N-[1,1'-biphenyl]-4-yl-N-(4-broMophenyl)-9,9-diMethyl-9H-Fluoren-2-aMine Chemical Properties

Melting point:

159.0 to 163.0 °C

Boiling point:

655.9±55.0 °C(Predicted)

Density 

1.293±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Tetrahydrofuran

form 

powder to crystal

pka

-3.55±0.40(Predicted)

color 

White to Almost white

InChI

InChI=1S/C33H26BrN/c1-33(2)31-11-7-6-10-29(31)30-21-20-28(22-32(30)33)35(27-18-14-25(34)15-19-27)26-16-12-24(13-17-26)23-8-4-3-5-9-23/h3-22H,1-2H3

InChIKey

CBLKFNHDNANUNU-UHFFFAOYSA-N

SMILES

C1(C)(C)C2=C(C=CC=C2)C2=C1C=C(N(C1=CC=C(C3=CC=CC=C3)C=C1)C1=CC=C(Br)C=C1)C=C2

Safety Information

HS Code 

2921.49.5000

N-[1,1'-biphenyl]-4-yl-N-(4-broMophenyl)-9,9-diMethyl-9H-Fluoren-2-aMine Usage And Synthesis

Uses

N-([1,1''-Biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine is used as a reactant in the synthesis of novel hole transport materials for efficient green electroluminescent devices.

Synthesis

GENERAL STEPS: A mixture of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (1.00 g, 2.77 mmol), 1-bromo-4-iodobenzene (1.00 g, 3.53 mmol), potassium hydroxide (0.30 g, 5.38 mmol), cuprous iodide (5.70 mg, 0.03 mmol) and 1,10- Phenanthroline monohydrate (5.40 mg, 0.03 mmol) in o-xylene (30 mL) was reacted with stirring under nitrogen protection at 150 °C for 8 hours. After completion of the reaction, it was cooled to room temperature and the reaction solution was concentrated under reduced pressure. Cold water was added to the residue, which was then extracted with dichloromethane (DCM). The organic phases were combined, filtered and dried over anhydrous magnesium sulfate (MgSO4). The crude product was purified by silica gel (SiO2) column chromatography with the eluent of petroleum ether/dichloromethane (4:1, v/v) to afford the target product N-[1,1'-biphenyl]-4-yl-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine (1.31 g, 91.8% yield).1H NMR (400 MHz, CDCl3) δ 7.58 (d, J = 7.5 Hz, 1H), 7.52 (t, J = 7.5 Hz, 3H), 7.43 (d, J = 8.7 Hz, 2H), 7.35 (dd, J = 15.4, 7.4 Hz, 3H), 7.29 (d, J = 8.9 Hz, 2H), 7.23 (m, 3H), 7.14 (d, J = 2.0 Hz, 1H). 7.10 (d, J = 8.6 Hz, 2H), 6.98 (m, 3H), 1.36 (s, 6H).

References

[1] Tetrahedron, 2017, vol. 73, # 31, p. 4610 - 4615
[2] Patent: CN107652189, 2018, A. Location in patent: Paragraph 0088; 0089-0091
[3] Patent: US2012/292576, 2012, A1. Location in patent: Page/Page column 131-132
[4] Patent: US9385325, 2016, B2. Location in patent: Page/Page column 71; 72
[5] Patent: EP2415773, 2012, A2. Location in patent: Page/Page column 16-17