142646-58-0

Basic information

• Product Name: 4,4'-Dinonyl-2,2'-bipyridine
• Synonyms: 4 4'-DINONYL-2 2'-DIPYRIDYL 97;4,4'-Dinonyl-2,2'-bipyridine;4,4 -DINOYL-2,2 -DIPYRIDYL;4,4'-Bis(nonyl)-2,2'-bipyridine;4,4'-Dinonyl-2,2'-bipyridyl;4,4'-Di-n-nonyl-2,2'-bipyridin;4,4'-Di-n-nonyl-2,2'-bipyridine, 97%;4,4′-Dinonyl-2,2′-dipyridyl,dNbpy
• CAS NO: 142646-58-0
• Molecular Formula: C₂₈H₄₄N₂
• Molecular Weight: 408.66
• Product Categories: C9 to C46;Heterocyclic Building Blocks;Pyridines
• Mol File: 142646-58-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 61-63 °C(lit.)
• Boiling Point: 522.4 °C at 760 mmHg
• Flash Point: 199.5 °C
• Appearance: /
• Density: 0.933 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.30±0.30(Predicted)
• CAS DataBase Reference: 4,4'-Dinonyl-2,2'-bipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dinonyl-2,2'-bipyridine(142646-58-0)
• EPA Substance Registry System: 4,4'-Dinonyl-2,2'-bipyridine(142646-58-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 142646-58-0(Hazardous Substances Data)

Usage

Chemical Properties

White or off-white powder

Uses

Used in the preparation of an artificial muscle with lamellar structure based on a nematic triblock copolymer. Also use as complex in cyclic voltammetric studies of copper complexes catalyzing atom transfer radical polymerization.

Synthetic route

4,4'-dimethyl-2,2'-bipyridines (1134-35-6) + 1-bromo-octane (111-83-1) → 4,4'-dinonyl-2,2'-bipyridine (142646-58-0)

Conditions	Yield
Stage #1: 4,4'-dimethyl-2,2'-bipyridines With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 1.08333h; Inert atmosphere; Stage #2: 1-bromo-octane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	80%
Stage #1: 4,4'-dimethyl-2,2'-bipyridines With lithium diisopropyl amide at -75℃; for 1.5h; Inert atmosphere; Stage #2: 1-bromo-octane In tetrahydrofuran at -75℃; for 0.5h; Inert atmosphere;	60%
With n-butyllithium; diisopropylamine In tetrahydrofuran at 0 - 20℃; for 15h; Inert atmosphere;	45%
With lithium diisopropyl amide 1.) THF, 0 deg C, 3 h, 2.) THF, 0 deg C, 3 h; Yield given. Multistep reaction;

picoline (108-89-4) → 4,4'-dinonyl-2,2'-bipyridine (142646-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 11 percent / Raney Ni / 60 h / Heating 2: 1.) LDA / 1.) THF, 0 deg C, 3 h, 2.) THF, 0 deg C, 3 h View Scheme

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → dichloro(p-cymene)-4,4′-dinonyl-2,2′-bipyridine ruthenium(II)

Conditions	Yield
In ethanol for 4h; Reflux;	100%

ferrous ammonium sulphate + sodium perchlorate + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → tris-4,4'-di-n-nonyl-2,2'-bipyridine iron(II) perchlorate

Conditions	Yield
In water aq. solns. of Fe(NH4)2(SO4)2 combined with acetone soln. of bipy deriv.;excess NaClO4 added; ppt. rinsed with water; dried under vac.;	99.6%

potassium tetrachloroplatinate(II) (10025-99-7) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → dichloro-bis(4,4'-dinonyl-2,2'-dipyridyl)platinum (518299-68-8)

Conditions	Yield
In water acidic aq. soln. of K2PtCl4 and bipyridine derivative heated at 343 K for 24 h; recrystn. from DMF; elem. anal.;	94%
With hydrogenchloride In water at 60℃;	85%

dichloro(benzene)ruthenium(II) dimer (37366-09-9) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → chloro(η6-benzene)(4,4'-dinonyl-2,2'-bipyridine)ruthenium(II) chloride (1332307-95-5)

Conditions	Yield
In acetonitrile (Ar) suspn. Ru complex and ligand in MeCN was heated to reflux (90°C) overnight; react. mixt. was cooled, soln. was filtered and evapd., residue was washed with ether and dried in vacuo;	92%
In water for 0.25h; Sonication; Green chemistry;

ammonium hexafluorophosphate + rhodium(III) chloride hydrate + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → C84H132N6Ru(2+)*2F6P(1-)

Conditions	Yield
Stage #1: rhodium(III) chloride hydrate; 4,4'-dinonyl-2,2'-bipyridine In ethanol at 80℃; for 2h; Sonication; Stage #2: ammonium hexafluorophosphate In methanol	85%

(tetra-n-butylammonium)2[Mo3S7Br6] + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → Mo3S7Br4(4,4’-dinonyl-2,2’-bipyridine)

Conditions	Yield
In dichloromethane at 20℃; for 5h; Inert atmosphere;	84%

[Ru(1,10-phenanthroline)2Cl2] + ammonium hexafluorophosphate + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → C52H60N6Ru(2+)*2F6P(1-)

Conditions	Yield
Stage #1: [Ru(1,10-phenanthroline)2Cl2]; 4,4'-dinonyl-2,2'-bipyridine In water at 140℃; for 1h; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water at 20℃; Inert atmosphere;	80%

4,4'-dimethyl-2,2'-bipyridines (1134-35-6) + cobalt(II) chloride hexahydrate + bis(trifluoromethane)sulfonimide lithium (90076-65-6) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → (4,4’-dimethyl-2,2’-bipyridine)bis(4,4’-dinonyl-2,2’-bipyridine)cobalt(II) bis(trifluoromethane)sulfonimide

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 4,4'-dinonyl-2,2'-bipyridine In methanol for 1h; Reflux; Stage #2: 4,4'-dimethyl-2,2'-bipyridines In methanol for 0.5h; Reflux; Stage #3: bis(trifluoromethane)sulfonimide lithium In methanol at 20℃; for 1h;	80%

silver(I) hexafluorophosphate (26042-63-7) + [(1,4,7-trithiacyclononane)platinum(II) dichloride] (109994-19-6, 326478-44-8) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → [Pt(1,4,7-trithiacyclononane)(4,4'-dinonyl-2,2'-bipyridine)](PF6)2

Conditions	Yield
In acetonitrile byproducts: AgCl; 2 equiv. of Ag-salt and Pt-compd. were stirred in dark in MeCN for 24 h,AgCl was filtered off, 1 equiv. of N-compd. was added, stirring for 48 h; soln. was concd. to 1/3 of its original vol., ether was diffunded overnight, crystals were filtered off, 3-3 times washed with EtOH and ether, resp., elem. anal.;	79.1%

4,4'-dinonyl-2,2'-bipyridine (142646-58-0) + zinc(II) chloride (7646-85-7) → [ZnCl2(4,4'-dinonyl-2,2'-bipyridine)] (1228769-49-0)

Conditions	Yield
In dichloromethane addn. of 1.5 equiv. of zinc compd. to CH2Cl2 soln. of bipyridine deriv.,stirring for 6 d at room temp.; filtration through celite, evapn., recrystn. (CHCl3/diethyl ether), elem. anal.;	78%

cis-dichro-bis(4,4'-dicarboxy-2,2'-bipyridine)ruthenium + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → C52H60N6O8Ru(2+)*2F6P(1-)

Conditions	Yield
Stage #1: cis-dichro-bis(4,4'-dicarboxy-2,2'-bipyridine)ruthenium; 4,4'-dinonyl-2,2'-bipyridine In water at 180℃; under 10343.2 Torr; for 2h; Microwave reactor; Stage #2: With hexafluorophosphoric acid In water pH=~ 2;	77%

zinc(II) sulfate heptahydrate + water (7732-18-5) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → 2C28H44N2*2Zn(2+)*2O4S(2-)*2H2O

Conditions	Yield
In methanol for 3h;	77%

[W3S4(thiourea)8(H2O)]Cl4*2H2O + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → [W3S4Cl3(4,4′-di-n-nonyl-2,2′-bipyridine)3]Cl

Conditions	Yield
In acetonitrile for 5h; Reflux;	76%

ammonium hexafluorophosphate + [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → bis(2-phenylpyridine-C(2),N')(4,4'-di-n-nonyl-2,2'-bipyridine)iridium(III) hexafluorophosphate

Conditions	Yield
In methanol; dichloromethane (air); a suspn. of Ir complex and ligand in CH2Cl2/MeOH refluxed; cooled to room temp., a soln. of NH4PF6 in MeOH added, stirred, evapd. (vac.), dissolved in CH2Cl2, filtered, Et2O layered onto the filtrate, crystd. at ca. 4°C; elem. anal.;	75%

potassium hexafluorophosphate (17084-13-8) + cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → C48H60N6Ru(2+)*2F6P(1-)

Conditions	Yield
Stage #1: cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate; 4,4'-dinonyl-2,2'-bipyridine In ethanol; water for 12h; Reflux; Stage #2: potassium hexafluorophosphate	74%

Zn(1-phenyl-3-methyl-4-COC6H4C(CH3)3-5-pyrazolonate)2 + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → [Zn(4,4'-dinonyl-2,2'-bipyridine)(1-phenyl-3-methyl-4-COC6H4C(CH3)3-5-pyrazolonate-O,O)2] (1228769-45-6)

Conditions	Yield
In chloroform addn. of bipyridine deriv. to CHCl3 soln. of zinc compd., stirring for 5d at room temp.; evapn., addn. of hexane, concg., filtration, drying in vac., elem. anal.;	73%

ammonium hexafluorophosphate + [Ru(cymene)(bis-4,4′-(trimethylaminomethyl)-2,2′-bipyridine)(Cl)]3+*Cl-*2PF6- + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → [Ru(4,4′-nonyl-2,2′-bipyridine)2(bis-4,4′-(trimethylaminomethyl)-2,2′-bipyridine)]4+*4PF6−

Conditions	Yield
Stage #1: [Ru(cymene)(bis-4,4′-(trimethylaminomethyl)-2,2′-bipyridine)(Cl)]3+*Cl-*2PF6-; 4,4'-dinonyl-2,2'-bipyridine With silver nitrate In ethanol at 150℃; for 0.416667h; Sealed tube; Microwave irradiation; Stage #2: ammonium hexafluorophosphate In methanol	71%

phenylpyridinebridgedichloro platinum (155475-93-7) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → [Pt(2-phenylpyridinato)(4,4'-bis(nonyl)-2,2'-bipyridine)]ClO4

Conditions	Yield
With silver perchlorate In dichloromethane for 23h; Reflux; Inert atmosphere;	69%

ammonium hexafluorophosphate + potassium hexachloroosmate(IV) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → (Os(II)(4,4'-dinonyl-2,2'-bipyridine)3)(PF6)2

Conditions	Yield
Stage #1: potassium hexachloroosmate(IV); 4,4'-dinonyl-2,2'-bipyridine In N,N-dimethyl-formamide Inert atmosphere; Reflux; Stage #2: With sodium dithionite at 20℃; Stage #3: ammonium hexafluorophosphate In water at 4℃;	67%

bis[2-(2,4-difluorophenyl)pyridinato-N,C6']iridium(III) chloride dimer + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → mer-bis[2-(4,6-difluorophenyl)pyridinato-C2,N](4,4'-dinonyl-2,2'-bipyridine)iridium(III) chloride

Conditions	Yield
In 2-ethoxy-ethanol Reflux;	67%

ammonium hexafluorophosphate + [iridium(III)(μ-chloride)2(2,3-diphenylbenzoquinoxaline)2]2 (895169-93-4) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → C76H74IrN6(1+)*F6P(1-)

Conditions	Yield
Stage #1: [iridium(III)(μ-chloride)2(2,3-diphenylbenzoquinoxaline)2]2; 4,4'-dinonyl-2,2'-bipyridine With silver trifluoromethanesulfonate In methanol; dichloromethane for 24h; Inert atmosphere; Reflux; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane for 1h;	61.7%

ruthenium(III) chloride trihydrate + 2,2'-Bipyridine-4,4'-dicarboxylic acid (6813-38-3) + ammonium thiocyanate + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → cis-di(thiocyanato)-(2,2'-bipyridyl-4,4'-dicarboxylicacid)(4,4'-dinonyl-2,2'-bipyridyl)ruthenium(II) (502693-09-6)

Conditions	Yield
Stage #1: ruthenium(III) chloride trihydrate; 2,2'-Bipyridine-4,4'-dicarboxylic acid; 4,4'-dinonyl-2,2'-bipyridine In 1-methyl-pyrrolidin-2-one at 140 - 150℃; for 1.5h; Stage #2: ammonium thiocyanate In 1-methyl-pyrrolidin-2-one for 1h; Solvent;	61%

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + 2,2'-Bipyridine-4,4'-dicarboxylic acid (6813-38-3) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → C52H60N6O8Ru(2+)*2F6P(1-)

Conditions	Yield
Stage #1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4,4'-dinonyl-2,2'-bipyridine In N,N-dimethyl-formamide at 60℃; for 2h; Inert atmosphere; Stage #2: 2,2'-Bipyridine-4,4'-dicarboxylic acid With sodium hydroxide In water; N,N-dimethyl-formamide at 160℃; for 6h; Stage #3: With hexafluorophosphoric acid; sodium hydroxide In water pH=2;	60%

ruthenium trichloride + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → cis-[Ru(4,4'-dinonyl-2,2'-bipyiridine)2Cl2]

Conditions	Yield
Stage #1: ruthenium trichloride With ethanol In water for 4h; Inert atmosphere; Reflux; Stage #2: 4,4'-dinonyl-2,2'-bipyridine With hydrogenchloride; tin(II) chloride dihdyrate In water for 1h; Heating;	60%

tetrakis(2-phenylquinoline-C2,N')(μ-dichloro)diiridium(III) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → mer-bis[2-phenylquinolinato-C2,N](4,4'-dinonyl-2,2'-bipyridine)iridium(III) chloride

Conditions	Yield
In 2-ethoxy-ethanol Reflux;	60%

(tetraethylammonium)4[(Nb2S4)(isothiocyanate)8] + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → (tetraethylammonium)2[(Nb2S4)(isothiocyanate)6(di-(4,4'-nonyl)-2,2'-bipyridine)]

Conditions	Yield
In acetonitrile for 12h; Reflux;	55%

[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → mer-bis[2-phenylpyridinato-C2,N](4,4'-dinonyl-2,2'-bipyridine)iridium(III) chloride

Conditions	Yield
In 2-ethoxy-ethanol Reflux;	51%

Zn(1-phenyl-3-methyl-4-COCH2C(CH3)3-5-pyrazolonate)2 + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → [Zn(4,4'-dinonyl-2,2'-bipyridine)(1-phenyl-3-methyl-4-COCH2C(CH3)3-5-pyrazolonate-O,O)2] (1228769-47-8)

Conditions	Yield
In chloroform addn. of bipyridine deriv. to CHCl3 soln. of zinc compd., stirring for 5d at room temp.; evapn., addn. of hexane, keeping at room temp., isolation of crystals, elem. anal.;	50%

4,4'-dimethyl-2,2'-bipyridines (1134-35-6) + cobalt(II) chloride hexahydrate + bis(trifluoromethane)sulfonimide lithium (90076-65-6) + 4,4'-dinonyl-2,2'-bipyridine (142646-58-0) → bis(4,4’-dimethyl-2,2’-bipyridine)(4,4’-dinonyl-2,2’-bipyridine)cobalt(II) bis(trifluoromethane)sulfonimide

Conditions	Yield
Stage #1: 4,4'-dimethyl-2,2'-bipyridines; cobalt(II) chloride hexahydrate In methanol for 1h; Reflux; Stage #2: 4,4'-dinonyl-2,2'-bipyridine In methanol for 0.5h; Reflux; Stage #3: bis(trifluoromethane)sulfonimide lithium In methanol at 20℃; for 1h;	45%

Upstream product

• 108-89-4 picoline 
• 1134-35-6 4,4'-dimethyl-2,2'-bipyridines 
• 111-83-1 1-bromo-octane 

Downstream Products

• 1228769-47-8 [Zn(4,4'-dinonyl-2,2'-bipyridine)(1-phenyl-3-methyl-4-COCH₂C(CH₃)3-5-pyrazolonate-O,O)2] 
• 1228769-45-6 [Zn(4,4'-dinonyl-2,2'-bipyridine)(1-phenyl-3-methyl-4-COC₆H₄C(CH₃)3-5-pyrazolonate-O,O)2] 
• 502693-09-6 Z907 
• 1228769-37-6 [ZnCl(4,4'-dinonyl-2,2'-bipyridine)(1-phenyl-3-methyl-4-COC₆H₄C(CH₃)3-5-pyrazolonate-O,O)(water)] 
• 1228769-39-8 [ZnCl(4,4'-dinonyl-2,2'-bipyridine)(1-phenyl-3-methyl-4-COCH₂C(CH₃)3-5-pyrazolonate-O,O)(water)] 

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