34626-51-2

Light yellow liquid

5-Bromopentanol is an organic building block that has been used as a reactant in the synthesis of 3-hydroxypyridine-2-thione to be used as a zinc binding group for histone deacetylase(HDAC) inhibition.

Tetrahedron, 27, p. 5979, 1971 DOI: 10.1016/S0040-4020(01)91762-4

General procedure for the synthesis of 5-bromo-1-pentanol from 1,5-pentanediol: 1,5-pentanediol (14 g, 0.135 mol), 40% hydrobromic acid (28 mL, 0.2 mol), and 60 mL of benzene were added to a 250 mL three-necked flask, and reacted for 15 h in an oil bath at 70-80 °C. The reaction progress was monitored by TLC until the raw material spots disappeared. After completion of the reaction, the reaction mixture was washed sequentially with 5% sodium hydroxide solution, 10% hydrochloric acid and saturated saline, and then dried with anhydrous sodium sulfate. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, V/V = 8:1) and concentrated to give 5-bromo-1-pentanol (20.1 g, 89.1% yield) as colorless to light yellow liquid.

[1] Patent: CN105766907, 2016, A. Location in patent: Paragraph 0026; 0041; 0042
[2] RSC Advances, 2015, vol. 5, # 37, p. 29114 - 29120
[3] Chemistry - A European Journal, 2015, vol. 21, # 30, p. 10721 - 10728
[4] Journal of Physical Chemistry, 1995, vol. 99, # 32, p. 12195 - 12203
[5] Organic Process Research and Development, 2003, vol. 7, # 3, p. 339 - 340