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4-Nitrobenzyl bromide is used in the synthesis of di and tri-substituted azoles. It is also used in the preparation of N6-Benzyladenosine-5-uronamides as selective A3 adenosine agonists.
Josef Prousek. The course of reaction of 4-nitrobenzyl bromide and 5-nitrofurfuryl bromide with bases: Operation of anion-radical mechanism. Collect. Czech. Chem. Commun. 1982, 47,(5), 1334-1338.
Paul G.Bulger; Ian F.Cottrell; Cameron J.Cowden; Antony J.Davies; Ulf-H Dolling. An investigation into the alkylation of 1,2,4-triazole. Tetrahedron Letters. 2000, 41,(8), 1297-1301.
Has been used as a protecting reagent for the carboxyl group in peptide synthesis: Helv. Chim. Acta, 42, 972 (1959); see 4-Nitrobenzyl chloride, A15749, and Appendix 6. Has also been used in ß-lactam synthesis. Cleavage by sodium sulfide avoids hydrogenolysis problems otherwise encountered with these sulfur-containing nuclei: J. Org. Chem., 43, 1243 (1978).
For the protection of alcohols, introduction of the group by the use of silver oxide has been recommended. Selective cleavage can be accomplished with DDQ (2,3-Dichloro-5,6-dicyanobenzoquinone, A11879) or by anodic oxidation. Many other benzyl-type protecting groups are unaffected by these conditions: Tetrahedron Lett., 31, 389 (1990). Indium metal in the presence of ammonium chloride is an effective deprotection system for 4-nitrobenzyl ethers and esters: J. Chem. Soc., Perkin 1, 955 (2001).
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P201-P280i-P304+P340-P405-P501a
Obtain special instructions before use. Wear eye/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.