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It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.
Ilaria Donelli; Paola Taddei; Philippe F Smet; Dirk Poelman; Vincent A Nierstrasz; Giuliano Freddi. Enzymatic surface modification and functionalization of PET: a water contact angle, FTIR, and fluorescence spectroscopy study. Biotechnology and Bioengineering. 2009, 103 (5), 845-856.
Kuppuswamy Arumugam; James E Bollinger; Mark Fink; James P Donahue. Preparation and isolation of dithiolene thiophosphoryl molecules as stable, protected forms of dithiolene ligands. Inorganic Chemistry. 2007, 46 (8), 3283-3288.
Primary or secondary OH groups can be protected as 2-naphthylmethyl (NAP) ethers, e.g. with NaH in DMF. The NAP ether is stable to dilute aqueous HCl or NaOH, but is cleanly hydrogenolyzed with Pd/C; preferential cleavage in the presence of a benzyl ether can be achieved in high yield: J. Org. Chem., 63, 4172 (1998). NAP protection has been utilized in carbohydrate synthesis where stability to 4% TFA in CHCl3, hot 80% AcOH, SnCl2/AgOTf, or HCl/EtOH were demonstrated, conditions under which the 4-methoxybenzyl (PMB) group is cleaved; both NAP and PMB groups are efficiently cleaved with DDQ: Tetrahedron Lett., 41, 169 (2000).
NAP protection of amino groups and other N functions has also been reported. Cleavage was effected under mild condtions with DDQ: Synlett, 2065 (2003).
Gefahrenhinweise (EU): H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.