5486-06-6

Basic information

• Product Name: (R*,R*)-(±)-1,2-dipyridin-4-ylethane-1,2-diol
• Synonyms: (R*,R*)-(±)-1,2-dipyridin-4-ylethane-1,2-diol;(±)-α,β-Di(4-pyridyl)glycol;DL-1,2-Bis(4-pyridyl)glycol;DL-α,β-Di(4-pyridyl)glycol;rac-(1R*,2R*)-1,2-Bis(4-pyridyl)-1,2-ethanediol;1,2-bis(4-pyridyl)ethane-1,2-diol;1,2-di(pyridin-4-yl)ethane-1,2-diol
• CAS NO: 5486-06-6
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.23588
• EINECS: 226-815-3
• Mol File: 5486-06-6.mol

Chemical Properties

• Boiling Point: 451.1°Cat760mmHg
• Flash Point: 226.6°C
• Appearance: /
• Density: 1.303g/cm³
• Vapor Pressure: 6.3E-09mmHg at 25°C
• Refractive Index: 1.636
• PKA: 12.01±0.20(Predicted)
• CAS DataBase Reference: (R*,R*)-(±)-1,2-dipyridin-4-ylethane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (R*,R*)-(±)-1,2-dipyridin-4-ylethane-1,2-diol(5486-06-6)
• EPA Substance Registry System: (R*,R*)-(±)-1,2-dipyridin-4-ylethane-1,2-diol(5486-06-6)

Safety Data

• Hazardous Substances Data: 5486-06-6(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
(R,R)-(±)-1,2-dipyridin-4-ylethane-1,2-diol is used as a chelating agent for forming stable complexes with metal ions, such as copper, in coordination chemistry. Its ability to bind with metal ions makes it a useful compound in this field.
Used in Catalysis:
In the field of catalysis, (R,R)-(±)-1,2-dipyridin-4-ylethane-1,2-diol is used as a ligand in metal-catalyzed reactions, contributing to the enhancement of reaction rates and selectivity.
Used in Material Science:
(R,R)-(±)-1,2-dipyridin-4-ylethane-1,2-diol is employed in material science for its potential applications in the development of new materials with unique properties,得益于其与金属离子形成稳定复合物的能力。
Used in Medicinal Chemistry:
In medicinal chemistry, (R,R)-(±)-1,2-dipyridin-4-ylethane-1,2-diol is used for its potential application in the development of new drugs and therapeutic agents, taking advantage of its chelating properties and interactions with metal ions.
Used in Asymmetric Synthesis:
(R,R)-(±)-1,2-dipyridin-4-ylethane-1,2-diol is utilized as a valuable tool in asymmetric synthesis, where its chiral properties aid in the selective formation of specific enantiomers of a compound.
Used in Enantiomeric Separation:
(R,R)-(±)-1,2-dipyridin-4-ylethane-1,2-diol is also used in enantiomeric separation, a technique that involves the isolation of individual enantiomers from a mixture. Its chiral nature makes it a useful agent in this process.
Used in Pharmaceutical Industry:
(R,R)-(±)-1,2-dipyridin-4-ylethane-1,2-diol is used as a chelating agent and ligand in the pharmaceutical industry for the development of drugs that require metal ion interactions or catalysis.
Used in Chemical Research:
In the field of chemical research, (R,R)-(±)-1,2-dipyridin-4-ylethane-1,2-diol is used as a model compound to study the effects of chirality on chemical reactions and to develop new methods for enantiomeric separation and asymmetric synthesis.

InChI:InChI=1/C12H12N2O2/c15-11(9-1-5-13-6-2-9)12(16)10-3-7-14-8-4-10/h1-8,11-12,15-16H

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 100-52-7 benzaldehyde 
• 67-64-1 acetone 
• 77280-42-3 (1-Nitro-cyclohexyl)-[4]pyridyl-methanol 
• 4972-49-0 dl-1,2-bis(4'-pyridyl)-1,2-ethanediol 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 4972-49-0 (+)-1,2-di-[4]pyridyl-ethane-1,2-diol 
• 4972-49-0 (-)-1,2-di-[4]pyridyl-ethane-1,2-diol 
• 1393707-71-5 4,4'-[1,2-bis(2,3,5,6-tetrafluoro-4-iodophenoxy)ethane-1,2-diyl]dipyridine 

Relevant articles and documents

Aromatic derivative mononitrate and preparation method thereof

The invention relates to aromatic derivative mononitrate and a preparation method thereof, the general formula of the aromatic derivative mononitrate is as shown in formula (I), Ar group is benzene ring, mono-substituted or multi-substituted benzene ring, pyridine ring or mono-substituted pyridine ring, and the substituent group on the benzene ring or pyridine ring is CH3, halogen, OH, NO2 or CF3.When the Ar group is the pyridine ring, the preparation method comprises the following steps: (1) reacting 4-aldehyde pyridine with a hydrochloric acid aqueous solution of titanium trichloride in glacial acetic acid to obtain a vicinal diol intermediate compound 1; and (2) reacting the compound 1 in concentrated nitric acid or mixed acid of concentrated nitric acid and fuming nitric acid to obtain the mononitrate compound 2; and the raw materials for preparation are low in cost, few in synthesis steps, simple to operate, convenient to extract and purify and high in yield. The compound has thecharacteristics of nitrate, has potential application in the aspects of expanding blood vessels, inhibiting platelet aggregation and adhesion and resisting thrombosis, and is beneficial to treatmentof angina pectoris caused by coronary atherosclerosis.

O-dicarbonyl ester and preparation method thereof (by machine translation)

The invention provides an ortho-dicarbonyl ester and a preparation method thereof, and the general formula is shown in a formula (I). , The Ar group is a benzene ring, a mono-or polysubstituted benzene ring, a pyridine ring or a mono-substituted pyridine ring, and the substituent on the benzene ring or the pyridine ring is CH. 3 Halogen, OH, NO2 Or CF3 When Ar is a pyridine ring, the preparation method is as follows: (1) 4 -aldehyde pyridine is reacted with an aqueous hydrochloric acid solution of titanium trichloride to obtain the intermediate compound 1 of o-diol; (2) the compound 1 is reacted in concentrated sulfuric acid and fuming nitric acid to obtain the ortho-dinitrate compound 2. Raw materials used in the preparation process are low in cost, few in synthesis steps, simple to operate, convenient to extract and purify and high in yield. The compound has the characteristics of nitrate, can inhibit platelet aggregation and adhesion after expanding blood vessels, and has potential application in the aspect of antithrombotic formation, and is beneficial to angina pectoris treatment caused by coronary atherosclerosis. (by machine translation)

Organic intermediate diaromatic hydrocarbon carboxylic acid and preparation method thereof

The invention provides an organic intermediate diaromatic hydrocarbon carboxylic acid and a preparation method thereof. The general formula of the organic intermediate di-aromatic hydrocarbon carboxylic acid is as shown in formula (I) shown in the specification, wherein an Ar group is a benzene ring, a mono-substituted or multi-substituted benzene ring, a pyridine ring, and a mono-substituted pyridine ring, a substituent group on benzene ring or pyridine ring is CH3, halogen, OH, NO2 or CF3. When the Ar group is a pyridine ring, the preparation method comprises the following steps: (1) reacting 4-formylpyridine with a hydrochloric acid aqueous solution of titanium trichloride in glacial acetic acid to obtain an intermediate compound 1 of vicinal diol; and (2) subjecting the compound 1 to acatalytic reaction with ferric trichloride in acetic acid and water so as to obtain a target compound, i.e., the diaromatic hydrocarbon carboxylic acid compound 2. The synthesis steps of the diaromatic hydrocarbon carboxylic acid are few, operation is simple, purification is convenient, and the yield is higher. In addition, the invention provides the novel method for preparing the organic intermediate diaromatic hydrocarbon carboxylic acid, and the obtained product has important application value in the aspects of metal organic complexes and new organic molecular structure modification.

A CONVENIENT SYNTHESIS OF SUBSTITUTED PYRIDYLGLYCOLS PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE

2- and 4-Acetylpyridines, and 2- and 4-pyridinealdehydes when allowed to react with two-equiv. of aqueous titanium trichloride add to the carbonyl carbon atom of simple ketones (acetone, cyclopentanone, cyclohexanone) and aldehydes (acetaldehyde, propionaldehyde, benzaldehyde) affording substituted pyridylglycols in very good yields.The present one-pot method has considerable advantage over the existing procedure.The reaction is discussed in terms of a radical mechanism in which the Ti(III) species plays the fundamental role.

A Novel Reaction Type Promoted by Aqueous Titanium Trichloride. Synthesis of Unsymmetrical 1,2-Diols

Electron-withdrawing substituted carbonyl compounds when allowed to react with 2 equiv of aqueous titanium trichloride in the presence of acetone, acetaldehyde, or benzaldehyde afford unsymmetrical 1,2-diols in high yields under very simple experimental conditions.

REDUCTIVE REACTIONS OF SUBSTITUTED PYRIDINES BY AQUEOUS TITANIUM TRICHLORIDE

Aqueous titanium trichloride reductively removes cyano and halo groups from the correspondingly substituted pyridines by a two electron-transfer process and promotes reduction of pyridyl-ketones and aldehydes to glycols by one electron-transfer process under very simple experimental conditions.

Stereospecificity in the Reductive Coupling of 4-Pyridinecarboxaldehyde

One-electron reduction of 4-pyridinecarboxyaldehyde in aqueous solutions yields a mixture of dl- and meso-pinacols.Controlled-potential electrolysis (using a DME) at a potential corresponding to the limiting current of the first one-electron wave yielded dl/meso ratios of 0.57, 0.35, and 1.92 at pH values of 6.1, 10.6, and 13.3, respectively.The variation of the dl/meso ratios can be attributed to a difference in the surface orientation of radical cations (pH 6.1), uncharged radicals (pH 10.6), and radical anions (pH 13.3) that are involved in the dimerization at these different values of pH.For all dimerizations studied, voltammetric and polarographic results indicate a radical-radical coupling mechanism.