2-Methylimidazole supplier

Name
2-Methylimidazole
EINECS 211-765-7
CAS No. 693-98-1
Article Data89
CAS DataBase
Density 1.062 g/cm³
Solubility Soluble in water and ethanol.
Melting Point 142-143 °C(lit.)
Formula C₄H₆N₂
Boiling Point 267 °C at 760 mmHg
Molecular Weight 82.105
Flash Point 144.9 °C
Transport Information UN 3259 8/PG 2
Appearance white to light yellow crystalline powder
Safety 26-36/37/39-45-25
Risk Codes 26-36/37/39-45-25
Molecular Structure
Hazard Symbols C
Synonyms 2-Methyl imidazole;2-methyl-1H-imidazole;Imidazole, 2-methyl-;2,4-diamino-6-[2'-methyl imidazolyl-(1')]-ethyl-s-triazine;1H-Imidazole, 2-methyl-;Curezol 2MZ;1H-Imidazole,2-methyl-;1H-imidazole, 1-butyl-;
PSA 28.68000
LogP 0.71810

Synthetic route

: 13750-62-4
N-benzyl-2-methylimidazole

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	97%
With potassium tert-butylate; oxygen; dimethyl sulfoxide at 0℃; for 0.25h;	85%
With ammonia; sodium

: 534-26-9
lysidine

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With sodium periodate; [N,N'-bis(salicylidene)-o-phenylenediaminato]manganese(III) chloride In water; acetonitrile at 20℃; for 0.416667h;	93%
With aluminum oxide; potassium permanganate In acetonitrile at 20℃; for 0.25h;	92%
With sodium periodate; (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride In water; acetonitrile at 20℃; for 5h;	92%

: 16681-56-4
2-bromo-1H-imidazole

: 823-96-1
Trimethylboroxine

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With C70H40Cl2F68N2O6Pd2; tetrabutylammomium bromide; potassium carbonate In water at 140℃; for 0.416667h; Suzuki-Miyaura reaction; Microwave irradiation;	93%

: 131543-46-9
Glyoxal

: 7664-41-7
ammonia

: 78-84-2
isobutyraldehyde

: 74-89-5
methylamine

A: 22509-02-0
2-isopropyl-1-methyl-1(H)-imidazole

B: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
Stage #1: ammonia; isobutyraldehyde; methylamine In methanol; water at 25℃; for 1h; Stage #2: Glyoxal; ammonia at 25℃; for 1h;	A 88% B 3%

...Expand

: 131543-46-9
Glyoxal

: 75-07-0
acetaldehyde

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With ammonium bicarbonate In water at 15 - 30℃; for 0.0208333h; Temperature; Microwave irradiation;	87.1%
With ammonium hydroxide at 20℃; for 2h;	8.9 g
at 0 - 25℃; for 24h;

: 131543-46-9
Glyoxal

: 75-07-0
acetaldehyde

: 74-89-5
methylamine

A: 616-47-7
1-methyl-1H-imidazole

B: 1739-84-0
1,2-dimethyl-1H-imidazole

C: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With ammonium hydroxide In water at 25 - 70℃; under 225023 Torr; Pressure; Temperature;	A 6.27% B 85.1% C 6.59%

...Expand

: (3aα,4α,7α,7aα)-2-methyl-3a,4,7,7a-tetrahydro-4,7-methano-1H-benzimidazole

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
In decalin at 195℃; for 2h;	79%

: 110-85-0
piperazine

A: 288-32-4
1H-imidazole

B: 290-37-9
1,4-pyrazine

C: 616-47-7
1-methyl-1H-imidazole

D: 109-08-0
2-Methylpyrazine

E: 13925-00-3
2-ethylpyrazine

F: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
Pt-Al2O3-In2O3-Re at 400℃; Product distribution; variation of catalyst, temperature;	A n/a B 78.7% C n/a D 1.6% E 3.5% F n/a

...Expand

: 28227-42-1, 30834-74-3
1,4-di-tert-butyl-1,4-diazabutadiene

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
In diethyl ether at 800℃; under 0.0003 Torr;	67%

: 79-20-9
acetic acid methyl ester

: 107-15-3
ethylenediamine

A: 534-26-9
lysidine

B: 21202-52-8
1-ethyl-2-methylimidazole

C: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
Pt/Al2O3 at 400℃; under 760 Torr;	A 7% B 10.5% C 62.5%

...Expand

: 79-20-9
acetic acid methyl ester

: 107-15-3
ethylenediamine

A: 534-26-9
lysidine

B: 1739-84-0
1,2-dimethyl-1H-imidazole

C: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
Pt/Al2O3 at 400℃; under 760 Torr;	A 6.6% B 15.2% C 61.1%
Pt/Al2O3 at 360℃; under 760 Torr;	A 15.5% B 9% C 58.5%
Pt/Al2O3 at 360℃; under 760 Torr; Product distribution; var. temp.;

...Expand

: 28227-41-0, 24764-90-7
1,4-diisopropyl-1,4-diazabuta-1,3-diene

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
In diethyl ether at 800℃; under 0.0003 Torr;	43%

: 131543-46-9
Glyoxal

: 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol

: 75-07-0
acetaldehyde

A: (S)-2-(1H-imidazol-1-yl)-1-phenylethanol

B: (S)-2-(2-Methyl-imidazol-1-yl)-1-phenyl-ethanol

C: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With ammonium acetate In methanol; water for 5h; Heating;	A n/a B 41% C n/a

...Expand

: 2026-48-4
(S)-valinol

: 131543-46-9
Glyoxal

: 75-07-0
acetaldehyde

A: 909026-22-8
(S)-3-Methyl-2-(2-methyl-imidazol-1-yl)-butan-1-ol

B: 693-98-1
2-methylimidazole

C: 497830-20-3
1-[(2S)-1-methoxy-3-methylbutan-2-yl]-1H-imidazole

Conditions

Conditions	Yield
With ammonium acetate In methanol; water for 5h; Heating;	A 34% B n/a C n/a

...Expand

: 151-56-4
ethyleneimine

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With zinc oxide-chromium oxide-iron oxide-aluminium oxide; ammonia; hydrogen at 400℃;

: 616-47-7
1-methyl-1H-imidazole

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
beim Gluehen der Zinkchlorid-Doppelsalze mit Calciumoxyd;

: 616-47-7
1-methyl-1H-imidazole

A: 693-98-1
2-methylimidazole

B: 74-90-8
hydrogen cyanide

Conditions

Conditions	Yield
beim Durchleiten durch ein rotgluehendes Rohr;
beim Durchleiten durch ein rotgluehendes Rohr;

: 21202-52-8
1-ethyl-2-methylimidazole

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
beim Gluehen der Zinkchlorid-Doppelsalze mit Calciumoxyd;

: 21202-52-8
1-ethyl-2-methylimidazole

A: 693-98-1
2-methylimidazole

B: 74-90-8
hydrogen cyanide

Conditions

Conditions	Yield
beim Durchleiten durch ein gluehendes Rohr;

: 23012-17-1
2-methyl-1,3-oxazol-4-carboxylic acid

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With ammonium hydroxide at 150℃;

: 4897-22-7
5-chloro-1-ethyl-2-methyl-1H-imidazole

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
beim Gluehen der Zinkchlorid-Doppelsalze mit Calciumoxyd;

: 5313-35-9
2-Methylimidazole-4,5-dicarboxylic acid

: 693-98-1
2-methylimidazole

: 131543-46-9
Glyoxal

: 58052-80-5, 76231-37-3
2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With water
In water-d2 for 0.00555556h; Sonication;

: 64-19-7
acetic acid

: 107-15-3
ethylenediamine

: 693-98-1
2-methylimidazole

Conditions

Conditions	Yield
With hydrogen; Pt/Al2O3; AP-64K platinum-alumina catalyst at 400℃;
With aluminium oxide contact; Pt/Al2O3; hydrogen at 430 - 440℃;

: 534-26-9
lysidine

A: 21202-52-8
1-ethyl-2-methylimidazole

B: 693-98-1
2-methylimidazole

C: 1001-53-2
monoacetylaminoethylamine

D: 4814-93-1
1-ethyl-2-methyl-4,5-dihydro-1H-imidazole

Conditions

Conditions	Yield
With water; AP-64k at 330℃; for 0.6h; Product distribution; also in the molten state; var. temp. and contact time;

...Expand

: 930-61-0
2,4-dimethyl-2-imidazoline

: 67-66-3
chloroform

A: 14331-54-5
2,4-dimethylpyrimidine

B: 4994-86-9
4-chloro-2-methylpyrimidine

C: 693-98-1
2-methylimidazole

D: 75712-73-1
5-Chloro-2,4-dimethylpyrimidine

Conditions

Conditions	Yield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 930-61-0
2,4-dimethyl-2-imidazoline

: 67-66-3
chloroform

A: 123-32-0
2,5-dimethyl-pyrazine

B: 4994-86-9
4-chloro-2-methylpyrimidine

C: 693-98-1
2-methylimidazole

D: 75712-73-1
5-Chloro-2,4-dimethylpyrimidine

Conditions

Conditions	Yield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 930-61-0
2,4-dimethyl-2-imidazoline

: 67-66-3
chloroform

A: 4994-86-9
4-chloro-2-methylpyrimidine

B: 4472-45-1
4-chloro-2,6-dimethylpyrimidine

C: 693-98-1
2-methylimidazole

D: 75712-73-1
5-Chloro-2,4-dimethylpyrimidine

Conditions

Conditions	Yield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 693-98-1
2-methylimidazole

: 73746-44-8
4,5-diiodo-2-methyl-1H-imidazole

Conditions

Conditions	Yield
With iodine; sodium carbonate In 1,4-dioxane; water at 20℃; for 24h;	100%
With water; iodine; sodium carbonate In 1,4-dioxane at 20℃; for 24h; Iodination;	98%
With iodine; silver(I) acetate In dichloromethane at 50℃; Inert atmosphere;	93%

: 693-98-1
2-methylimidazole

: 403-43-0
4-fluorobenzoyl chloride

: 90172-64-8
1-(p-fluorophenylcarbonyl)-2-methylimidazole

Conditions

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

: 693-98-1
2-methylimidazole

: 84446-19-5
1-oxo-11-(2'-chloroacetyl)-5,11-dihydro-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one

: 84446-13-9
1-oxo-5,11-dihydro-11-(2''-methylimidazol-1''-yl)acetyl-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one

Conditions

Conditions	Yield
In toluene at 80℃; for 2h;	100%

: 1722-12-9
2-chloropyrimidine

: 693-98-1
2-methylimidazole

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

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; 2-aminopyrimidine-4,6-diol; copper(I) bromide at 145 - 150℃; for 24h;	100%
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride at 140 - 145℃; for 24h;	98%
Stage #1: 2-methylimidazole 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℃;	89%
With potassium phosphate; benzoin oxime; copper diacetate In dimethyl sulfoxide at 80℃; Inert atmosphere;	80%
With copper; caesium carbonate; methyl-alpha-D-glucopyranoside In water; dimethyl sulfoxide at 110℃; for 14h; Sealed tube; Green chemistry;	80%

: 693-98-1
2-methylimidazole

: 76-83-5
trityl chloride

: 23593-68-2
2-methyl-1-tritylimidazole

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%
With triethylamine In acetonitrile at 20℃; for 18.3333h;	97%
With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;	95%

: 403487-49-0
C26H31ClN2O5S

: 693-98-1
2-methylimidazole

: C29H33ClN4O2

Conditions

Conditions	Yield
Stage #1: 2-methylimidazole With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.333333h; Stage #2: C26H31ClN2O5S In DMF (N,N-dimethyl-formamide) at 20℃;	100%

: ammonium hexafluorophosphate

: 693-98-1
2-methylimidazole

: Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2O)2(2+)*2PF6(1-)=[Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2O)2](PF6)2

: Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(C3H3N2CH3)2(2+)*2PF6(1-)=[Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(C3H3N2CH3)2](PF6)2

Conditions

Conditions	Yield
In methanol N2; Co comp. dissolved under reflux, to a soln. added an excess of ligand, refluxed for 25 min, a soln. of NH4PF6 added; ppt. filtered, washed copiously (diethyl ether), dried (vac.); elem. anal.;	99%

...Expand

: 693-98-1
2-methylimidazole

: 14741-28-7
[copper(I)(triphenylphosphine)4](perchlorate)

: 182012-99-3
[(triphenylphosphine)2(2-methylimidazole)2Cu]ClO4

Conditions

Conditions	Yield
In diethyl ether large excess of N-ligand, stirring for 3 h (pptn.); collection (filtration), washing (ether); elem. anal.;	99%

: 693-98-1
2-methylimidazole

: Cu(C6H5C5H2N(C5H3NN(CH3)NCH)2)(H2O)2(2+)*2PF6(1-)=[Cu(C6H5C5H2N(C5H3NN(CH3)NCH)2)(H2O)2](PF6)2

: [Cu(PhC5H2N(C5H3NN(CH3)NCH)2)(2-methylimidazole)](PF6)2

Conditions

Conditions	Yield
In methanol excess of N-compd. was added to hot MeOH soln. of Cu-complex, reflux for25 min, concd. MeOH soln. of NH4PF6 was added; ppt. was collected, washed with copious amt. of Et2O, dried in vac., elem. anal.;	99%

: 693-98-1
2-methylimidazole

: 764-09-0
chlorosulfuric acid 2,2,2-trichloroethyl ester

: 1185733-66-7
2,2,2-trichloroethyl 2-methyl-1H-imidazole-1-sulfonate

Conditions

Conditions	Yield
for 2h; Inert atmosphere;	99%
In tetrahydrofuran at 0 - 20℃; for 16h;	95%
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	88%

: 693-98-1
2-methylimidazole

: 16419-60-6
2-Methylphenylboronic acid

: 2-methyl-1-o-tolyl-1H-imidazole

Conditions

Conditions	Yield
Stage #1: With N,N,N,N,-tetramethylethylenediamine; copper(II) nitrate In methanol at 20℃; for 0.25h; Stage #2: 2-methylimidazole; 2-Methylphenylboronic acid With oxygen In methanol at 20℃; under 760.051 Torr; for 24h;	99%
With Cu-exchanged fluoroapatite; air In methanol at 20℃; for 12h;	87%

: 693-98-1
2-methylimidazole

: 5720-06-9
2-Methoxyphenylboronic acid

: 1-(2-methoxyphenyl)-2-methyl-1H-imidazole

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; oxygen; copper(II) nitrate In methanol at 20℃; under 760.051 Torr; for 48h;	99%
With Cu-exchanged fluoroapatite; air In methanol at 20℃; for 12h;	89%

: 693-98-1
2-methylimidazole

: 133730-34-4
2,4-dimethoxyphenylboronic acid

: 1192014-98-4
1-(2,4-dimethoxyphenyl)-2-methyl-1H-imidazole

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; oxygen; copper(II) nitrate In methanol at 20℃; under 760.051 Torr; for 48h;	99%
With Cu-exchanged fluoroapatite; air In methanol at 20℃; for 10h;	92%

: 693-98-1
2-methylimidazole

: 28507-46-2
4-chloro-8-hydroxy-2-methylquinoline

: 54666-30-7
2-methyl-4-(2-methyl-imidazol-1-yl)-quinolin-8-ol

Conditions

Conditions	Yield
In 1,4-dioxane for 28h; Reflux;	99%

: 693-98-1
2-methylimidazole

: 98-09-9
benzenesulfonyl chloride

: 1352921-06-2
2-methyl-1-(phenylsulfonyl)-1H-imidazole

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃;	99%
In dichloromethane at 0℃; for 5h; Inert atmosphere;	97%

: 693-98-1
2-methylimidazole

: 814-49-3
diethyl chlorophosphate

: 1384485-94-2
O,O-diethyl (2-methyl-1H-imidazol-1-yl)phosphonate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 26℃; for 0.333333h;	99%

: 693-98-1
2-methylimidazole

: 100-39-0
benzyl bromide

: 13750-62-4
N-benzyl-2-methylimidazole

Conditions

Conditions	Yield
Stage #1: 2-methylimidazole With sodium hydride at -0.16℃; Schlenk technique; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran Inert atmosphere; Schlenk technique; Reflux;	99%
With sodium hydroxide In water at 20℃; for 0.333333h; Temperature; Micellar solution;	93%
With potassium carbonate In acetonitrile at 70℃;

: 693-98-1
2-methylimidazole

: 536-74-3
phenylacetylene

: 1198306-57-8
(Z)-2-methyl-1-styryl-1H-imidazole

Conditions

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Schlenk technique; stereoselective reaction;	99%
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 3h; Schlenk technique; Inert atmosphere; stereoselective reaction;	75%

: 693-98-1
2-methylimidazole

: 3'-O-benzoyl-2'-deoxythymidine-5'-monophosphate triethylammonium salt

: 3’-O-benzoyl-2’-deoxythymidine-5’-phosphor-2-methylimidazolide

Conditions

Conditions	Yield
With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	98.9%

: 693-98-1
2-methylimidazole

: 623-43-8
crotonic acid methyl ester

: methyl 3-(2-methyl-1H-imidazol-1-yl)butanoate

Conditions

Conditions	Yield
In neat (no solvent) at 80℃; for 24h; Michael Addition; Schlenk technique; Sealed tube;	98.5%

: 693-98-1
2-methylimidazole

: 1-(2’-O-benzoyl-α-L-threofuranosyl)thymidine-3’-monophosphate

: 1-(2’-O-benzoyl-α-L-threofuranosyl)thymidine-3’-monophosphor-2-methylimidazolide

Conditions

Conditions	Yield
With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	98.3%

2-Methylimidazole Specification

2-Methylimidazole(CAS NO.693-98-1), its Synonyms are 1H-Imidazole, 2-methyl-; Imidazole, 2-methyl-; 2-Methyl-1H-imidazol; 2-Methyl-imidazol; Glyoxalethyline; p-Oxal-methyline. It is white to light yellow crystalline powder. 2-Methylimidazole is a monomethylated imidazole that can be used as a building block in the preparation of a wide range of biologically active compounds. 2-Methylimidazole as well as other imidazoles can be use as catalyst for refolding of enhanced coloured fluorescent protein. 2-Methylimidazole has been identified as a byproduct of fermentation and is detected in foods and mainstream and side-stream tobacco smoke.

Physical properties about 2-Methylimidazole are: (1)ACD/LogP: 0.031; (2)ACD/LogD (pH 5.5): -2.34; (3)ACD/LogD (pH 7.4): -1.04; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 2.10; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Index of Refraction: 1.523; (11)Molar Refractivity: 23.602 cm³; (12)Molar Volume: 77.255 cm³; (13)Polarizability: 9.357 10-24cm³; (14)Surface Tension: 43.7360000610352 dyne/cm; (15)Density: 1.063 g/cm³; (16)Flash Point: 144.854 °C; (17)Enthalpy of Vaporization: 48.465 kJ/mol; (18)Boiling Point: 267 °C at 760 mmHg; (19)Vapour Pressure: 0.0140000004321337 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing, gloves and eye/face protection;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. Avoid contact with eyes;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6);
(2)InChIKey=LXBGSDVWAMZHDD-UHFFFAOYSA-N;
(3)Smilesc1([nH]ccn1)C;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	480mg/kg (480mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
mouse	LD50	oral	1400mg/kg (1400mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.

Product Name

2-Methylimidazole

Synthetic route

2-Methylimidazole Specification

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