11-BROMO-1-UNDECENE Chemical Properties

Melting point:

55 °C

Boiling point:

149-150 °C35 mm Hg(lit.)

Density 

1.063 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.468(lit.)

Flash point:

>110°C

storage temp. 

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

solubility 

Chloroform (Slightly)

form 

Oil

color 

Colourless

Specific Gravity

1.063

Water Solubility 

Soluble in water, 0.2422 mg/L @ 25°C (est).

BRN 

1753231

Stability:

Stable. Incompatible with strong oxidizing agents.

LogP

5.950 (est)

CAS DataBase Reference

7766-50-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

F 

10-23

HS Code 

29033990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

11-BROMO-1-UNDECENE Usage And Synthesis

Chemical Properties

colourless liquid

Uses

11-Bromo-1-undecene is used in advanced polymer dielectrics.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 34, p. 1024, 1991 DOI: 10.1021/jm00107a022
Synthesis, p. 511, 1987 DOI: 10.1055/s-1987-27988

General Description

11-Bromo-1-undecene is a halogenated hydrocarbon. It can be synthesized by employing alkenyl esters or dibromides as starting materials.

Synthesis

General procedure for the synthesis of 1-bromo-10-undecene from 10-undecadecen-1-ol: To a dichloromethane solution of 10-undecadecen-1-ol (200 mg, 1.17 mmol) was added sequentially at 0 °C CBr4 (403 mg, 1.29 mmol, 1.1 eq.) and Ph3P (340 mg, 1.29 mmol, 1.1 eq. ). The reaction mixture was kept stirred at 0 °C for 2 hours. After completion of the reaction, the reaction was quenched by the addition of water. The reaction mixture was extracted with dichloromethane, the organic layers were combined and dried over anhydrous Na2SO4. The organic solvent was removed by concentration under reduced pressure to give the crude product. The crude product was used directly in the next step of the reaction without chromatographic purification. Purification of the crude product by silica gel column chromatography afforded 1-bromo-10-undecene (273 mg, quantitative yield) [56] as a colorless oil.

References

[1] Synthetic Communications, 1984, vol. 14, # 7, p. 591 - 598
[2] Journal of Organic Chemistry, 1998, vol. 63, # 21, p. 7505 - 7515
[3] Lipids, 2017, vol. 52, # 12, p. 1019 - 1032
[4] Journal of Organic Chemistry, 1991, vol. 56, # 17, p. 5132 - 5138
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 13, p. 2433 - 2440

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