Diphenyl diselenide

Base Information

• Chemical Name: Diphenyl diselenide
• CAS No.: 1666-13-3
• Molecular Formula: C12H10Se2
• Molecular Weight: 312.131
• Hs Code.: 2931 90 00
• European Community (EC) Number: 216-780-2
• NSC Number: 49763
• UNII: 9ATU3Z459Q
• DSSTox Substance ID: DTXSID6061864
• Nikkaji Number: J31.930I
• Wikipedia: Diphenyl_diselenide
• Wikidata: Q3538196
• Pharos Ligand ID: A2APC4839FBP
• ChEMBL ID: CHEMBL3122204
• Mol file: 1666-13-3.mol

Synonyms:Phenyldiselenide (6CI,7CI,8CI);NSC 49763;

Chemical Property of Diphenyl diselenide

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 1.48E-05mmHg at 25°C
• Melting Point: 60 °C
• Refractive Index: 1.7430
• Boiling Point: 377.343 °C at 760 mmHg
• Flash Point: 182.011 °C
• PSA: 0.00000
• Density: 1.5570
• LogP: 0.96080
• Storage Temp.: Store at 0-5°C
• Water Solubility.: Insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 313.91129
• Heavy Atom Count: 14
• Complexity: 128

Purity/Quality:

99% ^*data from raw suppliers

Diphenyl Diselenide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N
• Hazard Codes: T,N
• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[Se][Se]C2=CC=CC=C2
• Uses: Diphenyl diselenide is used in the methoxyselenenylation of alkenes, dihydroxylation of double bonds, hydrothiolation of terminal alkynes. It is used in the synthesis of the unsymmetrical diorganyl selenides, 1-(phenylselenomethyl)vinyl selenides, allylic phenyl selenides.

Technology Process of Diphenyl diselenide

There total 646 articles about Diphenyl diselenide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1-(4-nitrophenyl)-2-(phenylselanyl)ethan-1-one (104755-32-0) → diphenyl diselenide (1666-13-3) + (4-nitrophenyl)ethanone (100-19-6)

Guidance literature:

With GLUTATHIONE; In methanol; Product distribution; Mechanism; 0.1 M phosphate buffer, pH=6.9; differnt quantity of glutathione; relative reactivity to α-(phenylselenenyl)acetophenone;

DOI:10.1016/S0040-4020(01)87004-6

Reference yield: 96.0%

tert-butyl(dimethyl)(phenylseleno)silane (72726-46-6) → diphenyl diselenide (1666-13-3) + tert-butyldimethylsilyl chloride (18162-48-6)

Guidance literature:

With chlorine; In tetrachloromethane;

DOI:10.1021/jo00320a012

Reference yield: 95.0%

Benzeneselenol (645-96-5) + benzal-p-toluidine (2272-45-9) → N-benzyl-N-(4-methylphenyl)amine (5405-15-2) + diphenyl diselenide (1666-13-3)

Guidance literature:

In chloroform; for 0.166667h; Product distribution; Ambient temperature; reduction of Schiff bases and reductive alkylation of amines with carbonyl compounds;

DOI:10.1016/S0040-4039(00)78695-3

upstream raw materials:

phenyl selenocyanate

ethanol

diethyl ether

ethylphenylselenium dibromide

Downstream raw materials:

p-methoxyphenyl phenyl selenide

benzyl phenyl selenide

Phenylselenyl chloride

selenoanisole

Refernces

• 1、 Saravanan, Perumal,Anbarasan, Pazhamalai. "Trifluoromethylthiolative 1,2-difunctionalization of alkenes with diselenides and AgSCF3". . p. 4639 - 4642. Retrieved 2019.
• 2、 Krief, A.,Mahieu, A. F. De,Dumont, W.,Trabelsi, M.. "Efficient Syntheses of Diselenides from Selenols". . p. 131 - 133. Retrieved 1988.
• 3、 Huang, Xian,Zhu, Liu-Sheng. "Stereoselective synthesis of (E)-vinylic selenides by palladium catalyzed cross-coupling reactions". . p. 9 - 11. Retrieved 1996.
• 4、 Su, Hai-You,Sheng, Shou-Ri,Zhang, Xiao-Lan,Ding, Xiao-Ying,Cai, Ming-Zhong. "One-pot synthesis of 1-(E)-phenylethenyl-1,2,3-triazoles by sequential click-elimination reaction from 2-azido-1-phenyl-1-(Phenylseleno)ethane". . p. 1591 - 1598. Retrieved 2013.
• 5、 Latham, John A.,Branchaud, Bruce P.,Chen, Y.-C. Jack,Walsh, Christopher. "Allylic and Propargylic Phenyl Selenide Oxygenation by Cyclohexanone Oxygenase: -Sigmatropic Rearrangement of the Enzyme-generated Selenoxide". . p. 528 - 530. Retrieved 1986.
• 6、 Luh, Tien-Yau,So, Wan Hung,Tam, S.W.. "TRANSITION METAL-PROMOTED REACTIONS.VI. PALLADIUM(II)-PROMOTED OXIDATIVE COUPLING OF ETHYL ACRYLATE AND RELATED TERMINAL OLEFINS IN THE PRESENCE OF BENZENESELENENYL BROMIDE". . p. 261 - 264. Retrieved 1981.
• 7、 Tainturier, Gerard,Fahim, Mohammed,Trouve-Bellan, Gwenaaelle,Gautheron, Bernard. "Thermal stability and reaction of chalcogen-containing metallocenic compounds with elemental chalcogens". . p. 321 - 332. Retrieved 1989.
• 8、 Fujita, Ken-Ichi,Hashimoto, Shigeru,Oishi, Akihiro,Taguchi, Yoichi. "Intramolecular oxyselenenylation and deselenenylation reactions in water, conducted by employing polymer-supported arylselenenyl bromide". . p. 3793 - 3795. Retrieved 2003.
• 9、 Chegini, Parisa,Khakyzadeh, Vahid,Varmaghani, Fahimeh. "Electrochemical investigation of the chloroselenobenzene under its atmosphere-sensitive characteristics". . . Retrieved 2020.
• 10、 House, Herbert O.,Nomura, Glenn S.,VanDerveer, Don. "Perhydroazulenes. 7. Effect of a tert-Butyl Substituent at C-6 upon the Properties of the 4-Keto Derivatives". . p. 2416 - 2423. Retrieved 1986.