1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene

Base Information

• Chemical Name: 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene
• CAS No.: 374934-77-7
• Molecular Formula: C₃₀H₅₂B₂O₄
• Molecular Weight: 498.362
• Mol file: 374934-77-7.mol

Synonyms:1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene

Chemical Property of 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene

Chemical Property:

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

1,4-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihexylbenzene,≥98%(GC) ≥98%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene

There total 4 articles about 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene 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-dihexyl-2,5-diiodobenzene (162715-91-5) + bis(pinacol)diborane (73183-34-3) → 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene (374934-77-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In N,N-dimethyl-formamide; at 90 ℃; for 48h;

DOI:10.1021/acs.inorgchem.5b02757

Reference yield: 67.0%

1,4-dibromo-2,5-di-n-hexylbenzene (117635-21-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene (374934-77-7)

Guidance literature:

With Pd₂(C₆H₅CHCHCOCHCHC₆H₅)3*CHCl₃; CH₃P(C(CH₃)3)2; N(CH₂CH₃)3; In toluene; N2, Schlenk tecgnique; PMe(tBu)2 in toluene added to Pd compd. in toluene at 0°C, stirring at room temp. for 2 h, Et3N added at -196°C, successive addn. of bromo compd., toluene, and B compd. at room temp., heating at 90°C for 4 d; cooling to room temp., addn. of satd. aq. NH4Cl, org. layer sepd., aq. phase extd. with ether, combined org. phases dried over Na2SO4, filtration, filtrate evapd., recrystn. from hot MeOH, dissolved in hexane. filtration, evapn.; elem. anal.;

DOI:10.1039/c0dt01271h

Reference yield: 42.0%

1,4-dioxane (123-91-1,28347-88-8,28347-91-3,39449-24-6,54841-74-6) + bis(pinacolato)diborane + pyrographite (7440-44-0) → 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,5-di-n-hexylbenzene (374934-77-7)

Guidance literature:

With potassium acetate; In water;

upstream raw materials:

2,3-dimethyl-2,3-butane diol

2,5-dihexyl-1,4-phenylenediboronic acid

1,4-dibromo-2,5-di-n-hexylbenzene

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

Downstream raw materials:

C₆H₂-1,4-(BH₂(NMe₂Et)2-2,5-(Hex)2

C₆H₂-1,4-(B(CHCHtBu)2)2-2,5-(Hex)2

2,5-bis-(3,5-di-tert-butyl-benzyl)-3-[2',5'-dihexyl-4'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-4-yl]-6-phenyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione

Refernces

• 1、 Skaisgirski, Michael,Larsen, Christopher B.,Kerzig, Christoph,Wenger, Oliver S.. "Stepwise Photoinduced Electron Transfer in a Tetrathiafulvalene-Phenothiazine-Ruthenium Triad". . . Retrieved 2019.
• 2、 Franz, Daniel,Bolte, Michael,Lerner, Hans-Wolfram,Wagner, Matthias. "Ditopic hydridoborates and hydridoboranes: Bridging ligands in coordination polymers and versatile hydroboration reagents". . p. 2433 - 2440. Retrieved 2011/06/09.