -23 °C 2: 180 mg / lithium azide / dimethylformamide / 18 h / 21 °C View Scheme

2-Mercaptopyridine (2637-34-5) + 2-(1H-imidazol-4-yl)ethanol (872-82-2) → 2-{[2-(1H-Imidazol-4-yl)ethyl]thio}pyridine

Conditions	Yield
In aqueous HBr

2-(1H-imidazol-4-yl)ethanol (872-82-2) + p-toluenesulfonyl chloride (98-59-9) → 2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethanol (930768-34-6)

Conditions	Yield
With triethylamine In tetrahydrofuran; dichloromethane for 0.333333h;

2-(1H-imidazol-4-yl)ethanol (872-82-2) + tert-butylchlorodiphenylsilane (58479-61-1) → 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-imidazole (1571145-65-7)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h;	1.6 g
With 1H-imidazole at 20℃; for 2h;	1.6 g

2-(1H-imidazol-4-yl)ethanol (872-82-2) + tert-butyl 2-chloro-4-iodobenzoate → tert-butyl 2-chloro-4-(4-(2-hydroxyethyl)-1H-imidazol-1-yl)benzoate

Conditions	Yield
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 20 - 50℃; for 2h; Inert atmosphere;

2-(1H-imidazol-4-yl)ethanol (872-82-2) + trityl chloride (76-83-5) → methyl 4-nitro-3-[2-(1-tritylimidazol-4-yl)ethoxy]benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C 2: sodium hydride / N,N-dimethyl-formamide / 4 h / 70 °C View Scheme

2-(1H-imidazol-4-yl)ethanol (872-82-2) → 1-(6-(4-(2-bromoethyl)-1H-imidazol-1-yl)pyrimidin-4-yl)-3-ethylthiourea

Conditions	Yield
Multi-step reaction with 3 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 140 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h 2.2: 0.5 h / 20 °C 3.1: phosphorus tribromide / dichloromethane / 20 °C View Scheme

Upstream product

• 50-00-0 formaldehyd 
• 140-86-3 1,4-dihydroxy-2-butanone 
• 90773-75-4 4-(2-hydroxy-ethyl)-1,3-dihydro-imidazole-2-thione 
• 7664-41-7 ammonia 
• 7732-18-5 water 
• 7758-99-8 copper(II) sulfate 
• 30290-08-5 4-(2′-methoxyethyl)imidazole 
• 51718-80-0 methyl 2-(1H-imidazol-4-yl)acetate hydrochloride 
• 55-36-7 histamine hydrochloride 

Downstream Products

• 930768-34-6 2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethanol 
• 127607-62-9 1-triphenylmethyl-4-(2-hydroxyethyl)-1H-imidazole 
• 1571145-65-7 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-imidazole 
• 74294-62-5 4-(2-Azido-ethyl)-1-(toluene-4-sulfonyl)-1H-imidazole 
• 56-92-8 histamine dichloride 
• 645-65-8 2-(1H-imidazol-4-yl)acetic acid 
• 74294-60-3 NO-bis-p-tolylsulphonylhistaminol 
• 74294-66-9 Phenyl-carbamic acid 2-(1H-imidazol-4-yl)-ethyl ester 
• 13518-55-3 4-(2-chloroethyl)-1H-imidazole 

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