Diphenyl ditelluride

(Redirected from Diphenylditelluride)

Diphenylditelluride is the chemical compound with the formula (C6H5Te)2, abbreviated Ph2Te2. This orange-coloured solid is the oxidized derivative of the unstable benzenetellurol, PhTeH. Ph2Te2 is used as a source of the PhTe unit in organic synthesis[2] and as a catalyst for redox reactions.[3] The compound is a strong nucleophile, easily displacing halides. It also adds electrophilically across multiple bonds, and traps radicals.[4]

Diphenyl ditelluride
Chemical structure of diphenyl ditelluride
Space-filling model of the diphenyl ditelluride molecule
Names
Preferred IUPAC name
1,1′-Ditellanediyldibenzene
Other names
Phenylditelluride
Diphenylditelluride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.046.332 Edit this at Wikidata
EC Number
  • 250-982-1
  • InChI=1S/C12H10Te2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H checkY
    Key: VRLFOXMNTSYGMX-UHFFFAOYSA-N checkY
  • InChI=1/C12H10Te2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
    Key: VRLFOXMNTSYGMX-UHFFFAOYAJ
  • C1([Te][Te]C2=CC=CC=C2)=CC=CC=C1
  • [Te]([Te]c1ccccc1)c2ccccc2
Properties
C12H10Te2
Molar mass 409.42 g/mol
Appearance Orange powder
Density 2.23 g/cm3
Melting point 66 to 67 °C (151 to 153 °F; 339 to 340 K)
Boiling point decomposes
Insoluble
Solubility in other solvents Dichloromethane
Structure
90° at Se
C2 symmetry
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302, H312, H315, H319, H332, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Related compounds
Related compounds
Ph2S2,
Ph2Se2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Preparation

edit

Ph2Te2 is prepared by the oxidation of tellurophenolate, which is generated via the Grignard reagent:[5]

PhMgBr + Te → PhTeMgBr
2PhTeMgBr + 0.5 O2 + H2O → Ph2Te2 + 2 MgBr(OH)

The molecule has C2 symmetry.

References

edit
  1. ^ "Diphenyl ditelluride". pubchem.ncbi.nlm.nih.gov. Retrieved 23 December 2021.
  2. ^ Mohan, Balaji; Yoon, Chohye; Jang, Seongwan; Park, Kang Hyun (2015). "Copper Nanoparticles Catalyzed Se(Te)-Se(Te) Bond Activation: A Straightforward Route Towards Unsymmetrical Organochalcogenides from Boronic Acids". ChemCatChem. 7 (3): 405–412. doi:10.1002/cctc.201402867. ISSN 1867-3880. S2CID 97000699.
  3. ^ Alberto, Eduardo E.; Muller, Lisa M.; Detty, Michael R. (2014). "Rate Accelerations of Bromination Reactions with NaBr and H2O2 via the Addition of Catalytic Quantities of Diaryl Ditellurides". Organometallics. 33 (19): 5571–5581. doi:10.1021/om500883f.
  4. ^ Crich, David; Yao Qingwei. "Diphenyl ditelluride". Encyclopedia of Reactants for Organic Synthesis. doi:10.1002/047084289X.rd416.
  5. ^ Crich, D.; Yao, Q. "Diphenyl Ditelluride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.rd416.