1739-84-0

Basic information

• Product Name: 1,2-Dimethylimidazole
• Synonyms: 1,2-dimethyl-1h-imidazol;1H-Imidazole,1,2-dimethyl-;Imidazole, 1,2-dimethyl-;AKOS BBS-00004287;1,2-dimethyl-1h-imidazole;1,2-DIMETHYLIMIDAZOLE;LUPRAGEN(R) DMI;1,2-Dimethylimdazole
• CAS NO: 1739-84-0
• Molecular Formula: C₅H₈N₂
• Molecular Weight: 96.13
• EINECS: 217-101-2
• Product Categories: Imidazoles;Building Blocks;Heterocyclic Building Blocks;Thiophenes
• Mol File: 1739-84-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 37-39 °C(lit.)
• Boiling Point: 204 °C(lit.)
• Flash Point: 198 °F
• Appearance: Colorless to yellow/Low Melting Mass
• Density: 1.084 g/mL at 25 °C(lit.)
• Vapor Pressure: 1 mm Hg ( 20 °C)
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 7.76±0.25(Predicted)
• Water Solubility: Soluble in water.
• BRN: 108457
• CAS DataBase Reference: 1,2-Dimethylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dimethylimidazole(1739-84-0)
• EPA Substance Registry System: 1,2-Dimethylimidazole(1739-84-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-38-41
• Safety Statements: 24-26-2
• RIDADR: UN 3263 8/PG 2
• WGK Germany: 2
• RTECS: NI4838854
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1739-84-0(Hazardous Substances Data)

Usage

Chemical Properties

colorless to yellow low melting mass

Uses

Different sources of media describe the Uses of 1739-84-0 differently. You can refer to the following data:
1. 1,2-Dimethylimidazole is used in the synthesis of 1,2-dimethyl-3-n-butylimidazoliumchloride and 1,2-dimethyl-3-n-propylimidazolium chloride. It also can be used in the synthesis of 1-(2-methoxyethyl)-2,3-dimethylimidazolium chloride and hexafluorophosphate salts.
2. 1,2-Dimethylimidazole was used in the synthesis of 1,2-dimethyl-3-n-butylimidazoliumchloride and 1,2-dimethyl-3-n-propylimidazolium chloride. It was also used in the synthesis of 1-(2-methoxyethyl)-2,3-dimethylimidazolium chloride and hexafluorophosphate salts.

General Description

1,2-Dimethylimidazole reacts with copper(II) tetraacetate to yield cis-bis(acetato)bis(1,2-dimethylimidazole) copper(II) complex. It undergoes Menschutkin reaction with benzyl bromide to yield 3-benzyl-1,2-dimethylimidazolium bromide and kinetics of reaction was studied in various ionic liquids and molecular organic solvents.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise the imidazole from *benzene, dry and store it at 0-4o. The picrate crystallises from H2O or EtOH with m 181o. [Balaban & Pymann J Chem Soc 125 1570 1924, Gorun et al. J Am Chem Soc 109 4244 1987, Beilstein 23 H 66, 23 II 56, 23 III/IV 594.]

InChI:InChI=1/C5H8N2/c1-5-6-3-4-7(5)2/h3-4H,1-2H3

Synthetic route

methanol (67-56-1) + 2-methylimidazole (693-98-1) → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
H-Y zeolite at 299.9℃;	92.5%
zeolite HNaY at 300 - 400℃;	83%

Glyoxal (131543-46-9) + acetaldehyde (75-07-0) + methylamine (74-89-5) → 1-methyl-1H-imidazole (616-47-7) + 1,2-dimethyl-1H-imidazole (1739-84-0) + 2-methylimidazole (693-98-1)

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

2-methylimidazole (693-98-1) + carbonic acid dimethyl ester (616-38-6) → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate at 100℃; for 8h;	85%
With 18-crown-6 ether; potassium carbonate at 100℃; for 10h;	85%
In N,N-dimethyl-formamide at 120 - 145℃; Solvent; Temperature;	85%

2-methylimidazole (693-98-1) + methyl iodide (74-88-4) → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With potassium hydroxide In 1,2-dimethoxyethane at 8℃; for 0.5h;	83%
at 30℃; for 8h;	70%

acetic acid methyl ester (79-20-9) + ethylenediamine (107-15-3) → lysidine (534-26-9) + 1,2-dimethyl-1H-imidazole (1739-84-0) + 2-methylimidazole (693-98-1)

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.;

5-bromo-1,2-dimethyl-1H-imidazole (24134-09-6) → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With ammonia; sodium In tert-butyl alcohol for 0.0833333h; Mechanism; Heating; other reagent and solvent;	48%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 48h; Heating; Irradiation; or Na/NH3, tBuOH, reflux;	50 % Spectr.

1,2-dimethyl-5-iodoimidazole (24134-13-2) → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With ammonia; sodium In tert-butyl alcohol for 0.0833333h; Mechanism; Heating; other reagent and solvent;	15%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene Heating; Irradiation; or Na/NH3, tBuOH, reflux;	53 % Spectr.

4-chloro-1,2-dimethyl-1H-imidazole (861362-00-7) → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With diethyl ether; sodium

2-chloromethyl-1-methylimidazole (19225-92-4) → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With acetic acid; zinc

5-chloro-2-chloromethyl-1-methyl-1H-imidazole (900640-98-4) → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With potassium hydroxide; palladium on activated charcoal; hydrazine
With potassium hydroxide; Pd-BaSO4; hydrazine

2-methylimidazole (693-98-1) + methyl iodide (74-88-4) → 1,2-dimethyl-1H-imidazole (1739-84-0) + 1,2,3-trimethylimidazolium iodide (36432-31-2)

Conditions	Yield
With diethyl ether

1,5-dimethyl-1H-pyrazole (694-31-5) → 1,4-dimethylimidazole (6338-45-0) + 1,2-dimethylimidazole (10447-93-5) + 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
In acetonitrile Mechanism; Product distribution; Irradiation; other substrate, other temperatures and irradiation times;

acetic acid (64-19-7) + ethylenediamine (107-15-3) → lysidine (534-26-9) + 1,2-dimethyl-1H-imidazole (1739-84-0) + 2-methylimidazole (693-98-1) + N,N'-diacetylethylenediamine (871-78-3) + 1-ethyl-2-methyl-4,5-dihydro-1H-imidazole (4814-93-1)

Conditions	Yield
With hydrogen; Pt/Al AP-64K catalyst at 280℃; Product distribution; var. temp. and molar ratio of ragents;

C15H20N7O7P (122676-65-7) → 1,2-dimethyl-1H-imidazole (1739-84-0) + guanosine 5'-phosphate (56499-56-0)

Conditions	Yield
In water at 37℃; Rate constant; ionic strength=1.75 NaCl; in the absence and presence of Mg(2+), Ca(2+);

1-methyl-2-((trimethylsilyl)methyl)-1H-imidazole (91631-71-9) → 1,2-dimethyl-1H-imidazole (1739-84-0) + Trimethylsilanol (1066-40-6)

Conditions	Yield
With water at 25℃; Rate constant; pH=12.5;

methanol (67-56-1) + 2-methylimidazole (693-98-1) → 1,2-dimethyl-1H-imidazole (1739-84-0) + 1,2,4,5-tetramethylimidazole (1739-83-9) + 1,2,4-trimethylimidazole (1842-63-3)

Conditions	Yield
γ-Al2O3 at 350 - 400℃; Product distribution; other catalysts, var. temp., other alkohols;

1,3-dimethyl-1H-pyrazole (694-48-4) → 1,4-dimethylimidazole (6338-45-0) + 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
In acetonitrile for 0.25h; Rearrangement; Photolysis;

1,5-dimethyl-1H-pyrazole (694-31-5) → 1,2-dimethylimidazole (10447-93-5) + 1,2-dimethyl-1H-imidazole (1739-84-0) + (E)-3-methyl-3-(N-methylamino)propenenitrile (60375-51-1) + (E)-2-methyl-2-(N-methylamino)ethenyl isocyanide

Conditions	Yield
In acetonitrile for 1h; Rearrangement; ring cleavage; Photolysis; Further byproducts given;

1-methyl-2-oxy-methyl-imidazole → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With phosphorus; hydrogen iodide at 155 - 170℃;

1-methyl-5-bromo-2-oxymethyl-imidazole → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With phosphorus; hydrogen iodide at 155 - 170℃;

1-methyl-5-chloro-2-oxymethyl-imidazole → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
With phosphorus; hydrogen iodide at 155 - 170℃;

methyl iodide (74-88-4) + imidazolyl-(1)-magnesium bromide → 1,2-dimethyl-1H-imidazole (1739-84-0)

1-methyl-2-hydroxymethylimidazole (17334-08-6) + hydrogen iodide (10034-85-2) + red phosphorus → 1,2-dimethyl-1H-imidazole (1739-84-0)

(5-chloro-1-methyl-1H-imidazol-2-yl)methanol (334893-99-1) + hydrogen iodide (10034-85-2) + red phosphorus → 1,2-dimethyl-1H-imidazole (1739-84-0)

(5-bromo-1-methyl-1H-imidazol-2-yl)methanol (861362-06-3) + hydrogen iodide (10034-85-2) + red phosphorus → 1,2-dimethyl-1H-imidazole (1739-84-0)

Conditions	Yield
at 160℃;

4-chloro-1,2-dimethyl-1H-imidazole (861362-00-7) + sodium + alcohol containing diethyl ether → 1,2-dimethyl-1H-imidazole (1739-84-0)

{Fe(meso-tetraphenylporphinato)(1,2-dimethylimidazole)2}Cl → 1,2-dimethyl-1H-imidazole (1739-84-0) + (1,2-dimethylimidazole)tetraphenylporphyrinatoiron(III) chloride

Conditions	Yield
In not given Kinetics; dissociation of Fe(TPP)(1,2-Me2Im)2Cl, 25 °C; not isolated; detection by dynamic NMR;

{Fe(meso-tetraphenylporphinato)(1,2-dimethylimidazole)2}Cl → 1,2-dimethyl-1H-imidazole (1739-84-0) + (1,2-dimethylimidazole)tetramesitylporphyrinatoiron(III) chloride

Conditions	Yield
In not given Kinetics; dissociation of Fe(TMP)(1,2-Me2Im)2Cl, 25 °C; not isolated; detection by satn. transfer method;

Pd(2+)*C6H5(1-)*3C5H8N2*I(1-) → 1,2-dimethyl-1H-imidazole (1739-84-0) + trans-[(phenyl)Pd(1,2-dimethyl-1H-imidazole)2I]

Conditions	Yield
In benzene-d6

1,2-dimethyl-1H-imidazole (1739-84-0) → MeN(CHO)COMe (141264-24-6)

Conditions	Yield
With ozone In methanol at -78℃; Mechanism; other 1-substituted imidazoles;	100%
With ozone In methanol at -78℃;	100%

1,2-dimethyl-1H-imidazole (1739-84-0) → 5-deuterio-1,2-dimethyl-1H-imidazole (86051-76-5)

Conditions	Yield
With n-butyllithium; water-d2 In diethyl ether; hexane for 0.333333h; Ambient temperature;	100%
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; potassium carbonate / ethyl acetate / 1.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.75 h / -100 - -80 °C / Inert atmosphere 2.2: -80 - 20 °C / Inert atmosphere View Scheme

1,2-dimethyl-1H-imidazole (1739-84-0) + 1-bromo-4-methoxy-benzene (104-92-7) → 1,2-dimethyl-5-(4-methoxyphenyl)-1H-imidazole

Conditions	Yield
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere;	100%
With palladium diacetate; potassium carbonate; tricyclohexylphosphine; Trimethylacetic acid In N,N-dimethyl-formamide at 180℃; for 0.5h; Inert atmosphere; Microwave irradiation;	85%
With C24H22ClN3OPdSe; potassium carbonate; Trimethylacetic acid In dimethyl amine at 110℃; for 10h; Reagent/catalyst; regioselective reaction;	84%

1,2-dimethyl-1H-imidazole (1739-84-0) + 3-(4-bromomethyl-phenyl)thiophene (108912-09-0) → 2,3-dimethyl-1-(4-thien-3-ylbenzyl)-1H-imidazol-3-ium bromide

Conditions	Yield
In toluene for 3h; Heating;	100%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1-bromo-octane (111-83-1) → 1,2-dimethyl-3-octyl-1H-imidazol-3-ium bromide

Conditions	Yield
at 140℃; for 0.666667h;	100%
In neat (no solvent) at 60℃; for 24h; Inert atmosphere;	100%
at 90℃; for 48h;	88%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1,4-butane sultone (1633-83-6) → 1,2-dimethyl-3-(4-sulfonatobutyl)-1H-imidazol-3-ium (1088461-53-3)

Conditions	Yield
at 40℃; for 10h;	100%
In ethanol at 20℃; for 48h;	95%
In ethanol at 25℃; for 48h;	95%

1,2-dimethyl-1H-imidazole (1739-84-0) + para-bromoacetophenone (99-90-1) → 1-(4-(1,2-dimethyl-1H-imidazol-5-yl)phenyl)ethan-1-one (1201005-37-9)

Conditions	Yield
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;	100%
With C24H22ClN3OPdSe; potassium carbonate; Trimethylacetic acid In dimethyl amine at 110℃; for 10h; Reagent/catalyst; regioselective reaction;	97%
With C28H24FN2O3PPd; potassium acetate In dimethyl amine at 140℃; for 18h; Catalytic behavior; Reagent/catalyst;	96%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1-dodecylbromide (143-15-7) → 1-dodecyl-2,3-dimethylimidazol-1-ium bromide (61546-10-9)

Conditions	Yield
In neat (no solvent) at 60℃; for 24h; Inert atmosphere;	100%
at 20℃; Inert atmosphere;	90%
at 140℃; for 0.133333h; Microwave irradiation; Neat (no solvent);

(S)-benzyl 1-bromo-2-propyl ether (861959-09-3) + 1,2-dimethyl-1H-imidazole (1739-84-0) → (S)-1-(2-benzyloxypropyl)-2,3-dimethylimidazolium bromide

Conditions	Yield
In toluene Reflux;	100%

1,2-dimethyl-1H-imidazole (1739-84-0) + C114H72Br12O24 → C174H168N24O24(12+)*12Br(1-)

Conditions	Yield
In chloroform for 48h; Reflux;	100%

1,2-dimethyl-1H-imidazole (1739-84-0) + [PdPh(μ-O2CMe)(PPh3)]2 (106354-46-5, 287183-78-2) → [(phenyl)Pd(triphenylphosphine)(OAc)(1,2-dimethyl-1H-imidazole)]

Conditions	Yield
In benzene at 20℃;	100%

1,2-dimethyl-1H-imidazole (1739-84-0) + 2-chloroethanesulfonyl fluoride (762-70-9) → C7H12FN2O2S(1+)*Cl(1-)

Conditions	Yield
In ethyl acetate at 20℃; for 2h; Menshutkin Reaction;	100%

1,2-dimethyl-1H-imidazole (1739-84-0) + Methyl formate (107-31-3) → 1,2,3-trimethylimidazolium formate (878492-91-2)

Conditions	Yield
In methanol at 140℃; under 22502.3 Torr; for 18h;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + (1R,2S,5R)-1-(chloromethoxy)-2-isopropyl-5-methylcyclohexane (26127-08-2) → 1-[(1R,2S,5R)-(-)-menthoxymethyl]-2,3-dimethylimidazolium chloride

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.5h; Menschutkin reaction;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[phenylethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))iron(II) (573658-67-0) → (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[phenylethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))(1,2-dimethyl-1H-imidazole)iron(II)

Conditions	Yield
In toluene (N2); not isolated, detected by UV-vis;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[[3-hydroxyphenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))iron(II) (573658-66-9) → (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[[3-hydroxphenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))(1,2-dimethyl-1H-imidazole)iron(II) (849726-41-6)

Conditions	Yield
In toluene (N2); not isolated, detected by UV-vis;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[[3-(hydroxymethyl)phenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))iron(II) (573658-65-8) → (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[[3-(hydroxymethyl)phenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))(1,2-dimethyl-1H-imidazole)iron(II) (849726-42-7)

Conditions	Yield
In toluene (N2); not isolated, detected by UV-vis;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[[3-(aminocarbonyl)phenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))iron(II) (573658-63-6) → (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[[3-(aminocarbonyl)phenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))(1,2-dimethyl-1H-imidazole)iron(II) (849726-40-5)

Conditions	Yield
In toluene (N2); not isolated, detected by UV-vis;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[[3-(aminosulfonyl)phenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))iron(II) (573658-64-7) → (tetrakis(3,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl) 4,4',4'', 4'''-[[10-(2-[[3-(aminosulfonyl)phenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))(1,2-dimethyl-1H-imidazole)iron(II)

Conditions	Yield
In toluene (N2); not isolated, detected by UV-vis;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + 4-bromo-benzaldehyde (1122-91-4) → 4-(1,2-dimethyl-1H-imidazol-5-yl)benzaldehyde (1201005-45-9)

Conditions	Yield
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Reagent/catalyst; regioselective reaction;	99%
With C40H40Cl3N3Pd; oxygen; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; under 760.051 Torr; for 12h; regioselective reaction;	98%
With potassium carbonate In glycerol at 130℃; for 17h; Catalytic behavior; Temperature; Reagent/catalyst; Solvent; Green chemistry; regioselective reaction;	95%

1,2-dimethyl-1H-imidazole (1739-84-0) → 1,2-dimethylimidazolium nitrate (501693-50-1)

Conditions	Yield
With nitric acid In ethanol; water at 40℃; for 10h;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1,4-dichlorobutane (110-56-5) → 1,4-bis(1,2-dimethylimidazolium-3-yl)butane dichloride

Conditions	Yield
In chloroform at 60℃; under 14251400 Torr; for 24h; Kinetics; Pressure; Time; Menshutkin Reaction; High pressure; Autoclave;	99%
In isopropyl alcohol for 16h; Reflux;	60%

1,2-dimethyl-1H-imidazole (1739-84-0) + 5-bromo-2-fluoropyridine (766-11-0) → 5-(1,2-dimethyl-1H-imidazol-5-yl)-2-fluoropyridine

Conditions	Yield
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6) → 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1,2-dimethyl-1H-imidazol-3-ium chloride

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1,3-Dichloropropane (142-28-9) → 1,3-bis(1,2-dimethylimidazolium-3-yl)propane dichloride

Conditions	Yield
In chloroform at 60℃; under 14251400 Torr; for 24h; Kinetics; Pressure; Time; Menshutkin Reaction; High pressure; Autoclave;	99%

1,2-dimethyl-1H-imidazole (1739-84-0) + methyl iodide (74-88-4) → 1,2,3-trimethylimidazolium iodide (36432-31-2)

Conditions	Yield
In acetonitrile at 40℃; for 2h; Schlenk technique; Inert atmosphere;	98%
In diethyl ether at 20℃; for 72h;	97%
In diethyl ether at 20℃;	93%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1-Bromonaphthalene (90-11-9) → 1,2-dimethyl-5-(naphthalen-1-yl)-1H-imidazole

Conditions	Yield
With C40H40Cl3N3Pd; oxygen; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; under 760.051 Torr; for 12h; regioselective reaction;	98%
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;	97%
With C24H22ClN3OPdSe; potassium carbonate; Trimethylacetic acid In dimethyl amine at 110℃; for 10h; Reagent/catalyst; regioselective reaction;	89%

(1S,3R,4S,6R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]heptane + 1,2-dimethyl-1H-imidazole (1739-84-0) → 4,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-(1-methyl-1H-imidazol-2-ylmethyl)-cyclohexanol

Conditions	Yield
With n-butyllithium; (1R,2S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine In tetrahydrofuran; hexane at 0 - 20℃; for 64h;	98%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1-bromo-3-propanol (627-18-9) → 1-(3'-hydroxypropyl)-2,3-dimethylimidazolium bromide

Conditions	Yield
at 70℃; for 2h;	98%
In acetonitrile at 80 - 90℃; for 24h;

1,2-dimethyl-1H-imidazole (1739-84-0) + 2-chloro-ethanol (107-07-3) → 1-(2-hydroxyethyl)-2,3-dimethylimidazol-3-ium chloride

Conditions	Yield
In toluene at 70℃; for 81h; Reflux;	98%
In toluene at 70℃; for 81h; Reflux;	98%
at 120℃; for 24h;	88%

Upstream product

• 900640-98-4 5-chloro-2-chloromethyl-1-methyl-1H-imidazole 
• 24134-09-6 5-bromo-1,2-dimethyl-1H-imidazole 
• 24134-13-2 5-iodo-1,2-dimethylimidazole 
• 79-20-9 acetic acid methyl ester 
• 107-15-3 ethylenediamine 
• 67-56-1 methanol 
• 693-98-1 2-methylimidazole 
• 694-31-5 1,5-dimethyl-1H-pyrazole 
• 74-88-4 methyl iodide 
• 17334-08-6 1-methyl-2-hydroxymethylimidazole 
• 10034-85-2 hydrogen iodide 
• 334893-99-1 (5-chloro-1-methyl-1H-imidazol-2-yl)methanol 
• 861362-06-3 (5-bromo-1-methyl-1H-imidazol-2-yl)methanol 
• 861362-00-7 4-chloro-1,2-dimethyl-1H-imidazole 

Downstream Products

• 36432-31-2 1,2,3-trimethylimidazolium iodide 
• 13230-04-1 1,2-dimethyl-4-nitro-1H-imidazole 
• 551-92-8 dimetridazole 
• 175649-97-5 1-(2-acetoxyphenyl)-2-(1-methyl-1H-imidazol-2-yl)vinyl 2-acetoxybenzoate 
• 19225-97-9 1,2-dimethyl-5-phenyl-1H-imidazole 
• 13369-82-9 4,5-diiodo-1,2-dimethylimidazole 
• 98892-76-3 1-Ethyl-2-methyl-3-methylimidazolium bromide 
• 108203-70-9 1-n-butyl-2,3-dimethylimidazolium iodide 
• 227617-70-1 1-butyl-2,3-dimethylimidazolium hexafluorophosphate 
• 402846-78-0 1-butyl-2,3-methylimidazolium tetrafluoroborate 
• 669009-67-0 (4-cyanophenyl)-(2,3-dimethyl-3H-imidazol-4-yl)methanol 

Relevant articles and documents

Magnesium Ion Catalyzed P-N Bond Hydrolysis in Imidazolide-Activated Nucleotides. Relevance to Template-Directed Synthesis of Polynucleotides

Magnesium, an ion necessary in enzymatic as well as in nonenzymatic template-directed polynucleotide-synthesizing reaction, has been found to catalyze the hydroxide ion attack on the P-N bond of selected 5'-monophosphate imidazolide derivatives of nucleotides, such as guanosine 5'-monophosphate 2-methylimidazolide (2-MeImpG), guanosine 5'-monophosphate imidazolide (ImpG), and adenosine 5'-monophosphate 2-methylimidazolide (2-MeImpA).Calcium ion behaves similarly, but quantitatively the effects are smaller.Pseudo-first-order rate constants of 2-MeImpG and ImpG hydrolysis as a function of Mg(2+) concentration have been obtained in the range 6 +/-, imidazolide moiety protonated) with OH(1-) rather than reaction of the anionic form (S(1-), imidazolide moiety deprotonated) with water.This conclusion is based on a study of the N-methylated substrates N-MeImpG and 1,2-diMeImpG, respectively, which were generated in situ by the equilibrium reaction of ImpG with N-methylimidazole and 2-MeImpG with 1,2-dimethylimidazole, respectively.In contrast, in the absence of Mg(2+) the reaction of S(1-) with water competes with the reaction of SH+/- with OH(1-).The present study bears on the mechanism of the Mg(2+)-catalyzed template-directed synthesis of oligo- and polynucleotides derived from 2-MeImpG and on thecompetition between oligonucleotide synthesis and hydrolysis of 2-MeImpG.

Activities of new iminium compounds on selected strains of bacteria and fungi, XX: Synthesis of 1-methyl-2-alkyl-3-(n-alkoxymethyl)- and 1-methyl-3-(n-alkoxymethyl)-5-chloroimidazolium chlorides

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Alkylation method for nitrogen-hydrogen containing compounds and application thereof

The invention discloses an alkylation method for nitrogen-hydrogen containing compounds and an application thereof, belonging to the technical field of synthesis of organic compounds. The invention provides a series of methods for a nitrogen alkylation reaction of N-H containing heterocyclic compounds (II) with N,N-dimethylformamide dialkyl acetal as an alkyl source under the condition of no participation of metals, and a product with a hydrogen atom on a nitrogen atom substituted by R1 is obtained. The method provided by the invention has the advantages of highly-efficient reaction, high yield, simple treatment after the reaction, simple and convenient operation, mild reaction conditions, no participation of the metals, high tolerance of functional groups of a reaction substrate, wide range and easy preparation of the substrate, high reaction efficiency after amplification of the reaction, and applicability to large-scale industrial production.

Preparation method for 1,2-dimethylimidazole

The invention discloses a preparation method for 1,2-dimethylimidazole. The method comprises the following steps: dissolving 2-methylimidazole in an organic solvent; carrying out heating, adding dimethyl carbonate and continuing a reaction; and after completion of the reaction, subjecting a reaction solution to pressure-reduced distillation and rectification so as to prepare 1,2-dimethylimidazole. Compared with the prior art, the invention has the beneficial effects that 2-methylimidazole is used as a raw material; 1,2-dimethylimidazole is synthesized in one step at high temperature; and the preparation method has the advantages of no waste water, high yield, simple operation, no by product, etc. and is easy for industrial large-scale production. According to the invention, dimethyl carbonate is used as a methylation reagent, so raw material cost is low and toxicity is small; and no catalyst is needed in the method, so considerable solid sylvite waste does not exist and post-treatment is simple.

A 1,2-dimethyl imidazole of preparation method

The invention discloses a preparation method of 1,2-dimethylimidazole. The method comprises the following steps: bisimidazole is prepared from aminoacetaldehyde diethyl acetal, succinamide and 2,4-dimethylbenzoic acid, and 1,2-dimethylimidazole is prepared from bisimidazole. Compared with the prior art, the method allows to the total conversion rate to reach 90% by continuously optimizing reaction conditions and the use amounts of other reagents, and has the advantages of high conversation rate, mild reaction conditions, recycling of a solvent and a catalyst used in the reaction process, low cost, and practicality.