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1739-84-0 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.]

Check Digit Verification of cas no

The CAS Registry Mumber 1739-84-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,3 and 9 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1739-84:
(6*1)+(5*7)+(4*3)+(3*9)+(2*8)+(1*4)=100
100 % 10 = 0
So 1739-84-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H8N2/c1-5-6-3-4-7(5)2/h3-4H,1-2H3

1739-84-0 Well-known Company Product Price

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  • Alfa Aesar

  • (B23544)  1,2-Dimethylimidazole, 98%   

  • 1739-84-0

  • 25g

  • 142.0CNY

  • Detail
  • Alfa Aesar

  • (B23544)  1,2-Dimethylimidazole, 98%   

  • 1739-84-0

  • 100g

  • 216.0CNY

  • Detail
  • Alfa Aesar

  • (B23544)  1,2-Dimethylimidazole, 98%   

  • 1739-84-0

  • 500g

  • 904.0CNY

  • Detail
  • Aldrich

  • (136131)  1,2-Dimethylimidazole  98%

  • 1739-84-0

  • 136131-5G

  • 205.92CNY

  • Detail
  • Aldrich

  • (136131)  1,2-Dimethylimidazole  98%

  • 1739-84-0

  • 136131-100G

  • 367.38CNY

  • Detail
  • Aldrich

  • (136131)  1,2-Dimethylimidazole  98%

  • 1739-84-0

  • 136131-500G

  • 1,310.40CNY

  • Detail

1739-84-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2-Dimethylimidazole

1.2 Other means of identification

Product number -
Other names dimethylglyoxaline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. CBI
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1739-84-0 SDS

1739-84-0Synthetic route

methanol
67-56-1

methanol

2-methylimidazole
693-98-1

2-methylimidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
H-Y zeolite at 299.9℃;92.5%
zeolite HNaY at 300 - 400℃;83%
Glyoxal
131543-46-9

Glyoxal

acetaldehyde
75-07-0

acetaldehyde

methylamine
74-89-5

methylamine

A

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

1-methyl-1H-imidazole

B

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

1,2-dimethyl-1H-imidazole

C

2-methylimidazole
693-98-1

2-methylimidazole

Conditions
ConditionsYield
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

2-methylimidazole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
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

2-methylimidazole

methyl iodide
74-88-4

methyl iodide

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
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

acetic acid methyl ester

ethylenediamine
107-15-3

ethylenediamine

A

lysidine
534-26-9

lysidine

B

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

1,2-dimethyl-1H-imidazole

C

2-methylimidazole
693-98-1

2-methylimidazole

Conditions
ConditionsYield
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

5-bromo-1,2-dimethyl-1H-imidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
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-5-iodoimidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
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

4-chloro-1,2-dimethyl-1H-imidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
With diethyl ether; sodium
2-chloromethyl-1-methylimidazole
19225-92-4

2-chloromethyl-1-methylimidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
With acetic acid; zinc
5-chloro-2-chloromethyl-1-methyl-1H-imidazole
900640-98-4

5-chloro-2-chloromethyl-1-methyl-1H-imidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
With potassium hydroxide; palladium on activated charcoal; hydrazine
With potassium hydroxide; Pd-BaSO4; hydrazine
2-methylimidazole
693-98-1

2-methylimidazole

methyl iodide
74-88-4

methyl iodide

A

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

1,2-dimethyl-1H-imidazole

B

1,2,3-trimethylimidazolium iodide
36432-31-2

1,2,3-trimethylimidazolium iodide

Conditions
ConditionsYield
With diethyl ether
1,5-dimethyl-1H-pyrazole
694-31-5

1,5-dimethyl-1H-pyrazole

A

1,4-dimethylimidazole
6338-45-0

1,4-dimethylimidazole

B

1,2-dimethylimidazole
10447-93-5

1,2-dimethylimidazole

C

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
In acetonitrile Mechanism; Product distribution; Irradiation; other substrate, other temperatures and irradiation times;
acetic acid
64-19-7

acetic acid

ethylenediamine
107-15-3

ethylenediamine

A

lysidine
534-26-9

lysidine

B

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

1,2-dimethyl-1H-imidazole

C

2-methylimidazole
693-98-1

2-methylimidazole

D

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

E

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

1-ethyl-2-methyl-4,5-dihydro-1H-imidazole

Conditions
ConditionsYield
With hydrogen; Pt/Al AP-64K catalyst at 280℃; Product distribution; var. temp. and molar ratio of ragents;
C15H20N7O7P
122676-65-7

C15H20N7O7P

A

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

1,2-dimethyl-1H-imidazole

B

guanosine 5'-phosphate
56499-56-0

guanosine 5'-phosphate

Conditions
ConditionsYield
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-methyl-2-((trimethylsilyl)methyl)-1H-imidazole

A

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

1,2-dimethyl-1H-imidazole

B

Trimethylsilanol
1066-40-6

Trimethylsilanol

Conditions
ConditionsYield
With water at 25℃; Rate constant; pH=12.5;
methanol
67-56-1

methanol

2-methylimidazole
693-98-1

2-methylimidazole

A

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

1,2-dimethyl-1H-imidazole

B

1,2,4,5-tetramethylimidazole
1739-83-9

1,2,4,5-tetramethylimidazole

C

1,2,4-trimethylimidazole
1842-63-3

1,2,4-trimethylimidazole

Conditions
ConditionsYield
γ-Al2O3 at 350 - 400℃; Product distribution; other catalysts, var. temp., other alkohols;
1,3-dimethyl-1H-pyrazole
694-48-4

1,3-dimethyl-1H-pyrazole

A

1,4-dimethylimidazole
6338-45-0

1,4-dimethylimidazole

B

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
In acetonitrile for 0.25h; Rearrangement; Photolysis;
1,5-dimethyl-1H-pyrazole
694-31-5

1,5-dimethyl-1H-pyrazole

A

1,2-dimethylimidazole
10447-93-5

1,2-dimethylimidazole

B

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

1,2-dimethyl-1H-imidazole

C

(E)-3-methyl-3-(N-methylamino)propenenitrile
60375-51-1

(E)-3-methyl-3-(N-methylamino)propenenitrile

D

(E)-2-methyl-2-(N-methylamino)ethenyl isocyanide

(E)-2-methyl-2-(N-methylamino)ethenyl isocyanide

Conditions
ConditionsYield
In acetonitrile for 1h; Rearrangement; ring cleavage; Photolysis; Further byproducts given;
1-methyl-2-oxy-methyl-imidazole

1-methyl-2-oxy-methyl-imidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
With phosphorus; hydrogen iodide at 155 - 170℃;
1-methyl-5-bromo-2-oxymethyl-imidazole

1-methyl-5-bromo-2-oxymethyl-imidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
With phosphorus; hydrogen iodide at 155 - 170℃;
1-methyl-5-chloro-2-oxymethyl-imidazole

1-methyl-5-chloro-2-oxymethyl-imidazole

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
With phosphorus; hydrogen iodide at 155 - 170℃;
methyl iodide
74-88-4

methyl iodide

imidazolyl-(1)-magnesium bromide

imidazolyl-(1)-magnesium bromide

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

1,2-dimethyl-1H-imidazole

1-methyl-2-hydroxymethylimidazole
17334-08-6

1-methyl-2-hydroxymethylimidazole

hydrogen iodide
10034-85-2

hydrogen iodide

red phosphorus

red phosphorus

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

1,2-dimethyl-1H-imidazole

(5-chloro-1-methyl-1H-imidazol-2-yl)methanol
334893-99-1

(5-chloro-1-methyl-1H-imidazol-2-yl)methanol

hydrogen iodide
10034-85-2

hydrogen iodide

red phosphorus

red phosphorus

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

1,2-dimethyl-1H-imidazole

(5-bromo-1-methyl-1H-imidazol-2-yl)methanol
861362-06-3

(5-bromo-1-methyl-1H-imidazol-2-yl)methanol

hydrogen iodide
10034-85-2

hydrogen iodide

red phosphorus

red phosphorus

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

1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
at 160℃;
4-chloro-1,2-dimethyl-1H-imidazole
861362-00-7

4-chloro-1,2-dimethyl-1H-imidazole

sodium

sodium

alcohol containing diethyl ether

alcohol containing diethyl ether

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

1,2-dimethyl-1H-imidazole

{Fe(meso-tetraphenylporphinato)(1,2-dimethylimidazole)2}Cl

{Fe(meso-tetraphenylporphinato)(1,2-dimethylimidazole)2}Cl

A

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

1,2-dimethyl-1H-imidazole

(1,2-dimethylimidazole)tetraphenylporphyrinatoiron(III) chloride

(1,2-dimethylimidazole)tetraphenylporphyrinatoiron(III) chloride

Conditions
ConditionsYield
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

{Fe(meso-tetraphenylporphinato)(1,2-dimethylimidazole)2}Cl

A

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

1,2-dimethyl-1H-imidazole

(1,2-dimethylimidazole)tetramesitylporphyrinatoiron(III) chloride

(1,2-dimethylimidazole)tetramesitylporphyrinatoiron(III) chloride

Conditions
ConditionsYield
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-)

Pd(2+)*C6H5(1-)*3C5H8N2*I(1-)

A

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

1,2-dimethyl-1H-imidazole

trans-[(phenyl)Pd(1,2-dimethyl-1H-imidazole)2I]

trans-[(phenyl)Pd(1,2-dimethyl-1H-imidazole)2I]

Conditions
ConditionsYield
In benzene-d6
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

MeN(CHO)COMe
141264-24-6

MeN(CHO)COMe

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

5-deuterio-1,2-dimethyl-1H-imidazole
86051-76-5

5-deuterio-1,2-dimethyl-1H-imidazole

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

1,2-dimethyl-5-(4-methoxyphenyl)-1H-imidazole

1,2-dimethyl-5-(4-methoxyphenyl)-1H-imidazole

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

3-(4-bromomethyl-phenyl)thiophene
108912-09-0

3-(4-bromomethyl-phenyl)thiophene

2,3-dimethyl-1-(4-thien-3-ylbenzyl)-1H-imidazol-3-ium bromide

2,3-dimethyl-1-(4-thien-3-ylbenzyl)-1H-imidazol-3-ium bromide

Conditions
ConditionsYield
In toluene for 3h; Heating;100%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

1-bromo-octane
111-83-1

1-bromo-octane

1,2-dimethyl-3-octyl-1H-imidazol-3-ium bromide

1,2-dimethyl-3-octyl-1H-imidazol-3-ium bromide

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

1,4-butane sultone
1633-83-6

1,4-butane sultone

1,2-dimethyl-3-(4-sulfonatobutyl)-1H-imidazol-3-ium
1088461-53-3

1,2-dimethyl-3-(4-sulfonatobutyl)-1H-imidazol-3-ium

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

para-bromoacetophenone
99-90-1

para-bromoacetophenone

1-(4-(1,2-dimethyl-1H-imidazol-5-yl)phenyl)ethan-1-one
1201005-37-9

1-(4-(1,2-dimethyl-1H-imidazol-5-yl)phenyl)ethan-1-one

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

1-dodecylbromide
143-15-7

1-dodecylbromide

1-dodecyl-2,3-dimethylimidazol-1-ium bromide
61546-10-9

1-dodecyl-2,3-dimethylimidazol-1-ium bromide

Conditions
ConditionsYield
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

(S)-benzyl 1-bromo-2-propyl ether

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

1,2-dimethyl-1H-imidazole

(S)-1-(2-benzyloxypropyl)-2,3-dimethylimidazolium bromide

(S)-1-(2-benzyloxypropyl)-2,3-dimethylimidazolium bromide

Conditions
ConditionsYield
In toluene Reflux;100%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

C114H72Br12O24

C114H72Br12O24

C174H168N24O24(12+)*12Br(1-)

C174H168N24O24(12+)*12Br(1-)

Conditions
ConditionsYield
In chloroform for 48h; Reflux;100%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

[PdPh(μ-O2CMe)(PPh3)]2
106354-46-5, 287183-78-2

[PdPh(μ-O2CMe)(PPh3)]2

[(phenyl)Pd(triphenylphosphine)(OAc)(1,2-dimethyl-1H-imidazole)]

[(phenyl)Pd(triphenylphosphine)(OAc)(1,2-dimethyl-1H-imidazole)]

Conditions
ConditionsYield
In benzene at 20℃;100%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

2-chloroethanesulfonyl fluoride
762-70-9

2-chloroethanesulfonyl fluoride

C7H12FN2O2S(1+)*Cl(1-)

C7H12FN2O2S(1+)*Cl(1-)

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 2h; Menshutkin Reaction;100%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

Methyl formate
107-31-3

Methyl formate

1,2,3-trimethylimidazolium formate
878492-91-2

1,2,3-trimethylimidazolium formate

Conditions
ConditionsYield
In methanol at 140℃; under 22502.3 Torr; for 18h;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

(1R,2S,5R)-1-(chloromethoxy)-2-isopropyl-5-methylcyclohexane
26127-08-2

(1R,2S,5R)-1-(chloromethoxy)-2-isopropyl-5-methylcyclohexane

1-[(1R,2S,5R)-(-)-menthoxymethyl]-2,3-dimethylimidazolium chloride

1-[(1R,2S,5R)-(-)-menthoxymethyl]-2,3-dimethylimidazolium chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 0.5h; Menschutkin reaction;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

(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-))iron(II)

(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)

(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
ConditionsYield
In toluene (N2); not isolated, detected by UV-vis;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

(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-hydroxyphenyl]ethynyl]phenyl)porphyrin-5,15-diyl]bis[benzene-2,1,3-triylbis(oxy)]]tetrabutanoate(2-))iron(II)

(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

(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)

Conditions
ConditionsYield
In toluene (N2); not isolated, detected by UV-vis;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

(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-))iron(II)

(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

(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)

Conditions
ConditionsYield
In toluene (N2); not isolated, detected by UV-vis;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

(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-))iron(II)

(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

(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)

Conditions
ConditionsYield
In toluene (N2); not isolated, detected by UV-vis;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

(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-))iron(II)

(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)

(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
ConditionsYield
In toluene (N2); not isolated, detected by UV-vis;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-(1,2-dimethyl-1H-imidazol-5-yl)benzaldehyde
1201005-45-9

4-(1,2-dimethyl-1H-imidazol-5-yl)benzaldehyde

Conditions
ConditionsYield
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-dimethyl-1H-imidazole

1,2-dimethylimidazolium nitrate
501693-50-1

1,2-dimethylimidazolium nitrate

Conditions
ConditionsYield
With nitric acid In ethanol; water at 40℃; for 10h;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

1,4-dichlorobutane
110-56-5

1,4-dichlorobutane

1,4-bis(1,2-dimethylimidazolium-3-yl)butane dichloride

1,4-bis(1,2-dimethylimidazolium-3-yl)butane dichloride

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

5-bromo-2-fluoropyridine
766-11-0

5-bromo-2-fluoropyridine

5-(1,2-dimethyl-1H-imidazol-5-yl)-2-fluoropyridine

5-(1,2-dimethyl-1H-imidazol-5-yl)-2-fluoropyridine

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

2-chloro-4,6-dimethoxy-1 ,3,5-triazine
3140-73-6

2-chloro-4,6-dimethoxy-1 ,3,5-triazine

3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1,2-dimethyl-1H-imidazol-3-ium chloride

3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1,2-dimethyl-1H-imidazol-3-ium chloride

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h;99%
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

1,3-Dichloropropane
142-28-9

1,3-Dichloropropane

1,3-bis(1,2-dimethylimidazolium-3-yl)propane dichloride

1,3-bis(1,2-dimethylimidazolium-3-yl)propane dichloride

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

methyl iodide
74-88-4

methyl iodide

1,2,3-trimethylimidazolium iodide
36432-31-2

1,2,3-trimethylimidazolium iodide

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1,2-dimethyl-5-(naphthalen-1-yl)-1H-imidazole

1,2-dimethyl-5-(naphthalen-1-yl)-1H-imidazole

Conditions
ConditionsYield
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

(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

1,2-dimethyl-1H-imidazole

4,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-(1-methyl-1H-imidazol-2-ylmethyl)-cyclohexanol

4,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-(1-methyl-1H-imidazol-2-ylmethyl)-cyclohexanol

Conditions
ConditionsYield
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

1,2-dimethyl-1H-imidazole

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

1-(3'-hydroxypropyl)-2,3-dimethylimidazolium bromide

1-(3'-hydroxypropyl)-2,3-dimethylimidazolium bromide

Conditions
ConditionsYield
at 70℃; for 2h;98%
In acetonitrile at 80 - 90℃; for 24h;
1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

2-chloro-ethanol
107-07-3

2-chloro-ethanol

1-(2-hydroxyethyl)-2,3-dimethylimidazol-3-ium chloride

1-(2-hydroxyethyl)-2,3-dimethylimidazol-3-ium chloride

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

1739-84-0Relevant articles and documents

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

Kanavarioti, Anastassia,Bernasconi, Claude F.,Doodokyan, Donald L.,Alberas, Diann J.

, p. 7247 - 7257 (1989)

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

Pernak,Krysinski,Skrzypczak,Michalak

, p. 193 - 197 (1988)

-

Alkylation method for nitrogen-hydrogen containing compounds and application thereof

-

Paragraph 0059; 0061, (2018/10/04)

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.

METHOD FOR PRODUCING 1,2-DISUBSTITUTED IMIDAZOLE

-

Paragraph 0051-0052, (2017/06/14)

PROBLEM TO BE SOLVED: To provide a 1,2-disubstituted imidazole production method which can suppress production of by-products and efficiently produce high-purity 1,2-disubstituted imidazole in a shorter reaction time than that of the conventional one. SOLUTION: A 1,2-disubstituted imidazole production method includes a first stage reaction step of reacting an aldehyde compound with ammonia and/or a primary amine, and a second stage reaction step of reacting a glyoxal compound and ammonia and/or a primary amine with reaction products in the first stage reaction step. The primary amine is reacted in at least one of the first stage reaction step and the second stage reaction step to produce 1,2-disubstituted imidazole in a flow manner. The reaction in at least one of the first stage reaction step and the second stage reaction step is performed in a pressurized state at a pressure of 1-50 MPa. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT

A 1,2-dimethyl imidazole of preparation method

-

Paragraph 0029-0032, (2017/02/24)

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.

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