Diphenyl diselenide
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| Diphenyl diselenide | |
|---|---|
 |
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| General | |
| Systematic name | Diphenyldiselenide |
| Other names | Phenyldiselenide |
| Molecular formula | C12H10Se2 |
| SMILES | C1(SeSeC2=CC=CC=C2)=CC=CC=C1 |
| Molar mass | 312.13 g/mol |
| Appearance | Orange powder |
| CAS number | [1666-13-3] |
| Properties | |
| Density and phase | 1.84 g/cm3 |
| Solubility in water | Insoluble |
| Other solvents | Dichloromethane |
| Melting point | 59-61 °C |
| Boiling point | ? °C |
| Structure | |
| Coordination geometry |
90° at Se C2 symmetry |
| Dipole moment | 0 D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Toxic |
| NFPA 704 | |
| R/S statement | R: 23/25-33-50/53 S: 20/21-28-45-60-61 |
| RTECS number | JM9152500 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | Ph2S2, C6H5SeH |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Diphenyldiselenide is the chemical compound with the formula (C6H5)2Se2, abbreviated Ph2Se2 This orange-coloured solid is the oxidized derivative of benzeneselenol. It is used as a source of the PhSe unit in organic synthesis.
Ph2Se2 is prepared by the oxidation of phenylselenoate, which is generated via the Grignard reagent:[1]
- PhMgBr + Se → PhSeMgBr
- 2 PhSeMgBr + Br2 → Ph2Se2 + 2 MgBr2
It has a centrosymmetric structure, with an Se-Se bond length of 2.29 A.[2]
[edit] Reactions
Two reactions characteristic of Ph2Se2 are reduction and chlorination:
- Ph2Se2 + 2 Na → 2 PhSeNa
- Ph2Se2 + Cl2 → 2 PhSeCl
[edit] Safety
Organoselenium compounds are toxic.
[edit] References
- ^ Reich, H. J.; Cohen, M. L.; Clark, P. S. "Reagents for Synthesis of Organoselenium Compounds: Diphenyl Diselenide and Benzeneselenyl Chloride" Organic Syntheses Collective Volume 6, page 533. 1988.
- ^ Marsh, R. E. "The Crystal Structure of Diphenyl Diselenide" Acta Crystallographica (1952), volume 5, pages 458-462. doi:10.1107/S0365110X52001349.
