56954-90-6

Basic information

• Product Name: 2-(9H-fluoren-9-yl)propan-2-ol
• Synonyms: 2-(9H-fluoren-9-yl)propan-2-ol
• CAS NO: 56954-90-6
• Molecular Formula: C₁₆H₁₆O
• Molecular Weight: 0
• Mol File: 56954-90-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 371.9°C at 760 mmHg
• Flash Point: 158.7°C
• Appearance: /
• Density: 1.146g/cm³
• Vapor Pressure: 3.45E-06mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 2-(9H-fluoren-9-yl)propan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(9H-fluoren-9-yl)propan-2-ol(56954-90-6)
• EPA Substance Registry System: 2-(9H-fluoren-9-yl)propan-2-ol(56954-90-6)

Safety Data

• Hazardous Substances Data: 56954-90-6(Hazardous Substances Data)

Usage

Derived from

Fluorene molecule

Contains

Propan-2-ol group

Common uses

Organic synthesis, chemical research (as a reagent and intermediate), production of pharmaceuticals and agrochemicals

Characteristics

Stability and reactivity

Value

Wide range of applications in the chemical industry, valuable for scientific and industrial purposes

InChI:InChI=1/C16H16O/c1-16(2,17)15-13-9-5-3-7-11(13)12-8-4-6-10-14(12)15/h3-10,15,17H,1-2H3

Upstream product

• 85055-86-3 1-(fluoren-9-yl)-1-methylethyl acetate 
• 124-41-4 sodium methylate 
• 85055-90-9 1-(fluoren-9-yl)-1-methylethyl benzoate 
• 81277-93-2 6,6-dimethyldibenzofulvene oxide 
• 56954-88-2 9-(2-bromo-2-propyl)fluorene 
• 108-95-2 phenol 

Downstream Products

• 86-73-7 9H-fluorene 
• 486-25-9 9-fluorenone 
• 67-64-1 acetone 

Relevant articles and documents

COMPETING SOLVOLYTIC SUBSTITUTION AND ELIMINATION REACTIONS VIA A COMMON IRREVERSIBLY FORMED ION-MOLECULE PAIR INTERMEDIATE

The acid-catalysed solvolysis of 9-(2-phenoxy-2-propyl)fluorene in mixtures of water with acetonitrile or methanol at 25 deg C provides 9-(2-hydroxy-2-propyl)fluorene, 9-(2-propenyl)fluorene, and 9-(2-acetamido-2-propyl)fluorene or 9-(2-methoxy-2-propyl)fluorene, respectively.The overall kinetic deuterium isotope effects for the reactions of the hexadeuterated analogue 9-(1,1,1,3,3,3-2H6)-9-(2-phenoxy-2-propyl)fluorene in 90 vol.percent acetonitrile in water were measured as (kEH+kSH)/(kED6+kSD6)=1.54+/-0.05, which is composed of the isotope effect kSH/kSD6=1.4+/-0.1 for formation of the substitution products and kEH/kED6=4.0+/-0.2 for production of 9-(2-methoxy-2-propyl)fluorene.Similar isotope effects were measured in other solvent mixtures.The results strongly indicate a branched mechanism involving rate-limiting formation of a common carbocation-molecule pair (with a secondary isotope effect of 1.54), which either undergoes nucleophilic attack by a solvent molecule (with a secondary isotope effect of ca 1), or is dehydronated (isotope effect ca 2.8) by the leaving group or by the solvent.The ion-molecule pair shows very low selectivities.Thus, in 50 vol.percent acetonitrile in water, an acetonitrile molecule is as efficient as a water molecule as a nucleophile towards the ion-molecule pair, kMeCN/kHOH>/=1 (ratio of second-order rate constants).The discrimination between methanol and water is anomalously small, kMeOH/kHOH=0.7.

Electrochemical Studies of the Reduction of 6,6-Dimethyldibenzofulvene Oxide and Tetraphenyloxirane

The electrochemical reduction of 6,6-dimethyldibenzofulvene oxide (1) in dimethylformamide-0.1 M (n-Bu)4NClO4 is an overall two-electron process that affords 9-fluorenyl anion and acetone in the absence of an added proton donor and 2-(9-fluorenyl)propanol (2) in the presence of diethyl malonate.The initial electroreduction of tetraphenyloxirane (3) is also a two-electron process and gives Ph2C(-)CPh2(O-) as an unobserved intermediate.This dianioon reacts rapidly by abstracting a proton at either the benzhydryl carbon center (75percent) or the oxygen center (25percent) to give either Ph2CHCPh2(O-) or Ph2C(-)CPh2OH.The former anion then undergoes an elimination of Ph2CH(-) to afford Ph2C=O whereas Ph2C(-)CPh2(OH) eleminate OH- to give Ph2C=CPh2.Ph2C=O and Ph2C=CPh2 are then reduced at the applied potential to Ph2CHOH and (Ph2CH)2, respectively.Ph2CHCPh2OH (4) and 2 undergo electrochemically induced chain reactions in the potential range of interest with 4, affording equimolar amounts of Ph2C=O and Ph2CH2, whereas 2 gives equimolar amounts of fluorene and acetone.There is no evidence that carbene anion radicals are formed as transient intermediates in any of the electroreductions.