Ethyne-1,2-diyldiboronic acid dipinacol ester

Base Information

• Chemical Name: Ethyne-1,2-diyldiboronic acid dipinacol ester
• CAS No.: 1010840-17-1
• Molecular Formula: C₁₄H₂₄B₂O₄
• Molecular Weight: 277.964
• Hs Code.: 2934999090
• Mol file: 1010840-17-1.mol

Synonyms:1,2-bis(4’,4’,5’,5’-tetramethyl[1’,3’,2’]dioxaborolan-2’-yl)ethyne

Chemical Property of Ethyne-1,2-diyldiboronic acid dipinacol ester

Chemical Property:

• Melting Point: 269°C
• Boiling Point: 257.5±23.0 °C(Predicted)
• Density: 1.00±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Reactant for the preparation of:Poly(p-phenyleneethynylene)s (PPEs), which are used in constructing organic light-emitting diodes (OLEDs), field-effect transistors (FETs) and several other materials used in electronic devices

Technology Process of Ethyne-1,2-diyldiboronic acid dipinacol ester

There total 2 articles about Ethyne-1,2-diyldiboronic acid dipinacol ester 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: 77.0%

Trichloroethylene (79-01-6) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 1,2-bis(4’,4’,5’,5’-tetramethyl[1’,3’,2’]dioxaborolan-2’-yl)ethyne (1010840-17-1)

Guidance literature:

Trichloroethylene; With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol702758f

Reference yield: 68.0%

Trichloroethylene (79-01-6) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) → 1,2-bis(4’,4’,5’,5’-tetramethyl[1’,3’,2’]dioxaborolan-2’-yl)ethyne (1010840-17-1)

Guidance literature:

Trichloroethylene; With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; for 12.25h; Inert atmosphere;

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; for 6h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; Inert atmosphere;

DOI:10.1021/jacs.9b12930

Reference yield: 73.0%

[5-bromo-10,20-bis(2’,6’-bis(3”,3”-dimethylbutoxy)phenyl)porphinato]zinc(II) (478184-34-8) + 1,2-bis(4’,4’,5’,5’-tetramethyl[1’,3’,2’]dioxaborolan-2’-yl)ethyne (1010840-17-1) → 1,2-bis[(10,20-bis[2’,6’-bis(3”,3”-dimethyl-1”-butyloxy)phenyl]porphinato)zinc(II)-5-yl]ethyne

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In water; N,N-dimethyl-formamide; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1002/bkcs.10695

upstream raw materials:

Trichloroethylene

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

1,2-bis(9-anthryl)acetylene

diphenyl acetylene

4,4'-dimethoxydiphenylacetylene

1,2-bis(4-(trifluoromethyl)phenyl)ethyne

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