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97038-96-5

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97038-96-5 Usage

Uses

2,2'',6,6''-Tetrabromo-1,1''-biphenyl is a research intermediate used in the preparation of triphenylenes, tetraphenylenes, and other related compound.

Check Digit Verification of cas no

The CAS Registry Mumber 97038-96-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,7,0,3 and 8 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 97038-96:
(7*9)+(6*7)+(5*0)+(4*3)+(3*8)+(2*9)+(1*6)=165
165 % 10 = 5
So 97038-96-5 is a valid CAS Registry Number.

97038-96-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-dibromo-2-(2,6-dibromophenyl)benzene

1.2 Other means of identification

Product number -
Other names 2,2',6,6'-tetrabromobiphenyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:97038-96-5 SDS

97038-96-5Synthetic route

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

1,3-dibromo-2-iodo-benzene

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

2,2’,6,6’-tetrabromobiphenyl

Conditions
ConditionsYield
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
108-36-1

1,3-dibromobenzene

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

2,2’,6,6’-tetrabromobiphenyl

Conditions
ConditionsYield
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
854242-36-7

4,6,2',6'-tetrabromo-biphenyl-2,4'-diyldiamine

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

2,2’,6,6’-tetrabromobiphenyl

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

1,3-dibromo-2-iodo-benzene

A

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

1,2,3-tribromobenzene

B

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

2,2’,6,6’-tetrabromobiphenyl

Conditions
ConditionsYield
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
19821-80-8

1,3-dibromo-2-iodo-benzene

A

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

1,3-dibromo-2-chlorobenzene

B

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

2,2’,6,6’-tetrabromobiphenyl

Conditions
ConditionsYield
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
59261-08-4

2,2',4,4',6,6'-hexabromo-1,1'-biphenyl

A

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

2,2’,6,6’-tetrabromobiphenyl

B

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

2,4,2’,4’-tetrabromobiphenyl

C

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

2,4,2',6'-tetrabromo-biphenyl

Conditions
ConditionsYield
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
608-30-0

2,6-dibromoaniline

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

2,2’,6,6’-tetrabromobiphenyl

Conditions
ConditionsYield
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
75-77-4

chloro-trimethyl-silane

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

2,2’,6,6’-tetrabromobiphenyl

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

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

Conditions
ConditionsYield
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
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

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

4,4'-bis(pinacolatoboronyl)-2,2'6,6'-tetrabromobiphenyl

Conditions
ConditionsYield
(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
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

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

2,2,,6-tribromobiphenyl

Conditions
ConditionsYield
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%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

(6,6'-dibromobiphenyl-2,2'-diyl)dicarbaldehyde
1141733-49-4, 1260376-09-7, 1260376-17-7

(6,6'-dibromobiphenyl-2,2'-diyl)dicarbaldehyde

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #3: With hydrogenchloride In water; ethyl acetate
90%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran
Stage #2: N,N-dimethyl-formamide
85%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran
72%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium; (1R,2R)-bis(dimethylamino)cyclohexane In toluene at -78℃; for 2h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In toluene at -78 - 20℃; Inert atmosphere;
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

1,2-dibromomethane
74-95-3

1,2-dibromomethane

4,4,8,8-Tetrabrom-4,8-dihydrodibenzopentalen
33213-26-2

4,4,8,8-Tetrabrom-4,8-dihydrodibenzopentalen

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 65℃; for 18h;87%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

1,9-dibromo-5,5-dimethyldibenzosilole
1187984-45-7

1,9-dibromo-5,5-dimethyldibenzosilole

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium
Stage #2: dimethylsilicon dichloride
85%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

methyl iodide
74-88-4

methyl iodide

2,6,6'-tribromo-2'-methoxy-1,1'-biphenyl
871707-37-8

2,6,6'-tribromo-2'-methoxy-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -75℃;
Stage #2: With sodium hydroxide; fluorodimethoxyborane diethyl etherate; dihydrogen peroxide In tetrahydrofuran; hexane at -75 - 25℃;
Stage #3: methyl iodide With potassium hydroxide In dimethyl sulfoxide for 1h; Further stages.;
82%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes at -75℃;
Stage #2: With sodium hydroxide; fluorodimethoxyborane diethyl etherate; dihydrogen peroxide In tetrahydrofuran; hexanes; water at -75℃;
Stage #3: methyl iodide With hydrogenchloride; potassium hydroxide more than 3 stages;
82%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

2,2’-dibromo-6,6’-diiodo-1,1’-biphenyl

2,2’-dibromo-6,6’-diiodo-1,1’-biphenyl

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃;
82%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

2,6,6'-tribromo-1,1'-biphenyl-2-ol
911297-81-9

2,6,6'-tribromo-1,1'-biphenyl-2-ol

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -75℃;
Stage #2: With sodium hydroxide; fluorodimethoxyborane diethyl etherate; dihydrogen peroxide In tetrahydrofuran; hexane at -75 - 25℃; Further stages.;
81%
Multi-step reaction with 2 steps
1.1: n-BuLi / hexane; tetrahydrofuran / -75 °C
1.2: hexane; tetrahydrofuran
2.1: aq. NaOH; H2O2 / tetrahydrofuran
View Scheme
With sodium hydroxide; n-butyllithium; dihydrogen peroxide; fluorodimethoxyborane-diethyl etherate In tetrahydrofuran; hexane; water at -75℃;
chloromethyl formate
30566-31-5

chloromethyl formate

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

2,2’,6,6’-tetrabromobiphenyl

4,5‐dibromo‐9H‐fluoren‐9‐one
69414-97-7

4,5‐dibromo‐9H‐fluoren‐9‐one

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: chloromethyl formate In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere;
78%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

methyl chloroformate
79-22-1

methyl chloroformate

4,5‐dibromo‐9H‐fluoren‐9‐one
69414-97-7

4,5‐dibromo‐9H‐fluoren‐9‐one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at 20℃;78%
With tert.-butyl lithium In tetrahydrofuran; hexane at 20℃;78%
With n-butyllithium In tetrahydrofuran; hexane at 20℃;78%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

C24H30NPSn2

C24H30NPSn2

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane
30404-92-3

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane

C36H23NO2P2

C36H23NO2P2

Conditions
ConditionsYield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;73%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

C24H32NPSn2

C24H32NPSn2

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane
30404-92-3

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane

C36H25NO2P2

C36H25NO2P2

Conditions
ConditionsYield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;73%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

C24H32NPSn2

C24H32NPSn2

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane
30404-92-3

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane

C36H25NO2P2

C36H25NO2P2

Conditions
ConditionsYield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;73%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

C36H37N2OPSn2

C36H37N2OPSn2

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane
30404-92-3

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane

C48H30N2O3P2

C48H30N2O3P2

Conditions
ConditionsYield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;73%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

C24H30NPSn2

C24H30NPSn2

C48H30N2O2P2

C48H30N2O2P2

Conditions
ConditionsYield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;73%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

A

1,8-di-bromobiphenylene
180404-96-0

1,8-di-bromobiphenylene

B

1,8,9,16-Tetrabromotetraphenylene

1,8,9,16-Tetrabromotetraphenylene

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Metallation;
Stage #2: With zinc dibromide In tetrahydrofuran; hexane at -50℃; for 2h; Transmetallation;
Stage #3: With copper dichloride In tetrahydrofuran; hexane at -78 - 20℃; Elimination; Substitution;
A 72%
B n/a
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: With zinc dibromide In tetrahydrofuran; hexane at -50℃; for 2h;
Stage #3: With copper dichloride In tetrahydrofuran; hexane at -78 - 20℃;
A 72%
B n/a
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Metallation;
Stage #2: With copper dichloride In tetrahydrofuran; hexane at -78 - 20℃; Elimination; Substitution;
A 15%
B 61%
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: With copper dichloride In tetrahydrofuran; hexane at -78℃;
A 15%
B 61%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

10-((2-methoxyethoxy)methyl)-9(10H)-acridinone
147643-41-2

10-((2-methoxyethoxy)methyl)-9(10H)-acridinone

9,9'-(6,6'-dibromo-2,2'-biphenyldiyl)diacridine
1141733-47-2

9,9'-(6,6'-dibromo-2,2'-biphenyldiyl)diacridine

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: 10-((2-methoxyethoxy)methyl)-9(10H)-acridinone In tetrahydrofuran; hexane at -78 - 23℃;
Stage #3: With hydrogenchloride In ethanol; water at 23℃; for 3h;
71%
xanth-9-one
90-47-1

xanth-9-one

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

2,2’,6,6’-tetrabromobiphenyl

6,6'-dibromo-2,2'-bis(9-hydroxyxanthen-9-yl)biphenyl
500719-34-6

6,6'-dibromo-2,2'-bis(9-hydroxyxanthen-9-yl)biphenyl

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;68%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

C36H26Br2P2

C36H26Br2P2

(M)-(6,6'-dibromo-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine)

(M)-(6,6'-dibromo-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine)

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium; (1R,2R)-1,2-diphenyl-1,2-dimethoxyethane In hexane; toluene at -78℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: chloro-diphenylphosphine In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 12h; Schlenk technique; Inert atmosphere; Overall yield = 80 %; Overall yield = 545 mg;
A n/a
B 61%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

C24H30NPSn2

C24H30NPSn2

C48H30N2O2P2

C48H30N2O2P2

Conditions
ConditionsYield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;60%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

C19H26NPSn2

C19H26NPSn2

C38H22N2O2P2

C38H22N2O2P2

Conditions
ConditionsYield
With 1,1'-azobis(1-cyanocyclohexanenitrile) at 125℃; for 72h;60%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

(S)-6,6'-dibromo[1,1'-biphenyl]-2,2'-dicarbaldehyde

(S)-6,6'-dibromo[1,1'-biphenyl]-2,2'-dicarbaldehyde

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With (S,S)-1,2-di(3H-dinaphtho[2,1-c:1',2'-e]azepin-4(5H)-yl)ethane; sec.-butyllithium In hexane; cyclohexane; toluene at -78℃; for 1.5h; Inert atmosphere; Schlenk technique;
Stage #2: N,N-dimethyl-formamide In hexane; cyclohexane; toluene at -78℃; Reagent/catalyst; Inert atmosphere; Schlenk technique; enantioselective reaction;
50%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

chlorodicyclohexylphosphane
16523-54-9

chlorodicyclohexylphosphane

C36H50Br2P2

C36H50Br2P2

(M)-(6,6'-dibromo-[1,1'-biphenyl]-2,2'-diyl)bis(dicyclohexylphosphine)

(M)-(6,6'-dibromo-[1,1'-biphenyl]-2,2'-diyl)bis(dicyclohexylphosphine)

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium; (1R,2R)-1,2-diphenyl-1,2-dimethoxyethane In hexane; toluene at -78℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 12h; Schlenk technique; Inert atmosphere; Overall yield = 92 %; Overall yield = 650 mg;
A n/a
B 46%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

phenyllithium
591-51-5

phenyllithium

C18H11Br3
1171115-57-3

C18H11Br3

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride In tetrahydrofuran at -80 - 20℃; Negishi coupling reaction;42%
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane
30404-92-3

1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane

A

C24H16P2
1356238-70-4

C24H16P2

B

trans/cis-4,8-diphenyl-4,8-dihydrophosphindolo [4,3,2-bcd]phosphindole 4,8-dioxide

trans/cis-4,8-diphenyl-4,8-dihydrophosphindolo [4,3,2-bcd]phosphindole 4,8-dioxide

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl; 1,1,1,3,3,3-hexamethyl-2-phenyldistannaphosphane With 1,1'-azobis(1-cyanocyclohexanenitrile) In 4-methyl-1,2,3-trifluorobenzene at 125℃; for 45h; Inert atmosphere;
Stage #2: With dihydrogen peroxide In dichloromethane; water; 4-methyl-1,2,3-trifluorobenzene at 20℃; for 1h; Inert atmosphere;
A 41%
B n/a
2,2’,6,6’-tetrabromobiphenyl
97038-96-5

2,2’,6,6’-tetrabromobiphenyl

phenyldiiodoarsine
6380-34-3

phenyldiiodoarsine

4,5-dibromo-9-phenyl-9-arsafluorene

4,5-dibromo-9-phenyl-9-arsafluorene

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: phenyldiiodoarsine In tetrahydrofuran; hexane at 20℃; for 14h; Inert atmosphere;
40%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

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

2,2’,6,6’-tetrabromobiphenyl

(M)-1,12-dibromo-5,6,7,8-tetrahydrodibenzo[a,c][8]annulene

(M)-1,12-dibromo-5,6,7,8-tetrahydrodibenzo[a,c][8]annulene

C16H14Br2

C16H14Br2

Conditions
ConditionsYield
Stage #1: 2,2’,6,6’-tetrabromobiphenyl With n-butyllithium; (1R,2R)-1,2-diphenyl-1,2-dimethoxyethane In hexane; toluene at -78℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: 1,4-dibromo-butane With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane; toluene at -78 - 20℃; for 72h; Schlenk technique; Inert atmosphere; Overall yield = 51 %; Overall yield = 395 mg;
A 27%
B n/a

97038-96-5Relevant articles and documents

Asymmetric Bromine-Lithium Exchange: Application toward the Synthesis of New Biaryl-Diphosphine Ligands

Graff, Julien,?astawiecka, Elzbieta,Guénée, Laure,Leroux, Frédéric,Alexakis, Alexandre

, p. 2833 - 2839 (2015)

The desymmetrization of the prochiral tetrabromobiphenyl via asymmetric bromine-lithium exchange as a key step of synthesis of novel biphenyl-diphosphine ligands is reported. This new approach allows an easy access to twelve new enantiomerically pure atropisomeric ligands in one- to three-step reactions in good to excellent yields.

Synthesis and Physical Properties of Strained Doubly Phosphorus-Bridged Biaryls and Viologens

Greulich, Tobias W.,Yamaguchi, Eriko,Doerenkamp, Carsten,Lübbesmeyer, Maximilian,Daniliuc, Constantin G.,Fukazawa, Aiko,Eckert, Hellmut,Yamaguchi, Shigehiro,Studer, Armido

supporting information, p. 6029 - 6033 (2017/05/08)

New P/N-containing π-electron systems comprising fully planar biaryl arrays are synthesized by multiple radical phosphanylation. The biaryl moiety in these highly strained planar π-systems is rigidified by double P-bridging. The electronic properties of the core biaryl entity are varied by introducing N-donor substituents or by installing N-atoms within the π-system, thereby moving to the viologen core structure. The electrochemical and photophysical properties of these compounds are discussed and compared with those of related systems.

PROCESS FOR THE SYNTHESIS OF 2,2',6-TRIBROMOBIPHENYL

-

Page/Page column 2, (2010/06/16)

A process for the synthesis of 2,2′,6-tribromobiphenyl.

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