9-BROMO-1-NONENE Chemical Properties

Boiling point:

100-101℃/15mm

Density 

1.1034 (estimate)

refractive index 

1.4675

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

Liquid

color 

Colorless to pale yellow

InChI

InChI=1S/C9H17Br/c1-2-3-4-5-6-7-8-9-10/h2H,1,3-9H2

InChIKey

RQXPBVHYVAOUBY-UHFFFAOYSA-N

SMILES

C=CCCCCCCCBr

Safety Information

HS Code 

2903691990

9-BROMO-1-NONENE Usage And Synthesis

Uses

Non-8-enyl Bromide is a reactant in the synthesis of breast cancer drug, Fulvestrant (Falsodex).

Uses

Non-8-enyl Bromide is a reactant in the synthesis of breast cancer drug, Fulvestrant (Falsodex).

Synthesis

General procedure for the synthesis of 9-bromo-1-nonene from 8-nonen-1-ol: Triphenylphosphine (5.42 g, 20.67 mmol) was dissolved in 20 ml of acetonitrile and placed in a cold bath at -10 °C. Subsequently, bromine (1.01 ml, 19.83 mmol) was slowly added dropwise and the reaction mixture was stirred at that temperature for 30 min. Next, a solution of 8-nonen-1-ol (2 g, 14.06 mmol) and pyridine (1.8 ml, 22.36 mmol) in 10 ml of acetonitrile was added. The cold bath was removed and the reaction mixture was continued to be stirred at room temperature for 1 hour. After completion of the reaction, the solvent was removed by evaporation and the residue was purified by silica gel column chromatography using heptane as eluent. Finally, vacuum distillation was carried out through a bulb tube oven at 120 °C/1 mm Hg to give a colorless liquid product (1.44 g, 50% yield).

References

[1] Tetrahedron Letters, 2013, vol. 54, # 29, p. 3865 - 3867
[2] Patent: WO2015/181116, 2015, A1. Location in patent: Page/Page column 51
[3] Journal of the Chemical Society, 1937, p. 1977
[4] Organic letters, 1999, vol. 1, # 2, p. 241 - 243

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