98873-55-3

Basic information

• Product Name: IMIDAZOL-1-YL-ACETONITRILE
• Synonyms: IMIDAZOL-1-YL-ACETONITRILE;1-Imidazolylacetonitrile (1-(Cyanomethyl) imidazole);1-(Cyanomethyl)imidazole;1-Imidazolylacetonitrile;1H-imidazole-1-acetonitrile;1H-imidazol-1-ylacetonitrile(SALTDATA: FREE);2-(1-IMidazolyl)acetonitrile;IMidazal-1-yl-acetonitrile
• CAS NO: 98873-55-3
• Molecular Formula: C₅H₅N₃
• Molecular Weight: 107.1133
• EINECS: 1592732-453-0
• Mol File: 98873-55-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 54.0 to 58.0 °C
• Boiling Point: 329.691 °C at 760 mmHg
• Flash Point: 153.192 °C
• Appearance: /Solid
• Density: 1.111 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 5.63±0.10(Predicted)
• CAS DataBase Reference: IMIDAZOL-1-YL-ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: IMIDAZOL-1-YL-ACETONITRILE(98873-55-3)
• EPA Substance Registry System: IMIDAZOL-1-YL-ACETONITRILE(98873-55-3)

Safety Data

• RIDADR: UN 3439 6.1/PG III
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 98873-55-3(Hazardous Substances Data)

Usage

Uses

2-(1H-Imidazol-1-yl)acetonitrile is a reactant that has been used in the synthesis of lanoconazole (L174500), an antifungal.

InChI:InChI=1/C5H5N3/c6-1-3-8-4-2-7-5-8/h2,4-5H,3H2

Synthetic route

1H-imidazole (288-32-4) + acetonitrile (75-05-8) → 1-cyanomethylimidazole (98873-55-3)

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

1H-imidazole (288-32-4) + cyanomethyl bromide (590-17-0) → 1-cyanomethylimidazole (98873-55-3)

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%

1H-imidazole (288-32-4) + chloroacetonitrile (107-14-2) → 1-cyanomethylimidazole (98873-55-3)

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;

carbon disulfide (75-15-0) + [2-(2,4-dichlorophenyl)-3-methylsulfonyloxy-propyl] methanesulfonate + 1-cyanomethylimidazole (98873-55-3) → 2-[5-(2,4-dichlorophenyl)-1,3-dithian-2-ylidene]-2-imidazol-1-ylacetonitrile

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%

1-cyanomethylimidazole (98873-55-3) → 4-amino-3,5-bis(imidazol-1-ylmethyl)-1,2,4-triazole (170998-10-4)

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

ethanol (64-17-5) + 1-cyanomethylimidazole (98873-55-3) → 2-imidazol-1-yl-acetimidic acid ethyl ester; hydrochloride

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

1-iodononane (4282-42-2) + 1-cyanomethylimidazole (98873-55-3) → methyl 5-(cyano[nonyl]methyl)-3-tetrahydropyranyl-imidazole-4-carboxylate (172940-17-9)

Conditions	Yield
With NaH In ethyl acetate	67%

potassium hydroxide (1310-58-3) + nemagon (96-12-8) + 1-cyanomethylimidazole (98873-55-3) → 2-(1-imidazolyl)-2-(4-chloro-methyl-1,3-dithiolan-2-ylidene)acetonitrile (101530-02-3)

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

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 1-cyanomethylimidazole (98873-55-3) → (E)-3-(dimethylamino)-2-(1H-imidazol-1-yl)acrylonitrile

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

1-cyanomethylimidazole (98873-55-3) + C8H15ClN2O3 (312324-17-7) → (S)-tert-butyl {1-[5-amino-4-(1H-imidazol-1-yl)isoxazol-3-yl]-ethyl}carbamate

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 + 1-cyanomethylimidazole (98873-55-3) → (R)-tert-butyl {1-[5-amino-4-(1H-imidazol-1-yl)isoxazol-3-yl]-ethyl}carbamate

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%

(S)-valinol (2026-48-4) + 1-cyanomethylimidazole (98873-55-3) → (S)-N-(1-hydroxy-3-methylbutan-2-yl)-2-(1H-imidazol-1-yl)acetamide (1210068-56-6)

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%

carbon disulfide (75-15-0) + (S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate + 1-cyanomethylimidazole (98873-55-3) → [(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile + luliconazole

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

potassium hydroxide (1310-58-3) + 1-chloro-2-(1,2-dichloroethyl) benzene + 1-cyanomethylimidazole (98873-55-3) → lanoconazole (101530-10-3)

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

potassium hydroxide (1310-58-3) + 2'-isopropyl-1,2-dibromoethylbenzene + 1-cyanomethylimidazole (98873-55-3) → 2-(1-imidazolyl)-2-[4-(2-isopropyl-phenyl)-1,3-dithiolan-2-ylidene]acetonitrile

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

carbon disulfide (75-15-0) + 1-cyanomethylimidazole (98873-55-3) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 2-(cyano(1H-imidazol-1-yl)methylene)-[1,3]dithiolo[4,5-b]pyrazine-5,6-dicarbonitrile

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%

potassium hydroxide (1310-58-3) + 1,2-dibromo-4-methyl-pentane (21750-35-6) + 1-cyanomethylimidazole (98873-55-3) → 2-(1-imidazolyl)-2-(4-isobutyl-1,3-dithiolan-2-ylidene)acetonitrile (101529-88-8)

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

carbon disulfide (75-15-0) + [2-chloro-1-(2-chloro-3-fluoro-4-prop-2-ynoxy-phenyl)ethyl] methanesulfonate + 1-cyanomethylimidazole (98873-55-3) → (2Z)-2-[4-(2-chloro-3-fluoro-4-prop-2-ynoxyphenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile + (2E)-2-[4-(2-chloro-3-fluoro-4-prop-2-ynoxy-phenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile

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%

potassium hydroxide (1310-58-3) + 1,2-dibromo-1-(2’-chlorophenyl)ethane + 1-cyanomethylimidazole (98873-55-3) → lanoconazole (126509-69-1)

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

potassium hydroxide (1310-58-3) + 1,2-dibromo-1-(2’-chlorophenyl)ethane + 1-cyanomethylimidazole (98873-55-3) → lanoconazole (101530-10-3)

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

carbon disulfide (75-15-0) + ethylene dibromide (106-93-4) + 1-cyanomethylimidazole (98873-55-3) → 1,3-dithiolane-2-thione (822-38-8) + (1,3-dithiolan-2-ylidene)(imidazol-1-yl)acetonitrile

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

carbon disulfide (75-15-0) + 1,3-dibromo-propane (109-64-8) + 1-cyanomethylimidazole (98873-55-3) → 1,3-dithiane-2-thione (1748-15-8) + (1,3-dithian-2-ylidene)(imidazol-1-yl)acetonitrile

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

carbon disulfide (75-15-0) + 1,3-dichlorobutane (1190-22-3) + 1-cyanomethylimidazole (98873-55-3) → 1,3-dithiane-2-thione (1748-15-8) + Imidazol-1-yl-[4-methyl-[1,3]dithian-(2E)-ylidene]-acetonitrile

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

carbon disulfide (75-15-0) + 2-propynyl chloride (624-65-7) + 1-cyanomethylimidazole (98873-55-3) → (4-methyl-1,3-dithiol-2-ylidene)(imidazol-1-yl) acetonitrile

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

carbon disulfide (75-15-0) + 1-cyanomethylimidazole (98873-55-3) + 1,3-dihalopropane → 1,3-dithiane-2-thione (1748-15-8) + (1,3-dithian-2-ylidene)(imidazol-1-yl)acetonitrile

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

1-cyanomethylimidazole (98873-55-3) + ethyl isocyanate (109-90-0) + 1,2-dihaloethane → [3-Ethyl-thiazolidin-(2Z)-ylidene]-imidazol-1-yl-acetonitrile

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

1-cyanomethylimidazole (98873-55-3) + ethyl isocyanate (109-90-0) + 1,2-dihalopropane → [3-Ethyl-4-methyl-thiazolidin-(2Z)-ylidene]-imidazol-1-yl-acetonitrile

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

1-cyanomethylimidazole (98873-55-3) → 4-Amino-2,6-bis(imidazol-1-ylmethyl)-5-(imidazol-1-yl)pyrimidine

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

1-cyanomethylimidazole (98873-55-3) → 3,5-Bis-imidazol-1-ylmethyl-1H-[1,2,4]triazole

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

1-cyanomethylimidazole (98873-55-3) → C14H16N10(2+)*2Cl(1-) = (C14H16N10)Cl2

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

Upstream product

• 288-32-4 1H-imidazole 
• 75-05-8 acetonitrile 
• 590-17-0 cyanomethyl bromide 
• 107-14-2 chloroacetonitrile 

Downstream Products

• 187164-19-8 (Z/E)-(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene(1H-imidazol-1-yl)acetonitrile 
• 187164-19-8 luliconazole 
• 187164-19-8 [(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile 
• 101530-10-3 lanoconazole 
• 187164-19-8 2-(1-imidazolyl)-2-[4-(2,4-dichloro-phenyl)-1,3-dithiolan-2-ylidene]acetonitrile 
• 126509-69-1 lanoconazole 
• 172940-20-4 methyl 5-(cyano[2-(1-naphthyl)ethyl]methyl)-3-tetrahydropyranyl-imidazole-4-carboxylate 
• 172940-19-1 Methyl 5-(benzyl[cyano]methyl)-3tetrahydropyranyl-imidazole-4-carboxylate 
• 822-38-8 1,3-dithiolane-2-thione 

Relevant articles and documents

Synthesis and fungicidal activity of novel imidazole-based ketene dithioacetals

Novel imidazole-based ketene dithioacetals show impressive in planta activity against the economically important plant pathogens Alternaria solani, Botryotinia fuckeliana, Erysiphe necator and Zymoseptoria tritici. Especially derivatives of the topical antifungal lanoconazole, which bear an alkynyloxy or a heteroaryl group in the para-position of the phenyl ring, exhibit excellent control of the mentioned phytopathogens. These compounds inhibit 14α -demethylase in the sterol biosynthesis pathway of the fungi. Synthesis routes starting from either benzaldehydes or acetophenones as well as structure-activity relationships are discussed in detail.

Synthesis of Conformationally Locked and C-Linked Analogues of Imidazole-Based Ketene Dithioacetal Fungicides

First examples with the unknown tricyclic 4,8 b -dihydro-3 aH -indeno[1,2- d ][1,3]dithiole ring system have been prepared. Also, imidazoles linked in ring position 5 to a ketene dithioacetal and 1,3-dithiane derivatives with an exocyclic cyano- and imidazole-substituted C-C double bond are completely new. All these compounds are either conformationally locked, C-linked or six-ring analogues of the antifungal agent luliconazole. Synthesis and fungicidal activity of these sterol biosynthesis inhibitors are reported.

PROCESS FOR PREPARATION OF LULICONAZOLE

A process for the preparation of luliconazole and salts thereof is disclosed.