5-Bromopentan-1-ol Chemical Properties

Boiling point:

117 °C / 20mmHg

Density 

1,38 g/cm³

refractive index 

n20/D 1.482

Flash point:

40 - 50°C

storage temp. 

2-8°C

pka

15.11±0.10(Predicted)

form 

clear liquid

color 

Light red to Yellow to Red

InChI

InChI=1S/C5H11BrO/c6-4-2-1-3-5-7/h7H,1-5H2

InChIKey

WJVQJXVMLRGNGA-UHFFFAOYSA-N

SMILES

C(O)CCCCBr

CAS DataBase Reference

34626-51-2(CAS DataBase Reference)

EPA Substance Registry System

1-Pentanol, 5-bromo- (34626-51-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22-10

Safety Statements 

26-36/37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

Ⅲ

HS Code 

29055900

5-Bromopentan-1-ol Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

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.

Synthesis Reference(s)

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

Synthesis

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.

References

[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

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