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
• Article Data: 11

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

General Description

2,2'-Bipyridine-3,3'-diol is a chemical compound, also known as 2,2'-dihydroxybipyridine, frequently used in chemical research due to its characteristics as a bidentate ligand. The compound's IUPAC name is Pyridine, 2,2'-bipyridyl-3,3'-diol. It is often used in creating more complex chemical structures as it has the ability to donate two pairs of electrons. Furthermore, it is involved in the making of metal-organic frameworks (MOFs) and utilized in the fields of coordination chemistry and optoelectronics. 2,2'-Bipyridine-3,3'-diol generally appears as a yellow to light brown crystalline powder. It should be handled with care as it may cause eye, skin, and respiratory irritation.

Upstream product

• 109-00-2 3-HYDROXYPYRIDINE 
• 93560-50-0 (2-Furyl)(3-methoxy-2-pyridyl)keton 
• 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 
• 75449-26-2 2,2'-bipyridine-3,3'-diamine 
• 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 
• 93560-59-9 3,3'-dimethoxy-2,2'-bipyridine 
• 492-94-4 furil 
• 6602-32-0 2-bromo-pyridin-3-ol 

Downstream Products

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

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.

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.

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