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288-32-4 Usage

Preparation method

With glyoxal as raw material, reactive in formaldehyde and ammonium sulfate (or ammonia) in 85~90℃, and get imidazole sulfate and then neutralized with calcium hydroxide to get imidazole crude product. Filtering, water washing, combining filtrate and washings, decompression evaporation concentration and crystallization, then it’s done. If using ammonia directly, then there should be no sulfate processing steps and it can be prepared at once. Either with ammonium sulfate or ammonia, the yield is relatively low, approximately 45%. With o-phenylenediamine and formic acid as raw material, via cyclization to benzimidazole, and then through oxidation in the sulfuric acid solution to generate dicarbonyl imidazole; later in the effect of copper oxidation, via decarboxylation from 100 to 150℃ to get crude; And then in benzene solution recrystallization to get imidazole finished products. With d-tartrate acid as raw material, in sulfuric acid, nitric acid was used to carry out nitrification, and get 2, 3-dinitro tartrate acid; and then in the formaldehyde and ammonia reaction, to get dicarboxylic imidazole; finally decarboxylation to get it.

Uses

Excellent for buffers in the range of pH 6.2-7.8 Imidazole has been used in the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein. in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography. as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cell.

Physical characteristics

In nature, there are only imidazole derivatives and no free imidazole. The precipitation from benzene is a colorless crystalline prism, with scents of ammonia. Relative molecular mass 68.08. Relative density 1.0303(101/4℃) . Melting point 89~91℃,boiling point 257℃,165℃~168℃(2.67×103Pa) and 138.2℃(1.60×103Pa). Flash point 145℃. Refractive index 1.4801(101℃). Viscosity 2.696mPa·s(100℃). Slightly soluble in benzene, petroleum ether, soluble in ether, acetone, chloroform and pyridine, easily soluble in water (at normal temperature 70) and ethanol. It appears weak alkaline. As the-NH-bond on 1 bite and-N= bond on 3 bit forms hydrogen bond, the boiling point is quite high; when 1 bit hydrogen is substituted, hydrogen bond cannot be formed, hence the boiling point decreases. As to thermal stability, it rarely dissolves under 250℃ (decomposition temperature is 590℃). It is also very stable to reducing agent and oxidant, but can form stable salt with inorganic acid. Owning some certain aromatic properties, also could get halogenation, nitration, sulfonation and hydroxymethylation in the presence of catalyst. Can be coupled with the heavy nitrogen salt in 2 bit. In addition, due to the =NH (1 bit) connected to the two double bonds, with some of the "acid", it can be replaced by metal to get salt. In addition, 3 bit nitrogen ions have coordination effect on metal ions, which can form chelate compounds. Although it is difficult to restore, but can be combined with the proton to generate cation type with resonance structure, and get of a stable form. Tautomers of imidazole ring are very easy to change, so it is hard to tell isomers on 4 bit or 5 bit. The above information is edited by the Chemicalbook He Liao Pu.

Uses

Imidazole is a versatile heterocycle used in the preparation of various biologically active compounds such as the amino acid histidine and is present in many antifungal medication. It is also used ext ensively as a corrosion inhibitor on transition metals such as copper.It is used in organic synthesis and as an antiirradiationagent.

Purification Methods

Crystallise imidazole from *benzene, CCl4, CH2Cl2, EtOH, pet ether, acetone/pet ether and distilled de-ionized water. Dry it at 40o under vacuum over P2O5. Distil it at low pressure. It is also purified by sublimation or by zone melting. [Snyder et al. Org Synth Coll Vol III 471 1955, Bredereck et al. Chem Ber 97 827 1964, Caswell & Spiro J Am Chem Soc 108 6470 1986.] 15N-imidazole crystallises from *benzene [Scholes et al. J Am Chem Soc 108 1660 1986]. [Beilstein 23 II 34, 23 III/IV 564, 23/4 V 191.]

Fire Hazard

Noncombustible solid.

Chemical Properties

Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar.The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.

Main application

Imidazole can be used as epoxy curing agent, improve the mechanical properties such as bending, stretching and compression etc., improve the electrical properties of the insulation, and improve performance of chemical resistance properties, which is widely used in computers and electrical appliances; Used as an anti-rust agent for copper in printed circuit boards and integrated circuits; Used as pharmaceutical raw materials for manufacturing anti-fungal drugs, antifungal agents, drug for treatment of hypoglycemia, artificial plasma, trichomonad drug, bronchial asthma drug, macula agent, etc.; Used as pesticide raw material for synergist, insecticides and fungicides of boric acid agent; In addition, imidazole is also used as raw material of urea-formaldehyde resin curing agent, photographic medicine, adhesive, coating, vulcanizer, antistatic agent, etc.; intermediate for organic synthesis.

Uses

1.Used as intermediate of bactericide for imazalil, prochloraz, etc., and that of pharmaceutical anti-fungal drug, econazole, ketoconazole, and clotrimazole as well. 2.Used as organic synthetic materials and intermediates for the preparation of drugs and pesticides. 3.Used as analytical reagent, as well as in organic synthesis. 4.Imidazole is mainly used as curing agent for epoxy resin. In Japan the imidazole accounts for less than half of the consumption. For imidazole compounds whose dosage is 0.5 to 10 percent of epoxy resin, it can be used in antifungal drug, ant mildew agent, hypoglycemic drug, artificial plasma, etc., also can be used in medicines to cure trichomoniasis and turkey blackhead. Imidazole is also one of the main raw material during production of imidazole antifungal miconazole, econazole, clotrimazole and ketoconazole. By imidazole and 2, 4, ω-trichloroacetophenon as the main raw material, it can get fruit fungicide enilconazde. Add 2, 4, ω-trichloroacetophenon into absolute methanol, with heating reflux, adding bromine. Wait until the solution color gradually disappeared, cooling to 0℃, and then intensely mixing it for 3h. And the vacuum distillation of methanol. Put the remaining liquid into the water, to extract it with dichloromethane. After the extract recovered with dichloromethane, add dilute nitric acid to get salt; recrystallization with water and then treated with ammonia to get 2', 4'-dichloro-2-imidazole acetophenone. Furthermore use sodium borohydride reduction into the corresponding alcohols, and then in the presence of sodium hydroxide and dimethyl formamide, use allyl chloride based to get enilconazde (also known as enilconazole). the after adding dilute nitric acid salt and water after recrystallization using ammonia water treatment of 2,2 ', 4'-dichloro 2-methyl imidazole phenyl ethyl ketone. It has something in common of the structure and production methods between enilconazde and miconazole. Miconazole is a broad-spectrum antifungal agent, and enilconazde is also antifungal agent, which is widely used in imazalil. 5.Agrochemical intermediates, bactericide intermediates, triazole fungicide.

Definition

ChEBI: An imidazole tautomer which has the migrating hydrogen at position 1.

chemical properties

Imidazole is between the two nitrogen atoms of five membered heterocyclic compounds containing. The unshared electron pair of 1-bit nitrogen atom in imidazole ring participates in the cyclic conjugation, reduces the electron density of the nitrogen atom, and makes hydrogen of the nitrogen atom easily leave in the form of hydrogen. Therefore imidazole has weak acidity, and can form salt with strong base. The unshared electron pair of 3-bit nitrogen atom in imidazole ring doesn’t participates in the cyclic conjugation, while it occupies the sp2 hybridized orbital, can accept protons, and form salt with strong acid. Alkaline of imidazole is slightly stronger than pyrazole and pyridine. There is tautomerism in the imidazole ring. The hydrogen on the 1-bit nitrogen atom can be transferred to the 3-atom, therefore, imidazole derivatives with same substituent respectively on 4-bit and 5-bit are tautomers. Imidazole is stable to acid, and has antioxidant activity. Imidazole derivatives are widely found in nature, such as histamine, histidine and benzimidazole, etc. There are some interesting reagents in acyl imidazole compounds. For example, 1-acetyl imidazole is a stable acylating agent, after reaction with pyrrole, it becomes 1-acetyl pyrrole. Furthermore, in general, 1-acetyl imidazole can get ketones and aldehydes using Grignard reagent and reducing agent. Reaction of N, N-carbonyldimidazole and carboxyl will get useful reagent acyl imidazole. The relationship between imidazole and natural compounds is very close. For example, pyrimidine ring turns into purine derivatives after condensation. In addition to being like 6-amino purine and guanine the nucleic acid bases, it also exists in the organisms of uric acid, caffeine and theophylline. The catalytic action of imidazole, such as accelerated enzyme hydrolysis, still under study. As the cause of allergic skin, its toxicity is similar todiamine. Rat oral LD501880mg/kg. imidazole structure

Health Hazard

It is less toxic relative to pyrrole and otherfive-membered heterocyclic compounds ofnitrogen. Intraperitoneal administration ofimidazole caused somnolence, muscle contractions,and convulsions in mice. Theoral LD50 value in mice is in the range900 mg/kg.

Production method

1.It can be made via cyclization and neutralization by glyoxal. Put glyoxal, formaldehyde and ammonium sulfate into reaction pot, stir and heat up to 85-85℃ with heat preservation 4h. Cool it to 50-60℃, with limewater neutralization to pH for more than 10. Heat up to 85-90℃, ammonia excretion for more than 1h, cool it slightly, filter and filter cake washing with hot water; Combined wash, filtrate, and vacuum concentration until anhydrous steamed out; continue to vacuum distillation until low boiling substances all steamed out, collect 105-160℃ (0.133-0.267kPa) fractions and then imidazole is done. The yield is about 45%. Another method is to make cyclization of o-diaminobenzene and formic acid to get benzimidazole, followed by 4, 5-dyhydroxy imidazole via reaction and open-loop of hydrogen peroxide, and finally get imidazole via decarboxylation. 4, 5-dyhydroxy imidazole also can be made by d-tartrate through nitration and cyclization. The process of getting imidazole via decarboxylation of 4, 5-dyhydroxy imidazole is as below: mix 4, 5-dyhydroxy imidazole with copper oxide, heat up to 100-280℃, emit lots of carbon dioxide gas, then the collected distillate is crude product, and at last recrystallize it with benzene to get the product, and the yield is 76%. 2.The production method is to put glyoxal, formaldehyde and ammonium sulfate into reaction pot, stir and heat up to 85-85℃ with heat preservation 4h. Cool it to 50-60℃, with limewater neutralization to pH for more than 10. Heat up to 85-90℃, ammonia excretion for more than 1h, cool it slightly, filter and filter cake washing with hot water; Combined wash, filtrate, and vacuum concentration until anhydrous steamed out; continue to vacuum distillation until low boiling substances all steamed out, collect 105~160℃/133~266Pa fractions and then imidazole is done. With o-phenylenediamine as raw material, put it into formic acid, stir and heat up, heat preservation at 95~98℃ for 2h, cool it to 50~60℃, adjust PH value to 10 with 10%NaOH; When it reaches room temperature, with filtering, washing and drying to get benzimidazole. Put benzimidazole into concentrated sulfuric acid, heat up to 100℃, and slowly drop in H2O2. Reaction while stirring under 140~150℃ for 1h, cooling to 40℃, water dilution, precipitation, crystallization, filtration, washing, drying, and then 4, 5-dyhydroxy imidazole is done. Mix 4, 5-dyhydroxy imidazole with copper oxide, heat up to 100-280℃, emit lots of carbon dioxide gas, then the collected distillate is white block crude product, and at last recrystallize it with benzene to get the fine imidazole.
InChI:InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)

288-32-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (I0288)  Imidazole [for Buffer]  >99.0%(GC)(T) 288-32-4 25g 550.00CNY Detail
TCI America (I0288)  Imidazole [for Buffer]  >99.0%(GC)(T) 288-32-4 100g 1,670.00CNY Detail
TCI America (I0288)  Imidazole [for Buffer]  >99.0%(GC)(T) 288-32-4 500g 5,190.00CNY Detail
TCI America (I0001)  Imidazole  >98.0%(T) 288-32-4 25g 80.00CNY Detail
TCI America (I0001)  Imidazole  >98.0%(T) 288-32-4 100g 158.00CNY Detail
TCI America (I0001)  Imidazole  >98.0%(T) 288-32-4 500g 345.00CNY Detail
Alfa Aesar (A10221)  Imidazole, 99%    288-32-4 100g 164.0CNY Detail
Alfa Aesar (A10221)  Imidazole, 99%    288-32-4 500g 477.0CNY Detail
Alfa Aesar (A10221)  Imidazole, 99%    288-32-4 2500g 1719.0CNY Detail
Alfa Aesar (47274)  Imidazole, ACS, 99+%    288-32-4 100g 378.0CNY Detail
Alfa Aesar (47274)  Imidazole, ACS, 99+%    288-32-4 500g 1120.0CNY Detail
Alfa Aesar (47274)  Imidazole, ACS, 99+%    288-32-4 2500g 3668.0CNY Detail

288-32-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1H-imidazole

1.2 Other means of identification

Product number -
Other names IMD

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:288-32-4 SDS

288-32-4Synthetic route

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

1-phenyl-acetone
103-79-7

1-phenyl-acetone

A

1H-imidazole
288-32-4

1H-imidazole

B

1-phenyl-2-trimethylsiloxy-1-propene
43108-63-0

1-phenyl-2-trimethylsiloxy-1-propene

Conditions
ConditionsYield
Ambient temperature; other silylazoles and carbonyl compounds;A n/a
B 100%
tert-butyl 1H-imidazole-1-carboxylate
49761-82-2

tert-butyl 1H-imidazole-1-carboxylate

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With water at 100℃; for 0.166667h;99%
With silica gel In dichloromethane for 0.0333333h; Irradiation;98%
With water at 150℃; for 2h; Subcritical conditions;95%
1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

benzyl alcohol
100-51-6

benzyl alcohol

A

1H-imidazole
288-32-4

1H-imidazole

B

N-benzyloxycarbonylimidazole
22129-07-3

N-benzyloxycarbonylimidazole

Conditions
ConditionsYield
In acetonitrile at 25℃; for 12h; Esterification;A n/a
B 97%
1-benzylimidazole
4238-71-5

1-benzylimidazole

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With Na2K-SG(I) In 1,2-dimethoxyethane at 20℃; Inert atmosphere;96%
With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;92%
formaldehyd
50-00-0

formaldehyd

Glyoxal
131543-46-9

Glyoxal

ammonia
7664-41-7

ammonia

ethanolamine
141-43-5

ethanolamine

A

1H-imidazole
288-32-4

1H-imidazole

B

1-(2-Hydroxyethyl)imidazole
1615-14-1

1-(2-Hydroxyethyl)imidazole

Conditions
ConditionsYield
Stage #1: formaldehyd; ammonia; ethanolamine In water at 25℃; for 1h;
Stage #2: Glyoxal; ammonia at 25℃; for 1h; Product distribution / selectivity;
A 2%
B 96%
ethanol
64-17-5

ethanol

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

A

1H-imidazole
288-32-4

1H-imidazole

B

ethyl 1-imidazolecarboxylate
19213-72-0

ethyl 1-imidazolecarboxylate

Conditions
ConditionsYield
In acetonitrile at 25℃; for 12h; Esterification;A n/a
B 95%
at 20℃;
Glyoxal
131543-46-9

Glyoxal

isobutyraldehyde
78-84-2

isobutyraldehyde

A

1H-imidazole
288-32-4

1H-imidazole

B

2-isopropylimidazole
36947-68-9

2-isopropylimidazole

Conditions
ConditionsYield
Stage #1: isobutyraldehyde With ammonia In methanol; water at 25℃; for 1h;
Stage #2: Glyoxal With ammonia In methanol; water at 25℃; for 2h; Product distribution / selectivity;
A 2 %Chromat.
B 95%
With ammonia In water at 25℃; for 1h; Product distribution / selectivity;A 23 %Chromat.
B 56%
2-Amino-2-methyl-1-propanol
124-68-5

2-Amino-2-methyl-1-propanol

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

A

1H-imidazole
288-32-4

1H-imidazole

B

4,4-dimethyl-1,3-oxazolidin-2-one
26654-39-7

4,4-dimethyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
In diethyl ether for 0.166667h; Ambient temperature;A n/a
B 94%
2-(1H-imidazol-1-yl)-1-phenylethanone
24155-34-8

2-(1H-imidazol-1-yl)-1-phenylethanone

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With magnesium; acetic acid In methanol at 20℃;93%
formaldehyd
50-00-0

formaldehyd

Glyoxal
131543-46-9

Glyoxal

ammonia
7664-41-7

ammonia

1-amino-2-propene
107-11-9

1-amino-2-propene

A

1H-imidazole
288-32-4

1H-imidazole

B

1-allylimidazole
31410-01-2

1-allylimidazole

Conditions
ConditionsYield
Stage #1: formaldehyd; ammonia; 1-amino-2-propene In water at 25℃; for 1h;
Stage #2: Glyoxal; ammonia at 25℃; for 1h;
A 4%
B 93%
N-tosylimidazole
2232-08-8

N-tosylimidazole

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With lithium hydroxide; mercaptoacetic acid In N,N-dimethyl-formamide at 20℃; for 2h;92%
With mercaptoacetic acid; lithium hydroxide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;92%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;75%
With acetic anhydride In pyridine for 5h; Ambient temperature;
N-(tert-butoxycarbonyl)-L-serine methyl ester
2766-43-0

N-(tert-butoxycarbonyl)-L-serine methyl ester

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

A

1H-imidazole
288-32-4

1H-imidazole

B

imidazole-1-carboxylic acid 2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl ester

imidazole-1-carboxylic acid 2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl ester

Conditions
ConditionsYield
In acetonitrile at 25℃; for 12h; Esterification;A n/a
B 91%
1,1'-bis(imidazolyl)methane
84661-56-3

1,1'-bis(imidazolyl)methane

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With lithium aluminium tetrahydride; acetic acid for 4.5h;91%
imidazole-2-thione
872-35-5

imidazole-2-thione

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid at 25℃; for 0.0166667h;90%
With 3,3-dimethyldioxirane In methanol; acetone at 25℃; other imidazole derivatives;81%
lysidine
534-26-9

lysidine

A

1H-imidazole
288-32-4

1H-imidazole

B

2-imidazolinecarbonitrile
1092546-18-3

2-imidazolinecarbonitrile

C

2-imidazolinecarboxamide
696650-10-9

2-imidazolinecarboxamide

Conditions
ConditionsYield
With ammonia; MoO3-Sb2O4-TiO2 at 330℃;A n/a
B n/a
C 90%
N-tritylimidazole
15469-97-3

N-tritylimidazole

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With Na2K-SG(I) In tetrahydrofuran at 20℃; Inert atmosphere;90%
Glyoxal
131543-46-9

Glyoxal

ammonia
7664-41-7

ammonia

ethanolamine
141-43-5

ethanolamine

acetaldehyde
75-07-0

acetaldehyde

A

1H-imidazole
288-32-4

1H-imidazole

B

N-(2'-hydroxyethyl)-2-methylimidazole
1615-15-2

N-(2'-hydroxyethyl)-2-methylimidazole

Conditions
ConditionsYield
Stage #1: ammonia; ethanolamine; acetaldehyde In water at 25℃; for 1h;
Stage #2: Glyoxal; ammonia at 25℃; for 1h;
A 5%
B 89%
salicylaldehyde
90-02-8

salicylaldehyde

2-triphenyl(α-carboxymethylene)phosphorane imidazolide
73818-41-4

2-triphenyl(α-carboxymethylene)phosphorane imidazolide

A

1H-imidazole
288-32-4

1H-imidazole

B

coumarin
91-64-5

coumarin

Conditions
ConditionsYield
Stage #1: salicylaldehyde With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 2h; Inert atmosphere;
Stage #2: 2-triphenyl(α-carboxymethylene)phosphorane imidazolide In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Intramolecular Wittig reaction; Reflux; Inert atmosphere;
A n/a
B 85%
1-allylimidazole
31410-01-2

1-allylimidazole

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); diisobutylaluminium hydride In toluene for 1h; Ambient temperature;81%
With Na2K-SG(I) In tetrahydrofuran at 20℃; Inert atmosphere;65%
piperazine
110-85-0

piperazine

A

1H-imidazole
288-32-4

1H-imidazole

B

1,4-pyrazine
290-37-9

1,4-pyrazine

C

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

1-methyl-1H-imidazole

D

2-Methylpyrazine
109-08-0

2-Methylpyrazine

E

2-ethylpyrazine
13925-00-3

2-ethylpyrazine

F

2-methylimidazole
693-98-1

2-methylimidazole

Conditions
ConditionsYield
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
Glyoxal
131543-46-9

Glyoxal

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 106℃; for 0.0583333h; Microwave irradiation;78%
1H,1H,2H,2H-Perfluorodecanethiol
34143-74-3

1H,1H,2H,2H-Perfluorodecanethiol

1-(2-nitrobenzenesulfonyl)-1H-imidazole

1-(2-nitrobenzenesulfonyl)-1H-imidazole

A

1H-imidazole
288-32-4

1H-imidazole

B

1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-2-nitro-benzene

1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decylsulfanyl)-2-nitro-benzene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃;A 76%
B n/a
1-(2-hydroxy-1-naphthyl)ethan-1-one
574-19-6

1-(2-hydroxy-1-naphthyl)ethan-1-one

2-triphenyl(α-carboxymethylene)phosphorane imidazolide
73818-41-4

2-triphenyl(α-carboxymethylene)phosphorane imidazolide

A

1H-imidazole
288-32-4

1H-imidazole

B

1-methyl-3H-naphtho[2,1-b]pyran-3-one
21568-13-8

1-methyl-3H-naphtho[2,1-b]pyran-3-one

Conditions
ConditionsYield
Stage #1: 1-(2-hydroxy-1-naphthyl)ethan-1-one With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 2h; Inert atmosphere;
Stage #2: 2-triphenyl(α-carboxymethylene)phosphorane imidazolide In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Intramolecular Wittig reaction; Reflux; Inert atmosphere;
A n/a
B 75%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

2-triphenyl(α-carboxymethylene)phosphorane imidazolide
73818-41-4

2-triphenyl(α-carboxymethylene)phosphorane imidazolide

A

1H-imidazole
288-32-4

1H-imidazole

B

4-methyl-2H-chromen-2-one
607-71-6

4-methyl-2H-chromen-2-one

Conditions
ConditionsYield
Stage #1: o-hydroxyacetophenone With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 2h; Inert atmosphere;
Stage #2: 2-triphenyl(α-carboxymethylene)phosphorane imidazolide In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Intramolecular Wittig reaction; Reflux; Inert atmosphere;
A n/a
B 75%
1-benzhydryl-1H-imidazole
7189-67-5

1-benzhydryl-1H-imidazole

1H-imidazole
288-32-4

1H-imidazole

Conditions
ConditionsYield
With Na2K-SG(I) In tetrahydrofuran at 20℃; Inert atmosphere;75%
1H-imidazole
288-32-4

1H-imidazole

dichloromethane
75-09-2

dichloromethane

1,1'-bis(imidazolyl)methane
84661-56-3

1,1'-bis(imidazolyl)methane

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide for 13h; Ambient temperature;100%
With sodium hydroxide; phase transfer catalysis by tetraethylammonium bromide for 16h; Ambient temperature;96%
With tetrabutylammomium bromide; sodium hydroxide Inert atmosphere; Reflux;87%
1H-imidazole
288-32-4

1H-imidazole

benzoyl chloride
98-88-4

benzoyl chloride

1-benzoylimidazole
10364-94-0

1-benzoylimidazole

Conditions
ConditionsYield
In benzene at 8 - 20℃;100%
With iodine at 20℃; for 0.233333h; Neat (no solvent);97.32%
In benzene at 20℃; for 24h;94%
1H-imidazole
288-32-4

1H-imidazole

phenyl isocyanate
103-71-9

phenyl isocyanate

N-phenyl-1H-imidazole-1-carboxamide
33876-94-7

N-phenyl-1H-imidazole-1-carboxamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;100%
In 1,4-dioxane at 0 - 20℃;87%
In diethyl ether for 3h; Heating;84%
1H-imidazole
288-32-4

1H-imidazole

propyl bromide
106-94-5

propyl bromide

1-propyl-1H-imidazole
35203-44-2

1-propyl-1H-imidazole

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;100%
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h;
Stage #2: propyl bromide In tetrahydrofuran; mineral oil at 20℃; for 16h;
93%
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; hexane at 20℃;
Stage #2: propyl bromide In tetrahydrofuran; hexane at 60 - 65℃; Reflux;
86%
1H-imidazole
288-32-4

1H-imidazole

p-Xylylene dichloride
623-25-6

p-Xylylene dichloride

1,4-bis(imidazol-l-yl-methyl)benzene
56643-83-5

1,4-bis(imidazol-l-yl-methyl)benzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 6h;100%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h;
Stage #2: p-Xylylene dichloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h;
100%
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 6h;100%
1H-imidazole
288-32-4

1H-imidazole

2,4,5-triiodoimidazole
1746-25-4

2,4,5-triiodoimidazole

Conditions
ConditionsYield
With iodine; sodium carbonate In 1,4-dioxane; water at 20℃; for 24h;100%
With dihydrogen peroxide; iodine In water at 50℃; for 24h; Green chemistry;97%
With pyridine; iodine; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane for 3h; Ambient temperature;95%
1H-imidazole
288-32-4

1H-imidazole

2,4-dichloro-6-ethyl-5-nitropyrimidine
52379-63-2

2,4-dichloro-6-ethyl-5-nitropyrimidine

6-ethyl-2,4-bis(1H-imidazol-1-yl)-5-nitropyrimidine
156489-94-0

6-ethyl-2,4-bis(1H-imidazol-1-yl)-5-nitropyrimidine

Conditions
ConditionsYield
In acetonitrile for 18h; Ambient temperature;100%
1H-imidazole
288-32-4

1H-imidazole

1-(2-(phenylsulfonyl)ethyl)-1H-imidazole

1-(2-(phenylsulfonyl)ethyl)-1H-imidazole

Conditions
ConditionsYield
In acetonitrile for 2h; Ambient temperature;100%
Stage #1: 1H-imidazole With o-phenylenebis(diphenylphosphine); potassium tert-butylate; copper(l) chloride In toluene for 0.166667h; Michael Addition; Inert atmosphere;
Stage #2: PVS In toluene at 22℃; for 3h; Michael Addition; Inert atmosphere;
99%
1H-imidazole
288-32-4

1H-imidazole

2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

2-imidazol-1-yl-benzonitrile
25373-49-3

2-imidazol-1-yl-benzonitrile

Conditions
ConditionsYield
With 1,2,3-Benzotriazole; potassium tert-butylate; copper(l) iodide In dimethyl sulfoxide at 110℃; for 0.5h;100%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 36h;97%
With potassium carbonate; trans-1,2-diaminocyclohexane-based copper(II) complex In N,N-dimethyl-formamide at 110℃; for 1.5h;92%
1H-imidazole
288-32-4

1H-imidazole

(2-trimethylethylsilylethoxy)methyl chloride
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole
101226-33-9

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran at 0 - 25℃; for 0.5h; Inert atmosphere;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 0 - 25℃; for 14h; Inert atmosphere;
100%
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.75h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃;
93%
Stage #1: 1H-imidazole With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 0.5h; Large scale;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In dimethyl sulfoxide at 0 - 15℃; for 16h; Large scale;
90%
1H-imidazole
288-32-4

1H-imidazole

benzyl bromide
100-39-0

benzyl bromide

1-benzylimidazole
4238-71-5

1-benzylimidazole

Conditions
ConditionsYield
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;
100%
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 25℃; for 3h;
97%
With caesium carbonate at 100℃; for 0.416667h; Microwave irradiation;90%
1H-imidazole
288-32-4

1H-imidazole

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

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

1-oxo-5,11-dihydro-11-imidazol-1'-ylacetyl-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one
84446-11-7

1-oxo-5,11-dihydro-11-imidazol-1'-ylacetyl-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one

Conditions
ConditionsYield
In toluene at 80℃; for 2h;100%
1H-imidazole
288-32-4

1H-imidazole

ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

1-(2-nitrophenyl)-1H-imidazole
23309-16-2

1-(2-nitrophenyl)-1H-imidazole

Conditions
ConditionsYield
With 1,2,3-Benzotriazole; potassium tert-butylate; copper(l) iodide In dimethyl sulfoxide at 110℃; for 0.5h;100%
With pyridine; potassium carbonate; copper(II) oxide at 115℃; Ullmann Condensation;96%
With potassium carbonate In acetonitrile for 24h; Heating;95%
1H-imidazole
288-32-4

1H-imidazole

3-methoxycarbonylbenzyl bromide
1129-28-8

3-methoxycarbonylbenzyl bromide

methyl 3-((1H-imidazol-1-yl)methyl)benzoate
218131-31-8

methyl 3-((1H-imidazol-1-yl)methyl)benzoate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 20h;100%
In N,N-dimethyl-formamide for 8h;67%
In acetone for 2h; Heating;55%
1H-imidazole
288-32-4

1H-imidazole

ethanol
64-17-5

ethanol

N-Ethylimidazole
7098-07-9

N-Ethylimidazole

Conditions
ConditionsYield
H-Y zeolite at 299.9℃;100%
calcined Mg-Al layered double hydroxides at 424.85℃; Alkylation;63%
1H-imidazole
288-32-4

1H-imidazole

formaldehyd
50-00-0

formaldehyd

diethylamine
109-89-7

diethylamine

N-((1H-imidazol-1-yl)methyl)-N-ethylethanamine

N-((1H-imidazol-1-yl)methyl)-N-ethylethanamine

Conditions
ConditionsYield
With hydrogenchloride for 48h; Ambient temperature;100%
1H-imidazole
288-32-4

1H-imidazole

1,4-bis(bromomethyl)benzene
623-24-5

1,4-bis(bromomethyl)benzene

1,4-bis(imidazol-l-yl-methyl)benzene
56643-83-5

1,4-bis(imidazol-l-yl-methyl)benzene

Conditions
ConditionsYield
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;
Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran; mineral oil for 6h; Reflux; Inert atmosphere;
100%
Stage #1: 1H-imidazole With potassium hydroxide In acetonitrile at 20℃; for 2h;
Stage #2: 1,4-bis(bromomethyl)benzene In acetonitrile at 20℃; for 1.5h;
88%
With potassium hydroxide In isopropyl alcohol80%
1H-imidazole
288-32-4

1H-imidazole

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 1H-imidazole-1-carboxylate
49761-82-2

tert-butyl 1H-imidazole-1-carboxylate

Conditions
ConditionsYield
With 1-methylimidazolium tetrafluoroborate at 30 - 35℃; for 0.0833333h;100%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.0166667h;100%
With amberlyst-15 In ethanol at 20℃; for 0.0166667h; chemoselective reaction;100%
1H-imidazole
288-32-4

1H-imidazole

3,4-dibromophenylsulfonic acid chloride
81903-80-2

3,4-dibromophenylsulfonic acid chloride

1-((3,4-dibromophenyl)sulfonyl)-1H-imidazole
224824-30-0

1-((3,4-dibromophenyl)sulfonyl)-1H-imidazole

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 19h;100%
With sodium carbonate In methanol; chloroform for 22h; Ambient temperature;34%
1H-imidazole
288-32-4

1H-imidazole

(2R,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxy-2-(2-methanesulfonyloxyethyl)pyrrolidine
156441-21-3

(2R,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxy-2-(2-methanesulfonyloxyethyl)pyrrolidine

(2R,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxy-2-[2-(imidazol-1-yl)ethyl]pyrrolidine
156441-22-4

(2R,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxy-2-[2-(imidazol-1-yl)ethyl]pyrrolidine

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 60℃; for 1h; Alkylation;100%
1H-imidazole
288-32-4

1H-imidazole

phenylboronic acid
98-80-6

phenylboronic acid

1-phenylimidazole
7164-98-9

1-phenylimidazole

Conditions
ConditionsYield
With [Cu4I4(1,4-diazabicyclo[2.2.2]octane)2]n In methanol at 27℃; for 5h;100%
With [Cu30I16(5-methyl-4-(p-tolyl)pyrimidine-2-thiolato)12(μ10-S4)] In methanol for 5h; Temperature; Reagent/catalyst; Reflux;99%
With polystrene supported copper furfural catalyst In methanol at 40℃; for 10h; Inert atmosphere;99%
1H-imidazole
288-32-4

1H-imidazole

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

triethylamine
121-44-8

triethylamine

(μ-(1H-imidazolato-κ-N1:κ-N3))hexakis(pentafluorophenyl)di-borate(1-), N,N-diethylethanamine

(μ-(1H-imidazolato-κ-N1:κ-N3))hexakis(pentafluorophenyl)di-borate(1-), N,N-diethylethanamine

Conditions
ConditionsYield
In toluene for 5h; Heating;100%
In toluene at 20℃;91.9%
In toluene to soln. B(C6F5)3 and imidazole in toluene triethylamine in toluene wasadded, react. mixt. was stirred overnight at room temp.; soln. was concd., hexane was added, ppt. was filtered, washed with hexane and dried under reduced pressure; elem. anal.;91.9%
1H-imidazole
288-32-4

1H-imidazole

m-Fluorobenzonitrile
403-54-3

m-Fluorobenzonitrile

3-(1-imidazolyl)benzonitrile
25699-85-8

3-(1-imidazolyl)benzonitrile

Conditions
ConditionsYield
potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;100%
With tripotassium phosphate "n" hydrate In N,N-dimethyl-formamide at 110℃; for 18h;50%
With potassium carbonate; N,N-dimethyl-formamide at 100℃; for 48h; Inert atmosphere;46%
With potassium carbonate In N,N-dimethyl-formamide at 110℃;
potassium carbonate In N,N-dimethyl-formamide
1H-imidazole
288-32-4

1H-imidazole

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

1-(4-nitrophenyl)-1H-imidazole
2301-25-9

1-(4-nitrophenyl)-1H-imidazole

Conditions
ConditionsYield
With copper phthalocyanine; sodium hydroxide In dimethyl sulfoxide at 100℃;100%
With Hippuric Acid; copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 140℃; for 30h; Ullmann coupling reaction;99%
With caesium carbonate In dimethyl sulfoxide at 110℃; for 1h; Ullmann Condensation;98%
1H-imidazole
288-32-4

1H-imidazole

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

1-(4-nitrophenyl)-1H-imidazole
2301-25-9

1-(4-nitrophenyl)-1H-imidazole

Conditions
ConditionsYield
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride at 140 - 145℃; for 24h;100%
With potassium tert-butylate; trans-1,2-diaminocyclohexane-based copper(II) complex In N,N-dimethyl-formamide at 110℃; for 2h;99%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 24.5h;98%
1H-imidazole
288-32-4

1H-imidazole

iodobenzene
591-50-4

iodobenzene

1-phenylimidazole
7164-98-9

1-phenylimidazole

Conditions
ConditionsYield
With potassium tert-butylate; copper(I) oxide In N,N-dimethyl-formamide at 80℃; for 24h;100%
With potassium tert-butylate In toluene at 180℃; for 18h; Ullmann condensation;100%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere;99%
1H-imidazole
288-32-4

1H-imidazole

1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

1,3-bis(1H-imidazol-1-yl)benzene
69506-91-8

1,3-bis(1H-imidazol-1-yl)benzene

Conditions
ConditionsYield
With 1-sulfanyl-2-(dimethylaminomethyl)-3-Me3Si-benzene-Cu(I); potassium carbonate In 1-methyl-pyrrolidin-2-one at 160℃; for 16h;100%
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 150℃; for 48h;99%
With copper(l) iodide; dimethylaminoacetic acid; potassium carbonate In dimethyl sulfoxide at 110℃; for 48h; Inert atmosphere;93%
1H-imidazole
288-32-4

1H-imidazole

para-bromoacetophenone
99-90-1

para-bromoacetophenone

4'-(imidazol-1-yl)acetophenone
10041-06-2

4'-(imidazol-1-yl)acetophenone

Conditions
ConditionsYield
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride at 140 - 145℃; for 24h;100%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 24.5h;99%
With potassium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 110℃; for 24h; Ullmann coupling reaction;98%
6-(bromoacetyl)-2-butyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one
871946-66-6

6-(bromoacetyl)-2-butyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

1H-imidazole
288-32-4

1H-imidazole

2-butyl-6-(1H-1-imidazolylacetyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one
871946-70-2

2-butyl-6-(1H-1-imidazolylacetyl)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

Conditions
ConditionsYield
In chloroform at 20℃; for 5h;100%
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