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Product Code B1371-5g
Price £200 ex. VAT

A useful readily available biphenyl intermediate

Used for the synthesis of carbazoles, dibenzosiloles and dibenzoselenophenes

Specifications | MSDS | Literature and Reviews

4,4'-Dibromo-2,2'-dinitrobiphenyl (CAS number 91371-12-9) is a biphenyl intermediate with strong electron withdrawing dinitro groups at 2,2'-positions and dibromo groups at 4,4'-positions. It is a well-known intermediate for the synthesis of 2,7-dibromo-9H-carbazole, shown below.

the synthesis of 2,7-dibromocarbazole
The synthesis of 2,7-dibromo-9H-carbazole with 4,4'-Dibromo-2,2'-dinitrobiphenyl as the intermediate

4,4'-Dibromo-2,2'-dinitrobiphenyl can be obtained from one step synthesis from 2,5-dibromonitrobenzene via Ullmann coupling reaction in dimethylformamide (DMF) in high yield. Further reduction of 4,4'-Dibromo-2,2'-dinitrobiphenyl affords 4,4’-dibromobiphenyl-2,2'-diamine which is another useful intermediate for the formation of fused heterocyclic rings such as carbazoles, dibenzosiloles and dibenzoselenophenes.

Derived from 4,4′-dibromo-2,2′-dinitrobiphenyl, 9-phenyl-9-phosphafluorene oxide (PhFlOP) based TADF emitters achieved outstanding electroluminescence performances with the maximum external quantum efficiency of 23.3%, current efficiency of 83.7 cd/A, and power efficiency of 59.1 lm W-1.

General Information

CAS Number 91371-12-9
Chemical Formula C12H6Br2N2O4
Full Name 4,4'-Dibromo-2,2'-dinitrobiphenyl
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

Chemical Structure

4,4'-dibromo-2,2'-dinitrobiphenyl chemical structure, CAS 91371-12-9
4,4'-dibromo-2,2'-dinitrobiphenyl, CAS 91371-12-9

Product Details

Purity >98% (1H NMR)
Melting Point Tm = 148 °C – 150 °C
Appearance Light-yellow powder/crystals

MSDS Documentation

4,4'-dibromo-2,2'-dinitrobiphenyl4,4'-Dibromo-2,2'-dinitrobiphenyl MSDS Sheet

Literature and Reviews

  1. Organic Emitters with a Rigid 9-Phenyl-9-phosphafluorene Oxide Moiety as the Acceptor and Their Thermally Activated Delayed Fluorescence Behavior, D. Zhong et al., ACS Appl. Mater. Interfaces, 11 (30), 27112–27124 (2019); DOI: 10.1021/acsami.9b05950.
  2. Synthesis and fluorescent properties of conjugated co-oligomers containing maleimide and carbazole units at the main chain, M. Nakamura et al., Polym. J., 46, 94–103 (2014): DOI: 10.1038/pj.2013.83.
  3. Investigations on the electrochemical properties of new conjugated polymers containing benzo[c]cinnoline and oxadiazole moieties, Polymer, 52 (26), 6011-6019 (2011); DOI: 10.1016/j.polymer.2011.10.059.
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