Diphenyl diselenide

Names
IUPAC name

1,1′-Diselanediyldibenzene

Other names

Phenyl diselenide

Identifiers

CAS Number

* 1666-13-3 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 14710 Y

EC Number |

* 216-780-2

PubChem CID

* 15460

RTECS number |

* JM9152500

UNII |

* 9ATU3Z459Q Y

InChI

* InChI=1S/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H Y

Key: YWWZCHLUQSHMCL-UHFFFAOYSA-N Y

* InChI=1/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H

Key: YWWZCHLUQSHMCL-UHFFFAOYAK

SMILES

* c1ccc(cc1)[Se][Se]c2ccccc2

Properties

Chemical formula

| C12H10Se2
Molar mass | 312.154 g·mol−1
Appearance  | Yellow crystals
Density | 1.84 g/cm3
Melting point |  59 to 61 °C (138 to 142 °F; 332 to 334 K)

Solubility in water

| Insoluble
Solubility in other solvents  | Dichloromethane, THF, hot Hexane
Structure

Coordination geometry

| 90° at Se[citation needed]
C2 symmetry[citation needed]

Dipole moment

| 0 D
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H301, H331, H373, H410

GHS precautionary statements

| P260, P261, P264, P270, P271, P273, P301+310, P304+340, P311, P314, P321, P330, P391, P403+233, P405, P501
Related compounds

Related compounds

| Ph2S2,
C6H5SeH

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Diphenyl diselenide 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.

## Contents

* 1 Preparation and properties
* 2 Medical applications
* 3 Reactions
* 4 References

## Preparation and properties

Ph2Se2 is prepared by the oxidation of benzeneselenoate, the conjugate base of benzeneselenol which is generated via the Grignard reagent:[1]

PhMgBr \+ Se → PhSeMgBr
2 PhSeMgBr + Br2 → Ph2Se2 \+ 2 MgBr2

The molecule has idealized C2-symmetry, like hydrogen peroxide and related molecules. The Se-Se bond length of 2.29 Å the C-Se-Se-C dihedral angle is 82° and the C-Se-Se angles are near 110°.[2]

## Medical applications

Diphenyl diselenide alleviates methylmercury poisoning in grass carp.[3]

## Reactions

A reaction characteristic of Ph2Se2 is its reduction:

Ph2Se2 \+ 2 Na → 2 PhSeNa

PhSeNa is a useful nucleophile used to introduce the phenylselenyl group by nucleophilic substitution of alkyl halides, alkyl sulfonates (mesylates or tosylates) and epoxides. The example below was taken from a synthesis of morphine.[4]

Another characteristic reaction is chlorination:

Ph2Se2 \+ Cl2 → 2 PhSeCl

PhSeCl is a powerful electrophile, used to introduce PhSe groups by reaction with a variety of nucleophiles, including enolates, enol silyl ethers, Grignard reagents, organolithium reagents, alkenes and amines. In the sequence below (early steps in the synthesis of Strychnofoline), a PhSe group is introduced by reaction of a lactam enolate with PhSeCl.[5] This sequence is a powerful method for the conversion of carbonyl compounds to their α,β-unsaturated analogs.[6]

Diphenyl diselenide itself is also a source of a weakly electrophilic PhSe group in reactions with relatively powerful nucleophiles like Grignard reagents, lithium reagents and ester enolates (but not ketone enolates or weaker nucleophiles). PhSeCl is both more reactive, and more efficient, since with Ph2Se2 half of the selenium is wasted.

Ph2Se2 \+ Nu− → PhSeNu + PhSe−

N-Phenylselenophthalimide (N-PSP) can be used if PhSeCl is too strong and diphenyl diselenide is too weak or wasteful.[7]

## References

1. ↑ Reich, H. J.; Cohen, M. L.; Clark, P. S. (1979). "Reagents for Synthesis of Organoselenium Compounds: Diphenyl Diselenide and Benzeneselenenyl Chloride". Organic Syntheses 59: 141. http://www.orgsyn.org/demo.aspx?prep=CV6P0533. ;  Collective Volume, 6, pp. 533
2. ↑ Marsh, R. E. (1952). "The Crystal Structure of Diphenyl Diselenide". Acta Crystallographica 5 (4): 458–462. doi:10.1107/S0365110X52001349.
3. ↑ Baldissera, Matheus D.; Souza, Carine F.; da Silva, Aleksandro S.; Henn, Alessandra S.; Flores, Erico M. M.; Baldisserotto, Bernardo (2020). "Diphenyl diselenide dietary supplementation alleviates behavior impairment and brain damage in grass carp (Ctenopharyngodon idella) exposed to methylmercury chloride". Comparative Biochemistry and Physiology. Toxicology & Pharmacology 229: 108674. doi:10.1016/j.cbpc.2019.108674. ISSN 1532-0456. PMID 31760078.
4. ↑ Taber, D. F.; Neubert, T. D.; Rheingold, A. L. (2002). "Synthesis of (−)-Morphine". Journal of the American Chemical Society 124 (42): 12416–12417. doi:10.1021/ja027882h. PMID 12381175.
5. ↑ Lerchner, A.; Carreira, E. M. (2002). "First Total Synthesis of (±)-Strychnofoline via a Highly Selective Ring-Expansion Reaction". Journal of the American Chemical Society 124 (50): 14826–14827. doi:10.1021/ja027906k. PMID 12475306.
6. ↑ Reich, H. J.; Wollowitz, S. (1993). "Preparation of α,β-Unsaturated Carbonyl Compounds and Nitriles by Selenoxide Elimination". Organic Reactions 44: 1–296. doi:10.1002/0471264180.or044.01. ISBN 0471264180.
7. ↑ Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Corttés, M.; Armstrong, V. (1999). "Synthesis and Antitumor Activity of Puupehedione and Related Compounds". Tetrahedron 55 (52): 15181–15208. doi:10.1016/S0040-4020(99)00992-8.

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Diphenyl_diselenide&oldid=3421831"
*[CID]: Compound ID
*[H301]: Toxic if swallowed
*[H331]: Toxic if inhaled
*[H373]: May cause damage to organs through prolonged or repeated exposure
*[H410]: Very toxic to aquatic life with long lasting effects
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P311]: Call a POISON CENTER or doctor/physician
*[P314]: Get Medical advice/attention if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P330]: Rinse mouth
*[P391]: Collect spillage
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …