1-Bromododecane

1-Bromododecane is the organobromine compound with the formula Br(CH2)11CH3. It is a colorless liquid. It is used as a long chain alkylating agent to improve the lipophilicity and hydrophobicity of organic molecules for biological applications.[2]

1-Bromododecane
Skeletal formula of 1-Bromododecane
Names
Preferred IUPAC name
1-Bromododecane[1]
Other names
Lauryl bromide, dodecyl bromide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.080
EC Number
  • 205-587-9
UNII
  • InChI=1S/C12H25Br/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2-12H2,1H3
    Key: PBLNBZIONSLZBU-UHFFFAOYSA-N
  • CCCCCCCCCCCCBr
Properties
C12H25Br
Molar mass 249.236 g·mol−1
Appearance Colorless liquid
Density 1.038 g mL−1
Melting point −9.5 °C (14.9 °F; 263.6 K)
Boiling point 276.0 °C (528.8 °F; 549.1 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Production

Most 1-bromoalkanes are prepared by free-radical addition of hydrogen bromide to the 1-alkene. These conditions lead to anti-Markovnikov addition, giving the 1-bromo derivative.[2]

1-Bromododecane can also be prepared by treating dodecanol with hydrobromic acid and sulfuric acid.[3]

CH3(CH2)11OH + HBr → CH3(CH2)11Br + H2O

References
  1. "1-BROMODODECANE - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 4 December 2019.
  2. Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405.
  3. Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 195-196, (1973)
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