9,9-Dioctylfluorene-2,7-diboronic acid

Base Information

• Chemical Name: 9,9-Dioctylfluorene-2,7-diboronic acid
• CAS No.: 258865-48-4
• Molecular Formula: C₂₉H₄₄B₂O₄
• Molecular Weight: 478.288
• Hs Code.: 29319090
• European Community (EC) Number: 800-209-4
• DSSTox Substance ID: DTXSID90401547
• Nikkaji Number: J1.726.997F
• Wikidata: Q72472604
• Mol file: 258865-48-4.mol

Synonyms:258865-48-4;9,9-Dioctylfluorene-2,7-diboronic acid;(9,9-Dioctyl-9H-fluorene-2,7-diyl)diboronic acid;(7-borono-9,9-dioctylfluoren-2-yl)boronic acid;9 9-DIOCTYLFLUORENE-2 7-DIBORONIC ACID;9,9-dioctyl-9H-fluorene-2,7-diyldiboronic acid;MFCD03701608;[7-(DIHYDROXYBORANYL)-9,9-DIOCTYL-9H-FLUOREN-2-YL]BORONIC ACID;C29H44B2O4;Boronic acid, (9,9-dioctyl-9H-fluorene-2,7-diyl)bis-;SCHEMBL374243;DTXSID90401547;AMY32824;AKOS015839922;s11553;AS-63854;SY251065;CS-0175007;FT-0652969;9,9-Dioctylfluorene-2,7-diboronic acid, 96%;(7-borono-9,9-dioctyl-2-fluorenyl)boronic acid;(9,9-Dioctyl-9H-fluorene-2,7-diyl)diboronicacid;A818060;[7-(dihydroxyboranyl)-9,9-dioctyl-fluoren-2-yl]boronic acid

Chemical Property of 9,9-Dioctylfluorene-2,7-diboronic acid

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 6.56E-19mmHg at 25°C
• Melting Point: 158-162 °C(lit.)
• Refractive Index: 1.556
• Boiling Point: 670.8 °C at 760 mmHg
• Flash Point: 359.5 °C
• PSA: 80.92000
• Density: 1.08g/cm³
• LogP: 4.81390
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 16
• Exact Mass: 478.3425702
• Heavy Atom Count: 35
• Complexity: 537

Purity/Quality:

≥99% ^*data from raw suppliers

9,9-Dioctylfluorene-2,7-diboronic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)C3=C(C2(CCCCCCCC)CCCCCCCC)C=C(C=C3)B(O)O)(O)O
• Uses: 9,9-Dioctylfluorene-2,7-diboronic acid can be used as a reactant to synthesize hyperbranched conjugated conductive copolymers by Pd-catalyzed Suzuki-Miyaura cross coupling (SMC) copolymerization reaction with different dibromoarenes.

Technology Process of 9,9-Dioctylfluorene-2,7-diboronic acid

There total 11 articles about 9,9-Dioctylfluorene-2,7-diboronic acid 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: 80.0%

2,7-dibromo-9,9-dioctylfluorene (198964-46-4) → 9,9-dioctyl-9H-fluorene-2,7-diyldiboronic acid (258865-48-4)

Guidance literature:

2,7-dibromo-9,9-dioctylfluorene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 4.5h; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/pola.25984

Reference yield:

1-bromo-octane (111-83-1) → 9,9-dioctyl-9H-fluorene-2,7-diyldiboronic acid (258865-48-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 °C

1.2: hexane; tetrahydrofuran / -78 - 20 °C

2.1: Br₂; I₂ / CH₂Cl₂ / 20 h / 20 °C

3.1: n-BuLi / diethyl ether / -78 - 20 °C

3.2: triisopropyl boronate / diethyl ether / 20 h / 20 °C

3.3: 65 percent / aq. HCl / diethyl ether / 1 h / 20 °C

With n-butyllithium; bromine; iodine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ma011093n

Reference yield:

2,7-dibromo-9H-fluorene (16433-88-8) → 9,9-dioctyl-9H-fluorene-2,7-diyldiboronic acid (258865-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 60 °C

1.2: 75.3 percent / tetrahydrofuran / Heating

2.1: magnesium; iodine / tetrahydrofuran / Heating

2.2: 31 percent / triethyl borate / tetrahydrofuran / 48 h / 20 °C

With iodine; sodium hydride; magnesium; In tetrahydrofuran;

DOI:10.1021/ja0211151

upstream raw materials:

2,7-dibromo-9,9-dioctylfluorene

9H-fluorene

1-bromo-octane

9,9-dioctyl-9H-fluorene

Downstream raw materials:

2,7-bis(1,3,2-dioxaborinan-2-yl)-9,9-dioctylfluorene

9,9-dioctylfluorene-2,7-bis(5-salicylaldehyde)