109073-77-0

Basic information

• Product Name: 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine
• Synonyms: 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine;2,2'-Bi(pyridine-4-methanol);2,2'-Bipyridine-4,4'-bismethanol;2,2'-Bipyridine-4,4'-dimethanol;{2-[4-(hydroxyMethyl)pyridin-2-yl]pyridin-4-yl}Methanol;2,2'-Bipyridine-4,4'-dimethanol 4,4'-Bis(hydroxymethyl)-2,2'-bipyridyl;[2,2'-Bipyridine]-4,4'-diyldiMethanol;4,4'is(hydroxymethyl)-2,2'-bipyridine
• CAS NO: 109073-77-0
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.24
• Product Categories: Pyridines derivates
• Mol File: 109073-77-0.mol
• Article Data: 38

Chemical Properties

• Melting Point: 170.6-171.4 °C
• Boiling Point: 450.4 °C at 760 mmHg
• Flash Point: 226.2 °C
• Appearance: /
• Density: 1.281 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 12.94±0.10(Predicted)
• CAS DataBase Reference: 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine(109073-77-0)
• EPA Substance Registry System: 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine(109073-77-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 109073-77-0(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
4,4'-Bis(hydroxymethyl)-2,2'-bipyridine is used as a ligand for forming complexes with metal ions, which is crucial in the study and application of coordination chemistry. Its role in complex formation allows for the exploration of new chemical and physical properties that can be harnessed in various applications.
Used in Catalysis:
In the field of catalysis, 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine is utilized for its ability to modify the activity and selectivity of catalysts. 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine's interaction with metal ions can lead to the development of more efficient catalytic systems.
Used in Fluorescence Sensing:
4,4'-Bis(hydroxymethyl)-2,2'-bipyridine is employed as a component in fluorescence sensing due to its potential to form complexes that exhibit changes in fluorescence properties upon interaction with specific analytes. This makes it a valuable tool in the detection and measurement of various chemical species.
Used in the Design of Functional Materials:
As a building block for designing new functional materials, 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine contributes to the development of materials with tailored properties for specific applications, such as in electronics, pharmaceuticals, or environmental technologies.
Used in the Synthesis of Coordination Polymers and Metal-Organic Frameworks:
In the synthesis of coordination polymers and metal-organic frameworks, 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine is used as a versatile building block. Its incorporation into these structures can lead to materials with unique properties, such as high surface areas, tunable pore sizes, and adjustable chemical functionalities.
Used in Antioxidant and Antimicrobial Applications:
4,4'-Bis(hydroxymethyl)-2,2'-bipyridine is studied for its potential antioxidant properties, which could be beneficial in various industries, including pharmaceuticals and food preservation. Additionally, its antimicrobial properties are of interest for applications in healthcare and material sciences to prevent microbial growth and contamination.

Upstream product

• 134457-14-0 4,4'-bis(bromomethyl)-2,2'-bipyridine 
• 72460-28-7 2,2'-bipyridyl-4,4'-dicarboxylic acid chloride 
• 199282-52-5 4,4’-bis[(trimethylsilyl)methyl]-2,2’-bipyridine 
• 87855-83-2 4,4’-dimethyl-2,2’-bipyridine N,N’-dioxide 
• 6813-38-3 2,2'-Bipyridine-4,4'-dicarboxylic acid 
• 1134-35-6 4,4'-dimethyl-2,2'-bipyridines 
• 99970-84-0 [2,2']bipyridinyl-4,4'-dicarbaldehyde 
• 279681-06-0 2,2'-bipyridine-4,4'-diyldimethanediyl diacetate 
• 138219-98-4 4,4’-bis(chloromethyl)-2,2’-bipyridine 
• 1762-42-1 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine 
• 71071-46-0 4,4'-bis(carbomethoxy)-2,2'-bipyridine 

Downstream Products

• 134457-14-0 4,4'-bis(bromomethyl)-2,2'-bipyridine 
• 859839-18-2 4,4'-bis[3,4,5-tris(dodecyloxy)benzoyloxymethyl]-2,2'-bipyridine 
• 859839-20-6 4,4'-bis[3,4,5-(trihexadecyloxy)benzoyloxymethyl]-2,2'-bipyridine 
• 1394226-39-1 [(η⁶-benzene)RuCl(4,4′-dimethoxy-2,2′-bipyridine)](tosylate) 
• 1394226-44-8 [(η⁶-p-cymene)RuCl(4,4′-dimethoxy-2,2′-bipyridine)](tosylate) 
• 825621-06-5 (E,E′)-4,4′-bisstyryl-2,2′-bipyridine 
• 1431384-63-2 1,1'-([2,2'-bipyridine]-4,4'-diylbis(methylene))bis(3-(3,5-bis(triflu-oromethyl)phenyl)-thiourea) 
• 727380-18-9 4,4'-bis(aminomethyl)-2,2'-bipyridine 
• 1329744-13-9 4,4'-bis(4-tert-butylstyryl)-2,2'-bipyridyl 
• 176220-38-5 4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine 
• 345648-31-9 [3-(4-Trifluoromethyl-phenyl)-ureido]-acetic acid 4'-{2-[3-(4-trifluoromethyl-phenyl)-ureido]-acetoxymethyl}-[2,2']bipyridinyl-4-ylmethyl ester 
• 345648-32-0 [3-(4-Isopropyl-phenyl)-ureido]-acetic acid 4'-{2-[3-(4-isopropyl-phenyl)-ureido]-acetoxymethyl}-[2,2']bipyridinyl-4-ylmethyl ester 
• 345648-34-2 [3-(4-Bromo-phenyl)-ureido]-acetic acid 4'-{2-[3-(4-bromo-phenyl)-ureido]-acetoxymethyl}-[2,2']bipyridinyl-4-ylmethyl ester 
• 345648-35-3 [3-(3-Methylsulfanyl-phenyl)-ureido]-acetic acid 4'-{2-[3-(3-methylsulfanyl-phenyl)-ureido]-acetoxymethyl}-[2,2']bipyridinyl-4-ylmethyl ester 

Relevant articles and documents

Simultaneous self-assembly of a [2]catenane, a trefoil knot, and a solomon link from a simple pair of ligands

A topological triptych: Three molecular links, a [2]catenane, a trefoil knot, and a Solomon link, were obtained in one pot through the self-assembly of two simple ligands in the presence of ZnII (see picture). The approach relied on dynamic covalent chemistry and metal templation.

Enhanced electrochemiluminescence efficiency of Ru(ii) derivative covalently linked carbon nanotubes hybrid

The synthesized derivative Ru(bpy)3 covalently linked CNTs hybrid shows good electrochemical activity and ca. 17 times higher luminescence quantum efficiency than the adsorbed derivative Ru(bpy)3. The Ru-CNTs based ECL sensor exhibits high stability toward determination of TPA with a detection limit as low as 8.75 pM.

Iodide ion pairing with highly charged ruthenium polypyridyl cations in CH3CN

A series of three highly charged cationic ruthenium(II) polypyridyl complexes of the general formula [Ru(deeb)3-x(tmam)x](PF6)2x+2, where deeb is 4,4′-diethyl ester-2,2′-bipyridine and tmam is 4,4′-bis[(trimethylamino)methyl]-2,2′-bipyridine, were synthesized and characterized and are referred to as 1, 2, or 3 based on the number of tmam ligands. Crystals suitable for X-ray crystallography were obtained for the homoleptic complex 3, which was found to possess D3 symmetry over the entire ruthenium complex. The complexes displayed visible absorption spectra typical of metal-to-ligand charge-transfer (MLCT) transitions. In acetonitrile, quasi-reversible waves were assigned to RuIII/II electron transfer, with formal reduction potentials that shifted negative as the number of tmam ligands was increased. Room temperature photoluminescence was observed in acetonitrile with quantum yields of φ ～ 0.1 and lifetimes of τ ～ 2 μs. The spectroscopic and electrochemical data were most consistent with excited-state localization on the deeb ligand for 1 and 2 and on the tmam ligand for 3. The addition of tetrabutylammonium iodide to the complexes dissolved in a CH3CN solution led to changes in the UV-vis absorption spectra consistent with ion pairing. A Benesi-Hildebrand-type analysis of these data revealed equilibrium constants that increased with the cationic charge 1 -1. 1H NMR studies in CD3CN also revealed evidence for iodide ion pairs and indicated that they occur predominantly with iodide localization near the tmam ligand(s). The diastereotopic H atoms on the methylene carbon that link the amine to the bipyridine ring were uniquely sensitive to the presence of iodide; analysis revealed that an iodide "binding pocket" exists wherein iodide forms an adduct with the 3 and 3′ bipyridyl H atoms and the quaternized amine. The MLCT excited states were efficiently quenched by iodide. Time-resolved photoluminescence measurements of 1 revealed a static component consistent with rapid electron transfer from iodide in the "binding pocket" to the Ru metal center in the excited state, ket > 108 s-1. The possible relevance of this work to solar energy conversion and dye-sensitized solar cells is discussed.

A new bipyridyl cobalt complex for reductive dechlorination of pesticides

Reductive dechlorinations are especially promising reactions for improving the biodegradability and hence decreasing the environmental impact of chlorinated organic pollutants. In this context, the catalytic activity of a bipyridyl cobalt complex containing two bipyridine ligands was examined for achieving clean electrochemical dehalogenation in aqueous media. The prepared [Co(bpy(CH2OH)2)2]2+ complex was found to exhibit high catalytic activity toward the dechlorination of chloroacetanilide herbicides. Based on preparative electrolyses, 2-electron reduction of the substrate was obtained with a dechlorination yield of 85%, underlining the selectivity and efficiency of the dehalogenation process. Cyclic voltammetry analyses highlighted the catalytic activity of the complex toward chloroacetanilide herbicides, as alachlor, metolachlor and metazachlor. An high apparent chemical rate constant k1 of 5000 mol-1 L s-1 is calculated for the first step of the cathodic reduction of alachlor, based on simulated cyclic voltammetry experiments.

Synthesis of bifunctional Ru complexes with 1,2-dithiolane and carboxylate-substituted ligands

Abstract An N3-type, Ru heteroleptic complex, AK1, having one bipyridyl ligand modified with COOH groups for tethering to TiO2 and a second bipyridyl ligand modified with two lipoic acid units for binding to platinum, was synthesized. The photophysical and spectroelectrochemical properties were studied in solution, on TiO2, in a dye-sensitized solar cell and on a Pt wire electrode. The results showed that AK1 can produce a photocurrent on TiO2. Furthermore, AK1 binds to Pt via the lipoic acid ligand but not via the carboxylic acid group, and can be electrochemically addressed by the Pt via the lipoic acid linkage.

New bi-functional zinc catalysts based on robust and easy-to-handle N-chelating ligands for the synthesis of cyclic carbonates from epoxides and CO2 under mild conditions

A series of novel zinc complexes were prepared by covalent linkage of various imidazolium-based ionic liquid moieties with the 2,2′-bipyridine ligand on the two sides of the 4,4′-position. The zinc(ii) complexes containing the rigid N-chelating ligand proved to be stable, highly efficient and easy-to-handle catalysts towards the synthesis of cyclic carbonate from epoxide and CO2 without the use of any co-catalyst or organic solvent. The catalysts can be easily recovered and reused without significant loss of activity and selectivity by control of the solvent. The kinetic study uncovered that the reaction was first-order with respect to the epoxide. Moreover, a plausible reaction mechanism was proposed, in which the zinc center could promote ring-opening of the epoxide for the synergetic effect with the anion X- in ILs. the Partner Organisations 2014.

Synthesis and characterization of novel heteroleptic Ru(II) bipyridine complexes for dye-sensitized solar cell applications

Abstract: Four heteroleptic ruthenium(II) complexes, [Ru(L1)(L2)(NCS)2] (where L1 = 4,4′-bis[2-(1,1′-biphenyl)-4-ylethenyl]-2,2′-bipyridine (bpbpy) or 4,4′-bis[2-(3,4-dimethoxyphenyl)ethenyl]-2,2′-bipyridine (dmpbpy); L2 = 4,4′-dicarboxy-2,2′-bipyridine (dcbpy) or 4,4′-bis(E-carboxyvinyl)-2,2′-bipyridine (dcvbpy)), were synthesized from a one-pot reaction of [RuCl2(p-cymene)]2 and L1 followed by the addition of the anchoring ligand, L2. From these new heteroleptic ruthenium(II) complexes containing carboxylic acid-functionalized ligands, the tetrabutylammonium salt forms of the ruthenium(II) complexes, [Ru(L1)(L2)(NCS)2][TBA], were obtained in reasonable yields and applied as dyes in dye-sensitized solar cell (DSSC) devices. Among the DSSCs fabricated with the [Ru(L1)(L2)(NCS)2][TBA] dyes, a DSSC fabricated with the [Ru(bpbpy)(dcbpy)(NCS)2][TBA] dye exhibited the best power conversion efficiency (η) of 4.27%, while the cells fabricated with other dyes had η between 1.94 and 2.68%. Graphic abstract: [Figure not available: see fulltext.].

A water-soluble cyclometalated iridium(III) complex with fluorescent sensing capability for hypochlorite

Herein, a novel cyclometalated iridium (III) complex (Ir-1) with good water-solubility was designed and synthesized to sensitively detect hypochlorite (ClO?) in aqueous buffer solution. The sensor Ir-1 was prepared by incorporating a methacrylate group into cyclometalated ligands, which was a specific response site toward ClO? through an oxidation process. Ir-1 displayed strong emission at 615 nm, while significant fluorescence quenching was observed upon addition of ClO? with a low detection limit of 0.41 μM. Moreover, probe Ir-1 exhibited a rapid response (? with high selectivity over potentially competing species. The sensing process was evidenced by NMR and MS characterization. Further application in bioimaging of ClO? was successfully performed in living HepG2 cells.

Functionalized bipyridyl rhodium complex capable of electrode attachment for regeneration of NADH

A Rh(III) complex having a functionalized bpy-OH ligand that is potentially linkable to electrode surfaces was synthesized and fully characterized. The hydrido complex, which could be generated either electrochemically by cathodic reduction of the [η5-Cp*Rh(bpy-OH)Cl]Cl complex at -771 mV (versus Ag/AgCl) or chemically with formate, transformed NAD + efficiently into NADH with a TOF = 710 at 60 C.

A water-soluble and retrievable ruthenium-based probe for colorimetric recognition of Hg(II) and Cys

A new ruthenium-based complex 1 [(bis(4,4′-dimethylphosphonic-2,2′-bipyridine) dithiocyanato ruthenium (II))] was developed as a colorimetric probe for the detection of Hg(II) and Cys (Cysteine). The obtained compound 1 can give interconversional color changes upon the alternating addition of Hg(II) and Cys in 100% aqueous solution. The specific coordination between NCS groups with Hg(II) can lead to the formation of 1-Hg2 + complex, which can induce a remarkable spectral changes of probe 1. Afterwards the formed 1-Hg2 + complex can act as effective colorimetric sensor for Cys. Owing to the stronger binding affinity of sulfhydryl group to Hg2 +, Cys can extract Hg2 + from 1-Hg2 + complex resulting in the release of 1 and the revival of absorption profile of the probe 1. By introducing the hydrophilic phosphonic acid groups, the proposed probe exhibited excellent water solubility. The limits of detection (LODs) of the assay for Hg2 + and Cys are calculated to be 15 nM and 200 nM, respectively.