2-(2,6-DIMETHYL-1-CYCLOHEXEN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

Base Information

• Chemical Name: 2-(2,6-DIMETHYL-1-CYCLOHEXEN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• CAS No.: 287944-08-5
• Molecular Formula: C₁₄H₂₅BO₂
• Molecular Weight: 236.162
• Mol file: 287944-08-5.mol

Synonyms:2-(2,6-DIMETHYL-1-CYCLOHEXEN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(2,6-dimethyl-1-cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-

Chemical Property of 2-(2,6-DIMETHYL-1-CYCLOHEXEN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

Chemical Property:

• Boiling Point: 261.5±33.0 °C(Predicted)
• Density: 0.94±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

2-(2,6-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-(2,6-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used in the synthetic preparation of alkenylboronates via palladium-catalyzed cross-coupling reactions.

Technology Process of 2-(2,6-DIMETHYL-1-CYCLOHEXEN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

There total 3 articles about 2-(2,6-DIMETHYL-1-CYCLOHEXEN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE 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: 94.0%

2,6-dimethyl-1-cyclohexen-1-yl triflate (28075-36-7) + bis(pinacol)diborane (73183-34-3) → 2,6-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-cyclohexene (287944-08-5)

Guidance literature:

With triphenylphosphine; bis(triphenylphosphine)palladium(II) chloride; In toluene; mixt. in toluene stirred at 50°C for 2 h; treated (H2O) at room temp.; extd. (benzene); washed with brine; dried (MgSO4); purified by chromy. on silica gel or by distn. (vac.);

DOI:10.1021/ja0202255

Reference yield: 94.0%

1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene (77412-96-5) + bis(pinacol)diborane (73183-34-3) → 2,6-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-cyclohexene (287944-08-5)

Guidance literature:

With triphenylphosphine; bis(triphenylphosphine)palladium(II) chloride; In toluene; mixt. in toluene stirred at 50°C for 2 h; treated (H2O) at room temp.; extd. (benzene); washed with brine; dried (MgSO4); purified by chromy. on silica gel or by distn. (vac.);

DOI:10.1021/ja0202255

Reference yield:

2,6-dimethyl-1-cyclohexen-1-yl triflate (28075-36-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2,6-dimethyl-cyclohex-2-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane + 2,6-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-cyclohexene (287944-08-5)

Guidance literature:

With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; In 1,4-dioxane; at 100 ℃; for 48h; Title compound not separated from byproducts;

DOI:10.1055/s-2000-6274

upstream raw materials:

2,6-dimethyl-1-cyclohexen-1-yl triflate

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

bis(pinacol)diborane

1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene