1072-62-4

Basic information

• Product Name: 2-Ethylimidazole
• Synonyms: 2-ethvllmidazole;2-ethyl-1h-imidazol;Imidazole, 2-ethyl-;RESICURE(TM) NO 45;2-ethyl-1h-imidazole;2EMI;2-ETHYLIMIDAZOLE;2-ETHYLIMIDAZOLE 98+%
• CAS NO: 1072-62-4
• Molecular Formula: C₅H₈N₂
• Molecular Weight: 96.13
• EINECS: 214-011-5
• Product Categories: Imidaxoles;Building Blocks;Heterocyclic Building Blocks;Imidazoles
• Mol File: 1072-62-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 78-81 °C(lit.)
• Boiling Point: 268 °C(lit.)
• Flash Point: 159 °C
• Appearance: White to slightly yellow flakes
• Density: 1.5519 (rough estimate)
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.38±0.10(Predicted)
• Water Solubility: Soluble in water (617 g/L at 20°C)
• BRN: 106381
• CAS DataBase Reference: 2-Ethylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethylimidazole(1072-62-4)
• EPA Substance Registry System: 2-Ethylimidazole(1072-62-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1072-62-4(Hazardous Substances Data)

Usage

Chemical Properties

White to slightly yellow flakes

Uses

Different sources of media describe the Uses of 1072-62-4 differently. You can refer to the following data:
1. 2-Ethylimidazole is a selective catalyst for epoxy and urethanes reactions. 2-Ethylimidazole is used for two components epoxy systems; for modification of epoxy resins and for preparation of polyurethanes. 2-Ethylimidazole has been used as internal standard in the quantification of 4-(5-)methylimidazole (4MI) in coffee by GC-MS method. Reactions of [RuH(CO)CI(PPh3)3] have been carried out with imidazole, 2-methylimidazole, 2-ethylimidazole and pyrazole in the presence of suitable anions [BF4- ,BPh4-,ClO4-,&PF6-] The reaction products are found to be cationic and have been characterized by elemental analyses, IR, UV/vis and NMR spectral studies. Microwave plasma reaction of 2-ethylimidazole on poly(dimethylsiloxane) surface has been investigated.
2. 2-Ethylimidazole is used as internal standard in the quantification of 4-(5-)methylimidazole (4MI) in coffee by GC-MS method. It is a versatile intermediate used as a building block for active ingredients as well as in epoxy curing.
3. 2-Ethylimidazole has been used as internal standard in the quantification of 4-(5-)methylimidazole (4MI) in coffee by GC-MS method.

General Description

Microwave plasma reaction of 2-ethylimidazole on poly(dimethylsiloxane) surface has been investigated.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C5H8N2/c1-2-5-6-3-4-7-5/h3-4H,2H2,1H3,(H,6,7)

Synthetic route

2-ethyl-4,5-dihydro-1H-imidazole (930-52-9) → 2-Ethylimidazole (1072-62-4)

Conditions	Yield
With potassium permanganate; formic acid for 10h; Heating;	90.3%
With Pt/Al2O3; hydrogen at 425℃;

(3aα,4α,7α,7aα)-2-ethyl-3a,4,7,7a-tetrahydro-4,7-methano-1H-benzimidazole → 2-Ethylimidazole (1072-62-4)

Conditions	Yield
In decalin at 195℃; for 2h;	60%

N-Ethylimidazole (7098-07-9) → 2-Ethylimidazole (1072-62-4)

Conditions	Yield
beim Durchleiten durch ein auf Rotglut erhitztes Glasrohr;

N-Ethylimidazole (7098-07-9) → 2-Ethylimidazole (1072-62-4) + hydrogen cyanide (74-90-8)

Conditions	Yield
beim Durchleiten durch ein rotgluehendes Rohr;

2-ethyl-1H-imidazole-4,5-dicarboxylic acid (58954-22-6) → 2-Ethylimidazole (1072-62-4)

Glyoxal (131543-46-9) + propionaldehyde (123-38-6) → 2-Ethylimidazole (1072-62-4)

Conditions	Yield
With ammonia; water
at 0 - 25℃; for 24h;

propionic acid (802294-64-0) + ethylenediamine (107-15-3) → 2-Ethylimidazole (1072-62-4)

Conditions	Yield
With hydrogen; Pt/Al2O3; AP-64K platinum-alumina catalyst at 400℃;

2-ethyl-imidazole-dicarboxylic acid-(4.5) → 2-Ethylimidazole (1072-62-4)

1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (174899-82-2) → 1-methyl-1H-imidazole (616-47-7) + 2-Ethylimidazole (1072-62-4) + N-Ethylimidazole (7098-07-9) + 2-methylimidazole (693-98-1)

Conditions	Yield
Pyrolysis; Further byproducts given. Title compound not separated from byproducts;

C7H16N2O2 → 2-Ethylimidazole (1072-62-4)

Conditions	Yield
Stage #1: C7H16N2O2 With thioacetamide In methanol at 0 - 45℃; Stage #2: With hydrogenchloride In methanol at 0 - 80℃;

2-Ethylimidazole (1072-62-4) → 2-ethyl-4,5-diiodo-1H-imidazole (870704-53-3)

Conditions	Yield
With iodine; sodium carbonate In 1,4-dioxane; water at 20℃;	99%
With iodine; sodium carbonate In 1,4-dioxane; water at 20℃; for 24h;	92%
With iodine; sodium carbonate In 1,4-dioxane; water at 20℃; for 24h; Inert atmosphere;	92%

2-Ethylimidazole (1072-62-4) → sodium 2-ethylimidazolide

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran at 20℃; for 2h;	99%

2-Ethylimidazole (1072-62-4) + methyl iodide (74-88-4) → 2-ethyl-1,3-dimethyl-imidazolium; iodide (86173-30-0)

Conditions	Yield
With potassium carbonate sesquihydrate In chloroform at 20℃; for 144h;	98%

2-Ethylimidazole (1072-62-4) + allyl alcohol (107-18-6) → 1-allyl-2 ethylimidazole (14967-24-9)

Conditions	Yield
With 2,3,4,5,6-pentafluorophenol; briphos; bis(dibenzylideneacetone)-palladium(0) In dichloromethane at 30℃; for 24h; Inert atmosphere;	98%

2-Ethylimidazole (1072-62-4) + ethyl iodide (75-03-6) → C9H17N2(1+)*I(1-)

Conditions	Yield
With potassium carbonate sesquihydrate In chloroform at 20℃; for 144h;	98%

2-Ethylimidazole (1072-62-4) + acetic acid (64-19-7) → 2-ethylimidazolium acetate

Conditions	Yield
In dichloromethane at 20℃; for 0.833333h;	97%

2-Ethylimidazole (1072-62-4) + zinc(II) oxide → [zinc(2-ethylimidazole(-H))2]

Conditions	Yield
acetic acid In water at 95℃; for 0.5h; Heating / reflux;	96%
With NH4NO3 or NH4CH3SO3 or (NH4)2SO4 In further solvent(s) solvent N,N-diethylformamide, 1:2 mixt. of ZnO and imidazole deriv.; ground for 30 min in Retsch MM200 mill (stainless steel jar, two 7 mm diam.stainless steel balls) at 30 Hz; XRD;
With (NH4)2SO4 or none In neat (no solvent) 1:2 mixt. of ZnO and imidazole deriv.; ground for 30 min in Retsch MM200mill (stainless steel jar, two 7 mm diam. stainless steel balls) at 30 Hz; XRD;	0%

2-Ethylimidazole (1072-62-4) → 2-ethylimidazolium pentaborate

Conditions	Yield
With boric acid In methanol; water for 1h;	96%

2-Ethylimidazole (1072-62-4) → 2-ethyl-1H-imidazolium hydrogen sulfate

Conditions	Yield
With sulfuric acid In dichloromethane at 25℃; for 0.833333h;	96%

2-Ethylimidazole (1072-62-4) + dimethyl acetylenedicarboxylate (762-42-5) + triphenylphosphine (603-35-0) → dimethyl 2-(2-ethylimidazol-1-yl)-3-(triphenylphosphoranylidene)butanedioate

Conditions	Yield
In ethyl acetate at 20℃; for 24h;	95%

2-Ethylimidazole (1072-62-4) + 4-Fluoronitrobenzene (350-46-9) → 2-ethyl-1-(4-nitro)phenyl-1H-imidazole

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 90℃; for 15h;	94%
With sodium hydroxide In dimethyl sulfoxide at 90℃; for 5h;	84.9%

2-Ethylimidazole (1072-62-4) → 2-ethyl-3,5-dihydroimidazol-4-one

Conditions	Yield
With perchloric acid; chloramine-B In water at 29.84℃; Kinetics; Temperature; Green chemistry;	93.6%

2-Ethylimidazole (1072-62-4) + triphenylphosphine (603-35-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 2-(2-ethylimidazol-1-yl)-3-(triphenylphosphoranylidene)butanedioate

Conditions	Yield
In ethyl acetate at 20℃; for 24h;	93%

2-Ethylimidazole (1072-62-4) + Di-tert-butyl acetylenedicarboxylate (66086-33-7) + triphenylphosphine (603-35-0) → di-tert-butyl 2-(2-ethylimidazol-1-yl)-3-(triphenylphosphoranylidene)butanedioate

Conditions	Yield
In ethyl acetate at 20℃; for 24h;	92%

2-bromo-pyridine (109-04-6) + 2-Ethylimidazole (1072-62-4) → C10H11N3

Conditions	Yield
With copper(l) iodide; N-hydroxyphthalimide; sodium methylate In dimethyl sulfoxide at 110℃; for 24h;	92%
With dimethylenecyclourethane; copper(l) iodide; sodium methylate In dimethyl sulfoxide at 80℃; for 12h;	81%

2-Ethylimidazole (1072-62-4) + benzyl chloride (100-44-7) → 1-benzyl-2-ethyl-1H-imidazole (39269-64-2)

Conditions	Yield
Stage #1: 2-Ethylimidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at -15℃; for 0.5h; Inert atmosphere; Stage #2: benzyl chloride In N,N-dimethyl-formamide; mineral oil at -15 - -5℃; for 3h; Inert atmosphere;	92%

2-Ethylimidazole (1072-62-4) + methyl chloroformate (79-22-1) → methyl 2-ethyl-1-imidazolecarboxylate (1344736-09-9)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;	91%

2-Ethylimidazole (1072-62-4) → potassium 2-ethylimidazolide

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	91%

2-Ethylimidazole (1072-62-4) + 7-fluoro-6-nitro-1,4-dihydroquinoxaline-2,3-dione (143151-09-1) → 6-(2-Ethyl-imidazol-1-yl)-7-nitro-1,4-dihydro-quinoxaline-2,3-dione

Conditions	Yield
at 140 - 150℃;	90%

2-Ethylimidazole (1072-62-4) + methyl iodide (74-88-4) → 1-methyl-2-ethylimidazole (5709-61-5)

Conditions	Yield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene at 20℃; for 0.25h;	89%
at 30℃; for 8h;	70%
Stage #1: 2-Ethylimidazole With sodium hydride In toluene at 20℃; for 1h; Stage #2: methyl iodide In toluene at 20℃; for 5h;	49%

2-Ethylimidazole (1072-62-4) + Ag(1+)*C11H7F3N3O2(1-) → C16H15AgF3N5O2

Conditions	Yield
In acetonitrile for 1h;	89%

2-Ethylimidazole (1072-62-4) + AgCl(PPh3)3 (17116-26-6) → [AgCl(2-ethylimidazole)(PPh3)2] (883992-34-5)

Conditions	Yield
In diethyl ether addn. of imidazole deriv. to suspn. of silver compd. in ether, stirring at room temp. for 24 h; filtration, washing with ether, recrystn. (CHCl3), elem. anal.;	88%

2-Ethylimidazole (1072-62-4) + 1-bromo-1-octyne (38761-67-0) → (Z)-1-(1-bromo-1-octen-2-yl)-2-ethylimidazole (1349701-68-3)

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 24h; stereoselective reaction;	88%

2-Ethylimidazole (1072-62-4) + C19H17ClN2O3S → 2-(2-ethyl-1H-imidazol-1-yl)-1-(9-(phenylsulfonyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 1h;	88%

2-Ethylimidazole (1072-62-4) + 2-chloropyrimidine (1722-12-9) → 2-(2-ethyl-1H-imidazol-1-yl)pyrimidine

Conditions	Yield
Stage #1: 2-Ethylimidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃;	88%

2-Ethylimidazole (1072-62-4) + 1-(chloromethoxy)butane (2351-69-1) → 1-butoxymethyl-2-ethylimidazole (591235-24-4)

Conditions	Yield
Stage #1: 1-(chloromethoxy)butane With triethylamine In toluene at 20℃; for 0.25h; Stage #2: 2-Ethylimidazole In toluene Heating;	85%

2-Ethylimidazole (1072-62-4) + 3-(3-bromomethylphenyl)-5-isobutylthiophene-2-(N-tert-butyl)sulfonamide (912942-73-5) → 3-(3-(2-ethylimidazol-1-ylmethyl)phenyl)-5-isobutylthiophene-2-(N-tert-butyl)sulfonamide (912962-78-8)

Conditions	Yield
In 1,4-dioxane at 80℃; for 1h;	85%
In 1,4-dioxane at 80℃; for 1h;	85%

2-Ethylimidazole (1072-62-4) + thallium chloride + chlorine (7782-50-5) → TlCl3(N2C3H3(C2H5))2 (132829-18-6)

Conditions	Yield
In acetonitrile bubbling Cl2 through suspension of TlCl (4.2 mmol) and 2-ethylimidazole (9.0 mmol) in CH3CN until all the TlCl is dissolved; concg.;; pptn.; elem. anal.;;	85%

2-Ethylimidazole (1072-62-4) + phenylboronic acid (98-80-6) → 2-ethyl-1-phenyl-1H-imidazole

Conditions	Yield
With [CuI2(3,2'-pypzpym)]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 24h; Chan-Lam Coupling; Green chemistry;	85%
With 2,5-dimethoxybenzaldene-4-phenylthiosemicarbazone; copper(II) acetate monohydrate; triethylamine In water; N,N-dimethyl-formamide at 20℃; for 20h; Chan-Lam Coupling;	81%

Upstream product

• 58954-22-6 2-ethyl-1H-imidazole-4,5-dicarboxylic acid 
• 131543-46-9 Glyoxal 
• 123-38-6 propionaldehyde 
• 174899-82-2 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 
• 802294-64-0 propionic acid 
• 107-15-3 ethylenediamine 
• 7098-07-9 N-Ethylimidazole 
• 930-52-9 2-ethyl-4,5-dihydro-1H-imidazole 

Downstream Products

• 115178-32-0 (6aR,9S,10aR)-9-(2-Ethyl-imidazol-1-ylmethyl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline 
• 192804-82-3 4-[4-(2-ethyl-1H-imidazol-1-yl)butyl]phenylacetic acid 
• 170105-17-6 4-(2-ethyl-imidazol-1-yl)-2,2-diphenyl-butyronitrile 
• 471-46-5 Oxalamide 
• 501443-53-4 2-ethyl-1-(2-nitro-3-thienyl)-1H-imidazole 
• 960239-79-6 C₂₉H₄₀N₂O 
• 111903-10-7 cobalt(II) 5β,15β-bis{2-(2,2-dimethylpropanamido)phenyl}-10α,20α-(nonanediamidodi-o-phenylene)porphyrin 2-ethylimidazole complex 
• 111903-09-4 cobalt(II) 5β,15β-bis(2-pentanamidophenyl)-10α,20α-(nonanediamidodi-o-phenylene)porphyrin 2-ethylimidazole complex 
• 111903-08-3 cobalt(II) 5,15-diphenyl-10α,20.alpha-(nonanediamidodi-o-phenylene)porphyrin 2-ethylimidazole complex 
• 97178-22-8 [Rh(CO)(2-ethylimidazole)(triphenylphosphine)2][BPh₄] 
• 97178-34-2 [Rh(CO)(2-ethylimidazole)(triphenylphosphine)2][ClO₄] 
• 80297-39-8 Co((ONC(C₆H₅)C(C₆H₅)NO)2(BF₂)2)(C₃H₃N₂CH₂CH₃) 
• 161128-18-3 bis(2-ethylimidazole)tetraphenylporphyrinatocobalt(III) chloride 
• 1161830-68-7 5-(2-ethyl-imidazol-1-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl ester 

Related news

Vibrational spectroscopic (FTIR and FT-Raman), first-order hyperpolarizablity, HOMO, LUMO, NBO, Mulliken charge analyses of 2-Ethylimidazole (cas 1072-62-4) based on Hartree–Fock and DFT calculations07/27/2019

The FTIR and FT-Raman spectra of 2-ethylimidazole (2EIDZ) have been recorded in the region 4000–400 cm−1 and 3500–50 cm−1, respectively. Utilizing the observed FTIR and FT-Raman data, a complete vibrational assignment and analysis of the fundamental modes of the compound were carried out. The ...detailed

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