Isopentyl nitrite is used in the conversion of 2,6-disubstituted phenols to diphenoquinones and aminophenols to quinone diazides. It acts as an oxidant and nitrosating agent. It finds application in aromatic arylation, deamination of arylamines using tetrahydrofuran as a hydrogen donor. It is also useful for the preparation of benzyne using anthranilic acid. It is an antihypertensive and vasodilator to treat heart diseases such as angina and an antidote for cyanide poisoning. Further, it is used as a solvent and cleaning agent for a printed circuit board. In addition to this, it is considered to be a replacement for freon.
Widely used in non-aqueous nitrosation and diazotization reactions.
For aromatic arylation as an alternative to the Gomberg reaction, see: J. Chem. Soc., 4257 (1962). For deamination of arylamines using THF as a hydrogen donor, see: J. Chem. Soc., Perkin 1, 541 (1973).
For use in the generation of benzyne from anthranilic acid, see: J. Org. Chem., 38, 3462 (1973).
ɑ-Amino esters are converted to ɑ-diazo esters: Tetrahedron, 31, 227 (1975).
Liu, Z.; Zhu, S.; Li, Y.; Li, Y.; Shi, P.; Huang, Z.; Huang, X. Preparation of graphene/poly(2-hydroxyethyl acrylate) nanohybrid materials via an ambient temperature grafting-from strategy. Polym. Chem. 2015, 6 (2), 311-321.
Wang, Y.; Meng, L.; Fan, L.; Wu, G.; Ma, L.; Huang, Y. Preparation and properties of carbon nanotube/carbon fiber hybrid reinforcement by a two-step aryl diazonium reaction. RSC Adv. 2015, 5 (55), 44492-44498.
Hazard Statements: H225-H302-H331
Highly flammable liquid and vapour. Harmful if swallowed. Toxic if inhaled.
Precautionary Statements: P210-P261-P280a-P303+P361+P353-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.