1-(Cyanomethyl)imidazole supplier

Name
IMIDAZOL-1-YL-ACETONITRILE
EINECS 1592732-453-0
CAS No. 98873-55-3
Article Data13
CAS DataBase
Density 1.111 g/cm³
Solubility
Melting Point 54.0 to 58.0 °C
Formula C₅H₅N₃
Boiling Point 329.691 °C at 760 mmHg
Molecular Weight 107.115
Flash Point 153.192 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms 1-Imidazolylacetonitrile;
PSA 41.61000
LogP 0.40668

Synthetic route

: 288-32-4
1H-imidazole

: 75-05-8
acetonitrile

: 98873-55-3
1-cyanomethylimidazole

Conditions

Conditions	Yield
With 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; sodium hydride at 50℃;	87%

: 288-32-4
1H-imidazole

: 590-17-0
cyanomethyl bromide

: 98873-55-3
1-cyanomethylimidazole

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran for 6h;	70%
With sodium hydride In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	70%
With NaH (60percent suspension in mineral oil) In tetrahydrofuran at 20℃; for 4h;	64%

: 288-32-4
1H-imidazole

: 107-14-2
chloroacetonitrile

: 98873-55-3
1-cyanomethylimidazole

Conditions

Conditions	Yield
Stage #1: 1H-imidazole With sodium sulfate; sodium hydroxide In acetonitrile at -5 - 5℃; for 0.166667h; Stage #2: chloroacetonitrile In acetonitrile for 0.166667h;	62%
With potassium hydroxide 1.) acetonitrile, RT, 1.5 h, 2.) acetonitrile, RT, 6 h; Yield given. Multistep reaction;
In tetrahydrofuran; chloroform; water
With triethylamine In toluene Solvent; Reagent/catalyst;

: 75-15-0
carbon disulfide

: [2-(2,4-dichlorophenyl)-3-methylsulfonyloxy-propyl] methanesulfonate

: 98873-55-3
1-cyanomethylimidazole

: 2-[5-(2,4-dichlorophenyl)-1,3-dithian-2-ylidene]-2-imidazol-1-ylacetonitrile

Conditions

Conditions	Yield
Stage #1: carbon disulfide; 1-cyanomethylimidazole With potassium hydroxide In dimethyl sulfoxide at 10 - 20℃; Inert atmosphere; Stage #2: [2-(2,4-dichlorophenyl)-3-methylsulfonyloxy-propyl] methanesulfonate With potassium hydroxide at 20℃; Inert atmosphere;	92%

...Expand

: 98873-55-3
1-cyanomethylimidazole

: 170998-10-4
4-amino-3,5-bis(imidazol-1-ylmethyl)-1,2,4-triazole

Conditions

Conditions	Yield
With hydrazine hydrate at 100℃; for 6.5h;	82%

: 64-17-5
ethanol

: 98873-55-3
1-cyanomethylimidazole

: 2-imidazol-1-yl-acetimidic acid ethyl ester; hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In benzene at 0℃; Pinner reaction;	74%

: 4282-42-2
1-iodononane

: 98873-55-3
1-cyanomethylimidazole

: 172940-17-9
methyl 5-(cyano[nonyl]methyl)-3-tetrahydropyranyl-imidazole-4-carboxylate

Conditions

Conditions	Yield
With NaH In ethyl acetate	67%

: 1310-58-3
potassium hydroxide

: 96-12-8
nemagon

: 98873-55-3
1-cyanomethylimidazole

: 101530-02-3
2-(1-imidazolyl)-2-(4-chloro-methyl-1,3-dithiolan-2-ylidene)acetonitrile

Conditions

Conditions	Yield
With carbon disulfide; dimethyl sulfoxide In water	62%

...Expand

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 98873-55-3
1-cyanomethylimidazole

: (E)-3-(dimethylamino)-2-(1H-imidazol-1-yl)acrylonitrile

Conditions

Conditions	Yield
at 90℃; for 0.25h; Microwave irradiation;	49.5%

: 98873-55-3
1-cyanomethylimidazole

: 312324-17-7
C8H15ClN2O3

: (S)-tert-butyl {1-[5-amino-4-(1H-imidazol-1-yl)isoxazol-3-yl]-ethyl}carbamate

Conditions

Conditions	Yield
Stage #1: 1-cyanomethylimidazole With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Inert atmosphere; Stage #2: C8H15ClN2O3 In tetrahydrofuran; n-heptane; ethylbenzene at -78 - 20℃; Inert atmosphere; enantioselective reaction;	47%

: C8H15ClN2O3

: 98873-55-3
1-cyanomethylimidazole

: (R)-tert-butyl {1-[5-amino-4-(1H-imidazol-1-yl)isoxazol-3-yl]-ethyl}carbamate

Conditions

Conditions	Yield
Stage #1: 1-cyanomethylimidazole With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Inert atmosphere; Stage #2: C8H15ClN2O3 In tetrahydrofuran; n-heptane; ethylbenzene at -78 - 20℃; Inert atmosphere; enantioselective reaction;	45%

: 2026-48-4
(S)-valinol

: 98873-55-3
1-cyanomethylimidazole

: 1210068-56-6
(S)-N-(1-hydroxy-3-methylbutan-2-yl)-2-(1H-imidazol-1-yl)acetamide

Conditions

Conditions	Yield
Stage #1: (S)-valinol; 1-cyanomethylimidazole With zinc(II) chloride In chlorobenzene for 15h; Inert atmosphere; Reflux; Stage #2: With silica gel In methanol for 2h; Inert atmosphere; Reflux;	44%

: 75-15-0
carbon disulfide

: (S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

: 98873-55-3
1-cyanomethylimidazole

A: [(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile

B: luliconazole

Conditions

Conditions	Yield
Stage #1: carbon disulfide; 1-cyanomethylimidazole With potassium hydroxide In dimethyl sulfoxide at 4 - 20℃; for 2h; Stage #2: (S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate In dimethyl sulfoxide at 4 - 20℃; for 24h; Catalytic behavior;	A 19% B 43%
Stage #1: carbon disulfide; 1-cyanomethylimidazole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h; Stage #2: (S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate In dimethyl sulfoxide at 4 - 20℃; for 4h;	A n/a B n/a

...Expand

: 1310-58-3
potassium hydroxide

: 1-chloro-2-(1,2-dichloroethyl) benzene

: 98873-55-3
1-cyanomethylimidazole

: 101530-10-3
lanoconazole

Conditions

Conditions	Yield
With carbon disulfide; dimethyl sulfoxide In water	38%
With carbon disulfide; dimethyl sulfoxide In water	38%

...Expand

: 1310-58-3
potassium hydroxide

: 2'-isopropyl-1,2-dibromoethylbenzene

: 98873-55-3
1-cyanomethylimidazole

: 2-(1-imidazolyl)-2-[4-(2-isopropyl-phenyl)-1,3-dithiolan-2-ylidene]acetonitrile

Conditions

Conditions	Yield
With carbon disulfide In N-methyl-acetamide; water	34%
With carbon disulfide In N-methyl-acetamide; water

...Expand

: 75-15-0
carbon disulfide

: 98873-55-3
1-cyanomethylimidazole

: 56413-95-7
2,3-dichloro-5,6-dicyanopyrazine

: 2-(cyano(1H-imidazol-1-yl)methylene)-[1,3]dithiolo[4,5-b]pyrazine-5,6-dicarbonitrile

Conditions

Conditions	Yield
Stage #1: 1-cyanomethylimidazole With potassium hydroxide In dimethyl sulfoxide at 0 - 25℃; for 0.5h; Stage #2: carbon disulfide In dimethyl sulfoxide for 0.25h; Stage #3: 2,3-dichloro-5,6-dicyanopyrazine In dimethyl sulfoxide at 25℃; for 2h;	30%

...Expand

: 1310-58-3
potassium hydroxide

: 21750-35-6
1,2-dibromo-4-methyl-pentane

: 98873-55-3
1-cyanomethylimidazole

: 101529-88-8
2-(1-imidazolyl)-2-(4-isobutyl-1,3-dithiolan-2-ylidene)acetonitrile

Conditions

Conditions	Yield
With carbon disulfide; dimethyl sulfoxide In water	23%

...Expand

: 75-15-0
carbon disulfide

: [2-chloro-1-(2-chloro-3-fluoro-4-prop-2-ynoxy-phenyl)ethyl] methanesulfonate

: 98873-55-3
1-cyanomethylimidazole

A: (2Z)-2-[4-(2-chloro-3-fluoro-4-prop-2-ynoxyphenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile

B: (2E)-2-[4-(2-chloro-3-fluoro-4-prop-2-ynoxy-phenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile

Conditions

Conditions	Yield
Stage #1: carbon disulfide; 1-cyanomethylimidazole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere; Stage #2: [2-chloro-1-(2-chloro-3-fluoro-4-prop-2-ynoxy-phenyl)ethyl] methanesulfonate In dimethyl sulfoxide at 20℃; for 16h;	A 17% B 23%

...Expand

: 1310-58-3
potassium hydroxide

: 1,2-dibromo-1-(2’-chlorophenyl)ethane

: 98873-55-3
1-cyanomethylimidazole

: 126509-69-1
lanoconazole

Conditions

Conditions	Yield
With carbon disulfide; dimethyl sulfoxide In water	20%

...Expand

: 1310-58-3
potassium hydroxide

: 1,2-dibromo-1-(2’-chlorophenyl)ethane

: 98873-55-3
1-cyanomethylimidazole

: 101530-10-3
lanoconazole

Conditions

Conditions	Yield
With carbon disulfide; dimethyl sulfoxide In water	20%

...Expand

: 75-15-0
carbon disulfide

: 106-93-4
ethylene dibromide

: 98873-55-3
1-cyanomethylimidazole

A: 822-38-8
1,3-dithiolane-2-thione

B: (1,3-dithiolan-2-ylidene)(imidazol-1-yl)acetonitrile

Conditions

Conditions	Yield
With potassium hydroxide 1.) DMSO, 0 deg C, 1 h, 2.) DMSO, overnight; Multistep reaction;

...Expand

: 75-15-0
carbon disulfide

: 109-64-8
1,3-dibromo-propane

: 98873-55-3
1-cyanomethylimidazole

A: 1748-15-8
1,3-dithiane-2-thione

B: (1,3-dithian-2-ylidene)(imidazol-1-yl)acetonitrile

Conditions

Conditions	Yield
With potassium hydroxide 1.) DMSO, 0 deg C, 1 h, 2.) DMSO, overnight; Multistep reaction;

...Expand

: 75-15-0
carbon disulfide

: 1190-22-3
1,3-dichlorobutane

: 98873-55-3
1-cyanomethylimidazole

A: 1748-15-8
1,3-dithiane-2-thione

B: Imidazol-1-yl-[4-methyl-[1,3]dithian-(2E)-ylidene]-acetonitrile

Conditions

Conditions	Yield
With potassium hydroxide; dimethyl sulfoxide at 0℃;

...Expand

: 75-15-0
carbon disulfide

: 624-65-7
2-propynyl chloride

: 98873-55-3
1-cyanomethylimidazole

: (4-methyl-1,3-dithiol-2-ylidene)(imidazol-1-yl) acetonitrile

Conditions

Conditions	Yield
With potassium hydroxide; dimethyl sulfoxide at 0℃;

...Expand

: 75-15-0
carbon disulfide

: 98873-55-3
1-cyanomethylimidazole

1,3-dihalopropane: 1,3-dihalopropane

A: 1748-15-8
1,3-dithiane-2-thione

B: (1,3-dithian-2-ylidene)(imidazol-1-yl)acetonitrile

Conditions

Conditions	Yield
With potassium hydroxide; dimethyl sulfoxide at 0℃;

...Expand

: 98873-55-3
1-cyanomethylimidazole

: 109-90-0
ethyl isocyanate

1,2-dihaloethane: 1,2-dihaloethane

: [3-Ethyl-thiazolidin-(2Z)-ylidene]-imidazol-1-yl-acetonitrile

Conditions

Conditions	Yield
With potassium hydroxide; dimethyl sulfoxide at 0℃;

...Expand

: 98873-55-3
1-cyanomethylimidazole

: 109-90-0
ethyl isocyanate

1,2-dihalopropane: 1,2-dihalopropane

: [3-Ethyl-4-methyl-thiazolidin-(2Z)-ylidene]-imidazol-1-yl-acetonitrile

Conditions

Conditions	Yield
With potassium hydroxide; dimethyl sulfoxide at 0℃;

...Expand

: 98873-55-3
1-cyanomethylimidazole

: 4-Amino-2,6-bis(imidazol-1-ylmethyl)-5-(imidazol-1-yl)pyrimidine

Conditions

Conditions	Yield
1,4-diaza-bicyclo[2.2.2]octane at 200℃; for 24h;	0.055 g

: 98873-55-3
1-cyanomethylimidazole

: 3,5-Bis-imidazol-1-ylmethyl-1H-[1,2,4]triazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / hydrazine hydrate / 6.5 h / 100 °C 2: 85 percent / aq.HCl, NaNO2 / 5 h / 0 - 20 °C View Scheme

: 98873-55-3
1-cyanomethylimidazole

: C14H16N10(2+)*2Cl(1-) = (C14H16N10)Cl2

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / hydrazine hydrate / 6.5 h / 100 °C 2: 85 percent / aq.HCl, NaNO2 / 5 h / 0 - 20 °C 3: 42 percent / acetonitrile / 48 h / 85 °C View Scheme

1-(Cyanomethyl)imidazole Specification

The 1-(Cyanomethyl)imidazole is an organic compound with the formula C₅H₅N₃. The systematic name of this chemical is 1H-imidazol-1-ylacetonitrile. With the CAS registry number 98873-55-3, it is also named as Imidazol-1-yl-acetonitrile. In addition, this chemical can be used as intermediate in organic syntheses.

The other characteristics of 1-(Cyanomethyl)imidazole can be summarized as: (1)ACD/LogP: -0.35; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 1 ; (6)Polar Surface Area: 41.61 Å²; (7)Index of Refraction: 1.577; (8)Molar Refractivity: 31.96 cm³; (9)Molar Volume: 96.428 cm³; (10)Polarizability: 12.67×10^-24 cm³; (11)Surface Tension: 47.866 dyne/cm; (12)Density: 1.111 g/cm³; (13)Flash Point: 153.192 °C; (14)Enthalpy of Vaporization: 57.22 kJ/mol; (15)Boiling Point: 329.691 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

People can use the following data to convert to the molecule structure.
1. SMILES:N#CCn1ccnc1
2. InChI:InChI=1/C5H5N3/c6-1-3-8-4-2-7-5-8/h2,4-5H,3H2
3. InChIKey:ZPGCVVBPGQJSPX-UHFFFAOYAI
4. Std. InChI:InChI=1S/C5H5N3/c6-1-3-8-4-2-7-5-8/h2,4-5H,3H2
5. Std. InChIKey:ZPGCVVBPGQJSPX-UHFFFAOYSA-N

Product Name

IMIDAZOL-1-YL-ACETONITRILE

Synthetic route

1-(Cyanomethyl)imidazole Specification

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