4-Methylimidazole supplier

Name
2-Methylimidazole-4-sulfonic acid
EINECS 212-497-3
CAS No. 822-36-6
Article Data65
CAS DataBase
Density 1.062 g/cm³
Solubility Soluble in water and ethanol
Melting Point 44-47 °C(lit.)
Formula C₄H₆N₂
Boiling Point 263 °C at 760 mmHg
Molecular Weight 82.105
Flash Point 141.6 °C
Transport Information UN 3263 8/PG 3
Appearance slightly yellow chunks
Safety 26-36/37/39-45-25
Risk Codes 21/22-34-22
Molecular Structure
Hazard Symbols C
Synonyms 1H-Imidazole,4-methyl- (9CI);Imidazole, 4(or 5)-methyl- (6CI,7CI);Imidazole, 4-methyl-(8CI);4(5)-Methylimidazole;4(or 5)-Methylimidazole;4-Methyl-1H-imidazole;5-Methylimidazole;NSC 40744;4-Methylimidazole;
PSA 28.68000
LogP 0.71810

Synthetic route

: 100-97-0
hexamethylenetetramine

: 78-98-8
2-oxopropanal

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With ammonium acetate; acetic acid at 103℃; for 0.0666667h; Microwave irradiation;	76%

: 50-00-0
formaldehyd

: 96-26-4
dihydroxyacetone

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 50-00-0
formaldehyd

: 592-20-1
Acetol acetate

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With ammonium hydroxide; copper diacetate

: 57-48-7
D-Fructose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia
With zinc hydroxide; ammonia

: 57-48-7
D-Fructose

A: 822-36-6
4-methyl-1H-imidazole

B: 872-79-7
2-hydroxymethyl-4-methylimidazole

Conditions

Conditions	Yield
With ammonium hydroxide; manganese(II) sulfate

: 3458-28-4
D-Mannose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 6014-42-2
L-rhamnose

A: 822-36-6
4-methyl-1H-imidazole

B: 930-62-1
2,4-Dimethylimidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 609-06-3
L-xylose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 5328-37-0
L-arabinose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 3615-41-6
L-Rhamnose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 50-99-7
D-glucose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia
With zinc hydroxide; ammonia
With zinc hydroxide; ammonia at 100℃;
With zinc hydroxide; ammonium hydroxide; formaldehyd at 90℃; under 4413.05 - 5884.06 Torr;

: 59-23-4
D-Galactose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 96-26-4
dihydroxyacetone

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 38585-61-4
4-(chloromethyl)-1H-imidazole hydrochloride

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

: 1457-58-5
2-methyl-3H-imidazole-4-carboxylic acid

: 822-36-6
4-methyl-1H-imidazole

: 50-00-0
formaldehyd

: 78-98-8
2-oxopropanal

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia; water
With zinc hydroxide; ammonia

: 133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2
Maltose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 63-42-3
D-(+)-lactose

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With zinc hydroxide; ammonia

: 109-97-7
pyrrole

: 70019-89-5, 196413-36-2
4-Methylimidazolate anion

A: 822-36-6
4-methyl-1H-imidazole

B: 23303-09-5
pyrrolide anion

Conditions

Conditions	Yield
at 600℃; under 0.8 - 2.4 Torr; Thermodynamic data; intrinsic gas phase acidity (acid dissociation energy) is measured as a model for strong interactions in proteins and enzymes;

...Expand

: 15500-60-4
N,N-bis(trimethylsilyl)formamide

: 917-54-4
methyllithium

: tosylmethylisocyanate lithium

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
1) THF, -78 deg C, 30 min, 2a) -78 deg C, 30 min, 2b) -78 to 0 deg C, 2 h, 2c) RT, 16 h; Yield given. Multistep reaction;

...Expand

: 75-07-0
acetaldehyde

: tosylmethylisocyanate lithium

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With lithium hexamethyldisilazane 1) THF, -60 to -30 deg C, 20 min, 2a) -78 deg C, 30 min, 2b) -78 to 0 deg C, 2 h, 2c) RT, 16 h; Yield given. Multistep reaction;

: 67-68-5
dimethyl sulfoxide

: 119352-64-6
1-(trimethylsilyl)-4-methylimidazole

A: 822-36-6
4-methyl-1H-imidazole

B: 107-46-0
Hexamethyldisiloxane

C: 73844-89-0
4-Methyl-1-methylsulfanylmethyl-1H-imidazole

Conditions

Conditions	Yield
at 140 - 180℃;

...Expand

: 2,2-Dimethyl-propionic acid 4-nitro-phenyl ester; compound with 4-methyl-1H-imidazole

A: 822-36-6
4-methyl-1H-imidazole

B: 4195-17-9
4-nitrophenyl pivalate

Conditions

Conditions	Yield
With 2-(cyclohexylamino)ethanesulfonic acid In acetonitrile at 27℃; Equilibrium constant;

: 67908-02-5
N-(aminomethyl)benzamide

: 78-98-8
2-oxopropanal

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With water; acetic acid 1.) 4 h, 50 deg C; Yield given. Multistep reaction;

: 50-00-0
formaldehyd

: 2648-49-9
2-ethoxyprop-2-enal

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With hydrogenchloride; ammonia 1.) water, 35-40 deg C, 4 h, 2.) water, 70 deg C, 30 min, other reagent: ammonium carbonate; Yield given. Multistep reaction;

: 56119-27-8
glucose monohydrate

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With formaldehyd; zinc hydroxide carbonate; phosphoric acid; sulfuric acid; ammonia 1.) H2O, 100 deg C, 1 h, 2.) H2O, 95 - 97 deg C, 30 min; 20 deg C, 20 min; Yield given; Multistep reaction;

2-bromo-4-methyl-imidazole: 2-bromo-4-methyl-imidazole

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
With sodium sulfite

: 3247-70-9
4-methyl-1,3-dihydro-imidazole-2-thione

: 7697-37-2
nitric acid

: 822-36-6
4-methyl-1H-imidazole

: 7664-93-9
sulfuric acid

: 4-methyl-1(3)H-imidazole-2-sulfinic acid

: 822-36-6
4-methyl-1H-imidazole

Conditions

Conditions	Yield
an der Luft;

: 700-16-3
Pentafluoropyridine

: 822-36-6
4-methyl-1H-imidazole

: 1-(2,3,5,6-tetrafluoropyridyl)-4-methylimidazole

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 20h;	100%

: 822-36-6
4-methyl-1H-imidazole

: 624-83-9
methyl isocyanate

: 87864-86-6
4-Methyl-imidazole-1-carboxylic acid methylamide

Conditions

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	99%

: 822-36-6
4-methyl-1H-imidazole

: 76-83-5
trityl chloride

: 82594-80-7
4-methyl-1-trityl-1H-imidazole

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 3.5h;	98.2%
With triethylamine In N,N-dimethyl-formamide for 3.5h;	98.2%
With triethylamine In N,N-dimethyl-formamide for 3.5h;	98.2%

: 822-36-6
4-methyl-1H-imidazole

: 104-12-1
p-chlorphenylisocyanate

: 87864-85-5
4-Methyl-imidazole-1-carboxylic acid (4-chloro-phenyl)-amide

Conditions

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	98%

: 822-36-6
4-methyl-1H-imidazole

: C9H9BrN2O2

: C13H14N4O2

Conditions

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 0.133333h; Inert atmosphere;	98%
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere;	98%
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere;	98%

: 822-36-6
4-methyl-1H-imidazole

: 103-80-0
phenylacetyl chloride

: 123331-32-8
4-Methyl-1-(phenylacetyl)imidazole

Conditions

Conditions	Yield
In dichloromethane for 1.5h; Ambient temperature;	97%

: 1148-79-4
2,2':6,2''-terpyridine

: 822-36-6
4-methyl-1H-imidazole

: copper(II) tetrafluroborate hexahydrate

: {(2,2':6',2''-terpyridine)(4-methylimidazole)(H2O)(BF4)copper(II)}(BF4)

Conditions

Conditions	Yield
In methanol to a soln. of the Cu-salt and the imidazole in methanol is added dropwise a methanolic soln. of terpyridine with stirring; ether is then allowed to diffuse slowly into the soln., blue crystals are obtained in a few days, washed, dried, elem. anal.;	97%

...Expand

: 822-36-6
4-methyl-1H-imidazole

: 54962-75-3
[3-bromo-5-(trifluoromethyl)phenyl]amine

: 641571-11-1
3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Conditions

Conditions	Yield
With copper(l) iodide; (+)-D-glucosamine hydrochloride; caesium carbonate In water; dimethyl sulfoxide at 90℃; for 12h; Temperature; Concentration;	96.18%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene; tert-butyl alcohol at 120℃; for 8h; Inert atmosphere;	91%
With copper(l) iodide; 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethan-1-one; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 18h; Inert atmosphere; Sealed tube;	91%

: 108-86-1
bromobenzene

: 822-36-6
4-methyl-1H-imidazole

: 1-phenyl-4-methyl-1H-imidazole

Conditions

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere;	96%
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere; regioselective reaction;	95%
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In xylene at 130 - 140℃; for 15h;	91%
With potassium carbonate; copper(I) bromide In nitrobenzene for 18h; Heating;	8.8%
With 2-[(dimethylamino)methyl]benzenethiolato-copper(I); potassium carbonate In 1-methyl-pyrrolidin-2-one at 160℃; for 16h; Inert atmosphere;	59 %Chromat.

: 591-50-4
iodobenzene

: 822-36-6
4-methyl-1H-imidazole

: 1-phenyl-4-methyl-1H-imidazole

Conditions

Conditions	Yield
With C46H48Cu2Fe4I2Te4; lithium tert-butoxide at 85℃; for 12h; Catalytic behavior; Ullmann-Goldberg Substitution; Sealed tube; Green chemistry;	96%
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In xylene at 130 - 140℃; for 13h;	95%
With potassium carbonate; copper(l) chloride In water at 80℃; for 24h; Inert atmosphere;	90%
With copper(l) iodide; caesium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine In N,N-dimethyl-formamide at 110℃; for 24h;	77%
With copper(l) iodide; sodium hydroxide In dimethyl sulfoxide at 120℃; for 20h;	70%

: 108-05-4
vinyl acetate

: 822-36-6
4-methyl-1H-imidazole

: 1-(4-methyl-imidazol-1-yl)-ethyl acetate

Conditions

Conditions	Yield
In various solvent(s) at 50℃; for 48h; Markovnikov's addition;	96%
With [bmIm]OH at 50℃; for 4h; Markovnikov addition;	88%
With D-aminoacylase from Escherichia coli (EC 3.5.1.81) In hexane at 50℃; for 96h;	80%
With potassium tert-butylate In acetonitrile at 20℃; for 12h; regioselective reaction;	75%
With Thermomyces lanuginosus lipase; potassium carbonate In dimethyl sulfoxide at 50℃; for 0.5h; Flow reactor; Enzymatic reaction;	20%

: 822-36-6
4-methyl-1H-imidazole

: 66086-33-7
Di-tert-butyl acetylenedicarboxylate

: 603-35-0
triphenylphosphine

: di-tert-butyl 2-(4-methylimidazol-1-yl)-3-(triphenylphosphoranylidene)butanedioate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 24h;	96%
In ethyl acetate at 27℃; Kinetics; Temperature; Solvent;

...Expand

: 822-36-6
4-methyl-1H-imidazole

: 4-methylimidazolium pentaborate

Conditions

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

: 822-36-6
4-methyl-1H-imidazole

: 103-71-9
phenyl isocyanate

: 87864-84-4
4-methyl-1-(phenylcarbamoyl)imidazole

Conditions

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	95%

: 822-36-6
4-methyl-1H-imidazole

: 13360-57-1
dimethylamino sulfonyl chloride

: 151161-77-2
4-methylimidazole-1-sulfonic acid dimethylamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h;	95%
With triethylamine	61%
With triethylamine In dichloromethane Inert atmosphere;

: 822-36-6
4-methyl-1H-imidazole

: 105164-41-8
Rh2(N,N'-di-p-tolylformamidinate)2(trifluoroacetate)2(H2O)2*0.5benzene

: 105164-44-1
Rh2(N,N'-di-p-tolylformamidinate)2(trifluoroacetate)2(4-methylimidazole)2

Conditions

Conditions	Yield
In diethyl ether the Et2O soln. of water adduct was stirred with the imidazole (15min); addn. of hexane, slow evapn. of the solvent; elem. anal.;	95%

: 822-36-6
4-methyl-1H-imidazole

: 1066-45-1
trimethyltin(IV)chloride

: 205391-68-0
[bis(4-methylimidazole)trimethyltin(IV)]chloride

Conditions

Conditions	Yield
In diethyl ether N2-atmosphere; stirring (0°C, 1 h); crystn. (Et2O); elem. anal.;	95%

: 822-36-6
4-methyl-1H-imidazole

: 3-(5-bromo-6-methoxypyridin-2-yl)-5-phenyl-5,6-dihydro-4H-1,2,4-oxadiazine

: 3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-5-phenyl-5,6-dihydro-4H-1,2,4-oxadiazine

Conditions

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 18.05h; Inert atmosphere;	95%

: 822-36-6
4-methyl-1H-imidazole

: 7789-45-9
copper(ll) bromide

: dibromidotetrakis(4-methylimidazole)copper(II)

Conditions

Conditions	Yield
In methanol at 20℃; for 2h;	95%

: 822-36-6
4-methyl-1H-imidazole

: 753-73-1
dimethyltin dichloride

: 205391-71-5, 205391-91-9
bis(4-methylimidazole)dimethyldichlorotin(IV)

Conditions

Conditions	Yield
In diethyl ether stirring (room temp., 10 h); filtering, washing (Et2O), crystn. (CH2Cl2); elem. anal.;	94%

: 53087-13-1
3-(benzyloxy)phenyl bromide

: 822-36-6
4-methyl-1H-imidazole

: 1351990-64-1
1-(3-(benzyloxy)phenyl)-4-methyl-1H-imidazole

Conditions

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere; regioselective reaction;	94%

: 74-96-4
ethyl bromide

: 822-36-6
4-methyl-1H-imidazole

: 74-88-4
methyl iodide

: 3,4-dimethyl-1-ethylimidazolium bis(fluorosulfonyl)imide

Conditions

Conditions	Yield
Stage #1: 4-methyl-1H-imidazole; methyl iodide With potassium carbonate In acetone at 20℃; for 20h; Stage #2: ethyl bromide In toluene at 80℃; for 16h; Stage #3: With potassium bis(fluorosulfuryl)amide In tetrahydrofuran at 75℃; for 5h; Inert atmosphere;	94%

...Expand

: 822-36-6
4-methyl-1H-imidazole

: 38533-61-8
2-chloro-6-methoxy-3-nitropyridine

: 1156499-27-2
6-methoxy-2-(4-methyl-1H-imidazol-1-yl)-3-nitropyridine

Conditions

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; Product distribution / selectivity;	93%
Stage #1: 4-methyl-1H-imidazole With dmap In chloroform at 0℃; for 0.166667h; Stage #2: With triethylamine In chloroform at 0℃; for 0.166667h; Stage #3: 2-chloro-6-methoxy-3-nitropyridine In chloroform at 0 - 20℃;	93%
With dmap; triethylamine In chloroform at 0 - 20℃;	93%

: 1072-85-1
o-fluorobromobenzene

: 822-36-6
4-methyl-1H-imidazole

: 1351990-67-4
1-(2-fluorophenyl)-4-methyl-1H-imidazole

Conditions

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 120℃; for 5h; Inert atmosphere; regioselective reaction;	93%

: 3-(4-bromophenyl)-1,4-diazaspiro[4.4]non-3-en-2-one

: 822-36-6
4-methyl-1H-imidazole

: 1132817-67-4
3-(4-(4-methyl-1H-imidazol-1-yl)phenyl)-1,4-diazaspiro[4.4]non-3-en-2-one

Conditions

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; toluene at 130℃; for 6h; Inert atmosphere; regioselective reaction;	93%
With potassium phosphate; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane; toluene at 115℃; for 12h; Sealed tube; Inert atmosphere;	85%

: 822-36-6
4-methyl-1H-imidazole

: C17H21BrO3

: C21H26N2O3

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	92.78%
With potassium carbonate In acetonitrile at 20℃;	92.78%
With potassium carbonate In acetonitrile at 20℃; for 24h;	82.35%

: 822-36-6
4-methyl-1H-imidazole

: 75-36-5
acetyl chloride

: 61553-60-4
1-(4-methyl-1H-imidazol-1-yl)ethan-1-one

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 12h;	92%
In chloroform; toluene for 1h; Ambient temperature;
With triethylamine In acetonotrile at 20℃;
With triethylamine In acetonitrile at 0 - 20℃;
With triethylamine In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere;

: 822-36-6
4-methyl-1H-imidazole

: 4693-91-8
4-methoxyphenyl-acetic chloride

: 123331-33-9
1-<(4-Methoxyphenyl)acetyl>-4-methylimidazole

Conditions

Conditions	Yield
In dichloromethane for 1.5h; Ambient temperature;	92%

: 822-36-6
4-methyl-1H-imidazole

: 193806-50-7
2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane

A: 892393-34-9
2-(5-methyl-1H-imidazol-1-yl)-1-[2-[(tert-butoxycarbonyl)-amino]phenyl]ethane

B: 892393-33-8
2-(4-methyl-1H-imidazol-1-yl)-1-[2-[(tert-butoxycarbonyl)-amino]phenyl]ethane

C: 143262-10-6
1-(tert-butoxycarbonyl)indoline

Conditions

Conditions	Yield
Stage #1: 4-methyl-1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: 2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane In N,N-dimethyl-formamide at 25℃; for 2.5h; Product distribution / selectivity;	A n/a B n/a C 92%
In dichloromethane; toluene at 25 - 80℃; for 71h; Product distribution / selectivity;	A n/a B n/a C 22%

...Expand

: 822-36-6
4-methyl-1H-imidazole

: copper(II) bis(trifluoromethanesulfonate) hexahydrate

: 667909-43-5
tetrakis(5-methyl-1H-imidazole-κN3)copper(II) bis(trifluoromethanesulfonate)

Conditions

Conditions	Yield
With 2,2-dimethoxypropane In acetonitrile soln. of 4-methyl-1H-imidazole and Cu(CF3SO3)2*6H2O (4:1 mol) in MeCN with 5% dimethoxypropane stirred at room temp. for 2 h; Et2O added dropwise until pptn. started, stored in refrigerator for 2 d;	92%

4-Methylimidazole Consensus Reports

Reported in EPA TSCA Inventory.

4-Methylimidazole Specification

The 4-Methylimidazole is an organic compound with the formula C₄H₆N₂. The IUPAC name of this chemical is 5-methyl-1H-imidazole. With the CAS registry number 822-36-6 and EINECS 212-497-3, it is also named as 1H-Imidazole, 4-methyl-. The product's categories are Imidazol & Benzimidazole; Miscellaneous; Imidaxoles; Building Blocks; Heterocyclic Building Blocks; Imidazoles. It is slightly yellow chunk which is soluble in water and ethanol. Additionally, this chemical should be sealed in the container and stored in the cool and dry place which must be away from oxidant and acid.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.89; (4)ACD/LogD (pH 7.4): -0.38; (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): 7.33; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 17.82 Å²; (13)Index of Refraction: 1.523; (14)Molar Refractivity: 23.6 cm³; (15)Molar Volume: 77.2 cm³; (16)Polarizability: 9.35×10^-24 cm³; (17)Surface Tension: 43.7 dyne/cm; (18)Density: 1.062 g/cm³; (19)Flash Point: 141.6 °C; (20)Enthalpy of Vaporization: 48.06 kJ/mol; (21)Boiling Point: 263 °C at 760 mmHg; (22)Vapour Pressure: 0.0172 mmHg at 25°C.

Preparation and Uses of 4-Methylimidazole: It can be obtained by the reaction of pyruvaldehyde, acetaldehyde and ammonia. It is used as curing agent of epoxy resin, as the main raw material for cimetidine and in the synthesis of antibacterial agents. It also can be used as pharmaceutical intermediate. In addition, this chemcial can react with 3,6-bis-trifluoromethyl-[1,2,4,5]tetrazine to get N-{4-[3,6-Bis(trifluormethyl)-5-methyl-pyridazinyl]}-methanamidin. This reaction needs solvent toluene by heating. The reaction time is 4 hours. The yield is 72%.
4-Methylimidazole can react with 3,6-bis-trifluoromethyl-[1,2,4,5]tetrazine to get N-{4-[3,6-Bis(trifluormethyl)-5-methyl-pyridazinyl]}-methanamidin

When you are using 4-Methylimidazole, please be cautious about it as the following:
4-Methylimidazole is harmful in contact with skin and if swallowed. And it can cause burns. So people should avoid contact with eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES:n1cc(nc1)C;
(2)InChI:InChI=1/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6) ;
(3)InChIKey:XLSZMDLNRCVEIJ-UHFFFAOYAA;

The toxicity data of 4-Methylimidazole as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
chicken	LD50	intraperitoneal	210mg/kg (210mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
chicken	LD50	oral	590mg/kg (590mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
mouse	LD50	intraperitoneal	165mg/kg (165mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
mouse	LD50	oral	370mg/kg (370mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
rabbit	LDLo	intraperitoneal	120mg/kg (120mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Toxicology and Applied Pharmacology. Vol. 14, Pg. 301, 1969.
rat	LD50	oral	751mg/kg (751mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: OTHER CHANGES	Toxicology and Applied Pharmacology. Vol. 89, Pg. 175, 1987.

Product Name

2-Methylimidazole-4-sulfonic acid

Synthetic route

4-Methylimidazole Consensus Reports

4-Methylimidazole Specification

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