2-Amino-1-methylimidazole supplier

Name
1-methyl-1H-imidazol-2-amine
EINECS
CAS No. 6646-51-1
Article Data14
CAS DataBase
Density 1.224g/cm3
Solubility
Melting Point
Formula C4H7 N3
Boiling Point 255.146oC at 760 mmHg
Molecular Weight 97.1197
Flash Point 108.109oC
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Imidazole,2-amino-1-methyl- (7CI,8CI); 1-Methyl-1H-imidazol-2-ylamine;1-Methyl-2-aminoimidazole; 2-Amino-1-methylimidazole
PSA 43.84000
LogP 0.58350

Synthetic route

: 7720-39-0
1H-imidazol-2-amine

: 74-88-4
methyl iodide

: 6646-51-1
1-methyl-2-aminoimidazole

Conditions

Conditions	Yield
With copper(l) iodide; 8-quinolinol; sodium t-butanolate In methanol at 50℃; for 36h; Solvent;	72%
Stage #1: 1H-imidazol-2-amine With tert-butyldimethylsilyl chloride Stage #2: methyl iodide With n-butyllithium

: 51081-36-8
2-lithium-N-methylimidazole

: 6646-51-1
1-methyl-2-aminoimidazole

Conditions

Conditions	Yield
With 1-azidostyrene In tetrahydrofuran for 2h; from -78 deg.C to room temp.;	45%

: 1671-82-5
1-methyl-2-nitroimidazole

: 6646-51-1
1-methyl-2-aminoimidazole

Conditions

Conditions	Yield
With iron; acetic acid at 80℃;	17%
With palladium 10% on activated carbon; hydrogen In 1,4-dioxane at 20℃; for 16h;	70 mg

: 506-68-3
bromocyane

: 122-07-6
N-(methyl)aminoacetaldehyde dimethyl acetal

: 6646-51-1
1-methyl-2-aminoimidazole

Conditions

Conditions	Yield
Stage #1: bromocyane; N-(methyl)aminoacetaldehyde dimethyl acetal With acetic acid In water at 100℃; for 1h; Stage #2: With hydrogenchloride In water at 100℃; for 0.25h;

: ethyl 2-imino-3-methyl-2,3-dihydro-1H-imidazole-1-carboxylate

: 6646-51-1
1-methyl-2-aminoimidazole

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 22℃; for 8h;

: 626-55-1
3-Bromopyridine

: 6646-51-1
1-methyl-2-aminoimidazole

: 1369433-28-2
C9H10N4

Conditions

Conditions	Yield
With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; tert-butyl XPhos In tert-butyl alcohol at 20℃; for 16h; Inert atmosphere;	97%

: 6646-51-1
1-methyl-2-aminoimidazole

: 74-88-4
methyl iodide

: 2-amino-1,3-dimethylimidazolium iodide

Conditions

Conditions	Yield
for 1h; 0 deg C to r.t.;	92%

: 6646-51-1
1-methyl-2-aminoimidazole

: (S)-3-(bromomethyl)-N-(cyclopropyl(4-fluoro-3-methylphenyl)methyl)-5-(2-(trifluoromethyl)pyridin-3-yl)benzamide

: (S)-N-(cyclopropyl(4-fluoro-3-methylphenyl)methyl)-3-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-5-(2-(trifluoromethyl)pyridin-3-yl)benzamide

Conditions

Conditions	Yield
In acetonitrile at 23 - 50℃; for 12h;	84%

: 6646-51-1
1-methyl-2-aminoimidazole

: 108-86-1
bromobenzene

: 1369433-26-0
C10H11N3

Conditions

Conditions	Yield
With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; tert-butyl XPhos In tert-butyl alcohol at 20℃; for 4h; Inert atmosphere;	83%

: 6646-51-1
1-methyl-2-aminoimidazole

: 15781-72-3
bis(2,4,6-trichlorophenyl) ethylmalonate

: 1-methyl-6-ethyl-7-hydroxy-4,5-dihydroimidazo<1,2-a>pyrimidin-5-one

Conditions

Conditions	Yield
at 160℃; for 0.05h;	81%

: 109-04-6
2-bromo-pyridine

: 6646-51-1
1-methyl-2-aminoimidazole

: 1369433-27-1
C9H10N4

Conditions

Conditions	Yield
With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; tert-butyl XPhos In tert-butyl alcohol at 20℃; for 16h; Inert atmosphere;	80%

: 6646-51-1
1-methyl-2-aminoimidazole

: 586-75-4
4-chlorobenzoyl chloride

: 4-bromo-N-(1-methyl-1H-imidazol-2-yl)benzamide

Conditions

Conditions	Yield
With potassium hydrogencarbonate In ethanol at 50℃; for 12h;	77%

: 6646-51-1
1-methyl-2-aminoimidazole

: 59197-85-2
4-hydroxy-8-trifluoromethyl-3-quinoline-carboxylic acid chloride

: 114350-72-0
4-Hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid (1-methyl-1H-imidazol-2-yl)-amide

Conditions

Conditions	Yield
With pyridine Ambient temperature;	72%

: 6646-51-1
1-methyl-2-aminoimidazole

: 3-(bromomethyl)-N-(3,4-dichlorobenzyl)-5-(6-fluoro-2-methylpyridin-3-yl)benzamide

: N-(3,4-dichlorobenzyl)-3-(6-fluoro-2-methylpyridin-3-yl)-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)benzamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 18h;	62%

: 6646-51-1
1-methyl-2-aminoimidazole

: 7-(bromomethyl)-2-(4-chloro-3-methylbenzyl)-5-(2-methylpyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one

: 76-05-1
trifluoroacetic acid

: (x)C2HF3O2*C28H28ClN5O

Conditions

Conditions	Yield
Stage #1: 1-methyl-2-aminoimidazole; 7-(bromomethyl)-2-(4-chloro-3-methylbenzyl)-5-(2-methylpyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one at 80℃; for 0.5h; Stage #2: trifluoroacetic acid With Phenomenex Gemini Cl 8 In water; acetonitrile	56%

...Expand

: 6646-51-1
1-methyl-2-aminoimidazole

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

: 3-bromo-5-(bromomethyl)-N-(3,4-dichlorobenzyl)benzamide

: tert-butyl (E)-(1-(3-bromo-5-((3,4-dichlorobenzyl)carbamoyl)benzyl)-3-methyl-1,3-dihydro-2H-imidazol-2-ylidene)carbamate

Conditions

Conditions	Yield
Stage #1: 1-methyl-2-aminoimidazole; 3-bromo-5-(bromomethyl)-N-(3,4-dichlorobenzyl)benzamide With N-ethyl-N,N-diisopropylamine In acetonitrile for 18h; Reflux; Stage #2: di-tert-butyl dicarbonate With dmap In tetrahydrofuran at 20℃; for 18h;	53%

...Expand

: 6646-51-1
1-methyl-2-aminoimidazole

: C17H12F2N4O2

: C21H17F2N7O

Conditions

Conditions	Yield
With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;	48%

: 6646-51-1
1-methyl-2-aminoimidazole

: 80777-17-9
2-(Dichloromethyl)-4-hydroxy-8-(trifluoromethyl)-3-quinolinecarboxylic acid ethyl ester

: 80777-33-9
685B

Conditions

Conditions	Yield
	42%

: 6646-51-1
1-methyl-2-aminoimidazole

: 5-(bromomethyl)-N-(3,4-dichlorobenzyl)-2',4'-difluoro-6'-methyl-[1,1'-biphenyl]-3-carboxamide

: N-(3,4-dichlorobenzyl)-2′,4′-difluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazo-1-yl)methyl)-6′-methyl-[1,1′-biphenyl]-3-carboxamide

Conditions

Conditions	Yield
In acetonitrile at 80℃; for 0.5h; Microwave irradiation;	40%

: 6646-51-1
1-methyl-2-aminoimidazole

: 75999-37-0
2,8-bis-(trifluoromethyl)-4-hydroxy-3-quinoline-carboxylic acid chloride

: 75999-41-6
2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1-methyl-1H-imidazol-2-yl)-3-quinolinecarboxamide

Conditions

Conditions	Yield
With pyridine Ambient temperature;	34%

: 6646-51-1
1-methyl-2-aminoimidazole

: 3-(bromomethyl)-N-(3,5-dimethoxybenzyl)-5-(6-fluoro-4-methylpyridin-3-yl)benzamide

: N-(3,5-dimethoxybenzyl)-3-(6-fluoro-4-methylpyridin-3-yl)-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)benzamide

Conditions

Conditions	Yield
In acetonitrile at 80℃; for 16h;	20%

: 6646-51-1
1-methyl-2-aminoimidazole

: 474659-26-2
7-methoxyquinoline-3-carboxylic acid

: 7-methoxy-N-(1-methyl-1H-imidazol-2-yl)quinoline-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 7-methoxyquinoline-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 1-methyl-2-aminoimidazole In N,N-dimethyl-formamide	12%

: 6646-51-1
1-methyl-2-aminoimidazole

: 64321-74-0
ethyl 4-hydroxy-2-ethyl-8-trifluoromethyl-quinoline-3-carboxylate

: 114350-79-7
2-Ethyl-4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid (1-methyl-1H-imidazol-2-yl)-amide

Conditions

Conditions	Yield
	10%

: 6646-51-1
1-methyl-2-aminoimidazole

: 26250-84-0
(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid

: tert-butyl (2S)-2-[(1-methylimidazol-2-yl)carbamoyl]piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1-methyl-2-aminoimidazole In dichloromethane at 20℃; for 5h;	10%

: 6646-51-1
1-methyl-2-aminoimidazole

: (S)-(5-((cyclopropyl(4-methylpyridin-2-yl)methyl)carbamoyl)-4'-fluoro-2'-methyl-[1,1'-biphenyl]-3-yl)methyl methanesulfonate

: (S)-N-(cyclopropyl(4-methylpyridin-2-yl)methyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 55℃; for 16h;	9%

: 6646-51-1
1-methyl-2-aminoimidazole

: 188975-34-0
(R)-(-)-3-[3-fluoro-4-(3,6-dihydro-2H-pyran-4-yl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone

: 5(S)-(N-methylimidazol-2-ylaminomethyl)-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: 1-methyl-2-aminoimidazole With n-butyllithium In tetrahydrofuran; water at -78℃; for 1h; Stage #2: (R)-(-)-3-[3-fluoro-4-(3,6-dihydro-2H-pyran-4-yl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone In tetrahydrofuran; water at 20℃; for 18h; Heating / reflux; Stage #3: With ammonium chloride In tetrahydrofuran; water	4.6%

: 6646-51-1
1-methyl-2-aminoimidazole

: C22H17Cl4N3O4

: (1‘R,2’S,7a’R)-5,7-dichloro-N1‘-(3,5-dichlorophenyl)-N2’-(1- methyl-1H-imidazol-2-yl)-2-oxo-1‘,2’,5’,6’,7’,7a’-hexahydrospiro[indoline-3,3’-pyrrolizine]-1‘,2’-dicarboxamide

Conditions

Conditions	Yield
Stage #1: C22H17Cl4N3O4 With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 1-methyl-2-aminoimidazole In tetrahydrofuran at 60℃; for 24h;	4%

: 6646-51-1
1-methyl-2-aminoimidazole

: 122-51-0
orthoformic acid triethyl ester

: 762-04-9
phosphonic acid diethyl ester

: [(diethoxy-phosphoryl)-(1-methyl-1H-imidazol-2-ylamino)-methyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With phosphonic acid diethyl ester at 120 - 125℃; for 3h;

...Expand

: 6646-51-1
1-methyl-2-aminoimidazole

: 73742-45-7
5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

: 5-chloro-6-{[2-imino-3-methyl(4-imidazolin-1-yl)]methyl}uracil hydrochloride

Conditions

Conditions	Yield
In water at 100℃; for 1h;	80 mg

Product Name

1-methyl-1H-imidazol-2-amine

Synthetic route

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