Name: 1,3-dibromo-2-(2,6-dibromophenyl)benzene
SKU: 97038-96-5

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Basic Information

Molecular Structure:
CAS No.:	97038-96-5
Name:	1,3-dibromo-2-(2,6-dibromophenyl)benzene

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

Synthetic route

: 19821-80-8
1,3-dibromo-2-iodo-benzene

: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

Conditions

Conditions	Yield
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%

: 108-36-1
1,3-dibromobenzene

: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

Conditions

Conditions	Yield
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

: 854242-36-7
4,6,2',6'-tetrabromo-biphenyl-2,4'-diyldiamine

: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

: 19821-80-8
1,3-dibromo-2-iodo-benzene

A: 608-21-9
1,2,3-tribromobenzene

B: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

Conditions

Conditions	Yield
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;

: 19821-80-8
1,3-dibromo-2-iodo-benzene

A: 19230-27-4
1,3-dibromo-2-chlorobenzene

B: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

Conditions

Conditions	Yield
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;

: 59261-08-4
2,2',4,4',6,6'-hexabromo-1,1'-biphenyl

A: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

B: 66115-57-9
2,4,2’,4’-tetrabromobiphenyl

C: 97038-95-4
2,4,2',6'-tetrabromo-biphenyl

Conditions

Conditions	Yield
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.

...Expand

: 608-30-0
2,6-dibromoaniline

: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

Conditions

Conditions	Yield
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

: 75-77-4
chloro-trimethyl-silane

: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

: 911297-83-1
trimethyl(2',6,6'-tribromo-1,1'-biphenyl-2-yl)silane

Conditions

Conditions	Yield
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%

: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

: 73183-34-3
bis(pinacol)diborane

: 1356238-72-6
4,4'-bis(pinacolatoboronyl)-2,2'6,6'-tetrabromobiphenyl

Conditions

Conditions	Yield
(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%

: 97038-96-5
2,2’,6,6’-tetrabromobiphenyl

: 507241-82-9
2,2,,6-tribromobiphenyl

Conditions

Conditions	Yield
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%