36145-03-6

Basic information

• Product Name: 2,2'-BIPYRIDINE-3,3'-DIOL
• Synonyms: [2,2'-BIPYRIDYL]-3,3'-DIOL;2,2'-BIPYRIDYL-3,3DIOL;2,2'-BIPYRIDINE-3,3'-DIOL;2,2'-BIS(3-PYRIDINOL);2-(3-HYDROXY-2-PYRIDYL)-3-PYRIDINOL;3,3'-DIHYDROXY-2,2'-BIPYRIDINE
• CAS NO: 36145-03-6
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18
• Product Categories: AlcoholsOrganic Electronics and Photonics;Ligands and Metal Complex Precursors;Monomers;Polymer Science;Synthetic Tools and Reagents
• Mol File: 36145-03-6.mol

Chemical Properties

• Melting Point: 194-196 °C(lit.)
• Boiling Point: 528.194 °C at 760 mmHg
• Flash Point: 273.242 °C
• Appearance: /
• Density: 1.363 g/cm³
• PKA: 8.26±0.10(Predicted)
• CAS DataBase Reference: 2,2'-BIPYRIDINE-3,3'-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-BIPYRIDINE-3,3'-DIOL(36145-03-6)
• EPA Substance Registry System: 2,2'-BIPYRIDINE-3,3'-DIOL(36145-03-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 36145-03-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
2,2'-Bipyridine-3,3'-diol is used as a bidentate ligand for its ability to donate two pairs of electrons, which is crucial in creating more complex chemical structures.
Used in Metal-Organic Frameworks (MOFs):
2,2'-Bipyridine-3,3'-diol is used as a building block in the construction of MOFs, which are materials with potential applications in gas storage, catalysis, and drug delivery.
Used in Coordination Chemistry:
2,2'-Bipyridine-3,3'-diol is used as a ligand in the synthesis of coordination compounds, which are important in various chemical and catalytic processes.
Used in Optoelectronics:
2,2'-Bipyridine-3,3'-diol is used in the development of optoelectronic devices, such as light-emitting diodes and solar cells, due to its electronic properties.

Upstream product

• 6602-32-0 2-bromo-pyridin-3-ol 
• 492-94-4 furil 
• 93560-59-9 3,3'-dimethoxy-2,2'-bipyridine 
• 75449-26-2 2,2'-bipyridine-3,3'-diamine 
• 93560-50-0 (2-Furyl)(3-methoxy-2-pyridyl)keton 
• 109-00-2 3-HYDROXYPYRIDINE 
• 24059-89-0 3-methoxy-pyridine-2-carbonitrile 
• 617-90-3 2-furancarbonitrile 
• 24100-18-3 2-bromo-3-methoxypyridine 
• 93560-55-5 2-iodo-3-methoxy-pyridine 
• 87905-88-2 2-iodo-3-(methoxymethoxy)pyridine 
• 40263-57-8 2-iodo-3-hydroxypyridine 
• 87385-13-5 3'-Methoxy-2,2'-bipyridin-3-ol 
• 93560-60-2 2-Brom-3-(tetrahydro-2-pyranyloxy)pyridin 

Downstream Products

• 958633-04-0 [(η6-biphenyl)Ru(2,2'-bipyridine-3,3'-diol(1-))Cl] 
• 1351363-11-5 [(η5-C5Me4C5H5)Ir(bipy(OH)2)Cl]PF6 

Relevant articles and documents

The regioselective homocoupling of meta-hydroxypyridines with hypervalent iodine(iii)

The C-H homocoupling of meta-hydroxypyridines with phenyliodine(III) diacetate (PIDA) was carried out in dichloromethane at room temperature in the presence of cesium carbonate. The coupling reaction is highly regioselective with respect to the hydroxy group at the pyridine ring. Comparative control experiments with meta-alkoxypyridine suggest that the meta-hydroxy group at the pyridine ring plays a key role during the homocoupling reaction.

A Simple Synthesis of Dihydroxybipyridyls

Dihydroxybipyridyls (dihydroxybipyridines), laser dyes with large Stokes shifts, are prepared by a simple one-step synthesis from the corresponding 2-bromo-3-hydroxypyridines, 3-bromo-4-hydroxyisoquinoline and 2-bromo-3-hydroxyquinoline, using zinc, and nickel(0) in yields up to 45percent.

Metal-ion sensing europium(III) complexes with bidentate phosphine oxide ligands containing a 2,2′-bipyridine framework

Novel EuIII complexes with bidentate phosphine oxide ligands containing a bipyridine framework, i.e., [3,3′-bis(diphenylphosphoryl)-2, 2′-bipyridine]tris(hexafluoroacetylacetonato)europium(III) ([Eu-(hfa) 3(BIPYPO)]) and [3,3′-bis(diphenylphosphoryl)-6,6′- dimethyl-2,2′-bipyridine]tris(hexafluoroacetylacetonato)europium(III) ([Eu(hfa)3(Me-BIPYPO)]), were synthesized for lanthanide-based sensor materials having high emission quantum yields and effective chemosensing properties. The emission quantum yields of [Eu(hfa)3(BIPYPO)] and [Eu(hfa)3(Me-BIPYPO)] were 71 and 73%, respectively. Metal-ion sensing properties of the EuIII complexes were also studied by measuring the emission spectra of EuIII complexes in the presence of ZnII or CuII ions. The metal-ion sensing and the photophysical properties of luminescent EuIII complexes with a bidentate phosphine oxide containing 2,2′-bipyridine framework are demonstrated for the first time.

New syntheses of orelline and analogues via metalation and cross-coupling reactions

New total syntheses of orelline and some analogues are reported. The methodology involves metalation of 3-alkoxy-2-iodopyridines to afford 3,4-dialkoxy-2-iodopyridines, on which cross-coupling reactions are performed to reach the 2,2′-bipyridine skeleton of the alkaloid.

Syntheses of Hydroxylated Bipyridines, III. - Synthesis of Unsymmetrically and Symmetrically Structured Dihydroxybipyridines

Fifteen symmetrical and asymmetrical dimethoxybipyridines and the pertinent diols are prepared and characterized.Reductive cross coupling of halopyridines with Ni(0) may result in complex mixtures.The same is true for an alternative reaction of (trimethylstannyl)pyridines with halopyridines in the presence of Pd(0).UV, 1H-, and 13C-NMR spectra of the bipyridine derivatives are tabulated.Key Words: Bipyridinediols / Pyridines / Stannylpyridines

Notiz zur chemischen Reaktivitaet von hydroxylierten Pyridinen

Ueber mehrere Schritte werden Maltol in 3,4-Dimethoxy-2-methylpyridin (2b) und Kojisaeure in 3-Brom-4-hydroxy-5-methoxypyridin ueberfuehrt.Die Bromierung von 3,3'-Dihydroxy-2,2'-bipyridin (6) liefert ein Gemisch von Monobrom-, Dibrom-, Tribrom- und Tetrabromverbindungen 7a bis 7g, bei denen die 6-Bromderivate vorherrschen.Aehnliche Substitutionsmuster werden bei der Nitrierung von 6 erhalten, wobei die Verbindungen 7h - 7j erhalten werden.Ausgehend von 2-Iod-3-methoxypyridin (8) lassen sich die Substitutionsprodukte 10 bis 15 darstellen.Als besonders interessant erweist sich 3-Methoxy-2-iod-6-nitropyridin (11), das sich zu dem 3,3',6,6'-Tetrahydroxy-2,2'-bipyridin (16d) umwandeln laesst, einen Isomeren des Naturstoffs Orellin.

BIPYRIDINES. PART XVII. A CONVENIENT SYNTHESIS OF SOME BIPYRIDINEDIOLS AND FURODIPYRIDINES

A convenient method of synthesizing some bipyridinediols and furodipyridines based on diazotization of corresponding diamines in H2SO4 has been described.

Bipyridines. Part XVIII. On the Synthesis of -3-ol and Other Novel 2,2'-Bipyridine Derivatives from -3,3'-diamine

-3-hydroxylamine (6) and its 3'-acetylderivative (7) were obtained by diazotization of -3,3'-diamine (3) in acetic acid, however, diazotization of copper(II) complex of 3 led to -3-amine (10).The amine 10 was transformed into -3-ol (2).The pethway of the reaction was proposed.

Fluorescent Dyes with Large Stokes Shifts - a Simple Synthesis of -3,3'-diol

-3,3'-diol (4) is obtained in one step from furoin (8) by Zincke rearrangement in 32percent yield.The fluorescence quantum yield of the dye is 50percent in chloroform - absorption and fluorescence spectra are completely separated (TZ = 1011).The large Stokes shift is caused by a proton transfer according to the Foerster mechanism.