553-26-4

Basic information

• Product Name: 4,4'-Bipyridine
• Synonyms: 'LGC' (1608);GAMMA,GAMMA'-DIPYRIDYL;GAMMA,GAMMA-DIPYRIDYL;4, 4'-DIPYRIDINE;4,4'-DIPYRIDYL;4,4-DIPYRIDYL;4,4'-BIPYRIDINE;4,4-BIPYRIDINE
• CAS NO: 553-26-4
• Molecular Formula: C₁₀H₈N₂
• Molecular Weight: 156.18
• EINECS: 209-036-3
• Product Categories: Pyridines;Pyridines derivates;PYRIDINE;Viologens (Photochromic, Related Compounds);Functional Materials;Photochromic Compounds
• Mol File: 553-26-4.mol
• Article Data: 87

Chemical Properties

• Melting Point: 109-112 °C(lit.)
• Boiling Point: 305 °C(lit.)
• Flash Point: 304-305°C
• Appearance: Off-white to beige/Powder
• Density: 1.2814 (rough estimate)
• Refractive Index: 1.6057 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 4.5g/l
• PKA: pK1:3.17(+2);pK2:4.82(+1) (25°C)
• Water Solubility: slightly soluble
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents, strong acids.
• Merck: 14,3348
• BRN: 113176
• CAS DataBase Reference: 4,4'-Bipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bipyridine(553-26-4)
• EPA Substance Registry System: 4,4'-Bipyridine(553-26-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36/37/38-20/21-23/24/25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DW1760000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 553-26-4(Hazardous Substances Data)

Usage

Chemical Properties

off-white to tan powder

Uses

4,4'-Bipyridine is used in transition-metal complex catalyst chemistry for uniform polymerization, in luminescence chemistry and in spectrophotometric analysis. It plays an important role as a photosensitizer and luminescent material. It is also used as a precursor to paraquat viz. N,N'-dimethyl-4,4'-bipyridinium.

Definition

ChEBI: A bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'.

General Description

4,4′-Dipyridyl (BPY) is an organic linker mainly used in the preparation of coordination polymers. It is a pyridine derivative in which pyridyl groups can rotate along the carbon-carbon structure. It can be used as a catalyst for photoelectrochemical reduction.

Purification Methods

It crystallises from water, *benzene/pet ether, ethyl acetate and sublimes in vacuo at 70o. Also purify it by dissolving in 0.1M H2SO4 and twice precipitating by addition of 1M NaOH to pH 8. Then recrystallise it from EtOH. For the dihydrochloride see Viologen below. [Collman et al. J Am Chem Soc 109 4606 1987, Beilstein 23 H 800, 23 III/IV 1371, 23/8 V 28.]

Synthetic route

(4,4′-bipyridine){Ti(N[tBu](3,5-Me2C6H3))3}2 + iodine (7553-56-2) → 4,4'-bipyridine (553-26-4) + ITi(N[tBu](3,5-Me2C6H3))3

Conditions	Yield
In tetrahydrofuran for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;	A n/a B 100%

4,4'-bipyridine N,N'-dioxide (24573-15-7) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With titanium tetrachloride; tin(ll) chloride In benzene for 0.5h; Ambient temperature;	98%
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;	97%
With titanium tetrachloride; sodium iodide In acetonitrile at 20℃; for 0.0333333h;	95%
With sodium hypophosphite; palladium on activated charcoal In acetic acid at 60℃; for 1h;	92%
With sodium hydroxide; thiourea S,S-dioxide In ethanol at 80 - 85℃; for 1.5h;	81%

4,4'-bipyridine N-monoxide (39182-30-4) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With titanium tetrachloride; tin(ll) chloride In benzene for 0.5h; Ambient temperature;	96%
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;	94%

4-chlorpyridine hydrochloride (7379-35-3) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 12h; Ullmann Condensation; Inert atmosphere;	95%

4-bromopyridine hydrochloride (19524-06-2) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; Tetrakis(dimethylamino)ethylen In N,N-dimethyl-formamide at 50℃; for 6h;	92%
With Tetrakis(dimethylamino)ethylen; bis(benzonitrile)palladium(II) dichloride In N,N-dimethyl-formamide at 50℃; for 6h;	52%

4-bromopyridin (1120-87-2) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With tetraethylammonium tosylate; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide Ambient temperature; electrolysis;	91%
With indium; lithium chloride; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 2.5h;	90%
With manganese; zirconocene dichloride; (Me)2Dipyr(H)2*NiCl2; lithium chloride In 1,2-dimethoxyethane at 20℃; for 72h; Inert atmosphere;	87%

4-pyridylboronic acid (1692-15-5) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With potassium phosphate In 1,4-dioxane at 85℃; for 3h; Catalytic behavior; Suzuki Coupling; Green chemistry;	88%
With Cu(OH)x has been encapsulated over montmorillonite-KSF; air In methanol at 20℃; for 0.666667h; Green chemistry;	81%
With potassium acetate; silver(l) oxide In methanol at 40℃; for 36h;	78%

sodium pyridine-4-sulfinate (116008-37-8) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With di-tert-butyl peroxide; palladium diacetate In acetonitrile at 60℃; for 12h;	88%

4-Chloropyridine (626-61-9) → pyridine (110-86-1) + 4,4'-bipyridine (553-26-4)

Conditions	Yield
With 1,2-dimethoxyethane; NaH-tBuONa-Ni(OAc)2-PPh3 at 45℃; for 2h;	A 10 % Chromat. B 86%

4-Chloropyridine (626-61-9) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With nickel diacetate; triphenylphosphine; sodium t-butanolate In 1,2-dimethoxyethane at 45℃; for 2h;	86%
With triphenylphosphine; nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;	82%
With triphenylphosphine; nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;	82%
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); bis(pinacol)diborane; XPhos In ethanol at 20℃; for 8h;	72%
With N-benzyl-N,N,N-triethylammonium chloride; sodium formate; palladium on charcoal In methanol; water

4-iodopyridine (15854-87-2) + 4-pyridylboronic acid (1692-15-5) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With palladium diacetate; potassium carbonate In toluene at 80℃; Reagent/catalyst; Solvent;	86%
With sodium carbonate; potassium carbonate In toluene at 80℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere;

N,N'-dimethoxy-4,4'-bipyridyldiium bis(tetrafluoroborate) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With sodium hydroxide; L-homocysteine; sodium hydrogencarbonate In water for 1h; pH=11; Reflux;	85%

4-bromopyridin (1120-87-2) + 4-pyridylboronic acid (1692-15-5) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In water at 60 - 70℃; for 6h; Suzuki Coupling; Green chemistry;	85%
With palladium diacetate; potassium carbonate In toluene at 80℃; Reagent/catalyst;	82%
With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; sodium hydrogencarbonate In dichloromethane; toluene at 100℃; for 5h; Suzuki coupling; Reflux;	75%
With palladium diacetate; potassium carbonate In toluene at 80℃; for 6h; Reagent/catalyst; Inert atmosphere;

pyridin-4-yl trifluoromethanesulfonate (154446-99-8) + 4-pyridylboronic acid (1692-15-5) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In toluene at 80℃; for 6h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;	83%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In toluene at 80℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere;

pyridine (110-86-1) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With carbon dioxide; tetrabutylammonium perchlorate In acetonitrile at 20℃; Electrochemical reaction; Inert atmosphere;	80%
With magnesium In tetrahydrofuran at -196.15℃;	17%
With BDH laboratory sand; oxygen at 300℃; for 8h; in a glass Carius tube;	15%

4-bromopyridin (1120-87-2) → pyridine (110-86-1) + 4,4'-bipyridine (553-26-4)

Conditions	Yield
With 1,2-dimethoxyethane; NaH-tBuONa-Ni(OAc)2-PPh3 at 45℃; for 2h;	A 20 % Chromat. B 78%

4-Chloropyridine (626-61-9) + 4-pyridylboronic acid (1692-15-5) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With palladium diacetate; potassium carbonate In toluene at 80℃;	77%
With palladium diacetate; potassium carbonate In toluene at 80℃; for 6h; Inert atmosphere;

2-bromo-pyridine (109-04-6) → 4-(2-pyridyl)pyridine (581-47-5) + [2,2]bipyridinyl (366-18-7) + 4,4'-bipyridine (553-26-4)

Conditions	Yield
With lithium In tetrahydrofuran for 10h; ultrasonic;	A 5% B 65% C 30%

triphenyl(pyridin-4-yl)phosphonium trifluoromethanesulfonate (113964-72-0) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 100℃; for 14h;	65%

potassium (pyridin-4-yl)trifluoroborate → 4,4'-bipyridine (553-26-4)

Conditions	Yield
With potassium acetate; silver(l) oxide In water at 70℃; for 48h;	65%

4-iodopyridine (15854-87-2) + triethoxy(thiophen-2-yl)silane (17984-89-3) → 4,4'-bipyridine (553-26-4) + 4-thiophen-2-yl-pyridine (21298-54-4)

Conditions	Yield
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 12h; Hiyama Coupling; Inert atmosphere;	A n/a B 56%

isoalantolactone (470-17-7) + 4-iodopyridine (15854-87-2) → 4,4'-bipyridine (553-26-4) + (4aS,8aR,9aS)-8a-methyl-5-methylidene-3-[(pyridin-4-yl)methyl]-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one + (3aR,4aS,8aR,9aR,E)-8a-methyl-5-methylidene-3-[(pyridin-4-yl)methylidene]decahydronaphtho[2,3-b]furan-2(3H)-one

Conditions	Yield
With palladium diacetate; caesium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 0 - 120℃; for 16h; Heck Reaction; Inert atmosphere; Molecular sieve; Sealed tube;	A n/a B 56% C 29%

4-(phenylsulfonyl)pyridine (39574-19-1) + laurylmagnesium bromide (15890-72-9) → 4,4'-bipyridine (553-26-4) + 4-n-dodecylpyridine (59936-36-6)

Conditions	Yield
for 4h;	A 54% B 26%

4-(phenylsulfonyl)pyridine (39574-19-1) → 4,4'-bipyridine (553-26-4) + 4-n-dodecylpyridine (59936-36-6)

Conditions	Yield
With laurylmagnesium bromide for 4h;	A 54% B 26%

pyridine N-oxide (694-59-7) + biphenyl-4-yl-phenyl-methanone (2128-93-0) → pyridine (110-86-1) + 4,4'-bipyridine (553-26-4) + phenyl-4'-biphenyl-2-pyridylcarbinol (74671-91-3) + phenyl-4'-biphenylyl-2-pyridylcarbinol N-oxide (74671-90-2)

Conditions	Yield
With potassium In 1,4-dioxane for 24h; Product distribution; Ambient temperature; other alkali metals (Na, Li), var. molar ratios of input compounds;	A 4% B 18% C 17% D 52%
With potassium 1) dioxan, 3 days; 2) 24 h; Yield given. Multistep reaction. Yields of byproduct given;

pyridin-4-ylmagnesium bromide (21970-15-0) + 4-pyridyl p-tolyl sulfoxide (113512-73-5) → 4,4'-bipyridine (553-26-4)

Conditions	Yield
In tetrahydrofuran for 10h; Ambient temperature;	50%

4-iodopyridine (15854-87-2) + triethoxyphenylsilane (780-69-8) → p-phenylpyridine (939-23-1) + 4,4'-bipyridine (553-26-4)

Conditions	Yield
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 12h; Hiyama Coupling; Inert atmosphere;	A 48% B n/a

pyridine (110-86-1) + C19H14N2O2 (93845-12-6) → 4-(2-pyridyl)pyridine (581-47-5) + 4,4'-bipyridine (553-26-4) + 3,4'-bipyridyl (4394-11-0) + benzophenone (119-61-9)

Conditions	Yield
Irradiation; Further byproducts given;	A 44% B 20% C 23% D n/a

C19H14N2O2 (93845-12-6) → 4-(2-pyridyl)pyridine (581-47-5) + 4,4'-bipyridine (553-26-4) + 3,4'-bipyridyl (4394-11-0) + benzophenone (119-61-9)

Conditions	Yield
In pyridine Ambient temperature; Irradiation; Yield given. Further byproducts given;	A 44% B 20% C 23% D n/a

4-iodopyridine (15854-87-2) + p-tolyltriethoxysilane (18412-57-2) → 4,4'-bipyridine (553-26-4) + 4-(p-tolyl)pyridine (4423-10-3)

Conditions	Yield
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 120℃; for 12h; Hiyama Coupling; Inert atmosphere;	A n/a B 40%

4,4'-bipyridine (553-26-4) + benzyl bromide (100-39-0) → 1,1’-bis(phenylmethyl)-4,4’bipyridinium bromide (27768-49-6)

Conditions	Yield
In acetonitrile at 80℃; for 2h;	100%
In acetonitrile for 21h; Inert atmosphere; Reflux;	99%
In N,N-dimethyl-formamide at 90℃; for 12h;	96%

4,4'-bipyridine (553-26-4) + allyl bromide (106-95-6) → N,N'-diallyl-γ,γ,'-dipyridinium dibromide

Conditions	Yield
In N,N-dimethyl-formamide	100%
In acetonitrile at 70℃; for 21h; Inert atmosphere;	95%
In acetonitrile at 80℃; for 4h;	91%
In acetonitrile for 4h; Inert atmosphere; Reflux;	65%

4,4'-bipyridine (553-26-4) + 1 ,6-dibromohexane (629-03-8) → oligo(hexylene-4,4'-bipyridinium dibromide)

Conditions	Yield
In ethanol at 100℃; for 24h;	100%

4,4'-bipyridine (553-26-4) + zinc diacetate (557-34-6) + (2E)-but-2-enedioic acid (110-17-8) → [Zn2(fumarate)2(4,4'-bipyridyl)]n

Conditions	Yield
	100%

4,4'-bipyridine (553-26-4) + (Zn(C60H74N4O2)(CH2CH2CH2)2)2*C60 → fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0)

Conditions	Yield
In not given	100%

4,4'-bipyridine (553-26-4) + pentaamminetriflatorhodium(III) triflate (84254-57-9) → {Rh(NH3)5(4,4'-bipyridine)}(CF3SO3)3 (115244-87-6)

Conditions	Yield
In not given react. of soln. of {Rh(NH3)5(OSO2CF3)}(CF3SO3)2 and excess 4,4'-bipyridine, heating, dilution, chromy., evapn.; quantitative yield with sufficiently dry reagents;	100%

4,4'-bipyridine (553-26-4) + trifluoromethanesulfonatopentaamminecobalt(III) trifluoromethanesulfonate (115245-01-7) → {Co(NH3)5(4,4'-bipyridine)}(CF3SO3)3 (115244-88-7)

Conditions	Yield
In not given react. of soln. of {Co(NH3)5(OSO2CF3)}(CF3SO3)2 and excess 4,4'-bipyridine, heating, dilution, chromy., evapn.; quantitative yield with sufficiently dry reagents;	100%

4,4'-bipyridine (553-26-4) + [Os(2,3,7,8,12,13,17,18-octaethylporphyrinato)]2 → poly-(μ-4,4'-bipyridine)(octaethylporphyrinato)osmium(II) (108713-60-6)

Conditions	Yield
In toluene dissolving (Os(C20H4(C2H5)8N4))2 in toluene; addn. of NC5H4C5H4N in toluene; stirring for 1 h at room temp.; heating at reflux for 16 h;; pptn; elem. anal.;;	100%

4,4'-bipyridine (553-26-4) + [Ru2(μ-η4-C2O4)(MeOH)2(η6-p-iPrC6H4Me)2][O3SCF3]2 → [(C22H28O4Ru2)(4,4′-bipyridine)]2

Conditions	Yield
In methanol (N2); stirring (room temp., 24 h); evapn. to dryness; elem. anal.;	100%

4,4'-bipyridine (553-26-4) + [Pr(III)2(3,5-dinitro-4-methylbenzoate)6(H2O)4]*6H2O + water (7732-18-5) → [Pr(III)2(3,5-dinitro-4-methylbenzoate)6(H2O)4]*2(4,4'-bipyridyl)

Conditions	Yield
In not given guest-exchange react. between Pr-complex and bpy;	100%

4,4'-bipyridine (553-26-4) + tetrakis(actonitrile)copper(I) hexafluorophosphate (64443-05-6) + 2,9-dimesityl-[1,10]-phenanthroline (192226-54-3) → [Cu2(2,9-dimesityl-1,10-phenanthroline)2(4,4'-bipyridine)](PF6)2

Conditions	Yield
In dichloromethane	100%

4,4'-bipyridine (553-26-4) + [Pb(4-(trimethylammonio)benzenethiolate)2]2(PF6)4 → [Pb(4,4'-bipyridine)(4-(trimethylammonio)benzenethiolate)2](PF6)2

Conditions	Yield
In neat (no solvent, solid phase) at 20℃; for 0.5h;	100%

4,4'-bipyridine (553-26-4) → (4,4'-bipyridinium) hexafluorosilicate

Conditions	Yield
With fluorosilicic acid In methanol; water at 20℃;	100%

4,4'-bipyridine (553-26-4) + niobium pentafluoride (7783-68-8) + trimethylsilylazide (4648-54-8) → (Nb(N3)5)2·(4,4’-bipy) (1628265-38-2)

Conditions	Yield
In acetonitrile at -196 - 20℃; for 6h;	100%

4,4'-bipyridine (553-26-4) + tantalum pentafluoride (7783-71-3) + trimethylsilylazide (4648-54-8) → (Ta(N3)5)2·(4,4’-bipy) (1628265-39-3)

Conditions	Yield
In acetonitrile at -196 - 20℃; for 6h;	100%

4,4'-bipyridine (553-26-4) + C72(13)C2H132Cl8P4Pt2Ru2 → C82(13)C2H140Cl8N2P4Pt2Ru2

Conditions	Yield
In dichloromethane	100%

4,4'-bipyridine (553-26-4) + tungsten(VI) fluoride (7783-82-6) → F6W(4,4′-bipyridine)WF6

Conditions	Yield
In dichloromethane at -196 - 45℃; for 2h; Glovebox; Sonication;	100%

4,4'-bipyridine (553-26-4) + [Cu2(1-(4-{[4-(3-oxo-3-phenylpropanoyl)phenyl]methyl}phenyl)-3-phenylpropane-1,3-dione)2] → {[Cu2(1-(4-{[4-(3-oxo-3-phenylpropanoyl)phenyl]methyl}phenyl)-3-phenylpropane-1,3-dione)2](4,4’-bipyridine)}n

Conditions	Yield
In tetrahydrofuran; N,N-dimethyl acetamide	100%

4,4'-bipyridine (553-26-4) + 1,2,3,4,5,6-hexa(bromomethyl)benzene (3095-73-6) → C72H60N12(6+)*6Br(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 0.166667h;	100%
In N,N-dimethyl-formamide at 90℃;	99%

4,4'-bipyridine (553-26-4) + antimony(III) chloride (10025-91-9) → C10H8N2*Sb(3+)*3Cl(1-)

Conditions	Yield
In neat (no solvent) for 72h; Inert atmosphere; Sealed tube;	100%

4,4'-bipyridine (553-26-4) + antimony(III) bromide (7789-61-9) → C10H8N2*Sb(3+)*3Br(1-)

Conditions	Yield
In neat (no solvent) for 72h; Inert atmosphere; Sealed tube;	100%

4,4'-bipyridine (553-26-4) + antimony triiodide (7790-44-5) → C10H8N2*Sb(3+)*3I(1-)

Conditions	Yield
In neat (no solvent) for 72h; Inert atmosphere; Sealed tube;	100%

4,4'-bipyridine (553-26-4) + hexamethylenediamine-N,N,N′,N′-tetrakis(methylphosphonic acid) (23605-74-5) + copper(II) acetate monohydrate (6046-93-1) → 3Cu(2+)*2C10H8N2*6H2O*C10H22N2O12P4(6-)

Conditions	Yield
In water for 0.5h;	99.6%

4,4'-bipyridine (553-26-4) + potassium permanganate (7722-64-7) + silver(I) acetate (563-63-3) → C10H8N2*Ag(1+)*MnO4(1-)

Conditions	Yield
In water at 20℃; for 120h; Sealed tube;	99.6%

4,4'-bipyridine (553-26-4) + water (7732-18-5) + silver(I) acetate (563-63-3) → C2H3O2(1-)*Ag(1+)*C10H8N2*6H2O

Conditions	Yield
for 1h; Time;	99.1%

4,4'-bipyridine (553-26-4) + methyl iodide (74-88-4) → 1-methyl-4-(4-pyridyl)pyridinium iodide (38873-01-7)

Conditions	Yield
In acetonitrile for 1h; Reflux;	99%
In dichloromethane at 20 - 37℃; Inert atmosphere;	96%
In dichloromethane Heating;	95%

4-[4-[bis(4-t-butylphenyl)-4-ethylphenylmethyl]phenoxymethyl]benzylbromide (544708-57-8) + 4,4'-bipyridine (553-26-4) → 1-{4-[4-tris{4-t-butylphenyl}methylphenoxymethyl]benzyl}-4-(4'-pyridinyl)-pyridinium hexafluorophosphate

Conditions	Yield
In toluene; acetonitrile at 80℃;	99%

4,4'-bipyridine (553-26-4) + copper(ll) bromide (7789-45-9) → (3).infin.[CuBr(4,4'-bipyridine)] (113720-78-8)

Conditions	Yield
In water molar ratio Cu:bipy:H2O=1:2:167, acid digestion bomb, 170°C, 7 d; washing (water, Me2CO), drying in air;	99%

4,4'-bipyridine (553-26-4) + water (7732-18-5) + copper(II) malonate (7268-92-0, 855650-62-3, 1229512-67-7) → [Cu2(malonato)2(H2O)2(4,4'-bipyridine)]

Conditions	Yield
In water by the react. of aq. soln. of Cu-contg. compd. with 4,4'-bipyridine in a2:1 molar ratio; elem. anal.;	99%

Upstream product

• 110-86-1 pyridine 
• 15336-72-8 4,4'-bipiperidine 
• 3451-88-5 1,1'-Diacetyl-1,1',4,4'-tetrahydro-4,4'-bipyridine 
• 546-67-8 lead(IV) tetraacetate 
• 108-24-7 acetic anhydride 
• 23245-77-4 4,4'-bipyridine-3,3'-dicarboxylic acid 
• 64-19-7 acetic acid 
• 93845-12-6 C₁₉H₁₄N₂O₂ 
• 694-59-7 pyridine N-oxide 
• 642-29-5 1-benzoylnaphthalene 
• 2128-93-0 biphenyl-4-yl-phenyl-methanone 
• 109-09-1 2-chloropyridine 
• 109-04-6 2-bromo-pyridine 
• 16110-09-1 2,5 dichloropyridine 

Downstream Products

• 3688-18-4 ethyl viologen 
• 71190-51-7 1,1'-Diacetyl-1,1'-dihydro-4,4'-bipyridin 
• 141433-62-7 1,1'-bibenzyl-[4,4']bipyridyldiium; dichloride 
• 1983-61-5 N,N'-diethyl-4,4'-bipyridinium iodide 
• 41168-79-0 1,1′-bis(2,4-dinitrophenyl)-[4,4′-bipyridine]-1,1′-diium chloride 
• 1910-42-5 paraquat dichloride 
• 1983-60-4 methyl vilogen diiodide 
• 15336-72-8 4,4'-bipiperidine 
• 581-45-3 4-(piperidin-4-yl)pyridine 
• 125330-07-6 4,4′:2′,2″:4″,4?-quaterpyridine 
• 189000-91-7 2,2'-diamino-4,4'-bipyridine 
• 52243-87-5 1,1′-bis(propyl)-4,4′-bipyridinium dibromide 

Relevant articles and documents

Intramolecular Electron Transfer from Pentacyanoferrate(II) to Pentaaminecobalt(III) with 3,3'-Dimethyl-4,4'-bipyridine, 4,4'-Bipyridylacetylene, 1,4-Bis(4-pyridyl)butadiyne, 2,7-Diazapyrene, and 3,8-Phenanthroline as Bridging Ligands: Adiabaticity and th

Rate constants for intramolecular electron transfer from iron to cobalt in (NH3)5CO(III)LFe(II)(CN)5 (L=3,3'-dimethyl-4,4'-bipyridine, 4,4'-bipyridylacetylene, 1,4-bis(4-pyridyl)butadiyne, 2,7-diazapyrene, and 3,8-phenanthroline) have been measured at 25

Synthetic transformations of sesquiterpene lactones 9.*Synthesis of 13-(pyridinyl)eudesmanolides

[Figure not available: see fulltext.]The reaction of isoalantolactone, a sesquiterpene α-methylidene-γ-lactone, with bromo(iodo)pyridines under the Heck reaction conditions gave 3-(pyridylmethylidene)-8а-methyldecahydronaphtho[2,3-b]furan-2(3Н)-ones and 3-(pyridylmethyl)-8а-methyloctahydronaphtho[2,3-b]-furan-2(4Н)-ones, products of double bond migration. The yield and product ratio depended on the reaction conditions and the nature of halopyridine. The effectiveness of Pd(OAc)2–caffeine catalytic system was demonstrated in this reaction.

Highly efficient removal of paraquat pesticide from aqueous solutions using a novel nano Kaolin modified with sulfuric acid via host–guest interactions

Contamination of wastewaters with pesticides has significant risk for environmental water. In spite of the rule of Europ, paraquat is used extensively as an herbicide in the all around the world and it is likely to be released into drinking water. Therefore the elimination of it from water is very important. In this paper a new sulfuric acid modified nano kaolin sorbent was synthesized with a simple and low cost method. Thereafter it was applied for removing of paraquat and the experimental conditions such as concentration of herbicide, dose of sorbent and pH of solution were optimized. The results showed the unmodified Kaolin wasn’t able to remove the paraquat efficiently. But with the proposed modified nano Kaolin removal percent reach to 98% in a short time 60 min. Also the results showed this system obeys from Frendluich adsorption isotherm.

Suzuki–Miyaura arylation of 2,3-, 2,4-, 2,5-, and 3,4-dibromothiophenes

A convenient and general method for Suzuki–Miyaura double cross-coupling of various dibromothiophenes was developed. Using a simple and cheap catalytic system Pd(OAc)2/PPh3 in 95% EtOH, various (hetero)arylboronic acids react with dibromothiophenes providing diarylthiophenes, useful in the synthesis of metal–organic frameworks (MOFs), in moderate to excellent yields. The overall efficiency of the catalytic process and slight excess of boronic acids allowed to suppress formation of side products and significantly simplify the purification of products.

METHOD FOR COUPLING HALOGENATED PYRIDINE COMPOUND WITH HALOGENATED AROMATIC COMPOUND

There is a demand for the development of a technique according to which a reaction for coupling a halogenated pyridine compound with a halogenated aromatic compound can be performed in a simple manner through a small number of steps without using expensive agents such as a palladium catalyst. A method for coupling a halogenated pyridine compound with a halogenated aromatic compound includes a step of coupling a halogenated pyridine compound with a halogenated aromatic compound to obtain a pyridine compound by reacting, in a reaction solvent, the halogenated pyridine compound and the halogenated aromatic compound with a solution containing an alkali metal.