2-Ethyl-4-methylimidazole supplier

Name
2-Ethyl-4-methylimidazole
EINECS 213-234-5
CAS No. 931-36-2
Article Data12
CAS DataBase
Density 1 g/cm³
Solubility 210 g/L (20 ºC)
Melting Point 47-54 °C(lit.)
Formula C₆H₁₀N₂
Boiling Point 276 °C at 760 mmHg
Molecular Weight 110.159
Flash Point 137.8 °C
Transport Information
Appearance clear yellow viscous liquid after melting
Safety 26-39
Risk Codes 22-41
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Imicure EMI 24;Epicure EMI 24;1H-Imidazole,2-ethyl-4-methyl-;2-ethyl-4-methyl-3H-imidazole;Imidazole, 2-ethyl-4-methyl-;4-Methyl-2-ethylimidazole;Imidazole, 2-ethyl-4-methyl- (8CI);2-Ethyl-4-methyl imidazole;2-Ethyl-4-methyl-1H-imidazole;EMI 70;Curezol 2E4MZ;1H-Imidazole, 2-ethyl-4-methyl-;
PSA 28.68000
LogP 1.28050

Synthetic route

: 931-35-1
2-ethyl-4-methyl-1-imidazoline

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

Conditions

Conditions	Yield
With potassium hydroxide In water at 190℃; for 0.25h;	90.4%
With 5%-palladium/activated carbon at 140℃; for 10h; Reagent/catalyst; Temperature;	86.8%

: 123-38-6
propionaldehyde

: 598-31-2
1-bromoacetone

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

Conditions

Conditions	Yield
With ammonium hydroxide; copper diacetate

: 66675-19-2
N,N'-(methyl-ethenediyl)-bis-benzamide

: 123-62-6
propionic acid anhydride

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

Conditions

Conditions	Yield
at 180℃; im Rohr;

: 802294-64-0
propionic acid

: 78-90-0, 10424-38-1
1,2-diaminopropan

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

Conditions

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

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 403-43-0
4-fluorobenzoyl chloride

: 90172-65-9
2-ethyl-1-(p-fluorophenylcarbonyl)-4-methylimidazole

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In chloroform-d1	100%

: 50-00-0
formaldehyd

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 94887-76-0
2-ethyl-4-methyl-5-hydroxymethyl-imidazole

Conditions

Conditions	Yield
With potassium hydroxide In water at 15 - 25℃; for 28h; pH=12.5; Reagent/catalyst; Time; Mannich Aminomethylation;	98%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 75-03-6
ethyl iodide

: C10H19N2(1+)*I(1-)

Conditions

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

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 618-83-7
5-Hydroxyisophthalic acid

: (x)C6H10N2*C8H6O5

Conditions

Conditions	Yield
In ethyl acetate Reflux;	93%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 2-ethyl-4-methylimidazolium pentaborate

Conditions

Conditions	Yield
With boric acid In methanol; water for 1h;	92%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 140-88-5
ethyl acrylate

: ethyl 3-(2-ethyl-4-methyl-1H-imidazol-1-yl)propanoate

Conditions

Conditions	Yield
With C22H48N4(4+)*4HO(1-) In neat (no solvent) at 20℃; for 0.75h; Michael Addition;	92%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 100-11-8
1-bromomethyl-4-nitro-benzene

: C13H15N3O2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 60℃; for 2h;	91%
With potassium carbonate In acetonitrile at 20℃; for 5h;

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 766-97-2
4-n-methylphenylacetylene

: (Z)-2-ethyl-4-methyl-1-(3-methylstyryl)-1H-imidazole

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 120℃; Inert atmosphere; diastereoselective reaction;	89%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 107-13-1
acrylonitrile

: 23996-25-0
3-(2-ethyl-4-methyl-1H-imidazol-1-yl)propanenitrile

Conditions

Conditions	Yield
With C22H48N4(4+)*4HO(1-) In neat (no solvent) at 20℃; for 1.16667h; Michael Addition;	87%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 24424-99-5
di-tert-butyl dicarbonate

: 1299491-23-8
N-(tert-butoxycarbonyl)-2-ethyl-4-methylimidazole

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide for 1h;	86%

: 50-00-0
formaldehyd

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 95684-24-5
bis(2-ethyl-4-methyl-imidazol-5-yl)methane

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 0.0833333h; pH=14;	85%
In methanol	85%

: 50-00-0
formaldehyd

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 95684-24-5
4,4′-methanediylbis(2-ethyl-5-methyl-1H-imidazole)

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃; for 24h;	85%

: 50-00-0
formaldehyd

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 56-40-6
glycine

: N,N-bis(2-ethyl-4-methylimidazo-5-yl-methylene)glycine

Conditions

Conditions	Yield
Stage #1: 2-ethyl-4-methyl-1H-imidazole; glycine With 1H-imidazole In water for 0.166667h; Stage #2: formaldehyd In water for 0.25h; Stage #3: With triethylamine In water at 20℃; for 168h; pH=11 - 12;	85%

...Expand

: 1722-12-9
2-chloropyrimidine

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 2-(2-ethyl-4-methyl-1H-imidazol-1-yl)pyrimidine

Conditions

Conditions	Yield
Stage #1: 2-ethyl-4-methyl-1H-imidazole 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℃;	85%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 1096706-56-7
2-bromo-N-(2-bromoethyl)-N-(2,4-dichlorobenzyl)ethanamine

: 1096706-50-1
N-(2,4-dichlorobenzyl)-2-(2-ethyl-4-methyl-1H-imidazol-1-yl)-N-(2-(2-ethyl-4-methyl-1H-imidazol-1-yl)ethyl)ethanamine

Conditions

Conditions	Yield
Stage #1: 2-ethyl-4-methyl-1H-imidazole With sodium hydride In tetrahydrofuran at 60℃; for 1h; Stage #2: 2-bromo-N-(2-bromoethyl)-N-(2,4-dichlorobenzyl)ethanamine In tetrahydrofuran at 20 - 60℃;	84.8%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 84255-42-5
2-ethyl-4-methylimidazole-5-dithiocarboxylic acid

Conditions

Conditions	Yield
With carbon disulfide; sodium hydroxide In dimethyl sulfoxide	83%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 768-60-5
4-methoxyphenylacetylen

: 1383663-42-0
(Z)-2-ethyl-1-(4-methoxystyryl)-4-methyl-1H-imidazole

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 2h; Inert atmosphere; stereoselective reaction;	82%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 577-19-5
2-nitrophenyl bromide

: 2-ethyl-4-methyl-1-(2-nitrophenyl)-1H-imidazole

Conditions

Conditions	Yield
With copper(l) iodide; 1-Hydroxymethyl-1H-benzotriazole; potassium tert-butylate In dimethyl sulfoxide at 120℃; for 18h; Inert atmosphere;	82%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 137768-73-1
1-isothiocyanatopropa-1,2-diene

A: 1037456-35-1
2-(2-ethyl-4-methylimidazol-1-yl)-5-methylthiazole

B: 1037456-79-3
2-(2-ethyl-4-methylimidazol-1-yl)-5-methylene-4,5-dihydrothiazole

Conditions

Conditions	Yield
In tetrahydrofuran for 1h;	A 80% B 10%

...Expand

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 1493-27-2
ortho-nitrofluorobenzene

: 2-ethyl-4-methyl-1-(2-nitrophenyl)-1H-imidazole

Conditions

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 20℃;	80%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 536-74-3
phenylacetylene

: C14H16N2

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 1.5h; Schlenk technique; Inert atmosphere;	80%

: 1037456-15-7
3-isothiocyanato-4-methoxybuta-1,2-diene

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

A: 1037456-37-3
2-(2-ethyl-4-methylimidazol-1-yl)-4-methoxymethyl-5-methylthiazole

B: 1037456-81-7
2-(2-ethyl-4-methylimidazol-1-yl)-4-methoxymethyl-5-methylene-4,5-dihydrothiazole

Conditions

Conditions	Yield
In tetrahydrofuran for 1h;	A 79% B 3%

...Expand

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 1073-06-9
3-fluorobromobenzene

: 109-63-7
boron trifluoride diethyl etherate

: 2-ethyl-4-methylimidazolium tetrakis(3-fluorophenyl)borate

Conditions

Conditions	Yield
Stage #1: 3-fluorobromobenzene; boron trifluoride diethyl etherate With magnesium In tetrahydrofuran for 1h; Reflux; Stage #2: 2-ethyl-4-methyl-1H-imidazole With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.5h;	79%

...Expand

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 503551-53-9
parthenolide

: C21H30N2O3

Conditions

Conditions	Yield
With methanol at 20℃; for 15h; Michael Addition; diastereoselective reaction;	78%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 105-58-8
Diethyl carbonate

: 56468-51-0
1-ethyl-2-ethyl-4-methylimidazole

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 90℃; for 10h;	78%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 433-27-2
Trifluoroacetaldehyde ethyl hemiacetal

: 1-(2-Ethyl-5-methyl-3H-imidazol-4-yl)-2,2,2-trifluoro-ethanol

Conditions

Conditions	Yield
for 2h; Heating;	76%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 100-44-7
benzyl chloride

: 1-benzyl-2-ethyl-4-methylimidazole

Conditions

Conditions	Yield
With potassium carbonate In chloroform for 8h; Reflux;	75.35%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 197958-29-5
pyridin-2-ylboronic acid

: 1167443-57-3
2-(2-ethyl-4-methyl-1H-imidazol-1-yl)pyridine

Conditions

Conditions	Yield
With 2Na(1+)*CuC6H4(NCHC6H3OO3S)2(2-)=CuC6H4(NCHC6H3ONaO3S)2 In water at 100℃; for 6h;	75%

: 931-36-2
2-ethyl-4-methyl-1H-imidazole

: 89-98-5
2-chloro-benzaldehyde

: {4,4'-((2-chlorophenyl) methylene)bis(2-ethyl-5-methyl-1H-imidazole)}

Conditions

Conditions	Yield
With potassium hydroxide In water at 80℃; for 72h;	75%

2-Ethyl-4-methylimidazole Specification

The 2-Ethyl-4-methylimidazole with CAS registry number of 931-36-2 is also called 1H-Imidazole, 2-ethyl-4-methyl-. The IUPAC name is 2-ethyl-5-methyl-1H-imidazole. Its EINECS registry number is 213-234-5. In addition, the formula is C₆H₁₀N₂ and the molecular weight is 110.157. It belongs to the classes of Industrial/Fine Chemicals; Imidazoles; Heterocyclic Compounds; Imidaxoles; Building Blocks; Heterocyclic Building Blocks. It is a kind of light yellow crystalline and will become clear yellow viscous liquid after melting. What's more, it should be stored in a airtight, cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 0.62; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.8; (4)ACD/LogD (pH 7.4): -0.69; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 2.5; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 17.82 Å²; (13)Index of Refraction: 1.514; (14)Molar Refractivity: 33.15 cm³; (15)Molar Volume: 110 cm³; (16)Polarizability: 13.14 ×10^-24cm³; (17)Surface Tension: 39.1 dyne/cm; (18)Density: 1 g/cm³; (19)Flash Point: 137.8 °C; (20)Enthalpy of Vaporization: 49.38 kJ/mol; (21)Boiling Point: 276 °C at 760 mmHg; (22)Vapour Pressure: 0.00827 mmHg at 25°C.

Preparation of 2-Ethyl-4-methylimidazole: it can be prepared by 2-ethyl-4-methylimidazoleoline. This reaction will need solvent nickel. The reaction time is 8 hours at the temperature of 180 °C by stirring. At last, you should recover nickel by filtration, vacuum distillation the filtrate and collect fraction of 150-160 °C(1.33kPa). The yield is about 70%-80%.

2-Ethyl-4-methylimidazole can be prepared by 2-ethyl-4-methylimidazoleoline.

Uses of 2-Ethyl-4-methylimidazole: it is a kind of excellent temperature curing agent which can prepare epoxy glue and epoxy silicone resin coating. It has good miscibility with E-51 epoxy resin and F44 phenolic resin. There is no volatile compounds at room temperature. And it is odor, low toxicity. What's more, it has a longer period of application. It also can be used for casting, adhesive, impregnated and laminated materials. What's more, it can react with 4-fluoro-benzoyl chloride to get (2-ethyl-4-methyl-imidazol-1-yl)-(4-fluoro-phenyl)-methanone. This reaction will need reagent 1,4-diazabicyclo<2.2.2>octane(DABCO) and solvent CDCl₃. The yield is about 100%.

2-Ethyl-4-methylimidazole can react with 4-fluoro-benzoyl chloride to get (2-ethyl-4-methyl-imidazol-1-yl)-(4-fluoro-phenyl)-methanone.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and has risk of serious damage to eyes. You should wear eye/face protection when you are using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: n1cc(nc1CC)C
(2)InChI: InChI=1/C6H10N2/c1-3-6-7-4-5(2)8-6/h4H,3H2,1-2H3,(H,7,8)
(3)InChIKey: ULKLGIFJWFIQFF-UHFFFAOYAC

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	intraperitoneal	250mg/kg (250mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Veterinary and Human Toxicology. Vol. 41, Pg. 363, 1999.

Product Name

2-Ethyl-4-methylimidazole

Synthetic route

2-Ethyl-4-methylimidazole Specification

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