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2,2'-Bipyridine-4,4'-dicarboxylic acid is an organic compound characterized by its unique structure that features two pyridine rings connected by a carboxylic acid bridge at the 4,4' positions. 2,2'-Bipyridine-4,4'-dicarboxylic acid is known for its potential applications in various chemical synthesis processes due to its versatile chemical properties.

6813-38-3

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6813-38-3 Usage

Uses

Used in Organic Chemical Synthesis:
2,2'-Bipyridine-4,4'-dicarboxylic acid is used as an organic chemical synthesis intermediate for its ability to participate in a wide range of chemical reactions. Its presence in the synthesis process can lead to the formation of various complex organic molecules, making it a valuable component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Coordination Chemistry:
In coordination chemistry, 2,2'-Bipyridine-4,4'-dicarboxylic acid can act as a ligand, forming coordination complexes with metal ions. This property allows it to be used in the development of catalysts, sensors, and materials with specific electronic or optical properties.
Used in Supramolecular Chemistry:
2,2'-Bipyridine-4,4'-dicarboxylic acid's ability to form complexes with metal ions also makes it a candidate for supramolecular chemistry, where it can be used to construct larger, organized structures through non-covalent interactions. This can lead to the development of new materials with unique properties and functions.
Used in Analytical Chemistry:
2,2'-Bipyridine-4,4'-dicarboxylic acid can be employed as a reagent or a component in analytical methods, such as in the detection and quantification of metal ions. Its coordination properties can be leveraged to develop assays and sensors for environmental or clinical applications.
Overall, 2,2'-Bipyridine-4,4'-dicarboxylic acid is a versatile organic compound with applications spanning across various fields in chemistry, including organic synthesis, coordination chemistry, supramolecular chemistry, and analytical chemistry. Its unique structure and properties make it a valuable intermediate in the development of new compounds and materials.

Check Digit Verification of cas no

The CAS Registry Mumber 6813-38-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,8,1 and 3 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 6813-38:
(6*6)+(5*8)+(4*1)+(3*3)+(2*3)+(1*8)=103
103 % 10 = 3
So 6813-38-3 is a valid CAS Registry Number.

6813-38-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B1876)  2,2'-Bipyridine-4,4'-dicarboxylic Acid  >96.0%(HPLC)(T)

  • 6813-38-3

  • 100mg

  • 290.00CNY

  • Detail
  • TCI America

  • (B1876)  2,2'-Bipyridine-4,4'-dicarboxylic Acid  >96.0%(HPLC)(T)

  • 6813-38-3

  • 1g

  • 1,200.00CNY

  • Detail
  • Alfa Aesar

  • (B22594)  2,2'-Bipyridine-4,4'-dicarboxylic acid, 98%   

  • 6813-38-3

  • 1g

  • 637.0CNY

  • Detail
  • Alfa Aesar

  • (B22594)  2,2'-Bipyridine-4,4'-dicarboxylic acid, 98%   

  • 6813-38-3

  • 5g

  • 2404.0CNY

  • Detail
  • Alfa Aesar

  • (B22594)  2,2'-Bipyridine-4,4'-dicarboxylic acid, 98%   

  • 6813-38-3

  • 25g

  • 9923.0CNY

  • Detail
  • Alfa Aesar

  • (17510)  2,2'-Bipyridine-4,4'-dicarboxylic acid   

  • 6813-38-3

  • 1g

  • 1841.0CNY

  • Detail
  • Alfa Aesar

  • (17510)  2,2'-Bipyridine-4,4'-dicarboxylic acid   

  • 6813-38-3

  • 5g

  • 6996.0CNY

  • Detail
  • Aldrich

  • (550566)  2,2′-Bipyridine-4,4′-dicarboxylicacid  98%

  • 6813-38-3

  • 550566-1G

  • 2,399.67CNY

  • Detail
  • Aldrich

  • (282812)  2,2′-Bipyridine-4,4′-dicarboxylicacid  technical grade, 90%

  • 6813-38-3

  • 282812-1G

  • 4,496.31CNY

  • Detail

6813-38-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,2'-Bipyridine-4,4'-dicarboxylic acid

1.2 Other means of identification

Product number -
Other names 2-(4-carboxypyridin-2-yl)pyridine-4-carboxylic acid

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:6813-38-3 SDS

6813-38-3Synthetic route

4,4'-dimethyl-2,2'-bipyridines
1134-35-6

4,4'-dimethyl-2,2'-bipyridines

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

4,4'-bis(carbomethoxy)-2,2'-bipyridine
71071-46-0

4,4'-bis(carbomethoxy)-2,2'-bipyridine

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol Reflux;96%
With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃; Cooling with ice;
4,4’-diethyl-2,2’-bipyridine
3052-28-6

4,4’-diethyl-2,2’-bipyridine

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
With K2Cr2O7; sulfuric acid95%
With chromium(VI) oxide; periodic acid In dichloromethane; acetonitrile at 20 - 60℃; for 24h; Time;94 %Spectr.
4,4'-dibromo-2,2'-bipyridine
18511-71-2

4,4'-dibromo-2,2'-bipyridine

carbon dioxide
124-38-9

carbon dioxide

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique;
Stage #2: 4,4'-dibromo-2,2'-bipyridine With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 10h; Schlenk technique; Sealed tube;
91%
2-chloroisonicotinic acid,
6313-54-8

2-chloroisonicotinic acid,

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; palladium In methanol; water85%
4,4',5,5'-tetramethyl-2,2'-bipyridine
1762-35-2

4,4',5,5'-tetramethyl-2,2'-bipyridine

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid; water; nitric acid at 160℃; for 36h;55%
4'-methyl-2,2'-bipyridine-4-carboxylaldehyde
104704-09-8

4'-methyl-2,2'-bipyridine-4-carboxylaldehyde

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: 4'-methyl-2,2'-bipyridine-4-carboxylaldehyde With silver nitrate; acetic acid In ethanol; water for 24h;
Stage #2: With sodium hydroxide In ethanol; water for 0.333333h;
49.8%
4,4'-dimethyl-2,2'-bipyridines
1134-35-6

4,4'-dimethyl-2,2'-bipyridines

A

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

B

4'-methyl-2,2'-bipyridine-4-carboxylic acid
103946-54-9

4'-methyl-2,2'-bipyridine-4-carboxylic acid

Conditions
ConditionsYield
With potassium permanganate; sulfuric acid for 12h; Heating;A 45%
B 4%
With manganese(II) sulfate; potassium permanganate In pyridine; water for 120h; Ambient temperature;A n/a
B 7%
With sodium hydroxide; selenium(IV) oxide; silver nitrate 1.) 1,4-dioxane, reflux, 24 h, 2.) EtOH, water, 15 h; Yield given. Multistep reaction. Yields of byproduct given;
With chromium(VI) oxide; periodic acid In dichloromethane; acetonitrile at 20℃; for 16h; Overall yield = 0.099 g;A 35 %Spectr.
B 6 %Spectr.
4,4’,6,6’-tetracarboxy-2,2’-bipyridine
1127385-14-1

4,4’,6,6’-tetracarboxy-2,2’-bipyridine

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
With nitric acid In water at 180℃; for 36.17h; Heating;45%
picoline
108-89-4

picoline

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Raney nickel
2: oxidation
View Scheme
Multi-step reaction with 2 steps
1: 2 percent / 10percent Pd/C / 72 h / Heating
2: KMnO4 / H2O / 12 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: FeCl3
2: KMnO4; H2O
View Scheme
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon / Heating
2: potassium permanganate; water / Heating
View Scheme
Multi-step reaction with 2 steps
1: manganese(IV) oxide; palladium on activated charcoal / neat (no solvent) / 168 h / 140 °C
2: potassium permanganate; water; sodium hydroxide / ethanol / 12 h / pH 11 / Reflux
View Scheme
picoline
108-89-4

picoline

sulfur

sulfur

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: KMnO4
View Scheme
2-Amino-4-methylpyridine
695-34-1

2-Amino-4-methylpyridine

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: bromine; aqueous sodium nitrite solution; aqueous hydrobromic acid
2: copper / 240 °C
3: KMnO4; H2O
View Scheme
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper / 240 °C
2: KMnO4; H2O
View Scheme
4-Ethylpyridine
536-75-4

4-Ethylpyridine

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium-carbon
2: sulfuric acid; K2Cr2O7
View Scheme
Multi-step reaction with 2 steps
1: palladium on activated charcoal / dichloromethane / 288 h / Reflux; Inert atmosphere
2: periodic acid; chromium(VI) oxide / dichloromethane; acetonitrile / 24 h / 20 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1: palladium on activated charcoal / dichloromethane / 288 h / Reflux; Inert atmosphere
2: periodic acid; chromium(VI) oxide / dichloromethane; acetonitrile / 24 h / 20 - 60 °C
View Scheme
4,4',6,6'-tetramethyl-2,2'-bipyridine
4444-27-3

4,4',6,6'-tetramethyl-2,2'-bipyridine

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
With nitric acid In water at 180℃;
[2,2']bipyridinyl-4,4'-dicarbaldehyde
99970-84-0

[2,2']bipyridinyl-4,4'-dicarbaldehyde

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Conditions
ConditionsYield
With nitric acid for 2h; Reflux;6.9 g
4,4’-diethyl-2,2’-bipyridine
3052-28-6

4,4’-diethyl-2,2’-bipyridine

A

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

B

4-carboxy-4'-ethyl-2,2'-bipyridine

4-carboxy-4'-ethyl-2,2'-bipyridine

Conditions
ConditionsYield
With chromium(VI) oxide; periodic acid In dichloromethane; acetonitrile at 20 - 60℃; for 24h; Time; Overall yield = 0.099 g;
2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

2,2'-bipyridyl-4,4'-dicarboxylic acid chloride
72460-28-7

2,2'-bipyridyl-4,4'-dicarboxylic acid chloride

Conditions
ConditionsYield
With thionyl chloride for 3h; Heating;100%
With thionyl chloride for 16h; Heating;100%
With thionyl chloride at 90℃; for 24h; Inert atmosphere;100%
2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

N,N`-dimethylethylenediamine
110-70-3

N,N`-dimethylethylenediamine

[2,2']bipyridinyl-4,4'-dicarboxylic acid bis-[methyl-(2-methylamino-ethyl)-amide]

[2,2']bipyridinyl-4,4'-dicarboxylic acid bis-[methyl-(2-methylamino-ethyl)-amide]

Conditions
ConditionsYield
Stage #1: 2,2'-Bipyridine-4,4'-dicarboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 60℃;
Stage #2: N,N`-dimethylethylenediamine In tetrahydrofuran at 20℃;
100%
methanol
67-56-1

methanol

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

4,4'-bis(carbomethoxy)-2,2'-bipyridine
71071-46-0

4,4'-bis(carbomethoxy)-2,2'-bipyridine

Conditions
ConditionsYield
With sulfuric acid for 60h; Heating;99%
With sulfuric acid Reflux;98%
Stage #1: methanol; 2,2'-Bipyridine-4,4'-dicarboxylic acid With sulfuric acid at 105℃; for 12h;
Stage #2: In water pH=9;
98%
hexafluorophosphoric acid

hexafluorophosphoric acid

[Ru(CH3CN)4(2-(4-nitrophenyl)pyridine(-1H))]PF6

[Ru(CH3CN)4(2-(4-nitrophenyl)pyridine(-1H))]PF6

[Ru(p-cymene)(CH3CN)2(2-(4-nitrophenyl)pyridine(-1H))]PF6

[Ru(p-cymene)(CH3CN)2(2-(4-nitrophenyl)pyridine(-1H))]PF6

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

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

N,N-dimethyl-formamide

[Ru(4,4'-dicarboxy-2,2'-bipyridine)2(2-(4-nitrophenyl)pyridine(-1H))]PF6*DMF*2H2O

[Ru(4,4'-dicarboxy-2,2'-bipyridine)2(2-(4-nitrophenyl)pyridine(-1H))]PF6*DMF*2H2O

Conditions
ConditionsYield
With NaOH In methanol; water soln. of ligand and NaOH in H2O/MeOH (1/4) was stirred for 40 min; mixt.of Ru complexes was added; refluxed for 3 h; cooled to room temp.; solvent removed (vac.); reconstituted in H2O; aq. HPF6 added dropwise; filtered; washed (H2O); reconstituted in DMF; drawnout of soln. with Et2O; filtered; washed (Et2O); dried in air; elem. an al.;99%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

4,4′-bis[2-(1,1′-biphenyl)-4-ylethenyl]-2,2′-bipyridine

4,4′-bis[2-(1,1′-biphenyl)-4-ylethenyl]-2,2′-bipyridine

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

cis‑4,4′‑bis[2‑(1,1′‑biphenyl)‑4‑ylethenyl]‑2,2′‑bipyridine‑(4,4′‑dicarboxy‑2,2′‑bipyridine)‑di(thiocyanato)ruthenium(II)

cis‑4,4′‑bis[2‑(1,1′‑biphenyl)‑4‑ylethenyl]‑2,2′‑bipyridine‑(4,4′‑dicarboxy‑2,2′‑bipyridine)‑di(thiocyanato)ruthenium(II)

Conditions
ConditionsYield
Stage #1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4,4′-bis[2-(1,1′-biphenyl)-4-ylethenyl]-2,2′-bipyridine In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere; Darkness;
Stage #2: 2,2'-Bipyridine-4,4'-dicarboxylic acid In N,N-dimethyl-formamide at 140℃; for 4h; Inert atmosphere; Darkness;
Stage #3: ammonium thiocyanate In N,N-dimethyl-formamide at 140℃; for 4h; Inert atmosphere; Darkness;
98%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

cis-dichro-bis(4,4'-dicarboxy-2,2'-bipyridine)ruthenium

cis-dichro-bis(4,4'-dicarboxy-2,2'-bipyridine)ruthenium

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 170℃; for 1.5h; Inert atmosphere;98%
[Ru(2,6-bis(1-pyrazolyl)pyridine)Cl3]*4H2O

[Ru(2,6-bis(1-pyrazolyl)pyridine)Cl3]*4H2O

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

water
7732-18-5

water

[Ru(2,6-bis(1-pyrazolyl)pyridine)(2,2'-bipyridine-4,4'-dicarboxylic acid-H)Cl]*2H2O

[Ru(2,6-bis(1-pyrazolyl)pyridine)(2,2'-bipyridine-4,4'-dicarboxylic acid-H)Cl]*2H2O

Conditions
ConditionsYield
With LiCl; Et3N In ethanol; water byproducts: Et3NHCl; under Ar; Schlenk tube charged with RuCl3*3H2O (0.399 mmol) and org. ligand (0.468 mmol) in EtOH/H2O (1:1, v/v); LiCl (0.59 mmol) in EtOH/H2O (1:1, v/v) and Et3N (0.788 mmol) added; refluxed (7 h); hot suspn. filtered in air through Celite; concd.; stored (2 d, 5°C); ppt. filtered; washed with cold H2O and Et2O; dried in air and in vac. over P2O5; filtrate concd.; stored (5°C); elem. anal.;97.1%
ethanol
64-17-5

ethanol

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine
1762-42-1

4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine

Conditions
ConditionsYield
With sulfuric acid for 18h; Heating;97%
With sulfuric acid93%
With sulfuric acid Reflux;92%
2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

trifluoroacetic acid
76-05-1

trifluoroacetic acid

Zr6(OH)4O4(bpydc)6

Zr6(OH)4O4(bpydc)6

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 120h;96.5%
pentafluorophenyl trifloroacetate
14533-84-7

pentafluorophenyl trifloroacetate

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

2,2'-bipyridine-4,4'-dicarboxylic acid pentafluorophenolic ester
331465-52-2

2,2'-bipyridine-4,4'-dicarboxylic acid pentafluorophenolic ester

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 20℃;96%
cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride

cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

water
7732-18-5

water

[4,4'-dicarboxy-2,2'-bipyridine]bis(2,2'-bipyridine)ruthenium(II) dichloride tetrahydrate

[4,4'-dicarboxy-2,2'-bipyridine]bis(2,2'-bipyridine)ruthenium(II) dichloride tetrahydrate

Conditions
ConditionsYield
In ethanol; water soln. of Ru-complex in EtOH/H2O was added to suspn. of ligand in EtOH/H2O, refluxed for 3 ds under N2, cooled; filtered, solvent was evapd., dried in vac.; elem. anal.;96%
ruthenium trichloride

ruthenium trichloride

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

water
7732-18-5

water

C24H16Cl6N4O9Ru2

C24H16Cl6N4O9Ru2

Conditions
ConditionsYield
With hydrogenchloride at 185℃; for 3h; Temperature; Reagent/catalyst; Sonication;95%
cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate

cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

(4,4'-dicarboxy-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride dihydrate

(4,4'-dicarboxy-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride dihydrate

Conditions
ConditionsYield
In acetic acid (N2); stirring (5 h); solvent removal (vac.), dissoln. (ethanol, concd. HCl), filtration, concn., pptn. (diethyl ether), stirring (1 h, room temp.), sepn., washing (diethyl ether), drying (60°C); elem. anal.;94%
methanol
67-56-1

methanol

ammonium hexafluorophosphate

ammonium hexafluorophosphate

chloridobis(2-phenyl-pyridine)rhodium(III) dimer
33915-80-9

chloridobis(2-phenyl-pyridine)rhodium(III) dimer

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

water
7732-18-5

water

rhodium(III) [bis(C,N-2-phenylpyridine)-N,N-4,4'-dicarboxy-2,2'-bipyridine] hexafluorophosphate monohydrate*2(methanol)

rhodium(III) [bis(C,N-2-phenylpyridine)-N,N-4,4'-dicarboxy-2,2'-bipyridine] hexafluorophosphate monohydrate*2(methanol)

Conditions
ConditionsYield
With sodium acetate In methanol; dichloromethane soln. of Rh complex in CH2Cl2 added to suspn. of ligand in MeOH; Na acetate in MeOH added; heated to reflux with stirring for 2 h; cooled to room temp.; satd. soln. of NH4PF6 in MeOH added; stirred for 30 min; solvent removed under reduced pressure; 1 M HCl added; stirred (10 min);filtered; ppt. washed with H2O; extd. into MeOH; satd. soln. of NH4PF6 in MeOH added; stirred (30 min); solvent removed; extd. (CH2Cl2); filter ed; solvent removed; elem. anal.;94%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

[(N-methyl-1,2-phenylenediamine)2iridium(III)(μ-Cl2)iridium(III)(N-methyl-1,2-phenylenediamine)2]

[(N-methyl-1,2-phenylenediamine)2iridium(III)(μ-Cl2)iridium(III)(N-methyl-1,2-phenylenediamine)2]

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

C40H30IrN6O4(1+)*F6P(1-)

C40H30IrN6O4(1+)*F6P(1-)

Conditions
ConditionsYield
Stage #1: [(N-methyl-1,2-phenylenediamine)2iridium(III)(μ-Cl2)iridium(III)(N-methyl-1,2-phenylenediamine)2]; 2,2'-Bipyridine-4,4'-dicarboxylic acid In methanol; dichloromethane at 65℃; Inert atmosphere;
Stage #2: ammonium hexafluorophosphate for 0.5h; Inert atmosphere;
94%
ruthenium trichloride hydrate

ruthenium trichloride hydrate

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

tris(4,4′-dicarboxylic acid-2,2′-bipyridyl) ruthenium-(II) dichloride

tris(4,4′-dicarboxylic acid-2,2′-bipyridyl) ruthenium-(II) dichloride

Conditions
ConditionsYield
In toluene RuCl3*nH2O and ligand in DMF were refluxed for 24 h; ppt. was filtered, washed with MeCN and CH2Cl2 and vac.-dried; elem. anal.;93%
With ascorbic acid In N,N-dimethyl-formamide (N2), Ru salt and ligand refluxed in DMF for 18 h, cooled to room temp, treated with ascorbic acid, refluxed for 4 h; filtered (vac.), recrystd. several times (aq.NaOH/aq.HCl), pptd.(aq.HCl)at pH=2-3;
dichlorobis(2,2'-bipyridine)ruthenium(II) tetrahydrate

dichlorobis(2,2'-bipyridine)ruthenium(II) tetrahydrate

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

water
7732-18-5

water

acetic acid
64-19-7

acetic acid

(4,4'-dicarboxy-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride dihydrate

(4,4'-dicarboxy-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride dihydrate

Conditions
ConditionsYield
In H2O other Radiation; to acetic acid added 4,4'-dicarboxy-2,2'-bipyridine and Ru(bpy)2Cl2; mixt. heated at 90°C under microwave irradiation for 30 min; solventremoved on rotary evaporator under reduced pressure; residue in methanol filtered through Celite; filtrate collected, evapd. under vac. and compd. dried at 40°C in vac.; elem. anal.;93%
O-2-tetrahydro-2H-pyranhydroxylamine
6723-30-4

O-2-tetrahydro-2H-pyranhydroxylamine

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

C22H26N4O6

C22H26N4O6

Conditions
ConditionsYield
Stage #1: 2,2'-Bipyridine-4,4'-dicarboxylic acid With thionyl chloride
Stage #2: O-2-tetrahydro-2H-pyranhydroxylamine With N-ethyl-N,N-diisopropylamine In dichloromethane for 24h;
93%
[RhCl2(p-cymene)]2

[RhCl2(p-cymene)]2

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

(E,E′)-4,4′-bisstyryl-2,2′-bipyridine
825621-06-5

(E,E′)-4,4′-bisstyryl-2,2′-bipyridine

ammonium thiocyanate

ammonium thiocyanate

cis-dithiocyanato(4,4'-dicarboxy-2,2'-bipyridine)-(4,4'-bis((E)-styryl)-2,2'-bipyridine) ruthenium(II)

cis-dithiocyanato(4,4'-dicarboxy-2,2'-bipyridine)-(4,4'-bis((E)-styryl)-2,2'-bipyridine) ruthenium(II)

Conditions
ConditionsYield
Stage #1: [RhCl2(p-cymene)]2; (E,E′)-4,4′-bisstyryl-2,2′-bipyridine In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere; Darkness;
Stage #2: 2,2'-Bipyridine-4,4'-dicarboxylic acid In N,N-dimethyl-formamide at 160℃; for 4h; Inert atmosphere; Darkness;
Stage #3: ammonium thiocyanate In N,N-dimethyl-formamide at 160℃; for 4h; Inert atmosphere; Darkness;
93%
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

[2,2'-bipyridine]-4,4'-dicarboxylic acid 4,4'-bis(2-methylpropyl) ester
1141011-53-1

[2,2'-bipyridine]-4,4'-dicarboxylic acid 4,4'-bis(2-methylpropyl) ester

Conditions
ConditionsYield
With sulfuric acid for 4h; Heating;92%
With sulfuric acid for 16h; Reflux;92%
With sulfuric acid for 24h; Reflux;2.01 g
2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

[Ir2(2-(3,4-difluorophenyl)pyridine)4Cl2]

[Ir2(2-(3,4-difluorophenyl)pyridine)4Cl2]

[Ir(2-(3,4-difluorophenyl)pyridine)2(4-carboxy-2,2′-bipyridine-4′-carboxylate)]

[Ir(2-(3,4-difluorophenyl)pyridine)2(4-carboxy-2,2′-bipyridine-4′-carboxylate)]

Conditions
ConditionsYield
With sodium carbonate In methanol; dichloromethane Reflux;92%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

[(cymene)ruthenium(chloride)(2,2'-bipyridine-4,4'-dicarboxylic acid)](chloride)

[(cymene)ruthenium(chloride)(2,2'-bipyridine-4,4'-dicarboxylic acid)](chloride)

Conditions
ConditionsYield
Stage #1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2,2'-Bipyridine-4,4'-dicarboxylic acid In N,N-dimethyl-formamide at 60℃; for 3h;
Stage #2: In methanol
92%
In water for 0.25h; Sonication; Green chemistry;
iridium(III) chloride trihydrate

iridium(III) chloride trihydrate

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

1-phenylpyrazole
1126-00-7

1-phenylpyrazole

[Ir(4-carboxy-2,2'-bipyridine-4'-carboxylate)(1-phenylpyrazole)2]*H2O

[Ir(4-carboxy-2,2'-bipyridine-4'-carboxylate)(1-phenylpyrazole)2]*H2O

Conditions
ConditionsYield
With Na2CO3 In 2-ethoxy-ethanol; dichloromethane; water soln. of Ir compd. and phenylpyrazole (2.2 equiv.) in 2-ethoxyethanol/H2O (3/1) was refluxed for 24 h; evapd.; dissolved in CH2Cl2; mixed with soln. of acid in MeOH; Na2CO3 was added; refluxed with stirring for 3 h; cooled to room temp.; solvent removed (vac.); H2O added; dil. HCl added to pH 5; filtered; dissolved in CH2Cl2/CH3OH (3/1); dried (Na2SO4); condensed; chromd. (silica, CH2Cl2/CH3OH, 1/1); elem. anal.;91%
rhenium(I) pentacarbonyl chloride
14099-01-5

rhenium(I) pentacarbonyl chloride

2,2'-Bipyridine-4,4'-dicarboxylic acid
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

Re(4,4'-dicarboxy-2,2'-bipyridine)(CO)3Cl
116840-69-8

Re(4,4'-dicarboxy-2,2'-bipyridine)(CO)3Cl

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 8h; Reflux;90%
In ethanol Inert atmosphere; Schlenk technique; Darkness; Reflux;85%
In toluene under Ar; one equiv. of ligand was added to a soln. of Re(CO)5Cl in toluene; a ppt. formed after 30 min; stirring for 15 h at 80 °C; after filtration the product was washed with Et2O; recrystn. from CH2Cl2 (or CH3CN)/Et2O; elem. anal.;>90
In methanol; toluene Re(CO)5Cl dissolved in hot toluene-MeOH; ligand added; stirred under reflux for 1 h; cooled; modified from A. Juris et al., Inorg. Chem., 1988, 27, 4007; pptd. in freezer over 1 h; filtered; filtrate rotary evapd. to dryness;

6813-38-3Relevant academic research and scientific papers

Synthesis and characterization of cross-linkable ruthenium complex dye and its application on dye-sensitized solar cells

Liu, Ken-Yen,Hsu, Chiao-Ling,Chang, Shun-Hsing,Chen, Jian-Ging,Ho, Kuo-Chuan,Lin, King-Fu

, p. 366 - 372 (2010)

A new crosslinkable light sensitizer, Ru(2,2′-bipyridine- 4,40-bicarboxylic acid)(4,4′-bis(11-dodecenyl)-2,2′-bipyridine)( NCS)2, denoted as Ru-C for titanium oxide nanocrystallinebased solar cells was synthesized with its crosslinking properties invesitigated by Fourier-transform infrared and UV-vis absorption spectroscopies. After crosslinking by itself or copolymerizing with methyacrylic acid, their sensitized solar cells with poly(methylacrylate)-gelled electrolyte system not only attained more than 5% of power conversion efficiency at AM 1.5 illumination (100 mW/cm2), but also gave rise to long storage life. To the best our knowledge, this is the first crosslinkable dye ever applied to the DSSC in the literature.

Magnetic observation of above room-temperature spin transition in vesicular nano-spheres

Luo, Yang-Hui,Liu, Qing-Ling,Yang, Li-Jing,Sun, Yu,Wang, Jin-Wen,You, Chao-Qun,Sun, Bai-Wang

, p. 8061 - 8069 (2016)

Nano-scale materials are acquiring a leading role in the fabrication of new generation devices, especially for the practical application of molecular bi-stability. However, the preparation of purely bi-stable nano-objects without the use of surfactants/polymers remains a challenging task. Here, we present a new approach to prepare spin-crossover (SCO) vesicular nano-spheres with single-external diameters of approximately 100 nm using a CHCl3-H2O mixture. The nano-spheres are based on a series SCO complexes, [Fe(H2Bpz2)2(dialkyl-bipy)] (H2Bpz2 = dihydrobis(1-pyrazolyl)borate, dialkyl-bipy = N4,N4′-dialkyl-(2,2′-bipyridine)-4,4′-dicarbo-xamide, alkyl = propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl and cetyl), and are prepared through a self-assembly process that is similar to liposomal assembly, with the dialkyl-bipy moiety acting as the hydrophobic tail and the Fe(H2Bpz2) moiety acting as the hydrophilic head. This study reveals that the alkyl chain length plays a key role in the formation of these nano-spheres and the determination of their spin transition temperatures. The spin transition temperatures for the bulk materials are centered at around 160 K, and show a positive correlation with the alkyl chain length. Meanwhile, for the vesicular nano-spheres in the solid state, their transition temperatures are above room-temperature, and the correlation with the alkyl chain length is negative. These results provide an effective strategy for the design of new metal-organic materials for nano-technological applications.

Hexameric supramolecular scaffold orients carbohydrates to sense bacteria

Gruenstein, Dan,Maglinao, Maha,Kikkeri, Raghavendra,Collot, Mayeul,Barylyuk, Konstantin,Lepenies, Bernd,Kamena, Faustin,Zenobi, Renato,Seeberger, Peter H.

, p. 13957 - 13966 (2011)

Carbohydrates are integral to biological signaling networks and cell-cell interactions, yet the detection of discrete carbohydrate-lectin interactions remains difficult since binding is generally weak. A strategy to overcome this problem is to create multivalent sensors, where the avidity rather than the affinity of the interaction is important. Here we describe the development of a series of multivalent sensors that self-assemble via hydrophobic supramolecular interactions. The multivalent sensors are comprised of a fluorescent ruthenium(II) core surrounded by a heptamannosylated β-cyclodextrin scaffold. Two additional series of complexes were synthesized as proof-of-principle for supramolecular self-assembly, the fluorescent core alone and the core plus β-cyclodextrin. Spectroscopic analyses confirmed that the three mannosylated sensors displayed 14, 28, and 42 sugar units, respectively. Each complex adopted original and unique spatial arrangements. The sensors were used to investigate the influence of carbohydrate spatial arrangement and clustering on the mechanistic and qualitative properties of lectin binding. Simple visualization of binding between a fluorescent, multivalent mannose complex and the Escherichia coli strain ORN178 that possesses mannose-specific receptor sites illustrates the potential for these complexes as biosensors.

Solid-supported chemiluminescence and electrogenerated chemiluminescence based on a tris(2,2′-bipyridyl)ruthenium(II) derivative

Greenway,Greenwood,Watts,Wiles

, p. 85 - 87 (2006)

We report a simple and efficient technique for the covalent immobilisation of a tris(2,2′-bipyridyl)ruthenium(ii) derivative suitable for both chemiluminescence and electrochemiluminescence detection. The Royal Society of Chemistry 2006.

Synthesis and recognition behaviour of allosteric hemicarcerands

Lützen, Arne,Ha?, Oliver,Bruhn, Torsten

, p. 1807 - 1811 (2002)

Bipyridine bridged bis(resorcinarenes) have been prepared. Upon co-ordinating to a transition metal ion, e.g. Ag+, the respective metal complex forms a hemicarcerand-like structure with the two resorcinarene moieties capable of binding non-polar organic molecules in a co-operative fashion, as shown qualitatively by NMR spectroscopy.

Silver coordination complexes as room-temperature multifunctional materials

Pucci, Daniela,Barberio, Giovanna,Bellusci, Anna,Crispini, Alessandra,Donnio, Bertrand,Giorgini, Loris,Ghedini, Mauro,La Deda, Massimo,Szerb, Elisabeta Ildyko

, p. 6738 - 6747 (2006)

A series of bischelate ionic silver complexes [Ag(L*)2][X] was prepared by complexation of a newly synthesized 2,2′-bipyridine containing chiral alkoxy chains in the 4,4′ positions. The appropriate choice of the construction motifs allows the preparation of new materials in which several functionalities can be introduced.Indeed, when the anion X - is a triflate or a dodecylsulfate group, the right combination of intermolecular interactions promotes the production of liquid crystalline mesophases. Therefore, the presence of coordinating anions, which drives the supramolecular assembly, is essential to generate, at the same time, room-temperature columnar hexagonal mesomorphism, the columnar helical supramolecular structure, and excimeric emission.

Protein Surface Mimetics: Understanding How Ruthenium Tris(Bipyridines) Interact with Proteins

Hewitt, Sarah H.,Filby, Maria H.,Hayes, Ed,Kuhn, Lars T.,Kalverda, Arnout P.,Webb, Michael E.,Wilson, Andrew J.

, p. 223 - 231 (2017)

Protein surface mimetics achieve high-affinity binding by exploiting a scaffold to project binding groups over a large area of solvent-exposed protein surface to make multiple cooperative noncovalent interactions. Such recognition is a prerequisite for competitive/orthosteric inhibition of protein–protein interactions (PPIs). This paper describes biophysical and structural studies on ruthenium(II) tris(bipyridine) surface mimetics that recognize cytochrome (cyt) c and inhibit the cyt c/cyt c peroxidase (CCP) PPI. Binding is electrostatically driven, with enhanced affinity achieved through enthalpic contributions thought to arise from the ability of the surface mimetics to make a greater number of noncovalent interactions than CCP with surface-exposed basic residues on cyt c. High-field natural abundance 1H,15N HSQC NMR experiments are consistent with surface mimetics binding to cyt c in similar manner to CCP. This provides a framework for understanding recognition of proteins by supramolecular receptors and informing the design of ligands superior to the protein partners upon which they are inspired.

Reduction of CO2 using a rhenium bipyridine complex containing ancillary BODIPY moieties

Teesdale, Justin J.,Pistner, Allen J.,Yap, Glenn P.A.,Ma, Ying-Zhong,Lutterman, Daniel A.,Rosenthal, Joel

, p. 149 - 157 (2014)

The reduction of carbon dioxide to chemical fuels such as carbon monoxide is an important challenge in the field of renewable energy conversion. Given the thermodynamic stability of carbon dioxide, it is difficult to efficiently activate this substrate in a selective fashion and the development of new electrocatalysts for CO2 reduction is of prime importance. To this end, we have prepared and studied a new fac-ReI(CO)3 complex supported by a bipyridine ligand containing ancillary BODIPY moieties ([Re(BB2)(CO)3Cl]). Voltammetry experiments revealed that this system displays a rich redox chemistry under N2, as [Re(BB2)(CO) 3Cl] can be reduced by up to four electrons at modest potentials. These redox events have been characterized as the ReI/0 couple, and three ligand based reductions - two of which are localized on the BODIPY units. The ability of the BB2 ligand to serve as a non-innocent redox reservoir is manifest in an enhanced electrocatalysis with CO2 as compared to an unsubstituted Re-bipyridine complex lacking BODIPY units ([Re(bpy)(CO) 3Cl]). The second order rate constant for reduction of CO2 by [Re(BB2)(CO)3Cl] was measured to be k = 3400 M-1 s-1 at an applied potential of -2.0 V versus SCE, which is roughly three times greater than the corresponding unsubstituted Re-bipyridine homologue. Photophysical and photochemical studies were also carried out to determine if [Re(BB2)(CO)3Cl] was a competent platform for CO 2 reduction using visible light. These experiments showed that this complex supports unusual excited state dynamics that precludes efficient CO 2 reduction and are distinct from those that are typically observed for fac-ReI(CO)3 complexes.

Evaluation of Tris-Bipyridine Chromium Complexes for Flow Battery Applications: Impact of Bipyridine Ligand Structure on Solubility and Electrochemistry

Cabrera, Pablo J.,Yang, Xingyi,Suttil, James A.,Brooner, Rachel E. M.,Thompson, Levi T.,Sanford, Melanie S.

, p. 10214 - 10223 (2015)

This report describes the design, synthesis, solubility, and electrochemistry of a series of tris-bipyridine chromium complexes that exhibit up to six reversible redox couples as well as solubilities approaching 1 M in acetonitrile. We have systematically modified both the ligand structure and the oxidation state of these complexes to gain insights into the factors that impact solubility and electrochemistry. The results provide a set of structure-solubility-electrochemistry relationships to guide the future development of electrolytes for nonaqueous flow batteries. In addition, we have identified a promising candidate from the series of chromium complexes for further electrochemical and battery assessment.

Synthesis and characterisation of poly(bipyridine)ruthenium complexes as building blocks for heterosupramolecular arrays

Schwalbe, Matthias,Schaefer, Bernhard,Goerls, Helmar,Rau, Sven,Tschierlei, Stefanie,Schmitt, Michael,Popp, Juergen,Vaughan, Gavin,Henry, William,Vos, Johannes G.

, p. 3310 - 3319 (2008)

Poly(bipyridine)ruthenium complexes with carboxylate anchor groups are key components in dye-sensitised solar cells. In this contribution, an improved microwave-assisted synthetic procedure is presented for the important building block [RuCl2(dcmb)2] (dcmb = 4,4′-dimethoxycarbonyl- 2,2′-bipyridine), which results in short reaction times and high purity. The methyl esters are easily deprotected to give free carboxylate functions. In addition, a full structural, spectral and electrochemical characterisation of a series of complexes with the general formula [Ru(dcmb)3-n(tbbpy) n](PF6)2 with n = 0-3 and tbbpy = 4,4′-di-tert-butyl-2,2′-bipyridine is presented. The location of the lowest-energy metal-to-ligand charge transfer (MLCT) excited state is investigated by resonance Raman spectroscopy for selected complexes. The results obtained indicate that the nature of the excited state that is populated is dependent on the excitation wavelength. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

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