4,4'-Dibromo-2,2'-dinitrobiphenyl (CAS 91371-12-9) is a biphenyl building block used as an intermediate in the synthesis of organic semiconductor materials. Its structure carries two bromine atoms at the 4,4'-positions and two strongly electron-withdrawing nitro groups at the 2,2'-positions. It is best known as a precursor to 2,7-dibromo-9H-carbazole.
The compound can be prepared in high yield in a single step from 2,5-dibromonitrobenzene by Ullmann coupling in dimethylformamide (DMF). Reducing its nitro groups gives 4,4'-dibromobiphenyl-2,2'-diamine, a further intermediate for building fused heterocycles such as carbazoles, dibenzosiloles and dibenzoselenophenes.
Materials derived from this intermediate have been used in OLED research. TADF emitters based on 9-phenyl-9-phosphafluorene oxide (PhFlOP) made from it reached a maximum external quantum efficiency of 23.3%, a current efficiency of 83.7 cd/A and a power efficiency of 59.1 lm W-1. Ossila supplies it as a light-yellow powder or crystals with >98% purity by 1H NMR.
- Synthesis of 2,7-dibromo-9H-carbazole for organic electronic materials.
- Preparation of 4,4'-dibromobiphenyl-2,2'-diamine by reduction of the nitro groups.
- Construction of fused heterocycles such as carbazoles, dibenzosiloles and dibenzoselenophenes.
- Development of PhFlOP-based TADF emitters for OLEDs.
- Synthesis of intermediates for OFET and organic photovoltaic materials.
| Brand | Ossila |
|---|---|
| CAS number | 91371-12-9 |
| Molecular formula | C12H6Br2N2O4 |
| Purity | >98% (1H NMR) |
| Category | — |
| Pack sizes | 5 g, 10 g, 25 g |
| Physical form | Light-yellow powder/crystals |
| Storage | — |
- Product code: B1371
- Molecular Weight: 402.00 g/mol
- Synonyms: 4,4'-Dibromo-2,2'-dinitro-1,1'-biphenyl, 4-bromo-1-(4-bromo-2-nitrophenyl)-2-nitrobenzene
- Classification / Family: Biphenyl derivatives, Semiconductor synthesis intermediates, OLED, OFETs, organic photovoltaics
- Melting Point: 148 °C – 150 °C
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