Bis-(9,9-diMethyl-9H-fluoren-2-yl)-aMine Chemical Properties

Melting point:

178℃

Boiling point:

571.0±39.0 °C(Predicted)

Density 

1.146

storage temp. 

2-8°C

solubility 

soluble in Dimethylformamide

form 

powder to crystal

pka

1.01±0.40(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C30H27N/c1-29(2)25-11-7-5-9-21(25)23-15-13-19(17-27(23)29)31-20-14-16-24-22-10-6-8-12-26(22)30(3,4)28(24)18-20/h5-18,31H,1-4H3

InChIKey

LCSMGMWMTSWXDD-UHFFFAOYSA-N

SMILES

C1(C)(C)C2=C(C=CC=C2)C2=C1C=C(NC1C=CC3C4=C(C(C)(C)C=3C=1)C=CC=C4)C=C2

Safety Information

HS Code 

2921420090

Bis-(9,9-diMethyl-9H-fluoren-2-yl)-aMine Usage And Synthesis

Uses

Bis-(9,9-diMethyl-9H-fluoren-2-yl)-aMine is mainly used as a pharmaceutical intermediate.

Uses

Building block of organic sensitizers for use in dye-sensitized solar cells.

Synthesis

The general procedure for the synthesis of bis(9,9-dimethyl-9H-fluoren-2-yl)amine from the compound (CAS: 1185882-60-3) was as follows: 0.4 g of tert-butoxycarbonyl-protected arylamine 1 (0.8 mmol) was dissolved in 1 mL of tetrahydrofuran and 8 mL of trifluoroacetic acid (TFA). The reaction mixture was stirred at room temperature for 10 min and the color of the solution was observed to change to dark green. Subsequently, TFA was removed by evaporation under vacuum. dichloromethane was added to the residue and neutralized with saturated aqueous sodium hydroxide solution. The mixture was extracted using dichloromethane and the organic layers were combined and dried over anhydrous sodium sulfate. Purification by column chromatography (stationary phase: silica gel, mobile phase: ethyl acetate/hexane = 1:10, v/v) afforded 0.3 g of light yellow target compound 2 in 95% yield. Melting point: 178°C. 1H NMR (300 MHz, (CD3)2CO): δ 7.7-7.67 (m, 4H), 7.48 (d, J = 6.9 Hz, 2H), 7.36 (s, 2H), 7.31-7.22 (m, 4H), 7.18 (d, J = 7.2 Hz, 2H), 1.46 (s, 12H). 13C NMR (300 MHz, (CD3)2CO): δ 155.97, 153.83, 144.45, 140.29, 132.48, 127.79, 126.73, 123.27, 121.67, 119.69, 117.32, 112.46, 47.28, 27.53.

References

[1] Tetrahedron, 2009, vol. 65, # 31, p. 6236 - 6243
[2] Patent: EP2371813, 2011, A1. Location in patent: Page/Page column 13
[3] Patent: US2011/232763, 2011, A1
[4] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 11, p. 3316 - 3326

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