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

Description

4,4'-Bis(hydroxymethyl)-2,2'-bipyridine is a bipyridine derivative that exists as a white crystalline powder. It is characterized by its solubility in both water and organic solvents. 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine is known for its ability to act as a ligand in coordination chemistry, forming complexes with a variety of metal ions. Its structural features, including the hydroxymethyl groups on the bipyridine scaffold, contribute to its versatility in the synthesis of coordination polymers and metal-organic frameworks. It also holds promise for applications beyond its chemical reactivity, with potential antioxidant and antimicrobial properties being explored.

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

• 72460-28-7 2,2'-bipyridyl-4,4'-dicarboxylic acid chloride 
• 199282-52-5 4,4’-bis[(trimethylsilyl)methyl]-2,2’-bipyridine 
• 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 
• 134457-14-0 4,4'-bis(bromomethyl)-2,2'-bipyridine 
• 1762-42-1 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine 
• 71071-46-0 4,4'-bis(carbomethoxy)-2,2'-bipyridine 
• 87855-83-2 4,4’-dimethyl-2,2’-bipyridine N,N’-dioxide 

Downstream Products

• 134457-14-0 4,4'-bis(bromomethyl)-2,2'-bipyridine 
• 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 
• 1394226-44-8 [(η⁶-p-cymene)RuCl(4,4′-dimethoxy-2,2′-bipyridine)](tosylate) 
• 1394226-39-1 [(η⁶-benzene)RuCl(4,4′-dimethoxy-2,2′-bipyridine)](tosylate) 
• 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.

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.

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.

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.].

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.

Post-synthetic modifications of cadmium-based knots and links

Three topologically non-trivial cadmium(ii)-based complexes - Cd-[2]C, Cd-TK and Cd-SL - were simultaneously self-assembled in a dynamic library, individually isolated and fully characterized using solid-state, gas-phase and solution-phase techniques. Post-synthetic modifications, including reduction and transmetalation, were subsequently achieved. Imine bond reduction followed by demetallation led to the isolation of the corresponding organic molecules [2]C, TK and SL. Transmetalation of Cd-TK and Cd-SL with the zinc(ii) cation resulted in isolation of the corresponding zinc(ii)-containing complexes Zn-TK and Zn-SL.

A Water-Soluble Iridium Photocatalyst for Chemical Modification of Dehydroalanines in Peptides and Proteins

Dehydroalanine (Dha) residues are attractive noncanonical amino acids that occur naturally in ribosomally synthesised and post-translationally modified peptides (RiPPs). Dha residues are attractive targets for selective late-stage modification of these complex biomolecules. In this work, we show the selective photocatalytic modification of dehydroalanine residues in the antimicrobial peptide nisin and in the proteins small ubiquitin-like modifier (SUMO) and superfolder green fluorescent protein (sfGFP). For this purpose, a new water-soluble iridium(III) photoredox catalyst was used. The design and synthesis of this new photocatalyst, [Ir(dF(CF3)ppy)2(dNMe3bpy)]Cl3, is presented. In contrast to commonly used iridium photocatalysts, this complex is highly water soluble and allows peptides and proteins to be modified in water and aqueous solvents under physiologically relevant conditions, with short reaction times and with low reagent and catalyst loadings. This work suggests that photoredox catalysis using this newly designed catalyst is a promising strategy to modify dehydroalanine-containing natural products and thus could have great potential for novel bioconjugation strategies.

Synthesis and characterization of an immobilizable photochemical molecular device for H2-generation

With [RuII(bpyMeP)2tpphzPtCl2]2+ (4) a molecular photocatalyst has been synthesized for visible-light-driven H2-evolution. It contains the ligand bpyMeP (4,4′-bis(diethyl-(methylene)-phosphonate)-2,2′-bipyridine) with phosphate ester groups as precursors for the highly potent phosphonate anchoring groups, which can be utilized for immobilization of the catalyst on metal-oxide semiconductor surfaces. The synthesis was optimized with regard to high yields, bpyMeP was fully characterized and a solid-state structure could be obtained. Photophysical studies showed that the photophysical properties and the localization of the excited states are not altered compared to similar Ru-complexes without anchoring group precursors. (4) was even more active in homogenous catalysis experiments than [RuII(tbbpy)2tpphzPtCl2]2+ (6) with tbbpy (4,4′-bis(tbutyl)-2,2′-bipyridine) as peripheral ligands. After hydrolysis (4) was successfully immobilized on NiO, suggesting that an application in photoelectrosynthesis cells is feasible. This journal is

Establishing dual electrogenerated chemiluminescence and multicolor electrochromism in functional ionic transition-metal complexes

A combination of electrochromism and electroluminescence in functional materials could lead to single-layer dual electrochromic/electroluminescent (EC/EL) display devices, capable of simultaneous operation in emissive and reflective modes. Whereas such next generation displays could provide optimal visibility in any ambient lighting situation, materials available that exhibit such characteristics in the active layer are limited due to the required intrinsic multifunctionality (i.e., redox activity, electroluminescence, electrochromism, and ion conductivity) and to date can only be achieved via the rational design of ionic transition-metal complexes. Reported herein is the synthesis and characterization of a new family of acrylate-containing ruthenium (tris)bipyridine-based coordination complexes with multifunctional characteristics. Potential use of the presented compounds in EC/EL devices is established, as they are applied as cross-linked electrochromic films and electrochemiluminescent layers in light-emitting electrochemical cell devices. Electrochromic switching of the polymeric networks between yellow, orange, green, brown and transmissive states is demonstrated, and electrochemiluminescent devices based on the complexes synthesized show red-orange to deep red emission with λmax ranging from 680 to 722 nm and luminance up to 135 cd/m2. Additionally, a dual EC/EL device prototype is presented where light emission and multicolor electrochromism occur from the same pixel comprised of a single active layer, demonstrating a true combination of these properties in ionic transition-metal complexes.

Potentiostatic modulation of the lifetime of light-induced charge separation in a heterosupermolecule

A heterosupermolecule has been assembled by covalently linking a TiO2 nanocrystal, a ruthenium complex, and a viologen. The associated heterosupramolecular function, long-lived light-induced charge separation, has been demonstrated. Potentiostatic modulation of this function has also been demonstrated. The reported findings and associated insights may find practical applications in the area of optical information storage. ? 1999 American Chemical Society.

Xylose derivatives and process for preparation thereof

Disclosure of the present invention relates to a method for synthesis of a xylose derivative, which comprises protecting a xylose with a protective group, followed by incorporating to a halogen atom as a leaving group; removing the protective groups and using water-soluble ligands to carry out a Suzuki cross-couplings reaction with a palladium catalyst in a water solution. Ten new xylose derivatives as obtained by the method are also provided.