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11-BROMO-1-UNDECENE

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11-BROMO-1-UNDECENE Basic information
Product Name:11-BROMO-1-UNDECENE
Synonyms:N-UNDECYLENIC BROMIDE;UNDEC-10-EN-1-YL-BROMIDE;UNDEC-10-ENYL BROMIDE;UNDECYLENYL BROMIDE;W-UNDECYLENYL BROMIDE;11-BROMO-1-UNDECENE;1-BROMO-10-UNDECENE;11-Undecen-1-yl bromide
CAS:7766-50-9
MF:C11H21Br
MW:233.19
EINECS:
Product Categories:Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks
Mol File:7766-50-9.mol
11-BROMO-1-UNDECENE Structure
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.)
Fp >110°C
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
solubility Chloroform (Slightly)
form Oil
color Colourless
Specific Gravity1.063
Water Solubility Soluble in water, 0.2422 mg/L @ 25°C (est).
BRN 1753231
Stability:Stable. Incompatible with strong oxidizing agents.
InChI1S/C11H21Br/c1-2-3-4-5-6-7-8-9-10-11-12/h2H,1,3-11H2
InChIKeyYPLVPFUSXYSHJD-UHFFFAOYSA-N
SMILESBrCCCCCCCCCC=C
LogP5.950 (est)
CAS DataBase Reference7766-50-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26
WGK Germany 3
10-23
HS Code 29033990
Storage Class10 - Combustible liquids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
11-BROMO-1-UNDECENE Usage And Synthesis
Chemical Propertiescolourless liquid
Uses11-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 Description11-Bromo-1-undecene is a halogenated hydrocarbon. It can be synthesized by employing alkenyl esters or dibromides as starting materials.
Synthesis
10-UNDECEN-1-OL

112-43-6

11-BROMO-1-UNDECENE

7766-50-9

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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