(9,9-Dihexyl-9H-fluoren-2-yl)boronic acid

Base Information

• Chemical Name: (9,9-Dihexyl-9H-fluoren-2-yl)boronic acid
• CAS No.: 371193-08-7
• Molecular Formula: C25H35BO2
• Molecular Weight: 378.363
• European Community (EC) Number: 834-840-1
• DSSTox Substance ID: DTXSID70479188
• Nikkaji Number: J2.019.265H
• Wikidata: Q82313143
• Mol file: 371193-08-7.mol

Synonyms:371193-08-7;(9,9-Dihexyl-9H-fluoren-2-yl)boronic acid;9,9-Dihexyl-9H-fluoren-2-boronic acid;(9,9-dihexylfluoren-2-yl)boronic acid;9,9-Dihexylfluorene-2-boronic Acid (contains varying amounts of Anhydride);9,9-Dihexyl-9H-fluorene-2-yl-2-boronic acid;SCHEMBL3789775;DTXSID70479188;AMY29992;WPA19308;MFCD18910616;AKOS015901374;SB66754;AS-82701;(9,9-Dihexyl-9H-fluoren-2-yl)boronicacid;CS-0175907;D5054;FT-0763661;F16253

Chemical Property of (9,9-Dihexyl-9H-fluoren-2-yl)boronic acid

Chemical Property:

• Melting Point: 98°C(lit.)
• Boiling Point: 542.2 °C at 760 mmHg
• PKA: 8.63±0.40(Predicted)
• Flash Point: 281.7 °C
• PSA: 40.46000
• Density: 1.05 g/cm³
• LogP: 5.57370
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 378.2730105
• Heavy Atom Count: 28
• Complexity: 440

Purity/Quality:

98% ^*data from raw suppliers

9,9-Dihexyl-9H-fluoren-2-boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)C3=CC=CC=C3C2(CCCCCC)CCCCCC)(O)O

Technology Process of (9,9-Dihexyl-9H-fluoren-2-yl)boronic acid

There total 10 articles about (9,9-Dihexyl-9H-fluoren-2-yl)boronic 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: 88.0%

2-bromo-9,9-dihexyl-9H-fluorene (226070-05-9) → 9,9-dihexylfluorene-2-boronic acid (371193-08-7)

Guidance literature:

2-bromo-9,9-dihexyl-9H-fluorene; With n-butyllithium; In tetrahydrofuran; hexane; at -80 ℃; for 0.75h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -80 - 20 ℃; for 12h;

With hydrogenchloride; In tetrahydrofuran; hexane; pH=2 - 3;

DOI:10.1021/ja039228n

Reference yield: 88.0%

Triisopropyl borate (5419-55-6) + water (7732-18-5) + 2-bromo-9,9-dihexyl-9H-fluorene (226070-05-9) → 9,9-dihexylfluorene-2-boronic acid (371193-08-7)

Guidance literature:

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; 1. BuLi, THF; 2. (i-PrO)3B; 3. H2O/HCl;

DOI:10.1021/ja039228n

Reference yield: 61.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-bromo-9,9-dihexyl-9H-fluorene (226070-05-9) → 9,9-dihexylfluorene-2-boronic acid (371193-08-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; cyclohexane; to soln. of (C6H13)2(C13H7)Br in THF at -78°C, soln. of C4H9Li inC6H12 added dropwise; mixt. stirred at -78°C for 1 h, then (CH3O )3B added, warmed to room temp., stirred overnight, HCl added to hydrolyze for 30 min; org. layer washed with brine, dried over MgSO4, solvent removed, residuepurified by chromy. (silica gel, hexane/ethyl acetate = 2/1);

DOI:10.1021/jp037131h

upstream raw materials:

2-bromo-9,9-dihexyl-9H-fluorene

1-bromo-hexane

2-bromo-9H-fluorene

Triisopropyl borate

Downstream raw materials:

C₆(C₆H₅)4C₅H₄(C₁₃H₇(C₆H₁₃)2)N

C₆₀H₅₅N

C₆₉H₇₈O

TFE

Refernces

• 1、 Kulkarni, Abhishek P.,Kong, Xiangxing,Jenekhe, Samson A.. "Fluorenone-containing polyfluorenes and oligofluorenes: Photophysics, origin of the green emission and efficient green electroluminescence". . p. 8689 - 8701. Retrieved 2004.
• 2、 So, Gary Kwok-Ming,Cheng, Gang,Wang, Jian,Chang, Xiaoyong,Kwok, Chi-Chung,Zhang, Hongxing,Che, Chi-Ming. "Efficient Color-Tunable Copper(I) Complexes and Their Applications in Solution-Processed Organic Light-Emitting Diodes". . p. 1490 - 1498. Retrieved 2017/07/11.
• 3、 Robert, Patricia,Bolduc, Andreanne,Skene, W. G.. "Oligofluorenes as polymeric model compounds for providing insight into the triplets of ketone and ketylimine derivatives". . p. 9305 - 9314,10. Retrieved 2020/08/24.