| Identification | Back Directory | [Name]
2,7-DIBROMO-9H-CARBAZOLE | [CAS]
136630-39-2 | [Synonyms]
KFC
2,7-DibromocarbazoL
2,7-Dibromocarbazole
2,7-Dibrom-9H-carbazol
2,7-Dibromocarbazole>
2,7-DIBROMO-9H-CARBAZOLE
9H-Carbazole, 2,7-dibroMo-
2,7-Dibromo-9H-carbazole ,97%
2,7-DibroMocarbazole
(2,7-DBC)
2,7-DIBROMO-9H-CARBAZOLE; 2,7-DIBROMOCARBAZOLE
N,N-Bis(M-tolyl)benzenaMine,2,7-DibroMo-9H-carbazole, 9H-Carbazole | [EINECS(EC#)]
679-869-9 | [Molecular Formula]
C12H7Br2N | [MDL Number]
MFCD09033507 | [MOL File]
136630-39-2.mol | [Molecular Weight]
324.999 |
| Chemical Properties | Back Directory | [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 | [Odor]
Off White?powder |
| Hazard Information | Back Directory | [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 |
| Safety Data | Back Directory | [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 | [Storage Class]
6.1D - Non-combustible acute toxic Cat.3
toxic hazardous materials or hazardous materials causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Acetic acid-->Nitric acid-->Acetic anhydride-->Triphenylphosphine-->1,2-Dichlorobenzene-->4,4'-Dibromobiphenyl-->9H-Carbazole, 2,7-dibromo-9-(4-nitrophenyl)--->PHOSPHOROUS ACID TRIS(2-ETHYLHEXYL) ESTER-->2,7-DibroMo-9-(2-ethylhexyl)-9H-carbazole-->4,4'-DIBROMO-2-NITRO-BIPHENYL-->4,4'-dibroMo-2,2'-dinitrobiphenyl-->4,4'-dibroMobiphenyl-2,2'-diaMine | [Preparation Products]
9-Octyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-->2,7-Dibromo-N-phenylcarbazole |
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