1H-Imidazol-1-ylacetonitrile Chemical Properties

Melting point:

54.0 to 58.0 °C

Boiling point:

116-120 °C(Press: 0.35 Torr)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

5.63±0.10(Predicted)

form 

Solid

color 

White to Light yellow

InChI

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

InChIKey

ZPGCVVBPGQJSPX-UHFFFAOYSA-N

SMILES

C1N(CC#N)C=CN=1

Safety Information

RIDADR 

UN 3439 6.1/PG III

HS Code 

2933.29.4300

HazardClass 

IRRITANT

HazardClass 

6.1

PackingGroup 

III

1H-Imidazol-1-ylacetonitrile Usage And Synthesis

Uses

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

Synthesis

To a tetrahydrofuran (THF) solution of 1H-imidazole (5 g, 73.5 mmol) was added sodium hydride (1.8 g, 45 mmol) in batches and stirred at room temperature for 30 minutes. Subsequently, bromoacetonitrile (8.8 g, 73.9 mmol) was slowly added dropwise and stirring was continued for 2 hours at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL) and saturated ammonium chloride solution (50 mL). The reaction mixture was extracted with ethyl acetate (100 mL x 3) and the organic layers were combined. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=10:1) to give 2-(1H-imidazol-1-yl)acetonitrile (4.6 g, 59% yield) as a yellow oil.LRMS m/z: 108 [M+H]+.

References

[1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 9, p. 3185 - 3198
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 18, p. 2110 - 2116
[3] New Journal of Chemistry, 2002, vol. 26, # 7, p. 926 - 932
[4] Patent: US2015/65522, 2015, A1. Location in patent: Paragraph 0469; 0470; 0471
[5] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 2009 - 2016

1H-Imidazol-1-ylacetonitrile(98873-55-3)Related Product Information

• Methyl 4-imidazolecarboxylate
• Ethyl imidazole-4-carboxylate
• Dimethyl 4,5-imidazoledicarboxylate
• Imidazo[1,5-a]pyridine
• IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLIC ACID
• 1H-Imidazole-2-carboxylic acid
• 1H-Imidazol-1-ylacetonitrile
• Lanoconazole
• Luliconazole
• 1,3-Bis(cyanomethyl)imidazolium bis(trifluoromethylsulfonyl)imide
• 1,3-Bis(cyanomethyl)imidazolium chloride
• 1-(Cyanomethyl)-3-methylimidazolium chloride
• 2-(4,5-DICHLORO-1H-IMIDAZOL-1-YL)ACETONITRILE
• 2-[2-(TRIFLUOROMETHYL)-1H-1,3-BENZIMIDAZOL-1-YL]ACETONITRILE
• CBI-BB ZERO/005479
• AKOS BBS-00000213
• (2-methyl-1H-benzimidazol-1-yl)acetonitrile
• SALOR-INT L299758-1EA