2,7-Dibromocarbazole Chemical Properties

Melting point:

230.0 to 234.0 °C

Boiling point:

459.0±25.0 °C(Predicted)

Density 

1.930±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

15.13±0.30(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C12H7Br2N/c13-7-1-3-9-10-4-2-8(14)6-12(10)15-11(9)5-7/h1-6,15H

InChIKey

QPTWWBLGJZWRAV-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(Br)=C2)C2=C1C=C(Br)C=C2

Safety Information

Hazard Codes 

T

Risk Statements 

25-36/37/38

Safety Statements 

26-45-36/37/39

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29339900

2,7-Dibromocarbazole Usage And Synthesis

Application

One of the most popular products made available from 2,7-dibromocarbazole is PCDTBT, a well-known polymer semiconductor used for polymer solar cells. A good example for adjusting the solubility of the carbazole compounds by using 2,7-dibromocarbazole as the starting materials is the synthesis of 2,7-dibromo-9-heptadecanylcarbazole.

Description

2,7-dibromocarbazole, also known as 2,7-dibromo-9H-carbazole, is a building block for the synthesis of small molecules of carbazole series or carbazole back-boned polymers in the application of OFETs, OLEDs, PLEDs and OPVs.

Chemical Properties

White to light yellow powder or crystals

Uses

2,7-Dibromocarbazole (2,7-DBCZ) is predominantly employed in environmental pollution monitoring. Possessing a structure analogous to dioxins, 2,7-DBCZ ranks among the most frequently detected polyhalocarazoles (phcz) in environmental media.

General Description

2,7-Dibromocarbazole (2,7-DBCZ) is an emerging environmental pollutant. Due to its dioxin-like toxicity, cardiovascular toxicity and cardiac teratogenic effects, it poses a potentially high risk to human health.

Synthesis

Reaction of 4,4'-dibromo-2-nitro-1,1'-biphenyl (0.004 mol) and 4-nitrotoluene (0.006 mol) with an excess of tris(2-ethylhexyl) phosphite (0.05 mol) was carried out at 160 °C for 5 h (for the specific compounds j, k) or 17 h (for the specific compounds i, m), protected by argon gas. Upon completion of the reaction, the reaction was cooled to room temperature and the excess tris(2-ethylhexyl) phosphite and the resulting tris(2-ethylhexyl) phosphate were subsequently removed under vacuum. The reaction mixture was purified by silica gel column chromatography with the eluent of toluene/heptane (1:1, v/v) and the column size of 3 cm × 60 cm. The major product 2,7-dibromo-9-(2-ethylhexyl)-9H-carbazole (Rf = 0.8-0.9) was effectively separated from the by-product 2,7-dibromocarbazole (Rf = 0.5-0.6). The resulting compounds 7a-m were characterized by thin layer chromatography (TLC), elemental analysis, melting point determination, 1H NMR, 13C NMR and Fourier transform infrared spectroscopy (FTIR). Chromatographically purified compound 7 was used for melting point determination and further purified by methanol recrystallization. Non-alkylated carbazoles 8 (including 2,7-diiodocarbazole 10 (8a-c), 2,7-dibromocarbazole 8 (8d-f), 2,7-dichlorocarbazole 7 (8g-i), and commercial carbazole 11 (8j-m)) were obtained either by independent preparation or by commercial purchase and used for structural characterization.

References

[1] Tetrahedron, 2012, vol. 68, # 25, p. 5075 - 5080

2,7-Dibromocarbazole(136630-39-2)Related Product Information

• 2-HYDROXYCARBAZOLE
• 3,6-Dibromo-9-phenyl-9H-carbazole
• 2-chloro-9H-carbazole
• 4-BroMo-9H-carbazole
• 3,6-BIS(TERT-BUTYL)CARBAZOLE
• 3,6-Dibromocarbazole
• 3-Bromo-9H-carbazole
• 3,6-DIPHENYL-9H-CARBAZOLE
• 3,3'-(2,7-DibroMo-9H-fluorene-9,9-diyl)bis(N,N-diMethylpropan- 1-aMine)
• 2,7-Dibromo-9H-fluoren-9-one
• 2,7-Dibromo-9,9'-spiro-bifluorene
• 2,7-Dibromo-9,9-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-9H-fluorene
• 2,7-dibroMo-4,9-dihydro-4,4,9,9-tetrakis(4-hexylphenyl)-s-indaceno[1,2-b:5,6-b']dithiophene
• 2-BROMOCARBAZOLE
• 2,7-Dibromocarbazole