1-Bromohexane

1-Bromohexane
Names
	Preferred IUPAC name 1-Bromohexane
	Other names Bromohexane; Hexyl bromide}; 1-Hexyl bromide; n-Hexyl bromide;
Identifiers
CAS Number	111-25-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1731290
ChemSpider	7810 ;
ECHA InfoCard	100.003.501
EC Number	203-850-2;
MeSH	1-bromohexane
PubChem CID	8101;
RTECS number	MO0925000;
UNII	WVA0FAX7GA ;
UN number	1993
CompTox Dashboard (EPA)	DTXSID4021929 ;
	InChI InChI=1S/C6H13Br/c1-2-3-4-5-6-7/h2-6H2,1H3 Key: MNDIARAMWBIKFW-UHFFFAOYSA-N ;
	SMILES CCCCCCBr;
Properties
Chemical formula	C6H13Br
Molar mass	165.074 g·mol−1
Appearance	Colorless liquid
Density	1.176 g/mL
Melting point	−84.70 °C; −120.46 °F; 188.45 K
Boiling point	154 to 158 °C; 309 to 316 °F; 427 to 431 K
Solubility in water	Insoluble
Solubility	Alcohol, ether
Refractive index (nD)	1.448 (20 °C, D)
Thermochemistry
Heat capacity (C)	219.7 J K−1 mol−1
Std molar; entropy (S⦵298)	452.92 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−196.1–−192.9 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−4026.2–−4023.0 kJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H319, H335
Precautionary statements	P261, P305+P351+P338
NFPA 704 (fire diamond)	1 2 0
Flash point	57 °C (135 °F; 330 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1.226 g/kg (IP, mouse)
Related compounds
Related alkanes	1-Bromobutane; 1-Bromododecane; 2-Bromobutane; 2-Bromohexane;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

1-Bromohexane is organobromine compound with formula Br(CH₂)₅CH₃. It is a colorless liquid.

Synthesis and reactions

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-Bromohexane undergoes reactions expected of simple alkyl bromides. It can form Grignard reagents.^[3] It reacts with potassium fluoride to give the corresponding fluorocarbons.^[4]

References

^ "1-bromohexane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 17 June 2012.
^ 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.
^ Garst, J., Ungvary, F., Batlaw, R., & Lawrence, K. (1991). Solvent attack in Grignard reagent formation from bromocyclopropane and 1-bromohexane in diethyl ether. Journal of American Chemical Society, 113, 5392-5397.
^ Vogel, A. I.; Leicester, J.; Macey, W. A. T. (1956). "n-Hexyl Fluoride". Organic Syntheses. 36: 40. doi:10.15227/orgsyn.036.0040.

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[1] "1-bromohexane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 17 June 2012.

[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] Garst, J., Ungvary, F., Batlaw, R., & Lawrence, K. (1991). Solvent attack in Grignard reagent formation from bromocyclopropane and 1-bromohexane in diethyl ether. Journal of American Chemical Society, 113, 5392-5397.

[4] Vogel, A. I.; Leicester, J.; Macey, W. A. T. (1956). "n-Hexyl Fluoride". Organic Syntheses. 36: 40. doi:10.15227/orgsyn.036.0040.

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Synthesis and reactions

See also

References