9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

Base Information

• Chemical Name: 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole
• CAS No.: 785051-54-9
• Molecular Formula: C24H24BNO2
• Molecular Weight: 369.271
• Hs Code.: 2933990090
• European Community (EC) Number: 805-445-1
• DSSTox Substance ID: DTXSID60474400
• Nikkaji Number: J2.353.905E
• Wikidata: Q82304403
• Mol file: 785051-54-9.mol

Synonyms:785051-54-9;9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole;9-Carbazolylbenzeneboronic acid pinacol ester;9-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole;9-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbazole;MFCD16294549;9H-Carbazole-9-(4-phenyl) boronic acid pinacol ester;4-(9H-Carbazol-9-yl)phenylboronic Acid Pinacol Ester;2-[4-(9H-Carbazol-9-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;9-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole;9-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbazole;9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbazole;9-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-9H-carbazole;SCHEMBL792421;DTXSID60474400;AHDSYMVAUJZCOP-UHFFFAOYSA-N;AKOS016339781;AS-2450;SY107232;CS-0097287;FT-0732904;T3452;T72943;EN300-7382169;4-(9-Carbazolyl)phenylboronic Acid Pinacol Ester;A923177;9H-Carbazole-9-(4-phenyl) boronic acid pinacol ester, 95%;9-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-9H-carbazole

Chemical Property of 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

Chemical Property:

• Melting Point: 165-173 °C
• Boiling Point: 468.5±37.0 °C(Predicted)
• PSA: 23.39000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 5.08290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 369.1900092
• Heavy Atom Count: 28
• Complexity: 533

Purity/Quality:

97% ^*data from raw suppliers

9-Carbazolylbenzeneboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)N3C4=CC=CC=C4C5=CC=CC=C53
• Uses: 9-Carbazolylbenzeneboronic acid pinacol ester 9H-Carbazole-9-(4-phenyl) boronic acid pinacol can be used as a donor molecule in the formation of novel donor-π-acceptor dyes for electrochemical applications. It can also be used in the formation of organic light emitting diodes (OLEDs).

Technology Process of 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

There total 28 articles about 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole 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: 96.8%

N-(4-bromophenyl)carbazole (57102-42-8) + bis(pinacol)diborane (73183-34-3) → 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (785051-54-9)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; In dimethyl sulfoxide; at 80 ℃; for 8h; Inert atmosphere;

DOI:10.1039/c2cc34712a

Reference yield: 93.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + Triisopropyl borate (5419-55-6) + N-(4-bromophenyl)carbazole (57102-42-8) → 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (785051-54-9)

Guidance literature:

N-(4-bromophenyl)carbazole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; In tetrahydrofuran; hexane; at 20 ℃; for 69h; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.202102052

Reference yield: 87.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + N-(4-bromophenyl)carbazole (57102-42-8) → 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (785051-54-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran;

DOI:10.1002/cjoc.201500308

upstream raw materials:

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

N-(4-bromophenyl)carbazole

1,4-bromoiodobenzene

9H-carbazole

Downstream raw materials:

10-(4-(9H-carbazol-9-yl)phenyl)-8,8-di-p-tolyl-8H-indolo[3,2,1-de]acridine

9-(4'-bromo-2'-methylbiphenyl-4-yl)-9H-carbazole

3,6-dibromo-9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

C₂₃H₁₅BrN₂