Tetrabutylammonium nitrite Property

Melting point:

99-103 °C

BRN 

6285720

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-10

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Tetrabutylammonium nitrite Chemical Properties,Usage,Production

Uses

Tetrabutylammonium nitrite is a tosylate salt. It reversibly binds to copper ions, forming a copper complex that is activated by the presence of nitroalkanes. The binding of tetrabutylammonium nitrite to glycosidic bonds in sugar residues, such as the hemoglobin molecule, leads to the formation of reactive oxygen species (ROS), which are responsible for cell damage. It has been shown to reduce infarct size and improve cardiac function in animal models following ischemic reperfusion injury. This compound also has antioxidant properties due to its ability to scavenge ROS and protect against oxidative stress.

Application

A Tetrabutylammonium nitrite (Bu4NNO2) - acetic anhydride (Ac2O) system was demonstrated to be remarkably efficient for the deanilidation of phosphoranilidates in an oligonucleotide synthesis, i.e., the reaction is over almost instantly[1].

References

[1] S. Akai. “Tetrabutylammonium nitrite - acetic anhydride system, tetrabutylammonium nitrite, tetrabutylammonium acetate, and cesium acetate - 18-crown-6 for efficient unmasking of alkyl N-phenylcarbamates.” Tetrahedron Letters 39 1 (1998): 5583–5586.