1-Bromododecane

1-Bromododecane
Names
	Preferred IUPAC name 1-Bromododecane
	Other names Lauryl bromide, dodecyl bromide, n-bromododecane
Identifiers
CAS Number	143-15-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3184907;
ChemSpider	8579 ;
ECHA InfoCard	100.005.080
EC Number	205-587-9;
PubChem CID	8919;
UNII	90T93TX09D;
CompTox Dashboard (EPA)	DTXSID2044395;
	InChI InChI=1S/C12H25Br/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2-12H2,1H3 Key: PBLNBZIONSLZBU-UHFFFAOYSA-N;
	SMILES CCCCCCCCCCCCBr;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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 compounds	1-Bromobutane; 1-Bromohexane; Dodecanol; Dodecanal; Dodecanoic acid; Sodium lauryl sulfate;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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1-Bromododecane is a bromoalkane 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]

Production

Most 1-bromoalkanes are prepared by free-radical addition of hydrogen bromide to the 1-alkene, which is 1-dodecene in the case of 1-bromododecane. 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-BROMODODECANE - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 4 December 2019.
^ ^a ^b 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. ISBN 978-3527306732.
^ 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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[1] "1-BROMODODECANE - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 4 December 2019.

[Ullmann-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. ISBN 978-3527306732.

[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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