135853-33-7

Basic information

• Product Name: 6-(1H-pyrazol-1-yl)-2,2'-bipyridine
• Synonyms: 6-(1H-pyrazol-1-yl)-2,2'-bipyridine
• CAS NO: 135853-33-7
• Molecular Formula: C₁₃H₁₀N₄
• Molecular Weight: 222.2453
• EINECS: -0
• Mol File: 135853-33-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-(1H-pyrazol-1-yl)-2,2'-bipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(1H-pyrazol-1-yl)-2,2'-bipyridine(135853-33-7)
• EPA Substance Registry System: 6-(1H-pyrazol-1-yl)-2,2'-bipyridine(135853-33-7)

Safety Data

• Hazardous Substances Data: 135853-33-7(Hazardous Substances Data)

Usage

General Description

6-(1H-pyrazol-1-yl)-2,2'-bipyridine is a chemical compound that belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other through a bond, an atom or a group of atoms. The molecular formula of this compound is C14H10N4 and it has a molar mass of 238.26 g/mol. Its specific name derives from the 1H-pyrazol-1-yl group attached to the 6th position of one of the pyridine rings. It's a heterocyclic compound, which means it contains atoms of at least two different elements in its rings. It is often used as a ligand in the field of coordination chemistry.

Synthetic route

NH-pyrazole (288-13-1) + 6-fluoro-2,2′-bipyridine (1223063-81-7) → 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7)

Conditions	Yield
Stage #1: NH-pyrazole With sodium t-butanolate In dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 6-fluoro-2,2′-bipyridine In dimethyl sulfoxide at 100℃; for 24h;	87%

NH-pyrazole (288-13-1) + 6-Chloro-[2,2']bipyridinyl (13040-77-2) → 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7)

Conditions	Yield
With potassium In diethylene glycol dimethyl ether at 130℃; for 168h;	64%
With potassium tert-butylate In dimethyl sulfoxide at 140℃; for 14h;	39%
With potassium tert-butylate at 140℃; for 14h;	39%

pyridin-2-ylzinc(II) bromide → 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: sodium t-butanolate / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere 2.2: 24 h / 100 °C View Scheme

2-bromo-6-fluoropyridine (144100-07-2) → 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: sodium t-butanolate / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere 2.2: 24 h / 100 °C View Scheme

rhenium pentacarbonyl iodide (13821-00-6) + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [ReI(CO)3(6-(pyrazol-1-yl)-2,2'-bipyridine)]

Conditions	Yield
In not given N2-atmosphere; elem. anal.;	90%

{trimethylplatinum(IV) iodide}4 + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [PtI(CH3)3(C10H7N2C3H3N2)] (180517-08-2, 180517-05-9)

Conditions	Yield
In benzene (N2); stirring (50°C, 16 h); evapn. (vac.), light petroleum addn., washing (light petroleum), drying (vac.), recrystn. (dichloromethane/hexane); elem. anal.;	85%

rhenium(I) pentacarbonyl chloride (14099-01-5) + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [ReCl(CO)3(6-(pyrazol-1-yl)-2,2'-bipyridine)]

Conditions	Yield
In not given N2-atmosphere; elem. anal.;	85%

ammonium hexafluorophosphate + cobalt(II) chloride hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Co(6-(N-pyrazolyl)-2,2'-bipyridine)2](PF6)2

Conditions	Yield
In water; acetone a soln. of CoCl2 in H2O and bipyridine in acetone were mixed and stirred with heating for 75 min, NH4PF6 in H2O was added; ppt. was filtered, washed with H2O, dried with Et2O; elem. anal.;	71.8%
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine In water; acetone at 55℃; for 2h; Stage #2: ammonium hexafluorophosphate In water; acetone at 3℃;	57%

rhenium(I) pentacarbonyl bromide (14220-21-4) + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → bromotricarbonyl[6-(pyrazol-1-yl)-2,2'-bipyridine]rhenium(I)

Conditions	Yield
In benzene N2-atmosphere; refluxing of Re-complex with 2 equiv. of ligand (4 h); partial evapn., pptn. on light petroleum addn., decantation, washing (light petroleum), drying (vac.), recrystn. (CH2Cl2/hexane); elem. anal.;	70%

ammonium hexafluorophosphate + cobalt(II) chloride hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Co(6-(N-pyrazolyl)-2,2'-bipyridine)2](PF6)2 + [Co(III)(bby-pz)2](PF6)2

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine In methanol; water at 55℃; for 2h; Stage #2: With hydrogenchloride; dihydrogen peroxide In methanol; water at 20℃; for 1h; Stage #3: ammonium hexafluorophosphate In methanol; water at 3℃;	A 35% B 65%

cobalt(II) chloride hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Co(II)(bpy-pz)2](PF6)2 + [Co(III)(bpy-pz)2](PF6)3

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine In methanol; water at 55℃; for 2h; Stage #2: With hydrogenchloride; dihydrogen peroxide In methanol; water for 1h; Stage #3: With ammonium hexafluorophosphate In methanol; water at 3℃;	A 35% B 65%

ammonium hexafluorophosphate + Ammonium iron sulfate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Fe(6-(N-pyrazolyl)-2,2'-bipyridine)2](PF6)2*H2O

Conditions	Yield
In water a soln. of Fe-salt and bipyridine in H2O was stirred with heating for 75 min, NH4PF6 in H2O was added; ppt. was filtered, washed with H2O, dried with Et2O; elem. anal.;	62.3%

cobalt(II) chloride hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Co(II)(bpy-pz)2](PF6)2

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine In water; acetone at 55℃; for 2h; Stage #2: With ammonium hexafluorophosphate In water; acetone at 3℃;	57%

ammonium hexafluorophosphate + ruthenium(III) chloride trihydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → bis{6-(N-pyrazolyl)-2,2'-bipyridine-N,N',N2''}ruthenium(II) hexafluorophosphate

Conditions	Yield
In ethanol; water addn. of 6-(N-pyrazolyl)-2,2'-bipyridine to a soln. of RuCl3*3H2O in ethanol-water (90:10); refluxing under a N2 atm. for 72 h; removal of solvent in vac.; dropwise addn. of a soln. of NH4PF6 to the aq. soln. of the residue;; recrystn. of the ppt. from acetonitrile/diethylether or column chromy.; elem. anal.;;	55%

{trimethylplatinum(IV) chloride}4 + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [PtCl(CH3)3(C10H7N2C3H3N2)] (180517-07-1)

Conditions	Yield
In benzene (N2); stirring; elem. anal.;	47%

iron(II) perchlorate hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [iron(II)((6-pyrazol-1-yl)-2,2'-bipyridine)](perchlorate)2 monohydrate

Conditions	Yield
In ethanol mixing solns. of educts in hot solvent; cooling, sepn.; elem. anal.;

nickel(II) perchlorate hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [nickel(II)((6-pyrazol-1-yl)-2,2'-bipyridine)](perchlorate)2 monohydrate

Conditions	Yield
In ethanol mixing solns. of educts in hot solvent; cooling, sepn.; elem. anal.;

iron(II) tetrafluoroborate hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [iron(II)((6-pyrazol-1-yl)-2,2'-bipyridine)](fluoroborate)2 monohydrate

Conditions	Yield
In ethanol mixing solns. of educts in hot solvent; cooling, sepn.; elem. anal.;

cobalt(II) chloride hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → Co(bpy-pz)2[B(CN)4]2

Conditions	Yield
With potassium tetracyanoborate In water; acetone at 3 - 55℃;

cobalt(II) chloride hexahydrate + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → Co(bpy-pz)2[B(CN)4]3

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine In water; acetone at 55℃; for 2h; Stage #2: With bromine In methanol; water; acetone for 0.0833333h; Stage #3: With potassium tetracyanoborate In water

cobalt(II) chloride hexahydrate + potassium monofluorotricyanoborate (565451-76-5) + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Co(6-(N-pyrazolyl)-2,2'-bipyridine)2][BF(CN)3]2

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine In ethanol; water at 20℃; for 3h; Stage #2: potassium monofluorotricyanoborate In ethanol; water for 0.5h;

cobalt(II) chloride hexahydrate + potassium monofluorotricyanoborate (565451-76-5) + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Co(6-(N-pyrazolyl)-2,2'-bipyridine)2][BF(CN)3]3

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine With chlorine In ethanol; water for 0.833333h; Stage #2: potassium monofluorotricyanoborate In ethanol; water

cobalt(II) chloride hexahydrate + K[HB(CN)3] + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Co(6-(N-pyrazolyl)-2,2'-bipyridine)2][BH(CN)3]3

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine With chlorine In ethanol; water for 0.833333h; Stage #2: K[HB(CN)3] In ethanol; water

cobalt(II) chloride hexahydrate + K[HB(CN)3] + 6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) → [Co(6-(N-pyrazolyl)-2,2'-bipyridine)2][BH(CN)3]2

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; 6-(1H-pyrazol-1-yl)-2,2'-bipyridine In ethanol; water at 20℃; for 3h; Stage #2: K[HB(CN)3] In ethanol; water for 0.5h;

6-(1H-pyrazol-1-yl)-2,2'-bipyridine (135853-33-7) + cobalt(II) chloride (7646-79-9) → [Co(6-(N-pyrazolyl)-2,2'-bipyridine)2](2+) (312322-07-9)

Conditions	Yield
Stage #1: 6-(1H-pyrazol-1-yl)-2,2'-bipyridine; cobalt(II) chloride In water; acetone for 12h; Reflux; Stage #2: With ammonium hexafluorophosphate

Upstream product

• 288-13-1 NH-pyrazole 
• 1223063-81-7 6-fluoro-2,2′-bipyridine 
• 144100-07-2 2-bromo-6-fluoropyridine 
• 13040-77-2 6-Chloro-[2,2']bipyridinyl 

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