1,1-Dibromoethane

1,1-Dibromoethane
Names
	Preferred IUPAC name 1,1-Dibromoethane
	Other names Ethylidene bromide, ethylidene dibromide
Identifiers
CAS Number	557-91-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	10728 ;
ECHA InfoCard	100.008.351
EC Number	209-184-9;
PubChem CID	11201;
RTECS number	KH9000000;
UNII	KJ8ZJY72QQ ;
CompTox Dashboard (EPA)	DTXSID3060324 ;
	InChI InChI=1S/C2H4Br2/c1-2(3)4/h2H,1H3 Key: APQIUTYORBAGEZ-UHFFFAOYSA-N ;
	SMILES CC(Br)Br;
Properties
Chemical formula	C2H4Br2
Molar mass	187.862 g·mol−1
Appearance	Colorless liquid
Melting point	−63.0 °C; −81.3 °F; 210.2 K
Boiling point	108.1 °C; 226.5 °F; 381.2 K
Solubility in water	3.4 g/L (25 °C)
Solubility	soluble in ether, ethanol, acetone, and benzene ; slight soluble chloroform
log P	1.9 (estimated)
Refractive index (nD)	1.51277 (at 20 °C)
Hazards
	GHS labelling:
Signal word	Danger
Hazard statements	H301, H311, H315, H319, H331
Precautionary statements	P261, P264, P270, P271, P280, P311, P312, P321, P322, P330, P361, P362, P363, P405, P501
NFPA 704 (fire diamond)	2 1 0
Flash point	> 93 °C (199 °F; 366 K)
Safety data sheet (SDS)	fishersci.com
Related compounds
Related alkanes	Dibromomethane; Bromoform; Tetrabromomethane; 1,2-Dibromoethane; Tetrabromoethane; 1,2-Dibromopropane; 1,3-Dibromopropane; 1,2,3-Tribromopropane;
	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

1,1-Dibromoethane is a clear, slightly brown, flammable chemical compound.^[3] It is classified as an organobromine compound, and has the chemical formula C₂H₄Br₂^[4] and it is a position isomer of 1,2-dibromoethane. It is commonly seen in industrial chemistry, where it is used as a fuel additive.^[5] It is also used as a grain and soil fumigant for insect control.^[6]

Synthesis

1,1-Dibromoethane is synthesized through addition of hydrogen bromide onto vinyl bromide with absence of peroxide radical.^[7]

Safety

1,1-Dibromoethane is considered as a mildly toxic compound, especially with bromines attached as substituents. Bromines on the ethane are strong oxidizing agents. If absorbed through inhalation, 1,1-dibromoethane could potentially cause neuronal effects, tissue damage, and bromism.^[8]

References

^ "Ethylidene dibromide - Compound Summary". PubChem Compound. US: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 19 June 2012.
^ "1,1-Dirbomoethane". National Center for Biotechnology Information. Retrieved 31 May 2017.
^ "MSDS". Fisher Scientific, Inc. Retrieved 13 June 2012.
^ "Dibromoethane". ChemSpider. Retrieved 13 June 2012.
^ "1,1-dibromoethane". PubChem. Retrieved 9 June 2017.
^ Larranaga, Michael (10 March 2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. ISBN 9781118135150. Retrieved 9 June 2017.
^ Kharasch, M.; McNab, M.; Mayo, Frank (June 1933). "The Peroxide Effect in the Addition of Reagents to Unsaturated Compounds. II. The Addition of Hydrogen Bromide to Vinyl Bromide". Journal of the American Chemical Society. 55 (6): 2521–2530. doi:10.1021/ja01333a048.
^ "1,1-Dibromoethane (T3D1793)". The Toxin and Toxin Target Database. Retrieved 9 June 2017.

[1] "Ethylidene dibromide - Compound Summary". PubChem Compound. US: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 19 June 2012.

[2] "1,1-Dirbomoethane". National Center for Biotechnology Information. Retrieved 31 May 2017.

[3] "MSDS". Fisher Scientific, Inc. Retrieved 13 June 2012.

[4] "Dibromoethane". ChemSpider. Retrieved 13 June 2012.

[5] "1,1-dibromoethane". PubChem. Retrieved 9 June 2017.

[6] Larranaga, Michael (10 March 2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. ISBN 9781118135150. Retrieved 9 June 2017.

[7] Kharasch, M.; McNab, M.; Mayo, Frank (June 1933). "The Peroxide Effect in the Addition of Reagents to Unsaturated Compounds. II. The Addition of Hydrogen Bromide to Vinyl Bromide". Journal of the American Chemical Society. 55 (6): 2521–2530. doi:10.1021/ja01333a048.

[8] "1,1-Dibromoethane (T3D1793)". The Toxin and Toxin Target Database. Retrieved 9 June 2017.

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