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366-18-7 Usage

Chemical Properties

White to light red crystalline powder. Soluble in ethanol, ether, benzene, chloroform and petroleum ether, 1 part of this product is about 200 parts of water.

Uses

Different sources of media describe the Uses of 366-18-7 differently. You can refer to the following data:
1. A high-affinity chelator of iron. A reagent used for the determination of iron.
2. 2,2'-bipyridine acts as a bidentate chelating ligand which form complexes with transition metal ions and shows antifungal, antibacterial and antiviral activity. It is used for the colorimetric determination of iron as well as oxidation reduction indicators to confirm the presence of ferrous ion in soils. It forms complexes with ruthenium and platinum, exhibit intense luminescence, which may have practical applications. Copper(I) bipyridine complexes involved in the oxidation of alcohols under aerobic conditions.

Definition

ChEBI: 2,2'-bipyridine is a bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'. It has a role as a ferroptosis inhibitor and a chelator.

Preparation

2,2'-bipyridine is synthesized by the reaction of pyridine with ferric chloride. Take 70g of anhydrous pyridine and mix with 13g of anhydrous ferric chloride, heat and react at 300℃ in a sealed tube for about 35h. After cooling, the reactant solidified into red-black crystals, the sealing tube was opened, and the red-black solution of the solid was washed out with a small amount of hot water. The oily impurities were removed by extraction with ether. After neutralization with sodium bicarbonate, excess pyridine was removed by heating with steam. The mixture was then made strongly basic, and the 2,2'-bipyridine was distilled off with steam.

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 5567, 1978 DOI: 10.1021/ja00485a053Synthesis, p. 564, 1986 DOI: 10.1055/s-1986-31705

General Description

2,2′-Bipyridyl, is a symmetrical bipyridine commonly used as a neutral ligand for complexation with metal ions. The molecule is planar with trans-conformation and crystallizes in the monoclinic crystal system.

Biochem/physiol Actions

Metalloprotease inhibitor, high-affinity chelator of iron; may inhibit Fe2+ containing enzymes at 10?8?M.

Safety Profile

Poison by ingestion,subcutaneous, and intraperitoneal routes. Experimentalteratogenic data. Questionable carcinogen withexperimental tumorigenic data. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.

Purification Methods

2,2'-Bipyridyl crystallises from hexane, or EtOH, or (after charcoal treatment of a CHCl3 solution) from pet ether. Also, it precipitates from a concentrated solution in EtOH by addition of H2O. Dry it in a vacuum over P2O5. It can be further purified by chromatography on Al2O3 or by sublimation. UV (EtOH): at 280nm (log 4.13). max [Airoldi et al. J Chem Soc, Dalton Trans 1913 1986, Beilstein 23 H 199, 23/8 V 16.]

Check Digit Verification of cas no

The CAS Registry Mumber 366-18-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,6 and 6 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 366-18:
(5*3)+(4*6)+(3*6)+(2*1)+(1*8)=67
67 % 10 = 7
So 366-18-7 is a valid CAS Registry Number.

366-18-7 Well-known Company Product Price

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

  • (B0468)  2,2'-Bipyridyl  >99.0%(T)

  • 366-18-7

  • 25g

  • 230.00CNY

  • Detail
  • TCI America

  • (B0468)  2,2'-Bipyridyl  >99.0%(T)

  • 366-18-7

  • 100g

  • 580.00CNY

  • Detail
  • TCI America

  • (B0468)  2,2'-Bipyridyl  >99.0%(T)

  • 366-18-7

  • 500g

  • 2,120.00CNY

  • Detail
  • Alfa Aesar

  • (A15782)  2,2'-Bipyridine, 99+%   

  • 366-18-7

  • 25g

  • 488.0CNY

  • Detail
  • Alfa Aesar

  • (A15782)  2,2'-Bipyridine, 99+%   

  • 366-18-7

  • 100g

  • 1576.0CNY

  • Detail
  • Alfa Aesar

  • (A15782)  2,2'-Bipyridine, 99+%   

  • 366-18-7

  • 500g

  • 5556.0CNY

  • Detail
  • Alfa Aesar

  • (30569)  2,2'-Bipyridine, ACS, 98%   

  • 366-18-7

  • 10g

  • 167.0CNY

  • Detail
  • Alfa Aesar

  • (30569)  2,2'-Bipyridine, ACS, 98%   

  • 366-18-7

  • 50g

  • 637.0CNY

  • Detail
  • Alfa Aesar

  • (30569)  2,2'-Bipyridine, ACS, 98%   

  • 366-18-7

  • 250g

  • 2538.0CNY

  • Detail
  • Fluka

  • (14454)  2,2′-Bipyridyl  redox indicator, for spectrophotometric det. of Fe, ≥99.0%

  • 366-18-7

  • 14454-5G

  • 228.15CNY

  • Detail
  • Fluka

  • (14454)  2,2′-Bipyridyl  redox indicator, for spectrophotometric det. of Fe, ≥99.0%

  • 366-18-7

  • 14454-25G

  • 776.88CNY

  • Detail
  • Fluka

  • (14454)  2,2′-Bipyridyl  redox indicator, for spectrophotometric det. of Fe, ≥99.0%

  • 366-18-7

  • 14454-100G

  • 1,946.88CNY

  • Detail

366-18-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,2'-bipyridine

1.2 Other means of identification

Product number -
Other names 2,2'-BIPYRIDINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Paint additives and coating additives not described by other categories
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:366-18-7 SDS

366-18-7Synthetic route

2-bromo-pyridine
109-04-6

2-bromo-pyridine

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 210℃; for 24h; Catalytic behavior; Solvent; Reagent/catalyst;100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride In dimethyl sulfoxide at 120℃; for 8h;96%
With bis(triphenylphosphine)nickel(II) chloride; sodium hydride; triphenylphosphine; zinc In toluene at 70 - 90℃; Ullmann-type coupling;93%
ethyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel
115981-39-0

ethyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

1,1,1,3,3,3-hexafluoropropan-2-yl propionate
24499-62-5

1,1,1,3,3,3-hexafluoropropan-2-yl propionate

Conditions
ConditionsYield
With carbon monoxide In tetrahydrofuran Addn. of CO (ambient pressure) to metal complex (THF, room temp.), stirring (2.5 h).; Trap-to-trap distn., GLC anal.;A 100%
B 97%
methyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel
115981-38-9

methyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

1,1,1,3,3,3-hexafluoropropan-2-yl acetate
6919-79-5

1,1,1,3,3,3-hexafluoropropan-2-yl acetate

Conditions
ConditionsYield
With carbon monoxide In tetrahydrofuran Addn. of CO (ambient pressure) to metal complex (THF, room temp.), stirring (2.5 h).; Trap-to-trap distn., GLC anal.;A 100%
B 98%
2-iodopyridine
5029-67-4

2-iodopyridine

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; johnphos; bis(dibenzylideneacetone)-palladium(0) In 1-methyl-pyrrolidin-2-one at 20℃; for 12h;99%
With sodium hydroxide; triethylammonium formate; zinc In methanol for 2.5h; Heating;92%
With sodium hydroxide; ammonium formate; zinc In methanol for 2.5h; Heating;90%
2-chloropyridine
109-09-1

2-chloropyridine

C10H13BNO3(1-)*C16H36N(1+)

C10H13BNO3(1-)*C16H36N(1+)

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With (2-hydroxyethyl)(methyl)amine; copper(l) iodide; dichloro(1,3-bis(dicyclohexylphosphino)propane)palladium In N,N-dimethyl-formamide at 100℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;99%
2,2'-bipyridyl N-oxide
33421-43-1

2,2'-bipyridyl N-oxide

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With (4,4′-di-tert-butyl-2,2′-bipyridine)bis[(2-pyridinyl)phenyl]iridium(III) hexafluorophosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 3h; Inert atmosphere; Irradiation; chemoselective reaction;98%
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; hydrazine hydrate In dimethyl sulfoxide at 20℃; for 27h; Inert atmosphere; Irradiation; chemoselective reaction;96%
With N-Bromosuccinimide In chlorobenzene at 150℃; for 17h;20 %Spectr.
2-Cyanopyridine
100-70-9

2-Cyanopyridine

acetylene
74-86-2

acetylene

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 170℃; for 16h;97.4%
With cyclooctadienyl cobalt at 140 - 190℃; for 2h; Temperature; Autoclave;250 g
pyridine-2-carbonyl chloride
29745-44-6

pyridine-2-carbonyl chloride

N-butylamine
109-73-9

N-butylamine

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With dmap; copper(II) ethylacetoacetate; C26H36NP; silver(I) acetate In 1,2-dichloro-ethane at 90℃; for 8h; Reagent/catalyst;96.7%
2-chloropyridine
109-09-1

2-chloropyridine

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 12h; Reagent/catalyst; Ullmann Condensation; Inert atmosphere;96%
With aluminum oxide; nickel(II) chloride hexahydrate; sodium hydroxide; zinc In methanol; water at 50℃; for 3h; Reagent/catalyst; Temperature;95%
With manganese; nickel(II) bromide trihydrate In N,N-dimethyl-formamide at 20 - 60℃; for 20h; Inert atmosphere;86%
[2,2']bipyridinyl 1,1'-dioxide
7275-43-6

[2,2']bipyridinyl 1,1'-dioxide

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With titanium tetrachloride; tin(ll) chloride In benzene for 0.5h; Ambient temperature;95%
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;90%
With sodium hypophosphite; palladium on activated charcoal In acetic acid at 60℃; for 1h;90%
methyl 4-iodobenzoate
619-44-3

methyl 4-iodobenzoate

2-trimethylstannylpyridine
13737-05-8

2-trimethylstannylpyridine

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

4-pyridin-2-yl-benzoic acid methyl ester
98061-21-3

4-pyridin-2-yl-benzoic acid methyl ester

Conditions
ConditionsYield
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran Heating;A n/a
B 95%
cis-dichlorobis(2,2′-bipyridine)ruthenium(II)
345911-20-8, 19542-80-4, 158060-65-2, 34795-02-3, 15746-57-3

cis-dichlorobis(2,2′-bipyridine)ruthenium(II)

{Ag(2,2'-bipyridine)2}ClO4
86783-78-0

{Ag(2,2'-bipyridine)2}ClO4

sodium perchlorate

sodium perchlorate

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

{ruthenium(II) (2,2'-bipyridine)3}(ClO4)2*H2O

{ruthenium(II) (2,2'-bipyridine)3}(ClO4)2*H2O

Conditions
ConditionsYield
In methanol byproducts: AgCl; heated to reflux for 15 min; cooled, filtered, concd., addn. of an aq. soln. of NaClO4, pptn. filtered off, washed with diethyl ether, recrystn. (water or water-methanol 9:1); elem. anal.;A n/a
B 95%
3-(pyridin-2-yl)-1,2,4-triazine
30091-53-3

3-(pyridin-2-yl)-1,2,4-triazine

vinyl caprate
4704-31-8

vinyl caprate

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
Aza-Diels-Alder reaction;93.3%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

phenylboronic acid
98-80-6

phenylboronic acid

A

2-phenylpyridine
1008-89-5

2-phenylpyridine

B

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate In water at 100℃; for 4h; Suzuki Coupling; Inert atmosphere; Green chemistry;A 92%
B n/a
With 1-(4-bromobenzyl)-3-(4-chlorobenzyl)benzimidazolium chloride; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.166667h; Reagent/catalyst; Suzuki-Miyaura Coupling; Microwave irradiation;A 67.0 %Spectr.
B 27.2 %Spectr.
2-chloropyridine
109-09-1

2-chloropyridine

2-pyridylboronic acid glycol ester

2-pyridylboronic acid glycol ester

trans-di-μ-acetato-bis[2-[bis(1,1 -dimethylethyl)phosphino]-2-methylpropyl-C,P]dipalladium

trans-di-μ-acetato-bis[2-[bis(1,1 -dimethylethyl)phosphino]-2-methylpropyl-C,P]dipalladium

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With potassium hydroxide; tetrabutyl-ammonium chloride; lithium chloride In tetrahydrofuran; ethanol91%
cis-dichlorobis(2,2′-bipyridine)ruthenium(II)
345911-20-8, 19542-80-4, 158060-65-2, 34795-02-3, 15746-57-3

cis-dichlorobis(2,2′-bipyridine)ruthenium(II)

Ag(2,2'-bipyridine)2NO3

Ag(2,2'-bipyridine)2NO3

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

{Ru(2,2'-bipyridine)3}(NO3)2*6H2O

{Ru(2,2'-bipyridine)3}(NO3)2*6H2O

Conditions
ConditionsYield
With NaNO3 In methanol byproducts: AgCl; heated to reflux for 15 min; cooled, filtered, concd., addn. of an aq. soln. of NaNO3, pptn. filtered off, washed with diethyl ether, recrystn. (water or water-methanol 9:1); elem. anal.;A n/a
B 90%
2-tri-n-butylstannylpyridine
17997-47-6

2-tri-n-butylstannylpyridine

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With palladium diacetate; copper dichloride In tetrahydrofuran at 23℃; for 1h;89%
With iodine; copper dichloride In N,N-dimethyl-formamide at 100℃; for 4h;85%
With bis(η3-allyl-μ-chloropalladium(II)); N-(2-(diphenylphosphino)phenyl)methylene benzenamine In N,N-dimethyl-formamide at 70℃; for 72h;79%
With air; Pd-organostannane In N,N-dimethyl-formamide at 70℃; for 72h;79%
3-(pyridin-2-yl)-1,2,4-triazine
30091-53-3

3-(pyridin-2-yl)-1,2,4-triazine

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
In xylene at 90 - 120℃; Aza-Diels-Alder reaction;88.2%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

Glyoxal
131543-46-9

Glyoxal

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
88.2%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
88.2%
Phenylselenyl chloride
5707-04-0

Phenylselenyl chloride

tris(2-pyridyl)phosphine oxide
26437-49-0

tris(2-pyridyl)phosphine oxide

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

5-phenylseleno-2,2'-bipyridyl

5-phenylseleno-2,2'-bipyridyl

Conditions
ConditionsYield
In methanol at 20℃; for 24h;A 12%
B 88%
In methanol at 20℃; for 24h;A 36%
B 57%
pyridin-2-ylboronic acid
197958-29-5

pyridin-2-ylboronic acid

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With palladium diacetate at 20℃; for 0.5h;87%
With potassium phosphate In 1,4-dioxane at 85℃; for 3h; Catalytic behavior; Suzuki Coupling; Green chemistry;82%
With nano-CuO-grafted triazine-functionalized covalent organic framework In methanol at 60℃; Catalytic behavior;59%
[(1-phenyl-3-methyl-4-(trimethylacetyl)pyrazol-5-one)3(2,2'-bipyridine)gadolinium(III)]*H2O

[(1-phenyl-3-methyl-4-(trimethylacetyl)pyrazol-5-one)3(2,2'-bipyridine)gadolinium(III)]*H2O

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

[(1-phenyl-3-methyl-4-(trimethylacetyl)pyrazol-5-one)3gadolinium(III)]

[(1-phenyl-3-methyl-4-(trimethylacetyl)pyrazol-5-one)3gadolinium(III)]

Conditions
ConditionsYield
In neat (no solvent) heated at 200°C under vacuum for 1 h; temperature increased to 300°C, and the complex sublimed over 5 h, resublimed (300°C, 1E-7 mbar), elem. anal.;A n/a
B 85%
(pyridin-2-yl)magnesium bromide
21970-13-8

(pyridin-2-yl)magnesium bromide

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With lithium perchlorate; palladium diacetate In toluene at 100℃; for 15h; Reagent/catalyst; Inert atmosphere;85%
With 4,4'-di-tert-butylbiphenyl; lithium; iron(II) chloride In tetrahydrofuran; diethyl ether at 20℃; for 4h; Inert atmosphere;75%
With C19H3F17 at 60℃; for 24h; Schlenk technique; Inert atmosphere;44%
benzyltri(2-(4-methylpyridyl))phosphonium bromide
126963-91-5

benzyltri(2-(4-methylpyridyl))phosphonium bromide

A

picoline
108-89-4

picoline

B

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

C

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

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

Conditions
ConditionsYield
With hydrogenchloride In water for 0.5h; Product distribution; Ambient temperature; variation of pH, temp. and time;A 17%
B n/a
C 84%
2-acetylpyridine
1122-62-9

2-acetylpyridine

Trimethylenediamine
109-76-2

Trimethylenediamine

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With oxygen; palladium diacetate; toluene-4-sulfonic acid In tetrahydrofuran for 12h; Reflux;84%
With hydrogenchloride; iodine; oxygen In dimethyl sulfoxide at 80℃; for 4h;82%
With oxygen; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid In hexan-1-ol at 110℃; for 24h; Sealed tube; Schlenk technique;27%
2-iodopyridine
5029-67-4

2-iodopyridine

A

pyridine
110-86-1

pyridine

B

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 12h; Inert atmosphere;A 16.5%
B 83.5%
2-pyridyllithium
17624-36-1

2-pyridyllithium

tris(2-pyridyl)phosphine oxide
26437-49-0

tris(2-pyridyl)phosphine oxide

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
In tetrahydrofuran for 5h; Heating;82%
2,2′-sulfinyldipyridine
92686-20-9

2,2′-sulfinyldipyridine

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With phenyllithium In tetrahydrofuran at -78℃; for 0.25h;A 82%
B 53%
phenyllithium
591-51-5

phenyllithium

A

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With 2,2′-sulfinyldipyridine In tetrahydrofuran at -78℃; for 0.25h;A 82%
B 53%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

2,2'-bipyridyl N-oxide
33421-43-1

2,2'-bipyridyl N-oxide

Conditions
ConditionsYield
With water; dihydrogen peroxide; trifluoroacetic acid for 2h; Ambient temperature;100%
With dihydrogen peroxide; trifluoroacetic acid at 10 - 20℃; for 3h;100%
With dihydrogen peroxide In trifluoroacetic acid at 10 - 20℃; for 3h;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

6H-7,8-dihydropyrido<1,2-a:2,1-c><1,4>diazepine-5,9-diium dibromide
2895-98-9

6H-7,8-dihydropyrido<1,2-a:2,1-c><1,4>diazepine-5,9-diium dibromide

Conditions
ConditionsYield
In acetone Heating;100%
for 12h; Reflux;90%
In acetonitrile
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

tin(IV) chloride
7646-78-8

tin(IV) chloride

[SnCl4(2,2'-bipyridine)]

[SnCl4(2,2'-bipyridine)]

Conditions
ConditionsYield
In tetrachloromethane under N2; soln. of SnCl4 in CCl4 mixed with ligand (molar ratio 1:2); stirred for several h; filtered; solid washed with petroleum ether; dried in vac.; stored in desiccator over CaCl2; elem. anal.;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

A

tetracarbonyl(2,2'-bipyridine)molybdenum
15668-64-1

tetracarbonyl(2,2'-bipyridine)molybdenum

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

diphenylboronchloride
3677-81-4

diphenylboronchloride

(C5H4N)2B(C6H5)2(1+)*Cl(1-)={(C5H4N)2B(C6H5)2}Cl
14075-86-6

(C5H4N)2B(C6H5)2(1+)*Cl(1-)={(C5H4N)2B(C6H5)2}Cl

Conditions
ConditionsYield
In benzene100%
In nitrobenzene78%
In not given
In not given
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

brominepentafluoride * α,α'-bipyridine

brominepentafluoride * α,α'-bipyridine

Conditions
ConditionsYield
In trichlorofluoromethane addn. of CCl3F to 1.00 mmol BrF5 at -78°C; dissolving; addn. of 1 mmol C5H4NC5H4N at -45°C; pptn.; heating to -40°C in 2h; filtration;; washing twice with CCl3F at -40°C; drying in high vac. at -30°C;;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

molybdenium(II) acetate dimer

molybdenium(II) acetate dimer

Mo2Cl4(C10H8N2)2
51731-39-6

Mo2Cl4(C10H8N2)2

Conditions
ConditionsYield
In tetrahydrofuran (Ar); stirring (1 h); washing (hexane), drying (vac.); elem. anal.;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

[palladium(II)(μ-Cl)(C6H4-2-PPh2NPh-κC,N)]2
690634-60-7

[palladium(II)(μ-Cl)(C6H4-2-PPh2NPh-κC,N)]2

silver perchlorate

silver perchlorate

palladium(II)(C6H4-2-PPh2NPh-κC,N)(2,2'-bipyridine)perchlorate
880545-59-5

palladium(II)(C6H4-2-PPh2NPh-κC,N)(2,2'-bipyridine)perchlorate

Conditions
ConditionsYield
In acetone byproducts: AgCl; suspn. of Pd complex in acetone treated with AgClO4, stirred at room temp. for 30 min (exclusion of light), filtered, treated with ligand, stirred at room temp. for 4 h; evapd., treated with Et2O, filtered, dried, elem. anal.;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Mo(OCH2CHC(CH3)2)2O2(C(2)H3CN)2
138606-31-2

Mo(OCH2CHC(CH3)2)2O2(C(2)H3CN)2

Mo(OCH2CHC(CH3)2)2O2(C5H4NC5H4N)
138606-32-3

Mo(OCH2CHC(CH3)2)2O2(C5H4NC5H4N)

Conditions
ConditionsYield
In [D3]acetonitrile determined by NMR;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

8Cu(1+)*8((CH3)2CH)3C6H2S(1-)=[CuS((CH3)2CH)3C6H2]8

8Cu(1+)*8((CH3)2CH)3C6H2S(1-)=[CuS((CH3)2CH)3C6H2]8

[CuS((CH3)2CH)3C6H2]4((C5H4N)2)2

[CuS((CH3)2CH)3C6H2]4((C5H4N)2)2

Conditions
ConditionsYield
In toluene Ar atm.; stirring (10 min); concn., addn. of hexane, crystn. (-30°C), filtn., drying (40°C, vac.); elem. anal.;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

6Cu(1+)*6((CH3)2CH)3C6H2Se(1-)=[CuSe((CH3)2CH)3C6H2]6

6Cu(1+)*6((CH3)2CH)3C6H2Se(1-)=[CuSe((CH3)2CH)3C6H2]6

[CuSe((CH3)2CH)3C6H2]2((C5H4N)2)2

[CuSe((CH3)2CH)3C6H2]2((C5H4N)2)2

Conditions
ConditionsYield
In toluene Ar atm.; stirring; concn., addn. of hexane, crystn. (-30°C), filtn., drying (40°C, vac.);100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

[Pd(η4-1,5-cyclooctadiene)(C6F5)2]
105286-78-0

[Pd(η4-1,5-cyclooctadiene)(C6F5)2]

cis-Pd(C6F5)2(2,2'-bipyridine)

cis-Pd(C6F5)2(2,2'-bipyridine)

Conditions
ConditionsYield
In tetrahydrofuran Pd-complex reacted with ligand in THF, according to a) C. De Haro, G. Garcia, G. Sanchez and G. Lopez, J. Chem. Res. (S), 1986, 119; b) P. Espinet, J. M. Martinez-Ilarduya, C. Perez-Briso, A. L. Casado and A. M. Alonso, J. Organomet. Chem., 1998, 551, 9;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

[Ir(III)(η5-pentamethylcyclopentadienyl)(H2O)3](SO4)
254734-81-1

[Ir(III)(η5-pentamethylcyclopentadienyl)(H2O)3](SO4)

[Ir(III)Cp*(bpy)(OH2)](SO4)
519140-49-9

[Ir(III)Cp*(bpy)(OH2)](SO4)

Conditions
ConditionsYield
In water at 20℃; for 12h;100%
In water at 20℃; for 18h; Inert atmosphere;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

[Co(dibenzoylmethanato)2(H2O)2]
53642-37-8, 21417-64-1

[Co(dibenzoylmethanato)2(H2O)2]

[Co(1,3-diphenylpropane-1,3-dionate)2(2,2'-bipyridine)]
163733-16-2

[Co(1,3-diphenylpropane-1,3-dionate)2(2,2'-bipyridine)]

Conditions
ConditionsYield
In tetrahydrofuran 2,2'-bipyridine (0.15 mmol) added to soln. of Co complex (0.15 mmol) (stirring); stirred (room temp., 1 h); evapd. slolwy (room temp.); elem. anal.;100%
pyridine
110-86-1

pyridine

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

[(99)technetium(I)(carbonyl)3(H2O)3]
163932-31-8

[(99)technetium(I)(carbonyl)3(H2O)3]

C18H13N3O3(99)Tc(1+)*Cl(1-)

C18H13N3O3(99)Tc(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: [2,2]bipyridinyl; [(99)technetium(I)(carbonyl)3(H2O)3] With hydrogenchloride; sodium chloride In water at 40℃; for 0.5h; pH=6; Inert atmosphere;
Stage #2: pyridine In water at 40℃; for 0.333333h; Inert atmosphere;
100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

(2,2'-bipyridinium) hexafluorosilicate

(2,2'-bipyridinium) hexafluorosilicate

Conditions
ConditionsYield
With fluorosilicic acid In methanol; water at 20℃;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

niobium pentafluoride
7783-68-8

niobium pentafluoride

trimethylsilylazide
4648-54-8

trimethylsilylazide

[NbF4(2,2’-bipy)2][Nb(N3)6]

[NbF4(2,2’-bipy)2][Nb(N3)6]

Conditions
ConditionsYield
In acetonitrile at -196 - 20℃; for 6h;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

niobium pentafluoride
7783-68-8

niobium pentafluoride

trimethylsilylazide
4648-54-8

trimethylsilylazide

[Nb(N3)4(2,2’-bipy)2][Nb(N3)6]
1628265-29-1

[Nb(N3)4(2,2’-bipy)2][Nb(N3)6]

Conditions
ConditionsYield
In acetonitrile at -196 - 20℃; for 6h;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

tantalum pentafluoride
7783-71-3

tantalum pentafluoride

trimethylsilylazide
4648-54-8

trimethylsilylazide

[TaF4(2,2’-bipy)2][Ta(N3)6]

[TaF4(2,2’-bipy)2][Ta(N3)6]

Conditions
ConditionsYield
In acetonitrile at -196 - 20℃; for 6h;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

tantalum pentafluoride
7783-71-3

tantalum pentafluoride

trimethylsilylazide
4648-54-8

trimethylsilylazide

[Ta(N3)4(2,2’-bipy)2][Ta(N3)6]
1628265-31-5

[Ta(N3)4(2,2’-bipy)2][Ta(N3)6]

Conditions
ConditionsYield
In acetonitrile at -196 - 20℃; for 6h;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

vanadium(V) oxoazide

vanadium(V) oxoazide

[(2,2’-bipyridine)VO(N3)3]

[(2,2’-bipyridine)VO(N3)3]

Conditions
ConditionsYield
In acetonitrile for 0.25h; Sealed tube;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

C44H68ClIr2N8O8(1+)*C32H12BF24(1-)

C44H68ClIr2N8O8(1+)*C32H12BF24(1-)

sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate
79060-88-1

sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate

C32H42IrN6O4(1+)*C32H12BF24(1-)

C32H42IrN6O4(1+)*C32H12BF24(1-)

Conditions
ConditionsYield
at 19.84℃; for 0.25h;100%
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

[Ru(1,10-phenanthroline)2Cl2]

[Ru(1,10-phenanthroline)2Cl2]

(2,2’-bipyridine)bis(1,10-phenanthroline)ruthenium(II)hexafluorophosphate

(2,2’-bipyridine)bis(1,10-phenanthroline)ruthenium(II)hexafluorophosphate

Conditions
ConditionsYield
In ethylene glycol at 160℃; for 0.25h; Microwave irradiation;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

antimony(III) fluoride
7783-56-4

antimony(III) fluoride

Sb(CN)3(2,2’-bipyridine)

Sb(CN)3(2,2’-bipyridine)

Conditions
ConditionsYield
In acetonitrile at -196 - 20℃; for 1h; Autoclave;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3CN(1-)*C10H8N2*As(3+)

3CN(1-)*C10H8N2*As(3+)

Conditions
ConditionsYield
With arsenic(III) fluoride In acetonitrile at -196 - 20℃; for 1h; Autoclave;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

indium(III) trifluoride

indium(III) trifluoride

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

[(2,2’-bipyridine)In(CN)3]*2,2’-bipyridine

[(2,2’-bipyridine)In(CN)3]*2,2’-bipyridine

Conditions
ConditionsYield
In acetonitrile at -196 - 20℃; for 8h; Autoclave;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

lithium oxalate
553-91-3

lithium oxalate

copper(II) bis(trifluoromethanesulfonate)
34946-82-2

copper(II) bis(trifluoromethanesulfonate)

[Cu2(2,2'-bipyridine)2(H2O)2(C2O4)](CF3SO3)2

[Cu2(2,2'-bipyridine)2(H2O)2(C2O4)](CF3SO3)2

Conditions
ConditionsYield
In water100%

366-18-7Relevant articles and documents

INVESTIGATION OF THE INTERACTION OF PYRIDINE WITH THE SURFACE OF LAMINAR SILICATES BY THE METHOD OF OPTICAL ELECTRONIC SPECTROSCOPY.

Sivalov,Tarasevich

, p. 214 - 218 (1981)

A study of the nature of the active sites on the surface of laminar silicates and an attempt to identify those that are responsible for the observed conversion of sorbed pyridine on the surface of laminar silicate to more complex formations characterized by a rather developed system of conjugated pi -bonds are discussed.

Cartwright et al.

, p. 211,212, 218, 219 (1979)

-

Dearmond et al.

, p. 3388,3391 (1979)

-

Cation-Assisted Ligand Photosubstitution in Transition-Metal Complexes. Photoreactions of Ru(bpy)32+ with Ag+ in Acetonitrile

Foreman, T. K.,Bonilha, J. B. S.,Whitten, D. G.

, p. 3436 - 3439 (1982)

Irradiation of Ru(bpy)32+ in the presence of Ag+ in acetonitrile leads to the photosubstitution product Ru(bpy)2(CH3CN)22+.The reaction does not occur in the absence of Ag+ or acetonitrile; although Ag+ quenches the luminescent MLCT state of Ru(bpy)32+, a kinetic analysis indicates the photosubstitution does not originate from this excited state.The most reasonable mechanism for the process involves decay of the MLCT state via a d-d excited state to a ligand-labilized intermediate which is interpreted by Ag+ in a process which assists the substitution by removal of a bpy ligand.This mechanism is thus parallel to anion-induced substitution reactions which evidently proceed via competitive anion-ligand capture of the same or similar intermediates.

Acid directed in situ oxidation and decarboxylation of 4,4′,6, 6′-tetra-methyl-2,2′-bipyridine: Synthesis and structural characterisation of 4,4′,6-tri-carboxy-2,2′-bipyridine and its copper(II) coordination polymer

Kelly, Niamh R.,Goetz, Sandrine,Hawes, Chris S.,Kruger, Paul E.

, p. 102 - 109 (2013)

The reaction of either 4,4′,6,6′-tetramethyl-2,2′- bipyridine, L, or 4,4′,6,6′-tetracarboxy-2,2′-bipyridine, H4L, with Cu(OAc)2·H2O under acidic hydrothermal conditions (50:1 H2O/HNO3; 160 °C) led to the formation of crystalline {[Cu(HL′)(H2O)]·H 2O}, 1, which was structurally characterised to identify H 3L′ as 4,4′,6-tricarboxy-2,2′-bipyridine. Clearly, in situ mono-decarboxylation of a tetracarboxylic acid ligand gave the tricarboxy-analogue, H3L′. The structure of 1 consists of a 1D coordination polymer that cross-links through hydrogen-bonding between adjacent carboxylic acid and carboxylate groups, as well as through an aqua ligand and lattice water molecule, to form a densely interconnected 3D network. Regioselective mono-decarboxylation of L or H4L at the 6′-carboxylic acid position may also be affected by heating L or H 4L in acidic solution under hydrothermal conditions (2:1 H 2O/HNO3; 160°C) to yield crystalline 4,4′,6-tricarboxy-2,2′-bipyridinium nitrate hydrate {[H 4L′][NO3]·H2O}, 2, which was also structural characterised. The structure of 2 features an array of hydrogen-bonding interactions that generate a 3D network. More forceful heating of the acidic solution at 180°C led to double decarboxylation and the formation of 4,4′-dicarboxy-2,2′-bipyridine, whereas heating at 200°C led to total decarboxylation and the formation of 2,2′- bipyridine. Details of the structures of 1 and 2 along with their synthesis are discussed.

DIMER FORMATION IN THE REACTION OF ARYL HALIDES CATALYZED BY NICKEL COMPLEXES

Budnikova, Yu. G.,Kargin, Yu. M.,Yanilkin, V. V.

, p. 1299 - 1300 (1992)

The synthesis of diaryls catalyzed by electrochemically generated zero-valent nickel with 2,2'-dipyridyl as the ligand was carried out from aryl halides in high yield.Feasibility was demonstrated for synthesizing the catalyst itself by the anodic dissolution of nickel in the presence of 2-bromopyridine in a diaphragmless cell.Keywords: synthesis, diaryls, aryl halides.

Phototoxicity of strained Ru(II) complexes: Is it the metal complex or the dissociating ligand?

Azar, Daniel F.,Audi, Hassib,Farhat, Stephanie,El-Sibai, Mirvat,Abi-Habib, Ralph J.,Khnayzer, Rony S.

, p. 11529 - 11532 (2017)

A photochemically dissociating ligand in Ru(bpy)2(dmphen)Cl2 [bpy = 2,2′-bipyridine; dmphen = 2,9-dimethyl-1,10-phenanthroline] was found to be more cytotoxic on the ML-2 Acute Myeloid Leukemia cell line than Ru(bpy)2(H2O)22+ and prototypical cisplatin. Our findings illustrate the potential potency of diimine ligands in photoactivatable Ru(ii) complexes.

Ligand-free Stille cross-coupling reaction using Pd/CaCO3 as catalyst reservoir

Coelho, Aline V.,de Souza, Andréa Luzia F.,de Lima, Paulo G.,Wardell, James L.,Antunes

, p. 7671 - 7674 (2007)

Stille reactions between halobenzenes and other substituted (hetero)arenes and tributylphenyltin were carried out in ethanol-water solution using Pd/CaCO3 as catalyst in a ligand-free system. The catalyst could be recycled three times without any loss of activity. The ethanol-water solution, after removal of the catalyst and extraction of the product, was found to have catalytic activity, thus showing the presence of soluble Pd(0)/Pd(II) species that can be regarded as the true catalysts.

Pincerlike manganese complex and preparation method thereof, related ligand and preparation method thereof, catalyst composition and application

-

Paragraph 0159-0165, (2021/07/31)

The invention discloses a pincerlike manganese complex, a preparation method thereof, a ligand for preparation, a preparation method of the ligand, a catalyst composition taking the complex as an active component and application of the catalyst composition. According to the pincerlike manganese complex, a cycloalkyl ring is introduced into a ligand framework, and by regulating and controlling the cyclic tension, flexibility and steric hindrance of the cycloalkyl ring, the reactivity and stability of the manganese metal center can be effectively adjusted, and the catalytic activity and substrate applicability of a manganese metal system are remarkably improved. The catalyst composition taking the pincerlike manganese complex as an active component has the advantages of high catalyst activity, wide substrate application range, mild reaction conditions and the like in the process of preparing quinoline or pyridine derivatives by catalyzing dehydrogenation coupling reaction of o-amino aromatic alcohol or gamma-amino alcohol, ketone or secondary alcohol; and the synthesis advantages of low cost and stable performance are embodied, the operation is simple, and the yield is high.

Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts

Horan, Alexandra M.,Duong, Vincent K.,McGarrigle, Eoghan M.

supporting information, p. 9089 - 9093 (2021/11/30)

Herein are reported ligand-coupling reactions of Grignard reagents with pyridylsulfonium salts. The method has wide functional group tolerance and enables the formation of bis-heterocycle linkages, including 2,4′-, 2,3′-, and 2,2′-bipyridines, as well as pyridines linked to pyrimidines, pyrazines, isoxazoles, and benzothiophenes. The methodology was successfully applied to the synthesis of the natural products caerulomycin A and E.

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