9-Fluorenol Property

Melting point:

153-154 °C(lit.)

Boiling point:

275.62°C (rough estimate)

Density 

1.0368 (rough estimate)

refractive index 

1.5994 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

13.34±0.20(Predicted)

form 

Crystalline Powder

color 

Cream

Water Solubility 

Insoluble in water.

BRN 

1869799

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

CAS DataBase Reference

1689-64-1(CAS DataBase Reference)

NIST Chemistry Reference

9H-fluoren-9-ol(1689-64-1)

EPA Substance Registry System

9-Hydroxyfluorene (1689-64-1)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36/37/39-27-26

RIDADR 

UN 3077 9/PG III

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29062990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

9-Fluorenol Chemical Properties,Usage,Production

Chemical Properties

white powder

Uses

9-Fluorenol is used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuffs.

Application

9-Fluorenol is a wake-promoting agent and is considered a next-generation anti-drowsiness drug. It is also a potential environmental carcinogen.
9-Fluorenol is a dopamine reuptake inhibitor with IC50 of 9 μM, and a major metabolite of a compound developed as a wakefulness-promoting agent.

Preparation

Synthesis of 9-Fluorenol: A 5-g sample of 9-fluorenone is dissolved in 30 mL of warm ethanol in a 100-mL beaker. To this solution is added, dropwise, 10 mL of a reducing reagent, freshly prepared, which consists of 200 mg sodium methoxide,10 mL methanol, and 0.4 g sodium borohydride.This solution is allowed to stand undisturbed for 10-20 min. A color change is observed as the reaction proceeds from the yellow 9-fluorenone to the white 9-fluorenol.The product is precipitated by the addition of 50 mL of water and neutralized with 0.1 M HCl, vacuum filtered, and washed with cold water to remove any residual inorganic salt formed by the excess of the sodium borohydride reagent and hydrochloric acid.The dried crude product is sufficiently pure for characterization by melting point, infrared spectra,and NMR.The crude product melting point is 153°C, with a product yield of 95-100%.
A Synthesis of 9-Fluorenol: Sodium Borohydride Reduction of 9-Fluorenone

Definition

ChEBI: 9-Fluorenol is a member of the class of hydroxyfluorenes that is 9H-fluorene substituted by a hydroxy group at position 9 (the non-aromatic carbon). It has a role as an animal metabolite. It is a member of hydroxyfluorenes and a secondary alcohol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 6313, 1992 DOI: 10.1021/jo00049a045
Tetrahedron Letters, 13, p. 343, 1972

Synthesis

9-Fluorenol is prepared by reacting 9-fluorenone with THF solution of phosphazene under the action of boron catalyst.Add 9-fluorenone (0.8 mmol), a 0.2 M THF solution of phosphazene (80 μL, 0.016 mmol) and a 0.0762 M THF solution of boron catalyst (420 μL, 0.032 mmol) to a scintillation vial with magnetic stir bar in a glove box. Place the scintillation vial in a Parr reactor. Seal the reactor. Pressurize the reactor with hydrogen gas. Heat reaction mixture at 75°C (inside the reactor). Stir the reaction mixture (1000 rpm) for 20 hours at 75°C. Cool the mixture to room temperature and vent the Parr reactor to obtain 9-hydroxyfluoren. Analyze the reaction mixture by 1H NMR spectroscopy using CDCl3 as solvent.
Fig the synthetic method of 9-Fluorenol