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1,8-Bis(dimethylamino)naphthalene is used in the synthesis of C-substituted t-BuNH-8,9-R,R?-nido-7,8,9-C3B8H9 (R,R? = H,H; MeH; Me,Me; Ph,H and Ph,Ph) tricarbollide compounds. It was also used in the preparation of saturated fluoroalkyl(hydrido) complexes of Iridium.
Fumiyuki Ozawa.; Akihiko Kubo.; Tamio Hayashi. Palladium-catalyzed asymmetric arylation of 2,3-dihydrofuran: 1,8-Bis(dimethylamino)naphthalene as an efficient base. Tetrahedron Letters. 1992, 33, (11), 1485-1488.
Danuta Pyzalska.; Robert Pyzalski.; Teresa Borowiak. Structure of 1,8-bis(dimethylamino)naphthalene hydrobromide dihydrate. Journal of Crystallographic and Spectroscopic Research. 1983, 13, (3), 211-220.
The steric strain is relieved on protonation, hence it is one of the strongest organic bases known, but is only weakly nucleophilic: Chem. Commun., 723 (1968). In DMF vic-dibromides are debrominated in high yield: Synth. Commun., 5, 87 (1975).
Has been used In combination with Diphenylphosphonic azide, A12124, for the conversion of carboxylic acids to isocyanates: Synth. Commun., 23, 335 (1993). Preferred base for the conversion of aliphatic amines to isocyanates with Trichloromethyl chloroformate, A17444.
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.