tert-Butyl Nitrite

General Information:

Structure:

CAS Number: 540-80-7

Molecular Weight: 103.12 g/mol

Boiling Point: 61-63 C

tert-Butyl nitrite is a common reagent used for diazotization, typically for Sandmeyer reactions. Isoamyl nitrite is used for similar purposes.

Common Uses:

Reagent in Sandmeyer reactions (ex. bromide formation)

Procedure excerpt:

. . . CuBr2 (9.0 g, 40.0 mmol) in ACN at 0 C was added t-BuONO (5.2 mL, 44 mmol). The mixture was stirred for 10 min, after which time was added the SM (9.0 g, 34 mmol) . . .

[full procedure]

Reagent in Sandmeyer reactions (ex. chloride formation)

Procedure excerpt:

To a suspension of CuCl2 (450 mg, 3.4 mmol) in ACN (8 mL) was added t-BuONO (0.52 mL, 3.9 mmol). The mixture was stirred for 5 min then a solution of the SM . . .

[full procedure]

References:

1) Patent Reference: WO2014149164, page 260, (23.7 MB)

2) Patent Reference: WO2015105749, page 97, (11.4 MB)

3) www.sigmaldrich.com: tert-Butyl nitrite (link)