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inquiryProduct name 5,5'-Dibromo-2,2'-bipyridine CAS 15862-18-7 Molecular Formula C10H6Br2N2 Molecular Weight 313.98 Appeara
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inquiry5,5'-Dibromo-2,2'-bipyridyl Basic information Product Name: 5,5'-Dibromo-2,2'-bipyridyl Synonyms: 5,5'-Dibromo-2,2'-bipyridyl;5,5'-Dibromo-2,2'-bipyridyl;5,5'-dibromo-2,2'-bipyridine;2,2'-Bipyridine,
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inquiry5,5'-Dibromo-2,2'-bipyridylAppearance:powder Storage:Refrigerator Package:Depended Application:15862-18-7 Transportation:by air or by sea
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[2,2]bipyridinyl
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
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
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
With bromine for 72h; Heating; Autoclave; | 85% |
2,5-dibromopyridine
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
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
5-bromo-2-(tri-n-butylstannyl)pyridine
A
5,5'-dibromo-2,2'-dipyridyl
B
5,5''-dibromo-2,2',6',2''-terpyridine
Conditions | Yield |
---|---|
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
5-bromo-2-(tri-n-butylstannyl)pyridine
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
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
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
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
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt at 100℃; for 20h; Irradiation; | 1.09 g |
A
5-bromo-2,2'-bipyridyl
B
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
With carbon dioxide; bromine at 250℃; |
2,6-Dibromopyridine
5-bromo-2-(tri-n-butylstannyl)pyridine
A
5,5'-dibromo-2,2'-dipyridyl
B
C10H6Br2N2
C
5,5''-dibromo-2,2',6',2''-terpyridine
Conditions | Yield |
---|---|
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
5-bromo-2-(tri-n-butylstannyl)pyridine
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
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
5-bromo-2-(trimethylstannyl)pyridine
A
5,5'-dibromo-2,2'-dipyridyl
B
C10H6BrIN2
C
5,5''-dibromo-2,2',6',2''-terpyridine
Conditions | Yield |
---|---|
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
5-bromo-2-(trimethylstannyl)pyridine
A
5,5'-dibromo-2,2'-dipyridyl
B
5,5''-dibromo-2,2',6',2''-terpyridine
Conditions | Yield |
---|---|
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
5-bromo-2-(tri-n-butylstannyl)pyridine
A
5,5'-dibromo-2,2'-dipyridyl
B
C10H6BrIN2
C
5,5''-dibromo-2,2',6',2''-terpyridine
Conditions | Yield |
---|---|
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
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
With triphenyl phosphite; palladium(II) acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; Inert atmosphere; |
3-Bromopyridine
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
1-pyrenylboronic acid
5,5’-di(pyren-1-yl)-2,2’-bipyridine
Conditions | Yield |
---|---|
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% |
bis(2,2'-bipyridine)osmium(II) dichloride
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
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
5,5'-dibromo-2,2'-dipyridyl
bis(2,2′-bipyridine)(5,5′-dibromo-2,2′-bipyridine)ruthenium(II) hexafluorophosphate
Conditions | Yield |
---|---|
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
trimethylsilylacetylene
5,5'-bis((trimethylsilyl)ethynyl)-2,2'-bipyridine
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
trans-dichlorobis(triphenylphosphine)palladium(II) In N,N-dimethyl-formamide at 110℃; for 6h; Stille coupling; | 95% |
5,5'-dibromo-2,2'-dipyridyl
5,5’-diiodo-2,2’-bipyridine
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
cis-[bis (1,10-phenanthroline) dichlororuthenium(II)]
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
1-trimethylsilyl-(4-trimethylstannyl)benzene
5,5'-bis(4-trimethylsilylphenyl)-2,2'-bipyridine
Conditions | Yield |
---|---|
With triphenyl-arsane; lithium chloride; palladium dichloride In N,N-dimethyl-formamide at 110℃; | 93% |
Conditions | Yield |
---|---|
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
rhenium(I) pentacarbonyl chloride
(5,5'-dibromo-2,2-bipyridine)rhenium(I) tricarbonyl chloride
Conditions | Yield |
---|---|
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
4-amino-phenol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
methyltrioxorhenium(VII)
Conditions | Yield |
---|---|
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
5,5'-dimethyl-6-ethynyl-2,2'-bipyridine
Conditions | Yield |
---|---|
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
phosphonic acid diethyl ester
2,2'bipyrid-4,4'-yldiphosphonic acid diethyl ester
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine In toluene at 110℃; for 6h; | 87% |
5,5'-dibromo-2,2'-dipyridyl
tetrakis(acetonitrile)copper(I) perchlorate
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5h; Inert atmosphere; Schlenk technique; | 86.1% |
5,5'-dibromo-2,2'-dipyridyl
[Ir(2-(2,4-difluorophenyl)pyridine(-1H))2(5,5'-dibromo-2,2'-bipyridine)][PF6]
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran Inert atmosphere; Reflux; | 85% |
5,5'-dibromo-2,2'-dipyridyl
1-(diallylethoxysilyl)-4-ethynylbenzene
5,5'-bis[4-(diallylethoxysilyl)phenylethynyl]-2,2'-bipyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); diisopropylamine In benzene for 40h; Inert atmosphere; Reflux; | 84% |
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 140℃; for 1.5h; Inert atmosphere; | 81.1% |
5,5'-dibromo-2,2'-dipyridyl
3,6,8-triphenylpyreneboric acid
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 10h; | 81% |
5,5'-dibromo-2,2'-dipyridyl
Conditions | Yield |
---|---|
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
phenylacetylene
Conditions | Yield |
---|---|
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% |
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