Imidazole

Other Names:

1H-Imidazole

1,3-diazacyclopenta-2,4-diene

General Information:

Structure:

CAS Number: 288-32-4

Molecular Weight: 68.08 g/mol

Appearance: White to pale yellow solid

Melting Point: 88-91 C

Boiling Point: 256 C

Imidazole is a five-membered nitrogen containing aromatic heterocycle. Imidazole is highly polar and is very soluble in H2O.

Common Uses:

Basic activator in TBS protections

Procedure excerpt:

To a solution of the SM (985 mg, 5.24 mmol), imidazole (371 mg, 5.30 mmol), and DMF (5 mL) was added portionwise TBSCl (814 mg, 5.24 mmol). The reaction mixture . . .

[full procedure]

Base in the conversion of alcohols to iodides via Appel reactions

Procedure excerpt:

To a solution of the SM (0.79 g, 2.03 mmol), PPh3 (1.20 g, 4.58 mmol), and imidazole (0.277 g, 4.07 mmol) in THF (15 mL) was added iodine (0.96 g, 3.78 mmol) at RT. . . .

[full procedure]

References:

1) Patent Reference: WO2012069948, page 52, (3.9 MB)

2) Patent Reference: WO2016018697, page 79, (5.3 MB)

3) Wikipedia: Imidazole (link)

4) www.sigmaaldrich.com: Imidazole (link)