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931-36-2

Basic Information
CAS No.: 931-36-2
Name: 2-Ethyl-4-methylimidazole
Article Data: 12
Molecular Structure:
Molecular Structure of 931-36-2 (2-Ethyl-4-methylimidazole)
Formula: C6H10N2
Molecular Weight: 110.159
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-;
EINECS: 213-234-5
Density: 1 g/cm3
Melting Point: 47-54 °C(lit.)
Boiling Point: 276 °C at 760 mmHg
Flash Point: 137.8 °C
Solubility: 210 g/L (20 ºC)
Appearance: clear yellow viscous liquid after melting
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-41
Safety: 26-39
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In chloroform-d1100%
50-00-0

formaldehyd

931-36-2

2-ethyl-4-methyl-1H-imidazole

94887-76-0

2-ethyl-4-methyl-5-hydroxymethyl-imidazole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In ethyl acetate Reflux;93%
931-36-2

2-ethyl-4-methyl-1H-imidazole

2-ethyl-4-methylimidazolium pentaborate

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