18153-44-1

Basic information

• Product Name: 9-(2,6-dimethylphenyl)-9-fluorenol
• CAS NO: 18153-44-1
• Molecular Weight: 286.373
• Mol File: 18153-44-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 9-(2,6-dimethylphenyl)-9-fluorenol(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(2,6-dimethylphenyl)-9-fluorenol(18153-44-1)
• EPA Substance Registry System: 9-(2,6-dimethylphenyl)-9-fluorenol(18153-44-1)

Safety Data

• Hazardous Substances Data: 18153-44-1(Hazardous Substances Data)

Upstream product

• 486-25-9 9-fluorenone 
• 576-22-7 2-Bromo-m-xylene 

Downstream Products

• 18153-41-8 2-(9-fluorenyl)-1,3-dimethylbenzene 
• 63398-23-2 9-(2,6-Dimethyl-phenyl)-9-ethylsulfanyl-9H-fluorene 
• 20685-19-2 9-Chlor-9-(2,6-dimethyl-phenyl)-fluoren 
• 63398-21-0 9-(2,6-Dimethyl-phenyl)-9-ethoxy-9H-fluorene 
• 63398-22-1 9-(2,6-Dimethyl-phenyl)-9-methylsulfanyl-9H-fluorene 
• 63398-20-9 9-(2,6-Dimethyl-phenyl)-9-methoxy-9H-fluorene 

Relevant articles and documents

Flash photolysis study of a Friedel-Crafts alkylation. Reaction of the photogenerated 9-fluorenyl cation with aromatic compounds

A combination of flash photolysis and product analysis is employed to investigate the reaction of aromatic compounds (ArH) with the 9-fluorenyl cation (Fl+) photogenerated from 9-fluorenol in 1,1,1,3,3,3-hexafluoroisopropyl alcohol (HFIP).The availability of the photochemical route to Fl+ means that the reaction of benzylic-type cation with ArH can be directly followed by flash photolysis.An additional feature with electron-rich ArH is that the cyclohexadienyl cation is observed to grow as Fl+ decays.Thus both cationic intermediates of a Friedel-Crafts alkylation are observed in the same experiment.The formation of the cyclohexadienyl cation is demonstrated to be reversible, or at least quasi-reversible, with the kinetic analysis furnishing absolute rate constants for the formation of this cation as well as for its loss of H+ and Fl+.Values of kH:kD for benzene:benzene and toluene:toluene are ca. 1.5 and demonstrate that Fl+ addition is at least partly reversible with these compounds as well.The Hammett ρ+ value obtained for a series of the less electron-rich ArH is -8, indicative of a transition state with considerable cyclohexadienyl cation character.Anisole shows a negative deviation from from Hammett correlation line, explained by the addition of Fl+ to ArH becoming encounter-controlled.This behaviour is dramatically illustrated in a comparison of data for Fl+ and Br2.For the less electron-rich ArH, rate constants for the two electrophiles are parallel.However, from m-xylene through pentamethylbenzene, the rate with Fl+ is unchanged, while the rate with Br2 increases over 1000-fold.The concept of encounter control with Fl+ is strongly supported by the absolute rate constants, which for the electron-rich ArH are all in the range 1-2 E9 dm3 mol-1 s-1, a magnitude typical of diffusion-controlled reactions.The electron-rich ArH also show no intermolecular selectivity since their reactions are encounter-controlled, but have a high intramolecular selectivity.It is suggested that a factor influencing the latter is the reversibility of formation of the cyclohexadienyl cation from the encounter complex.