DIBENZOSUBERENOL

DIBENZOSUBERENOL Property

Melting point:

122.5-124 °C(lit.)

Boiling point:

401.9±14.0 °C(Predicted)

Density 

1.196±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Solid

pka

13.40±0.20(Predicted)

color 

White to Pale Yellow

BRN 

1957458

Safety

Safety Statements 

22-24/25

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

DIBENZOSUBERENOL Chemical Properties,Usage,Production

Uses

Dibenzosuberenol is an intermediate in the synthesis of 5H-Dibenzo[a,d]cycloheptene which itself was used in the synthesis of cyclotribenzylenes. Also functions as a calmodulin inhibitor affecting various crucial cellular processes.

Synthesis

General procedure for the synthesis of 5H-dibenzo[a,d]cyclohepten-5-ol from 5-dibenzo[a,d]cycloheptenone: 1.50 g (7.27 mmol) of 5-dibenzo[a,d]cycloheptenone was added to a suspension containing 4 mL of water, 0.45 mL of 1N aqueous sodium hydroxide solution and 20 mL of methanol, followed by 200 mg (5.29 mmol) of sodium borohydride. The reaction mixture was stirred overnight. Upon completion of the reaction, the precipitated crystals were collected by filtration, washed with water, and then the crystals were dissolved in ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and the solvent was subsequently evaporated under reduced pressure to give 5H-dibenzo[a,d]cyclohepten-5-ol. Yield: 1.48 g (7.11 mmol) in 98% yield.1H-NMR (CDCl3) data: δ 2.41 (1H, d), 5.43 (1H, d), 7.11 (2H, s), 7.25-7.31 (2H, m), 7.36-7.44 (4H, m), 7.66 (2H, d).

References

[1] Patent: US2004/167118, 2004, A1. Location in patent: Page 29-30
[2] Patent: US4910312, 1990, A
[3] Patent: US4772615, 1988, A
[4] Patent: EP221572, 1991, B1
[5] Patent: EP1481673, 2004, A1. Location in patent: Page/Page column 42-43