Chemical Properties
colourless or pale yellow liquid. soluble in ethanol, ether, benzene and chloroform, insoluble in water. It is used in the synthesis of the hypotensive drug hexamethonium bromide.
Uses
1,6-Dibromohexane is used as a reagent in the synthesis of novel benzo[b]xanthone derivatives which have a potential antitumor activity. It is also used as a cross-linker for the cross-linking of glycuronans.
Uses
1,6-Dibromohexane is generally used to introduce C6 spacer in the molecular architecture. Some of the examples are:
Synthesis of solvent processable and conductive polyfluorene ionomers for alkaline fuel cell applications.
Synthesis of cross-linkable regioregular poly(3-(5-hexenyl)thiophene) (P3HNT) for stabilizing the film morphology in polymer photovoltaic cells.
Synthesis of pyrrolo-tetrathiafulvalene molecular bridge (6PTTF6) to study redox switching behavior of single molecules.
Synthesis of water-soluble thermoresponsive polylactides.
Preparation
1,6-Dibromohexane is synthesized from hexanediol by bromination.
Synthesis
The general procedure for the synthesis of 1,6-dibromohexane from 1,6-hexanediol was as follows: N-bromosuccinimide (NBS, 534 mg, 3 mmol) was dissolved in dichloromethane (CH2Cl2, 10 mL) in a 50 mL round-bottomed flask. Triphenylphosphine (Ph3P, 786 mg, 3 mmol) and 1,6-hexanediol (1 mmol) were added dropwise to the NBS solution at -78 °C. The reaction mixture was stirred at room temperature away from light for 12 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC, eluent: petroleum ether-ethyl acetate, 20:1). Upon completion of the reaction, the mixture was concentrated under vacuum and purified by fast chromatography on silica gel column (eluent: petroleum ether-ethyl acetate, 30:1) to afford the target product 1,6-dibromohexane.
References
[1] Synthesis (Germany), 2015, vol. 47, # 8, p. 1154 - 1162
[2] Journal of the American Chemical Society, 1936, vol. 58, p. 488
[3] Archiv der Pharmazie (Weinheim, Germany), 1935, p. 323
[4] Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1508
[5] Journal of the Chemical Society, 1948, p. 46
