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15862-18-7

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15862-18-7 Usage

Uses

5,5''-Dibromo-2,2''-bipyridine

Check Digit Verification of cas no

The CAS Registry Mumber 15862-18-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,8,6 and 2 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 15862-18:
(7*1)+(6*5)+(5*8)+(4*6)+(3*2)+(2*1)+(1*8)=117
117 % 10 = 7
So 15862-18-7 is a valid CAS Registry Number.

15862-18-7 Well-known Company Product Price

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  • TCI America

  • (D4358)  5,5'-Dibromo-2,2'-bipyridyl  >98.0%(HPLC)

  • 15862-18-7

  • 1g

  • 3,450.00CNY

  • Detail

15862-18-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 5,5'-Dibromo-2,2'-bipyridine

1.2 Other means of identification

Product number -
Other names 5,5'-Dibromo-2,2'-bipyridyl

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:15862-18-7 SDS

15862-18-7Synthetic route

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With bromine at 150℃; for 15h;86%
With bromine at 150℃; under 1140.08 Torr; for 15h;86%
Stage #1: [2,2]bipyridinyl With Acetyl bromide In methanol at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: With bromine at 185℃; for 72h; Inert atmosphere;
Stage #3: With ethylene diamine tetraacetic acid tetrasodium salt; sodium hydroxide; sodium sulfite In dichloromethane; water at 20℃; for 2h; Inert atmosphere;
39%
2,2'-bipyridine dihydrochloride
65520-13-0

2,2'-bipyridine dihydrochloride

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With bromine for 72h; Heating; Autoclave;85%
2,5-dibromopyridine
624-28-2

2,5-dibromopyridine

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With hexamethyldistannane; tetrakis(triphenylphosphine) palladium(0) In benzene for 65h; Heating;80%
With tetrakis(triphenylphosphine) palladium(0); hexamethyldistannane In benzene for 72h; Heating;80%
With tetrakis(triphenylphosphine) palladium(0); bis(tri-n-butyltin) In m-xylene at 130℃; for 72h; Darkness;80%
2,6-diiodo-pyridine
53710-17-1

2,6-diiodo-pyridine

5-bromo-2-(tri-n-butylstannyl)pyridine
611168-46-8

5-bromo-2-(tri-n-butylstannyl)pyridine

A

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

B

5,5''-dibromo-2,2',6',2''-terpyridine
223463-10-3

5,5''-dibromo-2,2',6',2''-terpyridine

Conditions
ConditionsYield
With triphenyl phosphite; palladium(II) acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 3h; Stille coupling; Inert atmosphere;A 6 %Spectr.
B 80%
2-iodo-5-bromopyridine
223463-13-6

2-iodo-5-bromopyridine

5-bromo-2-(tri-n-butylstannyl)pyridine
611168-46-8

5-bromo-2-(tri-n-butylstannyl)pyridine

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With triphenyl phosphite; palladium(II) acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 5h; Stille coupling; Inert atmosphere;80%
2-iodo-5-bromopyridine
223463-13-6

2-iodo-5-bromopyridine

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); bis(tri-n-butyltin) In toluene at 125℃; for 72h; Sonogashira coupling;74%
With tetrakis(triphenylphosphine) palladium(0); bis(tri-n-butyltin) In toluene for 120h; Reflux;74%
Stille Cross-Coupling (Migita-Kosugi-Stille Coupling);69%
5,5'-(2,2'-bipyridine)diacid chloride
82799-91-5

5,5'-(2,2'-bipyridine)diacid chloride

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt at 100℃; for 20h; Irradiation;1.09 g
<2,2'>bipyridyl hydrobromide

<2,2'>bipyridyl hydrobromide

A

5-bromo-2,2'-bipyridyl
15862-19-8

5-bromo-2,2'-bipyridyl

B

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With carbon dioxide; bromine at 250℃;
2,6-Dibromopyridine
626-05-1

2,6-Dibromopyridine

5-bromo-2-(tri-n-butylstannyl)pyridine
611168-46-8

5-bromo-2-(tri-n-butylstannyl)pyridine

A

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

B

C10H6Br2N2
1042150-70-8

C10H6Br2N2

C

5,5''-dibromo-2,2',6',2''-terpyridine
223463-10-3

5,5''-dibromo-2,2',6',2''-terpyridine

Conditions
ConditionsYield
With triphenyl phosphite; palladium(II) acetylacetonate In toluene at 120℃; for 7h; Stille coupling; Inert atmosphere;A 5 %Spectr.
B 7 %Spectr.
C 87 %Spectr.
2,5-dibromopyridine
624-28-2

2,5-dibromopyridine

5-bromo-2-(tri-n-butylstannyl)pyridine
611168-46-8

5-bromo-2-(tri-n-butylstannyl)pyridine

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With triphenyl phosphite; palladium(II) acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 6h; Stille coupling; Inert atmosphere;
2,6-diiodo-pyridine
53710-17-1

2,6-diiodo-pyridine

5-bromo-2-(trimethylstannyl)pyridine
198985-48-7

5-bromo-2-(trimethylstannyl)pyridine

A

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

B

C10H6BrIN2
1042150-68-4

C10H6BrIN2

C

5,5''-dibromo-2,2',6',2''-terpyridine
223463-10-3

5,5''-dibromo-2,2',6',2''-terpyridine

Conditions
ConditionsYield
With palladium(II) acetylacetonate; triphenyl-arsane In toluene at 120℃; for 3h; Stille coupling; Inert atmosphere;A 22 %Spectr.
B 36 %Spectr.
C 40 %Spectr.
2,6-diiodo-pyridine
53710-17-1

2,6-diiodo-pyridine

5-bromo-2-(trimethylstannyl)pyridine
198985-48-7

5-bromo-2-(trimethylstannyl)pyridine

A

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

B

5,5''-dibromo-2,2',6',2''-terpyridine
223463-10-3

5,5''-dibromo-2,2',6',2''-terpyridine

Conditions
ConditionsYield
With palladium(II) acetylacetonate; triphenylphosphine In toluene at 120℃; for 18h; Stille coupling; Inert atmosphere;A 6 %Spectr.
B 93 %Spectr.
2,6-diiodo-pyridine
53710-17-1

2,6-diiodo-pyridine

5-bromo-2-(tri-n-butylstannyl)pyridine
611168-46-8

5-bromo-2-(tri-n-butylstannyl)pyridine

A

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

B

C10H6BrIN2
1042150-68-4

C10H6BrIN2

C

5,5''-dibromo-2,2',6',2''-terpyridine
223463-10-3

5,5''-dibromo-2,2',6',2''-terpyridine

Conditions
ConditionsYield
With triphenyl phosphite; palladium(II) acetylacetonate In toluene at 100℃; for 7h; Stille coupling; Inert atmosphere;A 5 %Spectr.
B 47 %Spectr.
C 38 %Spectr.
5-bromo-2-(tri-n-butylstannyl)pyridine
611168-46-8

5-bromo-2-(tri-n-butylstannyl)pyridine

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
With triphenyl phosphite; palladium(II) acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; Inert atmosphere;
3-Bromopyridine
626-55-1

3-Bromopyridine

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: diethyl ether / 0 °C / Inert atmosphere
2.1: lithium diisopropyl amide / diethyl ether / -78 °C / Inert atmosphere
2.2: -78 °C / Inert atmosphere
View Scheme
With Ni(NO3)2-Ce(NO3)3-La(NO3)3-Mn(NO3)2-impregnated solid catalyst In ethanol at 300℃; under 13351.3 Torr;
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

2-(3-Hexyloxymethyl-5-trimethylsilanylphenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane
276670-17-8

2-(3-Hexyloxymethyl-5-trimethylsilanylphenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

5,5'-bis[3-hexyloxymethyl-5-(trimethylsilanyl)phenyl]-2,2'-bipyridinyl
851605-32-8

5,5'-bis[3-hexyloxymethyl-5-(trimethylsilanyl)phenyl]-2,2'-bipyridinyl

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene for 72h; Suzuki-Miyaura cross-coupling; Reflux;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 72h; Heating;90%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

1-pyrenylboronic acid
164461-18-1

1-pyrenylboronic acid

5,5’-di(pyren-1-yl)-2,2’-bipyridine
1416448-44-6

5,5’-di(pyren-1-yl)-2,2’-bipyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 72h; Reflux; Inert atmosphere; Darkness;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 72h; Reflux; Inert atmosphere; Darkness;91%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

bis(2,2'-bipyridine)osmium(II) dichloride
15702-72-4, 79982-56-2

bis(2,2'-bipyridine)osmium(II) dichloride

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

bis(2,2'-bipyridine)(5,5'-dibromo-2,2'-pyridine)osmium(II) hexafluorophosphate

bis(2,2'-bipyridine)(5,5'-dibromo-2,2'-pyridine)osmium(II) hexafluorophosphate

Conditions
ConditionsYield
In ethylene glycol under Ar atm. ethyleneglycol soln. Os(bpy)2Cl2 and 5,5-dibromo-2,2'-bipyridine was refluxed for 1 h, water was added, mixt. was filtered, excess NH4PF6 was added; ppt. was filtered off, dissolved in acetone, filtered, solvent was removed under vac., residue was washed with ether and dried;99%
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate

bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate

bis(2,2′-bipyridine)(5,5′-dibromo-2,2′-bipyridine)ruthenium(II) hexafluorophosphate
99666-65-6

bis(2,2′-bipyridine)(5,5′-dibromo-2,2′-bipyridine)ruthenium(II) hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 5,5'-dibromo-2,2'-dipyridyl; bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate In ethylene glycol at 120℃; for 1.5h; Reflux;
Stage #2: potassium hexafluorophosphate In ethylene glycol
98%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

5,5'-bis((trimethylsilyl)ethynyl)-2,2'-bipyridine
187026-85-3

5,5'-bis((trimethylsilyl)ethynyl)-2,2'-bipyridine

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃; cross-coupling;96%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃; Inert atmosphere;95.6%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 50℃; Sonogashira coupling;87%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-stannane
175922-79-9

tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-stannane

5,5'-bis(3,4-(ethylenedioxy)thien-2-yl)-2,2'-bipyridine
199168-56-4

5,5'-bis(3,4-(ethylenedioxy)thien-2-yl)-2,2'-bipyridine

Conditions
ConditionsYield
trans-dichlorobis(triphenylphosphine)palladium(II) In N,N-dimethyl-formamide at 110℃; for 6h; Stille coupling;95%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

5,5’-diiodo-2,2’-bipyridine
209624-09-9

5,5’-diiodo-2,2’-bipyridine

Conditions
ConditionsYield
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 18h; Finkelstein Reaction; Inert atmosphere; Schlenk technique;95%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

ammonium hexafluorophosphate

ammonium hexafluorophosphate

Δ-[Ru(1,10-phenanthroline)2(pyridine)2](PF6)2

Δ-[Ru(1,10-phenanthroline)2(pyridine)2](PF6)2

Δ-[Ru(1,10-phenanthroline)2(5,5'-dibromo-2,2'-bipyridine)](PF6)2

Δ-[Ru(1,10-phenanthroline)2(5,5'-dibromo-2,2'-bipyridine)](PF6)2

Conditions
ConditionsYield
Stage #1: 5,5'-dibromo-2,2'-dipyridyl; Δ-[Ru(1,10-phenanthroline)2(pyridine)2](PF6)2 In ethylene glycol at 160℃; for 0.5h; Microwave irradiation;
Stage #2: ammonium hexafluorophosphate
94%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

ammonium hexafluorophosphate

ammonium hexafluorophosphate

cis-[bis (1,10-phenanthroline) dichlororuthenium(II)]
15453-59-5, 85718-09-8, 94292-22-5, 94292-23-6

cis-[bis (1,10-phenanthroline) dichlororuthenium(II)]

[Ru(1,10-phenanthroline)2(5,5'-dibromo-2,2'-bipyridine)](PF6)2

[Ru(1,10-phenanthroline)2(5,5'-dibromo-2,2'-bipyridine)](PF6)2

Conditions
ConditionsYield
Stage #1: 5,5'-dibromo-2,2'-dipyridyl; cis-[bis (1,10-phenanthroline) dichlororuthenium(II)] In ethylene glycol at 160℃; for 0.25h; Microwave irradiation;
Stage #2: ammonium hexafluorophosphate In water
94%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

ammonium hexafluorophosphate

ammonium hexafluorophosphate

Λ-[Ru(1,10-phenanthroline)2(pyridine)2](PF6)2*3H2O

Λ-[Ru(1,10-phenanthroline)2(pyridine)2](PF6)2*3H2O

Λ-[Ru(1,10-phenanthroline)2(5,5'-dibromo-2,2'-bipyridine)](PF6)2

Λ-[Ru(1,10-phenanthroline)2(5,5'-dibromo-2,2'-bipyridine)](PF6)2

Conditions
ConditionsYield
Stage #1: 5,5'-dibromo-2,2'-dipyridyl; Λ-[Ru(1,10-phenanthroline)2(pyridine)2](PF6)2*3H2O In ethylene glycol at 160℃; for 0.5h; Microwave irradiation;
Stage #2: ammonium hexafluorophosphate
94%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

1-trimethylsilyl-(4-trimethylstannyl)benzene
944-32-1

1-trimethylsilyl-(4-trimethylstannyl)benzene

5,5'-bis(4-trimethylsilylphenyl)-2,2'-bipyridine
309931-48-4

5,5'-bis(4-trimethylsilylphenyl)-2,2'-bipyridine

Conditions
ConditionsYield
With triphenyl-arsane; lithium chloride; palladium dichloride In N,N-dimethyl-formamide at 110℃;93%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

potassium vinyltrifluoroborate

potassium vinyltrifluoroborate

5,5’-divinyl-2,2’-bipyridine

5,5’-divinyl-2,2’-bipyridine

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; triphenylphosphine In tetrahydrofuran; water at 85℃; for 48h; Suzuki-Miyayra cross-coupling; Inert atmosphere; Sealed tube;93%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

rhenium(I) pentacarbonyl chloride
14099-01-5

rhenium(I) pentacarbonyl chloride

(5,5'-dibromo-2,2-bipyridine)rhenium(I) tricarbonyl chloride
264916-65-6

(5,5'-dibromo-2,2-bipyridine)rhenium(I) tricarbonyl chloride

Conditions
ConditionsYield
In benzene (N2); overnight at 50-60°C; solid filtered off, washed (hexane), dried (vac.);92%
In toluene under N2; Re(CO)5Cl and ligand in toluene heated at reflux for 6 h; cooled to room temp.; solvent distd. off; purified by column chromy. (silica gel, CH2Cl2-petroleum ether 2:1 contg. small amt. of Et3N); elem. anal.;61%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

4-amino-phenol
123-30-8

4-amino-phenol

5,5′-bis [(4-amino) phenoxy]-2,2′bipyridine

5,5′-bis [(4-amino) phenoxy]-2,2′bipyridine

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 195℃; for 12h; Solvent;92%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 175℃; for 12h;87%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

carbon monoxide
201230-82-2

carbon monoxide

butan-1-ol
71-36-3

butan-1-ol

5,5'-dicarbobutoxy-2,2'-bipyridine

5,5'-dicarbobutoxy-2,2'-bipyridine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; tributyl-amine at 120℃; under 760 Torr; for 20h;90%
With tributyl-amine; bis-triphenylphosphine-palladium(II) chloride at 120℃; under 760.051 Torr; for 40h; Carboxylation; esterification;90%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

ferroceneacetylene
1271-47-2

ferroceneacetylene

water
7732-18-5

water

C34H24Fe2N2*0.75H2O

C34H24Fe2N2*0.75H2O

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;89%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

methyltrioxorhenium(VII)
70197-13-6

methyltrioxorhenium(VII)

(4,4'-dibromo-2,2'-bipyridine)methyltrioxidorhenium

(4,4'-dibromo-2,2'-bipyridine)methyltrioxidorhenium

Conditions
ConditionsYield
In dichloromethane (N2 or Ar), MeReO3 dissolved in CH2Cl2, treated with 1 equiv. of ligand in CH2Cl2, reacted for 0.5 h; concd.(vac.), filtered, washed (n-hexane), dried (vac.), elem. anal.;88%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

5,5'-dimethyl-6-ethynyl-2,2'-bipyridine
133810-37-4

5,5'-dimethyl-6-ethynyl-2,2'-bipyridine

5,5'-bis<(5,5'-dimethyl-2,2'-bipyridin-6-yl)ethynyl>-2,2'-bipyridine

5,5'-bis<(5,5'-dimethyl-2,2'-bipyridin-6-yl)ethynyl>-2,2'-bipyridine

Conditions
ConditionsYield
With diisopropylamine; tetrakis(triphenylphosphine) palladium(0) In benzene at 80℃;87%
With tetrakis(triphenylphosphine) palladium(0); diisopropylamine In benzene at 80℃;87%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

2,2'bipyrid-4,4'-yldiphosphonic acid diethyl ester
209624-10-2

2,2'bipyrid-4,4'-yldiphosphonic acid diethyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine In toluene at 110℃; for 6h;87%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

tetrakis(acetonitrile)copper(I) perchlorate
14057-91-1

tetrakis(acetonitrile)copper(I) perchlorate

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene
161265-03-8

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

[Cu(5,5'-dibromo-2,2'-bipyridine)(9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthene)]ClO4

[Cu(5,5'-dibromo-2,2'-bipyridine)(9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthene)]ClO4

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5h; Inert atmosphere; Schlenk technique;86.1%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

bis[2-(2,4-difluorophenyl)pyridinato-N,C6']iridium(III) chloride dimer

bis[2-(2,4-difluorophenyl)pyridinato-N,C6']iridium(III) chloride dimer

5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

[Ir(2-(2,4-difluorophenyl)pyridine(-1H))2(5,5'-dibromo-2,2'-bipyridine)][PF6]
1185464-48-5

[Ir(2-(2,4-difluorophenyl)pyridine(-1H))2(5,5'-dibromo-2,2'-bipyridine)][PF6]

Conditions
ConditionsYield
In methanol; dichloromethane Ir complex added to a soln. of ligand, refluxed for 18 h; aq. NH4PF6 added, evapd. (vac.), dissolved in CH2Cl2, washed (H2O), the org. phase dried (Na2SO4), evapd., chromd. (silica gel, CH2Cl2/MeOH); elem. anal.;85%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

C28H27BO4

C28H27BO4

C32H21BrN2O2

C32H21BrN2O2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran Inert atmosphere; Reflux;85%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

1-(diallylethoxysilyl)-4-ethynylbenzene
1059193-35-9

1-(diallylethoxysilyl)-4-ethynylbenzene

5,5'-bis[4-(diallylethoxysilyl)phenylethynyl]-2,2'-bipyridine
1059193-41-7

5,5'-bis[4-(diallylethoxysilyl)phenylethynyl]-2,2'-bipyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); diisopropylamine In benzene for 40h; Inert atmosphere; Reflux;84%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

C19H14N3O4RuS(1+)*CNS(1-)

C19H14N3O4RuS(1+)*CNS(1-)

ammonium thiocyanate

ammonium thiocyanate

C24H14Br2N6O4RuS2

C24H14Br2N6O4RuS2

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 140℃; for 1.5h; Inert atmosphere;81.1%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

3,6,8-triphenylpyreneboric acid
887918-18-5

3,6,8-triphenylpyreneboric acid

2,2'-bipyridyl-5,5'-bis(3,6,8-triphenylpyrene)

2,2'-bipyridyl-5,5'-bis(3,6,8-triphenylpyrene)

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 10h;81%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

N3,N3,N6,N6-tetrakis(4-methoxyphenyl)-9-H-carbazole-3,6-diamine

N3,N3,N6,N6-tetrakis(4-methoxyphenyl)-9-H-carbazole-3,6-diamine

C90H74N8O8

C90H74N8O8

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 110℃; for 48h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;81%
5,5'-dibromo-2,2'-dipyridyl
15862-18-7

5,5'-dibromo-2,2'-dipyridyl

phenylacetylene
536-74-3

phenylacetylene

5,5'-bis(phenylethynyl)-2,2'-bipyridine

5,5'-bis(phenylethynyl)-2,2'-bipyridine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; Heck Reaction; Inert atmosphere;80%
With copper(l) iodide; diisopropylamine; tetrakis(triphenylphosphine) palladium(0) In toluene at 65℃; for 14h; Substitution;65.3%

15862-18-7Relevant articles and documents

Synthesis of new bis-BINOLs linked by a 2,2e′-bipyridine bridge

Bai, Xiao-Li,Liu, Xu-Dong,Wang, Mang,Kang, Chuan-Qing,Gao, Lian-Xun

, p. 458 - 464 (2005)

A series of new C2-symmetric chiral ligands 8, 9, 11 and 12, consisting of two binaphthyl units linked by a 2,2′-bipyridine bridge, has been synthesized via Suzuki cross-coupling reactions.

A straightforward synthesis of 5-bromo and 5,5'-dibromo-2,2'-bipyridines

Romero,Ziessel

, p. 6471 - 6474 (1995)

We herein report on the selective synthesis of 5-bromo-2,2'-bipyridine 2 and 5,5'-dibromo-2,2'-bipyridine 3 by direct bromination of 2,2'-bipyridine hydrobromide salt 1, as well as by radical decarboxylative bromination of the corresponding acid chlorides.

Cyclometalated iridium(III) complexes as photosensitizers for long-range electron transfer: Occurrence of a coulomb barrier

Hanss, David,Freys, Jonathan C.,Bernardinelli, Gerald,Wenger, Oliver S.

, p. 4850 - 4859 (2009)

Six cyclometalated iridium(III) complexes were investigated to assess their potential as photosensitizers for long-range electron transfer, and two of them were incorporated directly into covalent donor-bridge-acceptor molecules. The influence of ligarid substitutions on the excited-state properties and the photoredox behavior of the iridium complexes was explored by optical absorption, steady-state and time-resolved luminescence spectroscopy, as well as by electrochemical methods. Bimolecular electron transfer between the photoexcited complexes and 10-methylphenothiazine and methylviologen was found to be only weakly dependent on the ligand substitutions. Intramolecular long-range electron transfer from phenothiazine to photoexcited iridium(III) in the dyads is slow due to the occurrence of a Coulomb barrier. Consequently, an electron-transfer photoproduct is only observable in the transient absorption spectrum, of a donorbridge-acceptor molecule with a fluorinated photosensitizer that exhibits a very long excited-state lifetime. A flashquench technique is necessary for detection of an electrontransfer product in the dyad with a non-fluorinated photosensitizer. The occurrence of a Coulomb barrier associated with intramolecular (excited-state) long-range electron transfer in the dyads with cyclometalated iridium(III) photosensitizers represents an important difference to previously investigated similar donor-bridge-acceptor molecules with photosensitizers based on d6 metal diimine complexes.

Development of high dielectric polyimides containing bipyridine units for polymer film capacitor

Peng, Xinwen,Xu, Wenhui,Chen, Linlin,Ding, Yichun,Xiong, Tianrou,Chen, Shuiliang,Hou, Haoqing

, p. 93 - 98 (2016)

Polymer dielectrics with high dielectric constant, low dielectric loss, high breakdown strength, and high temperature capability are attractive for applications such as capacitive energy-storage. Commercially available polymer dielectrics such as biaxially oriented polypropylene (BOPP), poly(ethylene terephthalate) (PET), poly(ethylene naphthalate) (PEN), polycarbonate (PC), and poly(vinylidene) fluoride (PVDF) can be just operated below 200 °C. Great effort has been put into exploring high temperature polymer dielectrics to fulfill the demand of high temperature applications, such as the aerospace and military power supply. In this study, a series of polyimides containing bipyridine units with good dielectric performance and high temperature capability were prepared by using a newly synthesized diamine monomer, (5,5′-bis [(4-amino) phenoxy]-2,2′-bipyridine (BPBPA)). These polyimides possessed high dielectric constant of the as-synthesized polyimides can be up to7.2, the dielectric loss was 3. Furthermore, the polyimides exhibited high glass transition temperature (Tg) of 275–320 °C and tensile strengths of 175–221 MPa. These obtained polyimides promise potential applications in high temperature flexible polymer film capacitor operated at high temperature.

π-conjugated chelating polymers with charged iridium complexes in the backbones: Synthesis, characterization, energy transfer, and electrochemical properties

Liu, Shu-Juan,Zhao, Qiang,Chen, Run-Feng,Deng, Yun,Fan, Qu-Li,Li, Fu-You,Wang, Lian-Hui,Huang, Chun-Hui,Huang, Wei

, p. 4351 - 4361 (2006)

A series of π-conjugated chelating polymers with charged iridium (Ir) complexes in the backbones were synthesized by a Suzuki polycondensation reaction, leading to homogeneous polymeric materials that phosphoresce red light. The fluorene and bipyridine (bpy) segments were used as polymer backbones. 5.5′-Dibromobipyridine served as a ligand to form a charged iridium complex monomer with 1-(9′9-dioctylfluorene-2-yl)isoquinoline (Fiq) as the cyclometalated ligand. Chemical and photophysical characterization confirmed that Ir complexes were incorporated into the backbones as one of the repeat units by means of the 5.5′-dibromobipyridine ligand. Chelating polymers showed almost complete energy transfer from the host fluorene segments to the guest Ir complexes in the solid state when the feed ratio was 2 mol%. In the films of the corresponding blend system, however, energy transfer was not complete even when the content of Ir complexes was as high as 16 mol%. Both intra- and in termolecular energy-transfer processes existed in this host-guest system, and the intramolecular energy transfer was a more efficient process. All chelating polymers displayed good thermal stability, redox reversibility, and film formation. These chelating polymers also showed more efficient energy transfer than the corresponding blended system and the mechanism of incorporation of the charged Ir complexes into the π-conjugated polymer backbones efficiently avoided the intrinsic problems associated with the blend system, thus offering promise in optoelectronic applications.

Cu(ii)Cl2containing bispyridine-based porous organic polymer support preparedviaalkyne-azide cycloaddition as a heterogeneous catalyst for oxidation of various olefins

Choi, Hye Min,Lee, Suk Joong,Yoon, Jongho

supporting information, p. 9149 - 9152 (2020/06/17)

A new type of porous organic polymer (POP) based heterogeneous catalystCu-POPwas prepared by immobilizing Cu(ii)Cl2into bpy containing POP preparedviaalkyne-azide cycloaddition. This new catalyst showed efficient catalytic activities and outstanding reusability. Remarkably, one batch ofCu-POPwas continuously used for all olefins without losing its activity by simply washing.

Merging Photoredox and Organometallic Catalysts in a Metal–Organic Framework Significantly Boosts Photocatalytic Activities

Zhu, Yuan-Yuan,Lan, Guangxu,Fan, Yingjie,Veroneau, Samuel S.,Song, Yang,Micheroni, Daniel,Lin, Wenbin

supporting information, p. 14090 - 14094 (2018/10/15)

Metal–organic frameworks (MOFs) have been extensively used for single-site catalysis and light harvesting, but their application in multicomponent photocatalysis is unexplored. We report here the successful incorporation of an IrIII photoredox catalyst and a NiII cross-coupling catalyst into a stable Zr12 MOF, Zr12-Ir-Ni, to efficiently catalyze C?S bond formation between various aryl iodides and thiols. The proximity of the IrIII and NiII catalytic components to each other (ca. 0.6 nm) in Zr12-Ir-Ni greatly facilitates electron and thiol radical transfers from Ir to Ni centers to reach a turnover number of 38 500, an order of magnitude higher than that of its homogeneous counterpart. This work highlights the opportunity in merging photoredox and organometallic catalysts in MOFs to effect challenging organic transformations.

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