Samarium(II) bromide
| Names | |
|---|---|
| IUPAC name
Dibromosamarium | |
| Identifiers | |
| 3D model (JSmol) |
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| ChemSpider | |
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| Properties | |
| SmBr2 | |
| Molar mass | 310.17 g/mol[1] |
| Appearance | Brown crystals |
| Melting point | 669 °C (1,236 °F; 942 K)[2] |
| Boiling point | 1,880 °C (3,420 °F; 2,150 K) |
| +5337.0·10−6 cm3/mol [3][4] | |
| Hazards | |
| GHS pictograms |  |
| GHS signal word | Warning[1] |
| H315, H319, H335[1] | |
| P261, P305+351+338[1] | |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Samarium(II) bromide is a crystalline compound with the chemical formula SmBr
2.[5] Samarium(II) bromide is a brown crystal at room temperature.[2]
History
Samarium(II) bromide was first synthesized in 1934 by P. W. Selwood, when he reduced samarium tribromide (SmBr3) with hydrogen (H2). Kagan also synthesized it by converting samarium(III) oxide (Sm2O3) to SmBr3 and then reducing with a lithium dispersion in THF. Robert A. Flowers synthesized it by adding two equivalent of lithium bromide (LiBr) to samarium diiodide (SmI2) in tetrahydrofuran. Namy managed to synthesize it by mixing tetrabromoethane (C2H2Br4) with samarium metal, and Hilmerson found that heating the tetrabromoethane or samarium greatly improved the production of samarium(II) bromide.[6]
Usage
Samarium(II) bromide is used as a reductant, although it is not used as commonly as samarium diiodide.[7] This is likely due to it being soluble in fewer organic liquids, however, it is an effective reagent for pinacol homocouplings of aldehydes, ketones, and cross-coupling carbonyl compounds. Reports have shown that samarium(II) bromide is capable of selectively reducing ketones if it is in the presence of an alkyl halide.[6]
If hexamethylphosphoramide is added to samarium(II) bromide, it will strengthen it enough that it can reduce imines to amines and alkyl chlorides to hydrocarbons.[8] However, the addition of hexamethylphosphoramide to samarium(II) bromide that is in tetrahydrofuran will strengthen it enough that it can reduce cyclohexyl chloride to cyclohexanol, at room temperature, within two hours.[9]
Samarium(II) bromide will reduce ketones in tetrahydrofuran if an activator is absent.[10]
References
- 1 2 3 4 "Samarium(II) bromide 99.95% | Sigma-Aldrich". www.sigmaaldrich.com. Retrieved 20 December 2016.
- 1 2 Haynes, William M. (2013). CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. (94th ed.). CRC Press. p. 86. ISBN 9781466571150.
- ↑ Haynes, William M. (2013). CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. (94th ed.). CRC Press. p. 135. ISBN 9781466571150.
- ↑ Lide, David R. (2004). CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data (85th ed.). Boca Raton [u.a.]: CRC Press. p. 147. ISBN 9780849304859.
- ↑ Elements, American. "Samarium Bromide SmBr2". American Elements. Retrieved 20 December 2016.
- 1 2 Skrydstrup, David J. Procter, Robert A. Flowers, Troels (2009). Organic synthesis using samarium diiodide a practical guide. Cambridge: Royal Society of Chemistry. p. 157. ISBN 9781847551108.
- ↑ Ho, Tse-Lok (2016). Fiesers' Reagents for Organic Synthesis Volume 28. John Wiley & Sons. p. 486. ISBN 9781118942819.
- ↑ Pecharsky, Vitalij K.; Bünzli, Jean-Claude G.; Gschneidner, Karl A. (2006). Handbook on the physics and chemistry of rare earths. Amsterdam: North Holland Pub. Co. p. 431. ISBN 9780080466729.
- ↑ Couty, Sylvain; Baird, Mark S.; Meijere, Armin de; Chessum, Nicola; Dzielendziak, Adam (2014). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 48: Alkanes. Georg Thieme Verlag. p. 153. ISBN 9783131722911.
- ↑ Brown, Richard; Cox, Liam; Eames, Jason; Fader, Lee (2014). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 36: Alcohols. Georg Thieme Verlag. p. 129. ISBN 9783131721310.