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CAS No.: | 97038-96-5 |
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Name: | 1,3-dibromo-2-(2,6-dibromophenyl)benzene |
Article Data: | 14 |
Molecular Structure: | |
Formula: | C12H6 Br4 |
Molecular Weight: | 469.796 |
Synonyms: | Biphenyl,2,2',6,6'-tetrabromo- (6CI); 2,2',6,6'-Tetrabromo-1,1'-biphenyl;2,2',6,6'-Tetrabromobiphenyl; PBB 54 |
Density: | 2.14g/cm3 |
Melting Point: | 215 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7)) |
Boiling Point: | 391.3°Cat760mmHg |
Flash Point: | 184.8°C |
PSA: | 0.00000 |
LogP: | 6.40360 |
1,3-dibromo-2-iodo-benzene
2,2’,6,6’-tetrabromobiphenyl
Conditions | Yield |
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Stage #1: 1,3-dibromo-2-iodo-benzene With n-butyllithium; copper(ll) bromide In diethyl ether; hexane at -78℃; for 0.75h; Inert atmosphere; Schlenk technique; Stage #2: With nitrobenzene In diethyl ether; hexane at -78 - 20℃; for 6h; | 60% |
Stage #1: 1,3-dibromo-2-iodo-benzene With n-butyllithium In diethyl ether at -78℃; Ullman coupling; Stage #2: With nitrobenzene; copper(I) bromide Ullman coupling; | 56% |
Stage #1: 1,3-dibromo-2-iodo-benzene With n-butyllithium In diethyl ether; hexane at -78℃; for 1.08333h; Stage #2: With copper(ll) bromide In diethyl ether; hexane at -78℃; for 1.5h; chemoselective reaction; | 48% |
1,3-dibromobenzene
2,2’,6,6’-tetrabromobiphenyl
Conditions | Yield |
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Stage #1: 1,3-dibromobenzene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With copper(I) cyanide lithium chloride; p-benzoquinone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 60% |
Stage #1: 1,3-dibromobenzene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With copper(l) cyanide; chloranil; lithium chloride | 47% |
Stage #1: 1,3-dibromobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With copper(l) cyanide; lithium chloride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #3: With p-benzoquinone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 42% |
Multi-step reaction with 2 steps 1.1: n-butyllithium; lithium diisopropyl amide / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 1.2: 20 °C 2.1: n-butyllithium; copper(ll) bromide / hexane; diethyl ether / 0.75 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 6 h / -78 - 20 °C View Scheme |
4,6,2',6'-tetrabromo-biphenyl-2,4'-diyldiamine
2,2’,6,6’-tetrabromobiphenyl
1,3-dibromo-2-iodo-benzene
A
1,2,3-tribromobenzene
B
2,2’,6,6’-tetrabromobiphenyl
Conditions | Yield |
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With n-butyllithium; copper(ll) bromide 1.) ether, hexane, -78 deg C, 2 h, 2.) ether, hexane, from -78 deg C to RT, 12 h; Multistep reaction. Yields of byproduct given; |
1,3-dibromo-2-iodo-benzene
A
1,3-dibromo-2-chlorobenzene
B
2,2’,6,6’-tetrabromobiphenyl
Conditions | Yield |
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With n-butyllithium; copper dichloride 1.) ether, hexane, -78 deg C, 2 h, 2.) ether, hexane, from -78 deg C to RT, 12 h; Multistep reaction. Yields of byproduct given; | |
With n-butyllithium; copper dichloride 1.) ether, hexane, -78 deg C, 2 h, 2.) ether, hexane, from -78 deg C to RT, 12 h; Yield given. Multistep reaction; |
2,2',4,4',6,6'-hexabromo-1,1'-biphenyl
A
2,2’,6,6’-tetrabromobiphenyl
B
2,4,2’,4’-tetrabromobiphenyl
C
2,4,2',6'-tetrabromo-biphenyl
Conditions | Yield |
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Stage #1: 2,2',4,4',6,6'-hexabromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | A 6 %Chromat. B 30 %Chromat. C 63 %Chromat. |
2,6-dibromoaniline
2,2’,6,6’-tetrabromobiphenyl
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: sulfuric acid / 0.17 h / 0 °C 1.2: 3 h / 0 °C 1.3: 0.5 h / 0 °C 2.1: n-butyllithium / diethyl ether; hexane / 1.08 h / -78 °C 2.2: 1.5 h / -78 °C View Scheme |
chloro-trimethyl-silane
2,2’,6,6’-tetrabromobiphenyl
trimethyl(2',6,6'-tribromo-1,1'-biphenyl-2-yl)silane
Conditions | Yield |
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Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran at -80℃; Stage #2: chloro-trimethyl-silane In tetrahydrofuran | 100% |
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -75℃; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -75 - 25℃; Further stages.; | 88% |
2,2’,6,6’-tetrabromobiphenyl
bis(pinacol)diborane
4,4'-bis(pinacolatoboronyl)-2,2'6,6'-tetrabromobiphenyl
Conditions | Yield |
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(1,5-cyclooctadiene)(methoxy)iridium(I) dimer In further solvent(s) tert-butylmethyl ether, 60°C; | 93% |
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether for 21h; Inert atmosphere; Reflux; | 91% |
2,2’,6,6’-tetrabromobiphenyl
2,2,,6-tribromobiphenyl
Conditions | Yield |
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Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes at -75℃; Stage #2: With methanol; water In tetrahydrofuran; hexanes | 91% |
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes at -75℃; Stage #2: With methanol In tetrahydrofuran; hexanes Product distribution / selectivity; | 91% |
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes Stage #2: With methanol Product distribution / selectivity; | 91% |
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes Stage #2: With methanol In tetrahydrofuran; hexanes | 91% |