Product Name

  • Name

    1H-Imidazole-4-carbonitrile

  • EINECS 611-464-4
  • CAS No. 57090-88-7
  • Article Data19
  • CAS DataBase
  • Density 1.29 g/cm3
  • Solubility
  • Melting Point 143.5-144.5 °C
  • Formula C4H3N3
  • Boiling Point 388.128 °C at 760 mmHg
  • Molecular Weight 93.0879
  • Flash Point 130.816 °C
  • Transport Information
  • Appearance
  • Safety 26
  • Risk Codes 36
  • Molecular Structure Molecular Structure of 57090-88-7 (1H-Imidazole-4-carbonitrile)
  • Hazard Symbols Xi
  • Synonyms 1H-Imidazole-4-carbonitrile(9CI);1H-Imidazol-4-nitrile;4-Cyano-1H-imidazole;4-Cyanoimidazole;4-Imidazolecarbonitrile;1H-Imidazole-5-carbonitrile;
  • PSA 52.47000
  • LogP 0.28138

Synthetic route

4-(trifluoromethyl)-1H-imidazole
33468-69-8

4-(trifluoromethyl)-1H-imidazole

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
With ammonium hydroxide at 60℃; for 8h;87%
4(5)formylimidazole
3034-50-2

4(5)formylimidazole

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
Stage #1: 4(5)formylimidazole With pyridine; hydroxylamine hydrochloride at 8 - 30℃; for 2h;
Stage #2: With acetic anhydride at 80 - 110℃; for 3.83333h;		82%
With pyridine; hydroxylamine hydrochloride; acetic anhydride at 0 - 110℃; for 5.83333h;82%
Stage #1: 4(5)formylimidazole With pyridine; hydroxylamine hydrochloride at 8 - 30℃; for 2h;
Stage #2: With acetic anhydride at 80 - 110℃; for 0.5h;		82%
1H-imidazole-4-carboxaldehyde oxime
57090-90-1

1H-imidazole-4-carboxaldehyde oxime

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
With acetic anhydride at 20 - 100℃; for 1h;81%
With acetic anhydride at 78 - 110℃;
Stage #1: 1H-imidazole-4-carboxaldehyde oxime With acetic anhydride at 80 - 110℃; for 3.83333h;
Stage #2: With sodium hydroxide In water at 30℃; pH=8;
Stage #3: With hydrogenchloride In water pH=2; Product distribution / selectivity;
With pyridine; acetic anhydride at 120℃; for 1.5h;
With acetic anhydride at 80 - 110℃;42.7 g
4-cyano-5-imidazolecarboxylic acid
56745-98-3

4-cyano-5-imidazolecarboxylic acid

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
In nitrobenzene for 20h; Heating;80%
imidazole-4-carboxamide
26832-08-6

imidazole-4-carboxamide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
Stage #1: imidazole-4-carboxamide With trichlorophosphate In acetonitrile for 15h; Inert atmosphere; Reflux;
Stage #2: With sodium hydroxide In water; acetonitrile pH=9 - 11;		65.9%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

4-bromo-1 H-imidazole
2302-25-2

4-bromo-1 H-imidazole

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
With t-BuBrettPhos; C44H62NO5PPdS(1-); potassium acetate In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube;34 %Spectr.
n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-[1H-imidazol-4(5)-yl]pentan-1-one

1-[1H-imidazol-4(5)-yl]pentan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Grignard reaction;96%
1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

cyclohexylmagnesium bromide
931-50-0

cyclohexylmagnesium bromide

cyclohexyl[1H-imidazol-4(5)-yl]methanone

cyclohexyl[1H-imidazol-4(5)-yl]methanone

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Grignard reaction;92%
isobutylmagnesium bromide
926-62-5

isobutylmagnesium bromide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-[1H-imidazol-4(5)-yl]-3-methylbutan-1-one

1-[1H-imidazol-4(5)-yl]-3-methylbutan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Grignard reaction;90%
1-fluoro-2-methoxy-4-nitrobenzene
454-16-0

1-fluoro-2-methoxy-4-nitrobenzene

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

4-cyano-1-(2-methoxy-4-nitrophenyl)-1H-imidazole
1263868-22-9

4-cyano-1-(2-methoxy-4-nitrophenyl)-1H-imidazole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃;89%
1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

methyl iodide
74-88-4

methyl iodide

1-methyl-1H-imidazole-4-carbonitrile
66121-69-5

1-methyl-1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
Stage #1: 1H-imidazole-4-carbonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 25℃; for 2h;		86%
With potassium fluoride on basic alumina at 20℃; for 24h;1.9 g
sec-butylmagnesium bromide
671795-46-3

sec-butylmagnesium bromide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-[1H-imidazol-4(5)-yl]-2-methylbutan-1-one

1-[1H-imidazol-4(5)-yl]-2-methylbutan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Grignard reaction;85%
n-propylmagnesium bromide
927-77-5

n-propylmagnesium bromide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-[1H-imidazol-4(5)-yl]butan-1-one

1-[1H-imidazol-4(5)-yl]butan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Grignard reaction;83%
With sodium hydroxide; sulfuric acid In tetrahydrofuran; hexane; water83%
1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

isopropyl bromide
75-26-3

isopropyl bromide

1-[1H-imidazol-4(5)-yl]-2-methylpropan-1-one
247174-71-6

1-[1H-imidazol-4(5)-yl]-2-methylpropan-1-one

Conditions
ConditionsYield
Stage #1: isopropyl bromide With iodine; magnesium In tetrahydrofuran Grignard reaction;
Stage #2: 1H-imidazole-4-carbonitrile In tetrahydrofuran at 20℃; for 3h;		82%
di-isopropyl ether
108-20-3

di-isopropyl ether

isopropylmagnesium bromide
920-39-8

isopropylmagnesium bromide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-[1H-imidazol-4(5)-yl]-2-methylpropan-1-one
247174-71-6

1-[1H-imidazol-4(5)-yl]-2-methylpropan-1-one

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid In tetrahydrofuran; water82%
...Expand
isopropylmagnesium bromide
920-39-8

isopropylmagnesium bromide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-[1H-imidazol-4(5)-yl]-2-methylpropan-1-one
247174-71-6

1-[1H-imidazol-4(5)-yl]-2-methylpropan-1-one

Conditions
ConditionsYield
Stage #1: isopropylmagnesium bromide; 1H-imidazole-4-carbonitrile In tetrahydrofuran at 10℃; for 3.5h; Inert atmosphere;
Stage #2: With sulfuric acid In water for 0.5h; Inert atmosphere;		82%
methyl isocyanate
624-83-9

methyl isocyanate

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

4-cyano-1-(methylcarbamoyl)imidazole
87864-83-3

4-cyano-1-(methylcarbamoyl)imidazole

Conditions
ConditionsYield
With dibutyltin(II) dilaurate; 2-methyl-1,4-diazabicyclo [2,2,2]octane In dichloromethane for 16h; Ambient temperature;81%
2,3-dimethylbromobenzene
576-23-8

2,3-dimethylbromobenzene

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

(2,3-dimethylphenyl)(1H-imidazol-5-yl)methanone

(2,3-dimethylphenyl)(1H-imidazol-5-yl)methanone

Conditions
ConditionsYield
Stage #1: 2,3-dimethylbromobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 40 - 65℃; for 1h;
Stage #2: 1H-imidazole-4-carbonitrile With isopropylmagnesium chloride In tetrahydrofuran at -5 - 0℃; for 2h;
Stage #3: With sulfuric acid In tetrahydrofuran; water at 30℃; for 3h;		80%
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-(1H-imidazol-4-yl)-1-propanone

1-(1H-imidazol-4-yl)-1-propanone

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Grignard reaction;79%
With sodium hydroxide; sulfuric acid In tetrahydrofuran; hexane; water63%
(2-trimethylethylsilylethoxy)methyl chloride
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carbonitrile
854044-51-2

2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
Stage #1: (2-trimethylethylsilylethoxy)methyl chloride; 1H-imidazole-4-carbonitrile With potassium carbonate In acetone at 20℃; for 10h;
Stage #2: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 60℃; for 4h;		77%
Stage #1: (2-trimethylethylsilylethoxy)methyl chloride; 1H-imidazole-4-carbonitrile With potassium carbonate In acetone at 60℃;
Stage #2: With 2,2'-azobis(isobutyronitrile) In tetrachloromethane; acetone
Stage #1: (2-trimethylethylsilylethoxy)methyl chloride; 1H-imidazole-4-carbonitrile With potassium carbonate In acetone at 20℃; for 48h; Inert atmosphere;
Stage #2: With N-Bromosuccinimide In tetrahydrofuran at 60℃; Inert atmosphere;		1.24 g
Stage #1: (2-trimethylethylsilylethoxy)methyl chloride; 1H-imidazole-4-carbonitrile With potassium carbonate In acetone at 10 - 20℃;
Stage #2: With N-Bromosuccinimide In tetrachloromethane at 60 - 75℃;		800 mg
1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

N-(diphenylmethylene)-2,2,2-trifluoro-1-ethanamine

N-(diphenylmethylene)-2,2,2-trifluoro-1-ethanamine

C19H13FN4

C19H13FN4

Conditions
ConditionsYield
Stage #1: 1H-imidazole-4-carbonitrile; N-(diphenylmethylene)-2,2,2-trifluoro-1-ethanamine With potassium phosphate In tetrahydrofuran at -78 - 25℃; for 0.5h; Inert atmosphere;
Stage #2: With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere; stereoselective reaction;		75%
1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

methyl iodide
74-88-4

methyl iodide

1-methyl-1H-imidazole-5-carbonitrile
66121-66-2

1-methyl-1H-imidazole-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 1H-imidazole-4-carbonitrile With 2,2,6,6-tetramethylpiperidinylmagnesium chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 70℃; for 20h; Inert atmosphere;		74%
(2-trimethylethylsilylethoxy)methyl chloride
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carbonitrile
854044-50-1

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 10h;70%
With potassium carbonate In acetone at 20℃; for 10h; Product distribution / selectivity;70%
With potassium carbonate In acetone at 20℃; for 10h;70%
5-fluoro-2-nitrophenol
446-36-6

5-fluoro-2-nitrophenol

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-(3-hydroxy-4-nitrophenyl)-1H-imidazole-4-carbonitrile

1-(3-hydroxy-4-nitrophenyl)-1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 16h;68%
phenyl isocyanate
103-71-9

phenyl isocyanate

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

4-cyano-1-(phenylcarbamoyl)imidazole
87864-82-2

4-cyano-1-(phenylcarbamoyl)imidazole

Conditions
ConditionsYield
With dibutyltin(II) dilaurate; 2-methyl-1,4-diazabicyclo [2,2,2]octane In dichloromethane for 16h; Ambient temperature;60%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

[4-Cyano-1H-imidazol-1-yl]acetic acid ethyl ester
1154030-58-6

[4-Cyano-1H-imidazol-1-yl]acetic acid ethyl ester

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 20℃; for 16h;60%
In ethanol; sodium ethanolate
1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

2-(trifluoromethyl)pyridine-4-iodide
590371-73-6

2-(trifluoromethyl)pyridine-4-iodide

C10H5F3N4

C10H5F3N4

Conditions
ConditionsYield
With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;59%
2-chloro-3-methoxy-5-nitropyridine
75711-00-1

2-chloro-3-methoxy-5-nitropyridine

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4-carbonitrile

1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 20 - 50℃; for 16h; Inert atmosphere;56%
With potassium carbonate In dimethyl sulfoxide at 50℃; for 16h; Inert atmosphere;56%
1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

thymidine
50-89-5

thymidine

A

1-(2-deoxy-β-D-ribofuranosyl)-1H-imidazole-4-carbonitrile

1-(2-deoxy-β-D-ribofuranosyl)-1H-imidazole-4-carbonitrile

B

1-(2-deoxy-β-D-ribofuranosyl)-1H-imidazole-5-carbonitrile

1-(2-deoxy-β-D-ribofuranosyl)-1H-imidazole-5-carbonitrile

Conditions
ConditionsYield
With nucleoside 2-deoxyribosyltransferases class II from L.leichmannii In dimethyl sulfoxide at 50℃; for 2h; pH=6.5; Enzymatic reaction; regioselective reaction;A 56%
B 4%
...Expand
4-tolyl iodide
624-31-7

4-tolyl iodide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-(p-tolyl)-1H-imidazole-4-carbonitrile

1-(p-tolyl)-1H-imidazole-4-carbonitrile

Conditions
ConditionsYield
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;51%
With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; caesium carbonate In N,N-dimethyl-d6-formamide at 100℃; for 2h; Inert atmosphere;44.7%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

1H-imidazole-4-carbonitrile
57090-88-7

1H-imidazole-4-carbonitrile

1-(1H-imidazol-4-yl)ethan-1-one
61985-25-9

1-(1H-imidazol-4-yl)ethan-1-one

Conditions
ConditionsYield
Stage #1: methylmagnesium bromide; 1H-imidazole-4-carbonitrile In tetrahydrofuran; diethyl ether at 10 - 20℃; for 2.75h;
Stage #2: With sulfuric acid; water In tetrahydrofuran; diethyl ether at 20℃; for 0.5h;		48%

1H-Imidazole-4-carbonitrile Specification

The 1H-Imidazole-4-carbonitrile with cas registry number of 57090-88-7, is also named 1H-Imidazole-4-carbonitrile(9CI) ; 1H-Imidazol-4-nitrile .The 1H-Imidazole-4-carbonitrile belongs to the following product categories: (1)pharmacetical; (2)Imidazoles & Benzimidazoles .

Physical properties of 1H-Imidazole-4-carbonitrile :(1)ACD/LogP: -0.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.72; (4)ACD/LogD (pH 7.4): -0.73; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 9.62; (8)ACD/KOC (pH 7.4): 9.58; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 41.61 Å2; (13)Index of Refraction: 1.551; (14)Molar Refractivity: 23.04 cm3; (15)Molar Volume: 72.1 cm3; (16)Polarizability: 9.13×10-24cm3; (17)Surface Tension: 71.5 dyne/cm; (18)Enthalpy of Vaporization: 63.73 kJ/mol; (19)Vapour Pressure: 3.13E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure: (1)SMILES:N#Cc1cncn1; (2)InChI:InChI=1/C4H3N3/c5-1-4-2-6-3-7-4/h2-3H,(H,6,7)InChIKey:NWVGXXPWOYZODV-UHFFFAOYAT; (3)Std. InChI:InChI=1S/C4H3N3/c5-1-4-2-6-3-7-4/h2-3H,(H,6,7); (4)Std. InChIKey:NWVGXXPWOYZODV-UHFFFAOYSA-N.

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