ZINC bisbenzenide

Base Information

• Chemical Name: ZINC bisbenzenide
• CAS No.: 1078-58-6
• Molecular Formula: C12H10Zn
• Molecular Weight: 219.601
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID50910524
• Wikidata: Q769109
• Mol file: 1078-58-6.mol

Synonyms:zinc bisbenzenide;zinc;benzene;DTXSID50910524;EINECS 214-082-2;AKOS015915820;FT-0633309;Q769109

Chemical Property of ZINC bisbenzenide

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder.
• Melting Point: 102-106 °C
• Boiling Point: 78.8 °C at 760 mmHg
• Flash Point: 280-285°C
• PSA: 0.00000
• LogP: 2.97110
• Storage Temp.: Flammables area
• Sensitive.: Air & Moisture Sensitive
• Solubility.: Soluble in most organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 218.007392
• Heavy Atom Count: 13
• Complexity: 91.7

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diphenylzinc, 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,F
• Statements: 45-46-37/38-41-48/20/21/22-17
• Safety Statements: 53-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=[C-]C=C1.C1=CC=[C-]C=C1.[Zn+2]
• Uses: Diphenylzinc is used as the synthetic equivalent of ph- synthon. It is also useful in a Michael 1,4-addition reactions. It is used as a catalyst for propylene oxide polymerization in benzene medium. Further, it is a reactive coupling compound in Negishi cross-coupling reactions. In addition to this, it utilized in the preparation of arylcopper, arylsilver and arylgold compounds.

Technology Process of ZINC bisbenzenide

There total 23 articles about ZINC bisbenzenide 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%

diphenylmercury(II) (587-85-9,1337-09-3) + aluminium (7429-90-5) + zinc (7440-66-6) → diphenylzinc (1078-58-6) + triphenylaluminium (841-76-9)

Guidance literature:

In neat (no solvent);

Reference yield: 84.0%

iodobenzene (591-50-4) + zinc(II) chloride (7646-85-7,24359-56-6) → diphenylzinc (1078-58-6)

Guidance literature:

iodobenzene; With n-butyllithium; In diethyl ether; at -50 - 20 ℃; Schlenk technique; Inert atmosphere;

zinc(II) chloride; In diethyl ether; at 20 ℃; for 16h; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201805758

Reference yield: 55.0%

phenylmagnesium bromide (100-58-3) → diphenylzinc (1078-58-6)

Guidance literature:

With zinc dibromide; In tetrahydrofuran; at 0 - 80 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201400459

upstream raw materials:

diethyl ether

(E)-3-Ureido-but-2-enoic acid ethyl ester

phenyllithium

diphenylmercury(II)

Downstream raw materials:

benzoic acid

triphenylmethyl alcohol

triphenylmethane

aniline

Refernces

• 1、 Li, Yongchun,Meng, Huifeng,Liu, Tao,Xiao, Yiqun,Tang, Zhonghai,Pang, Bo,Li, Yuqing,Xiang, Ying,Zhang, Guangye,Lu, Xinhui,Yu, Gui,Yan, He,Zhan, Chuanlang,Huang, Jianhua,Yao, Jiannian. "8.78% Efficient All-Polymer Solar Cells Enabled by Polymer Acceptors Based on a B←N Embedded Electron-Deficient Unit". . . Retrieved 2019.
• 2、 Markies, Peter R.,Schat, Gerrit,Akkerman, Otto S.,Bickelhaupt, F.,Spek, Anthony L.. "Complexation of diphenylzinc simple ethers. Crystal structures of the complexes Ph2Zn*glyme and Ph2Zn*diglyme". . p. 1 - 13. Retrieved 1992.
• 3、 Wigman, Benjamin,Popov, Stasik,Bagdasarian, Alex L.,Shao, Brian,Benton, Tyler R.,Williams, Chloé G.,Fisher, Steven P.,Lavallo, Vincent,Houk,Nelson, Hosea M.. "Vinyl Carbocations Generated under Basic Conditions and Their Intramolecular C-H Insertion Reactions". . p. 9140 - 9144. Retrieved 2019.
• 4、 Henneberger, Thomas,Klein, Wilhelm,Dums, Jasmin V.,F?ssler, Thomas F.. "[(μ2-H)(η2-Ge4)ZnPh2]3?, an edge-on protonated E4 cluster establishing the first three-center two-electron Ge-H-Ge bond". . p. 12381 - 12384. Retrieved 2018.
• 5、 McCann, Lucas C.,Organ, Michael G.. "On the remarkably different role of salt in the cross-coupling of arylzincs from that seen with alkylzincs". . . Retrieved 2014.
• 6、 Sandfort, Frederik,O'Neill, Matthew J.,Cornella, Josep,Wimmer, Laurin,Baran, Phil S.. "Alkyl?(Hetero)Aryl Bond Formation via Decarboxylative Cross-Coupling: A Systematic Analysis". . p. 3319 - 3323. Retrieved 2017.
• 7、 Borys, Andryj M.,Gil-Negrete, Jose M.,Hevia, Eva. "Atom-efficient transition-metal-free arylation ofN,O-acetals using diarylzinc reagents through Zn/Zn cooperativity". supporting information. p. 8905 - 8908. Retrieved 2021/09/10.
• 8、 Hamby, Taylor B.,Sevov, Christo S.,Truesdell, Blaise L.. "General C(sp2)-C(sp3) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts". supporting information. p. 5884 - 5893. Retrieved 2020/04/10.