4,4'-Dibromo-2,2'-dinitrobiphenyl

CAS Number 91371-12-9

Chemistry Building Blocks, Dibromo Monomers, Materials, Monomers, Non-Heterocyclic Building Blocks

4,4'-Dibromo-2,2'-dinitrobiphenyl CAS 91371-12-9

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

Product Details

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

MSDS Documentation

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

Literature and Reviews

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.
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.
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.

Deep-blue emitting poly(2′,3′,6′,7′-tetraoctyl-2,7-spirosilabifluorene) simultaneously with good color purity and high external quantum efficiency, X. Xu et al., Org. Electron., 59, 77-83 (2018); DOI: 10.1016/j.orgel.2018.04.046.
Organic reactions catalyzed by solid superacids. 10. Perfluorinated sulfonic acid resin (Nafion-H) catalyzed ring closure reaction of 2,2'-diaminobiphenyls, A preparative route to carbazoles, T. Yamato et al., J. Org. Chem., 56 (21), 6248–6250 (1991); DOI:10.1021/jo00021a057.
Optical, Electrochemical, Thermal, and Structural Properties of Synthesized Fluorene/Dibenzosilole-Benzothiadiazole Dicarboxylic Imide Alternating Organic Copolymers for Photovoltaic Applications, A. Murad et al., Coatings, 10(12), 1147 (2020); DOI: 10.3390/coatings10121147.