72647-08-6

Basic information

• Product Name: 1,4,6-tribromonaphthalene
• Synonyms: 1,4,6-tribromonaphthalene
• CAS NO: 72647-08-6
• Molecular Weight: 364.862
• Mol File: 72647-08-6.mol

Chemical Properties

• CAS DataBase Reference: 1,4,6-tribromonaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,6-tribromonaphthalene(72647-08-6)
• EPA Substance Registry System: 1,4,6-tribromonaphthalene(72647-08-6)

Safety Data

• Hazardous Substances Data: 72647-08-6(Hazardous Substances Data)

Upstream product

• 91-17-8 decalin 

Relevant articles and documents

Polybrominated methoxy- and hydroxynaphthalenes

Regio- and stereoselective synthesis are described for convenient preparation of hydroxy- and methoxynaphthalenes starting from naphthalene (1). cis,cis,trans-2,3,5,8-Tetrabromo-4-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (6), cis,cis,trans-2,3,5,8-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydronaphthalene (7), and cis,cis,cis-2,3,5,8-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydronaphthalene (8) were obtained with silver-induced substitution of trans,cis,trans-1,2,3,4, 5,8-hexabromo-1,2,3,4-tetrahydronaphthalene (3). Base-promoted aromatization of dimethoxides 7 and 8 afforded 3,5,8-tribromo-1-methoxynaphthalene (9) and 2,5,8-tribromo-1-methoxynaphthalene (10). The reaction of 6 with sodium methoxide formed compounds 10 and 3,5,8-tribromonaphthalen-1-ol (16). Bromination of 9 and 16 with Br2 in dichloromethane at room temperature produced 2,3,5,8-tetrabromo-1-methoxynaphthalene (14) and 2,3,4,5,8-pentabromonaphthalen-1-ol (18), respectively, while compound 10 did not react in the same conditions. Pyridine-induced elimination of hexabromide 3 afforded 1,4,6-tribromnaphthalene (21) in 99% yield and thermolysis of the hexabromide 3 gave mainly 1,4,6,7-tetrabromonaphthalene (22). Tetrabromide 22 was transformed to 1,4,6,7-tetramethoxynaphthalene (23) by copper-assisted nucleophilic substitution reaction.

Bromination of naphthalene and derivatives: High temperature bromination XI

Thermal and photobromination of naphthalene and derivatives have been studied. Several hexabromo- (12, 13, 16 and 17), and tetrabromotetralin derivatives (23, 24, and 25) have been obtained as the major products, besides bromonaphthalene derivatives. Base-promoted elimination reactions of 12, 13, 16 and 17 provided di- (8) tri- (10) and tetrabromo-naphthalenes (22). A convenient method was developed for the synthesis of 1,3- dibromonaphthalene (26) starting from (24). The structures of these products were determined by 1H-,13C- NMR data and X-ray structural analysis.

Bromination of Decalin and Its Derivatives. 9. High Temperature Bromination

Thermal and photobromination of decalin, 1, was studied, trans,cis,trans-2,5,7,9-tetrabromooctalin, 2, was obtained as the major product along with smaller amounts of bromonaphthalene derivatives. The structures of the products were determined by 1H- and 13C-NMR data and single X-ray structural analysis. Bromination of the two decalin derivatives 9 and 10 results in the formation of single isomers 11 and 12, respectively. The three tetrabromides 2, 11, and 12 were shown by molecular mechanics calculations to be the most stable stereoisomer in each case. The formation of these tetrabromides under thermodynamic control is postulated.