9,9-diMethyl-N-phenyl-9H-fluoren-2-aMine Chemical Properties

Melting point:

99.0 to 103.0 °C

Boiling point:

448.7±24.0 °C(Predicted)

Density 

1.128

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroforom (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)

pka

0.95±0.40(Predicted)

form 

Solid

color 

White to Off-White

Safety Information

HS Code 

2921.49.5000

9,9-diMethyl-N-phenyl-9H-fluoren-2-aMine Usage And Synthesis

Uses

9,9-Dimethyl-N-phenyl-9H-fluoren-2-amine is useful for the synthetic preparation of secondary amines.

Synthesis

General procedure for the synthesis of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine from 9,9-dimethyl-2-bromofluorene and aniline: tri-tert-butylphosphine (2.7 mL of a 1.0 M toluene solution, 2.7 mmol), palladium acetate (307 mg, 1.4 mmol), and sodium tert-butoxide (9.8 g, 102 mmol) were added to a solution containing 9,9-dimethyl-9H-fluoren-2-amine (20.5 g, 71 mmol) and 4-bromo-9,9'-spirobifluorene (27 g, 68 mmol). 9H-fluoren-2-amine (20.5 g, 71 mmol) and 4-bromo-9,9'-spirobifluorene (27 g, 68 mmol) in a solution of degassed toluene (500 mL). The reaction mixture was heated under reflux conditions for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with toluene and filtered through diatomaceous earth. The filtrate was concentrated by vacuum evaporation and the residue was crystallized using a solvent mixture of ethyl acetate/heptane. The crude product was extracted by Soxhlet extractor (toluene as solvent) and subsequently purified twice by vacuum zone sublimation (pressure = 3 x 10^-5 mbar, temperature = 298 °C). The final product was obtained as a light yellow solid (8 g, 20% yield, HPLC purity >99.99%).

References

[1] Patent: WO2017/16632, 2017, A1. Location in patent: Page/Page column 67; 68
[2] Patent: EP2149555, 2010, A1. Location in patent: Page/Page column 20
[3] Chemistry of Materials, 2014, vol. 26, # 7, p. 2414 - 2426
[4] Patent: CN106431938, 2017, A. Location in patent: Paragraph 0049; 0050; 0051; 0052
[5] Patent: KR2015/140499, 2015, A. Location in patent: Paragraph 0363; 0370; 0371

9,9-diMethyl-N-phenyl-9H-fluoren-2-aMine(355832-04-1)Related Product Information

• 4-BroMo-9,9-diphenyl fluorene
• 7-Bromo-2-iodo-9,9-dimethyl-9H-fluorene
• 2-Bromo-9,9-diethylfluorene
• 3-BroMo-9,9-diphenyl-9H-fluorene
• 2-Bromo-9,9-di-n-butylfluoren
• 2-Bromo-9,9-dihexyl fluorene
• N,N-Diphenyl-p-phenylenediamine