ChemicalBook--->CAS DataBase List--->98873-55-3

98873-55-3

98873-55-3 Structure

98873-55-3 Structure
IdentificationBack Directory
[Name]

IMIDAZOL-1-YL-ACETONITRILE
[CAS]

98873-55-3
[Synonyms]

1-(Cyanomethyl)imidazole
1-Imidazolylacetonitrile
IMIDAZOL-1-YL-ACETONITRILE
IMidazal-1-yl-acetonitrile
Luliconazole Intermediates
1H-imidazole-1-acetonitril
Imidazole-1-yl-acetonitrile
1H-imidazole-1-acetonitrile
2-(1-IMidazolyl)acetonitrile
2-(1H Imidazole -1-yl) acetonitrile
1H-imidazol-1-ylacetonitrile(SALTDATA: FREE)
Imidazole-1-yl-acetonitrile(1-cyanomethyl)imidazole
1-Imidazolylacetonitrile (1-(Cyanomethyl) imidazole)
[EINECS(EC#)]

1592732-453-0
[Molecular Formula]

C5H5N3
[MDL Number]

MFCD06421433
[MOL File]

98873-55-3.mol
[Molecular Weight]

107.113
Chemical PropertiesBack Directory
[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)
[form ]

Solid
[pka]

5.63±0.10(Predicted)
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Danger
[Hazard statements ]

H302-H312-H315-H319-H332-H335
[Precautionary statements ]

P261-P280-P304+P340-P305+P351+P338-P405-P501a
[RIDADR ]

UN 3439 6.1/PG III
[HS Code ]

2933.29.4300
[HazardClass ]

6.1
[HazardClass ]

IRRITANT
[PackingGroup ]

III
Hazard InformationBack Directory
[Uses]

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

Imidazole

288-32-4

Bromoacetonitrile

590-17-0

1H-Imidazol-1-ylacetonitrile

98873-55-3

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
Spectrum DetailBack Directory
[Spectrum Detail]

1H-Imidazol-1-ylacetonitrile(98873-55-3)1HNMR
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