1530-12-7

Basic information

• Product Name: 9,9'-BIFLUORENE
• Synonyms: 9,9'-DIFLUORENYL;9,9'-BIFLUORENE;9,9’-Bi-9H-fluorenyl;9,9'-Bifluorenyl;Bifluorenyl;Bisfluorenyl
• CAS NO: 1530-12-7
• Molecular Formula: C₂₆H₁₈
• Molecular Weight: 330.42
• Product Categories: Fluorenes, Flurenones
• Mol File: 1530-12-7.mol
• Article Data: 88

Chemical Properties

• Melting Point: 244.0 to 248.0 °C
• Boiling Point: 402.85°C (rough estimate)
• Flash Point: 228.3°C
• Appearance: /
• Density: 1.1398 (estimate)
• Refractive Index: 1.8430 (estimate)
• CAS DataBase Reference: 9,9'-BIFLUORENE(CAS DataBase Reference)
• NIST Chemistry Reference: 9,9'-BIFLUORENE(1530-12-7)
• EPA Substance Registry System: 9,9'-BIFLUORENE(1530-12-7)

Safety Data

• Hazardous Substances Data: 1530-12-7(Hazardous Substances Data)

Usage

Description

9,9'-Bifluorene is an organic compound consisting of two fused fluorene rings. It is a white crystalline solid with a unique molecular structure that exhibits distinct chemical and physical properties.

Uses

Used in Chemical Synthesis:
9,9'-Bifluorene is used as a precursor in the synthesis of various organic compounds for different applications. It serves as a starting material for the production of other valuable compounds such as indene, chrysene, benzoanthracene, and others.
Used in Microwave Flash Pyrolysis:
In the field of chemical engineering, 9,9'-bifluorene is utilized in microwave flash pyrolysis, a technique that involves the rapid heating of a substance to high temperatures in the presence of a carrier gas. This process allows for the efficient formation of the aforementioned compounds, which can be further used in various industries, such as pharmaceuticals, materials science, and petrochemicals.

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 60-29-7 diethyl ether 
• 6630-65-5 9-chlorofluorene 
• 86-73-7 9H-fluorene 
• 486-25-9 9-fluorenone 
• 574-45-8 N-(diphenylmethylidene)phenylamine 
• 542-11-0 aniline hydrobromide 
• 10183-82-1 N-phenylfluorenimine 
• 5152-68-1 benzhydryl sodium 
• 693-25-4 n-pentylmagnesium bromide 
• 64-17-5 ethanol 
• 108734-93-6 [9,9']bifluorenyl-9,9'-diyl disodium 
• 1689-64-1 9-Fluorenol 
• 746-47-4 tetrabenzo[5.5]fulvalene 

Downstream Products

• 746-47-4 tetrabenzo[5.5]fulvalene 
• 86-73-7 9H-fluorene 
• 486-25-9 9-fluorenone 
• 197-61-5 rubicene 
• 191-68-4 dibenzo[g,p]chrysene 
• 340-19-2 benzindeno<1,2,3-hi>acephenanthrylene 

Relevant articles and documents

Stabilization of Carbanions by Polarization of Alkyl Groups on Nonadjacent Atoms

Equilibrium acidities in dimethyl sulfoxide solution have been found to increase along the series Me, Et, i-Pr, t-Bu for 9-substituted fluorenes when the alkyl group, R, is separated from the fluorene ring by a CH2, S, or SO2 moiety.This is a reversal of

A Kinetic Study on Reduction of 9,9'-Bifluorenylidene by Sodium Isopropoxide

The kinetics and mechanism of reduction of 9,9'-bifluorenylidene (1) by sodium isopropoxide (2) in isopropyl alcohol to yield 9,9'-bifluorenyl (3) were investigated spectrophotometrically.The kinetic data suggest that the reduction proceeds autocatalytically, the reduction product 3 acting as the catalyst.It was found that (1) (2) Reactions 1 and 2 are of the first order with respect to 1, but that the former is of the third order with respect to 2, whereas the latter is of the first.The fourth- and third-order rate constants, k1 and k2 for Reactions 1 and 2 were determined to be 3.0 * 10-5 dm9 mol-3 s-1 and 1.1 * 103 dm6 mol-2 s-1, respectively, at 130 deg C.Probable mechanisms for Reactions 1 and 2 have been offered on the basis of the reaction order for each molecular species involved.

PHOTOCHEMICAL GENERATION OF RADICAL ANIONS. AN ACCESS TO NOVEL STRUCTURES

The preparation of the radical anions of tetrabenzocyclooctatetraene (TBCOT) and fluorene (FLH) by photochemical methods leads to the observation of novel structures.

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Ion Pair Acidities of 9,9'-Bifluorenyl in THF: pK2 Is Lower than pK1

The second pK's in THF for lithium and cesium salts of 9,9'-bifluorenyl are 0.4 and 2.0 pK units, respectively, lower than the first pK's.

A facile synthesis of dithieno[3,2-b:6,7-b]fluorenes via a tandem annulation-reduction

A concise and facile synthesis of 2,8-disubstituted dithieno[3,2-b:6,7-b] fluorenes starting from 2,7-dihydroxyfluorenone is reported. The key step involved is the tandem annulation-reduction of a 3,6-dichloro-2,7-di(alkynyl) fluorenone using Na2S·9H2O as a sulfur surrogate and reductant. The final dithiophene-fused fluorenes are obtained in reasonable yields (23-43%). The Royal Society of Chemistry.

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A Kinetic Study of the Photosolvolysis of 9-Fluorenol

Excitation of 9-fluorenol in methanol and methanol-water mixtures leads to both heterolytic and homolytic cleavage via the singlet excited state.The partitioning between homolysis and heterolysis is controlled by solvent composition, the rate constant for cation formation being a function of the solvent dielectric constant.The rate constants of intersystem crossing, fluorescence, and singlet-derived radical formation are linear functions of the mole fraction of water.

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Evidence for the Generation of Aromatic Cationic Systems in the Excited State. Photochemical Solvolysis of Fluoren-9-ol

Photolysis of fluoren-9-ol (1) in aqueous methanol solution results in efficient formation of 9-methoxyfluorene (2); the driving force for the photosolvolysis is believed to be the formation of an aromatic 4? cationic system in the excited-state.

Vanadium Pyridonate Catalysts: Isolation of Intermediates in the Reductive Coupling of Alcohols

The reductive coupling of alcohols using vanadium pyridonate catalysts is reported. This attractive approach for C(sp3)-C(sp3) bond formation uses an oxophilic, earth-abundant metal for a catalytic deoxygenation reaction. Several pyridonate complexes of vanadium were synthesized, giving insight into the coordination chemistry of this understudied class of compounds. Isolated intermediates provide experimental mechanistic evidence that complements reported computational mechanistic proposals for the reductive coupling of alcohols. In contrast to previous mononuclear vanadium(V)/vanadium(III)/vanadium(IV) cycles, this pyridonate catalyst system is proposed to proceed by a vanadium(III)/vanadium(IV) cycle involving bimetallic intermediates.

Oxo-Free Hydrocarbon Oxidation by an Iron(III)-Isoporphyrin Complex

Metal-halides that perform proton coupled electron-transfer (PCET) oxidation are an important new class of high-valent oxidant. In investigating metal-dihalides, we reacted [FeIII(Cl)(T(OMe)PP)] (1, T(OMe)PP = meso-tetra(4-methoxyphenyl)porphyrinyl) with (dichloroiodo)benzene. An FeIII-meso-chloro-isoporphyrin complex [FeIII(Cl)2(T(OMe)PP-Cl)] (2) was obtained. 2 was characterized by electronic absorption, 1H NMR, EPR, and X-ray absorption spectroscopies and mass spectrometry with support from computational analyses. 2 was reacted with a series of hydrocarbon substrates. The measured kinetic data exhibited a nonlinear behavior, whereby the oxidation followed a hydrogen-atom-transfer (HAT) PCET mechanism. The meso-chlorine atom was identified as the HAT agent. In one case, a halogenated product was identified by mass spectrometry. Our findings demonstrate that oxo-free hydrocarbon oxidation with heme systems is possible and show the potential for iron-dihalides in oxidative hydrocarbon halogenation.

Photochemical generation of 9-Fluorenyl radicals

A series of 9H-fluorenols and 9H, 9′H-bifluorenyls were irradiated in less polar solvents giving photoproducts derived from their corresponding 9H-fluorenyl radicals. These transient species were directly observed by laser flash photolysis and their UV/visible spectra compared with those of their corresponding cations. Theoretical calculations (density functional theory [DFT]) of these intermediates indicate their destabilizing nature in similar fashion to the antiaromatic character of the corresponding cations.