16879-02-0

Basic information

• Product Name: 6-Chloropyridn-2-ol
• Synonyms: 2(1H)-Pyridinone, 6-chloro-;2(1H)-Pyridinone,6-chloro-;2(1H)-Pyridone, 6-chloro-;2(1H)-Pyridone,6-chloro-;2-Chloro-6-pyridinol;2-Hydroxy-6-chloropyridine;6-Chloro-1H-pyridin-2-one;6-Chloro-2(1H)-pyridinone
• CAS NO: 16879-02-0
• Molecular Formula: C₅H₄ClNO
• Molecular Weight: 129.54
• EINECS: 240-909-1
• Product Categories: PYRIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Chloropyridines;Halopyridines;alcohol|alkyl chloride
• Mol File: 16879-02-0.mol

Chemical Properties

• Melting Point: 128-130 °C(lit.)
• Boiling Point: 206 °C
• Flash Point: 163°C
• Appearance: /
• Density: 1.35
• Vapor Pressure: 0.000338mmHg at 25°C
• Refractive Index: 1.4510 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.33±0.10(Predicted)
• BRN: 108665
• CAS DataBase Reference: 6-Chloropyridn-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloropyridn-2-ol(16879-02-0)
• EPA Substance Registry System: 6-Chloropyridn-2-ol(16879-02-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 16879-02-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
6-Chloropyridn-2-ol is used as a key component in the synthesis of various chemical complexes, particularly those involving osmium. Its ability to undergo melt reactions at specific temperatures makes it a valuable compound in the creation of new materials with unique properties.
Used in Electrochemistry:
In the field of electrochemistry, 6-chloro-2-hydroxypyridine is utilized for studying the electrochemical properties of the complexes it forms with other elements, such as osmium. This helps in understanding the behavior of these complexes in different environments and their potential applications.
Used in Spectroscopic Studies:
6-Chloropyridn-2-ol is employed in the study of the spectroscopic properties of the complexes it forms. This allows researchers to gain insights into the electronic structure and bonding of these complexes, which can be useful in developing new materials with specific characteristics.
Used in X-ray Crystallography:
6-chloro-2-hydroxypyridine is used in the determination of the X-ray crystal structure of the complexes it forms. This information is crucial for understanding the three-dimensional arrangement of atoms within the complex and can provide valuable insights into its properties and potential applications.

InChI:InChI=1/C5H4ClNO/c6-4-2-1-3-5(8)7-4/h1-3H,(H,7,8)

Upstream product

• 4645-11-8 6-ethoxy-2-bromo-pyridine 
• 17228-64-7 6-chloro-2-methoxypyridine 
• 3385-94-2 hexamethyldisilathiane 
• 64-19-7 acetic acid 
• 2402-78-0 2,6-dichloropyridine 

Downstream Products

• 2402-78-0 2,6-dichloropyridine 
• 6515-38-4 3,5,6-trichloropyridin-2 ol 
• 108122-24-3 1-(6-hydroxy-2-pyridyl)piperazine 
• 122751-37-5 Z-Ala-OPyCl 
• 122751-38-6 Z-Val-O-PyCl 
• 122751-40-0 Z-Gln-OPyCl 
• 122751-41-1 Z-Asp(OBzl)-OPyCl 
• 122751-39-7 Z-Phe-OPyCl 
• 125320-81-2 Dicyclohexyl-amine; compound with 6-chloro-pyridin-2-ol 
• 74546-79-5 Phenyl-phosphonothioic acid O,O-bis-(6-chloro-pyridin-2-yl) ester 
• 17228-63-6 6-chloro-1-1methylpyridin-2(1H)-one 
• 442199-11-3 4-(6-chloropyridin-2-yloxy)piperidine-1-carboxylic acid tert-butyl ester 
• 901120-46-5 C₁₈H₁₉N₃O₄S 

Relevant articles and documents

Quantitative Model of Solvent Effects on Hydroxypyridine-Pyridone and Mercaptopyridine-Thiopyridone Equilibria: Correlation with Reaction-Field and Hydrogen-Bonding Effects

A model for the effect of reaction field and hydrogen bonding on the relative energies of protomers is applied to the equilibria between 6-chloro-2-hydroxypyridine and 6-chloro-2-pyridone, 2-mercaptopyridine and 2-thiopyridone, 6-chloro-2-mercaptopyridine and 6-chloro-2-thiopyridone, and 4-mercaptopyridine and 4-thiopyridone in a wide range of solvents.Quantitative correlation is obtained by a multivariable analysis.In addition to satisfactory statistical tests of the correlations, estimates of the differences in free energies between the isomers in the vapor phase and of the dipole moment component of the reaction-field term are obtained which compare well with the available independent values.These criteria are shown to signal an unacceptable correlation for the case of 2-chloro-4-hydroxypyridine and 2-chloro-4-pyridone.The advantage of this model, which provides an understanding of the effect of molecular environment on protomeric equilibria in terms of reasonable physical interactions, over empirical approaches is noted.

BF3·SMe2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles

Herein, a general, solvent-free and straightforward thiomethylation of electron deficient heterocycles using BF3·SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3·SMe2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non-malodorous reagent while the discovery of novel chemical transformations using BF3·SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent.

One-pot synthesis of benzo[f]quinolin-3-ones and benzo[a]phenanthridein-5- ones by the photoanuulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1- ones to phenylacetylene

The one-pot synthesis of benzo[f]quinolin-3-ones and benzo[a] phenanthridein-5-ones was achieved by the inter- and intramolecular photoannulation of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones with phenylacetylene or tethered phenylacetylene. The reactions were proceeded by photoaddition of 6-chloropyridin-2-ones and 3-chloroisoquinolin-1-ones to phenylacetylene to give the chlorine-substituted stilbenoids, and then 6π electrocyclization of the stilbenoids and oxidation aromatization to afford the polycyclic products.

Synthesis of 1,3-diazepines and ring contraction to cyanopyrroles

Several tetrazolo[1,5-a]pyridines/2-azidopyridines undergo photochemical nitrogen elimination and ring expansion to 1,3-diazacyclohepta-1,2,4, 6-tetraenes (7,10,13,16,19,22) as well as ring cleavage to cyanovinylketenimines (8,17,20b) in low temperature Ar matrices. 6,8-Dichlorotetrazolo[1,5-a]pyridine/2-azido-3,5-dichloropridine 6 undergoes ready exchange of the chlorine in position 8 (3) with ROH/RONa. 8-Chloro-6-trifluoromethylletrazolo[1,5-a]pyridine 15 undergoes solvolysis of the CF3 group to afford 8-chloro-6-methoxycarbonyltetrazolo[1,5-a]pyridine 18. Several tetrazolopyridines/2-azidopyridines afford 1H- or 5H-1,3-diazepines in good yields on photolysis in the presence of alcohols or amines (11,14,23,25). 5-Chlorotetrazolo[1,5-a]pyridines/2-azido-6-chloropyridines 21 and 38 undergo a rearrangement to 1H-and 3H-3-cyanopyrroles 27 and 45, respectively. The mechanism of this rearrangement was investigated by 15N-labelling and takes place via transient 1,3-diazepines. The structures of 6,8-dichloro-tetrazolo[1,5-a]pyridine 6T, 6-chloro-8-ethoxytetrazoIo[1,5-a]pyridine 9Tb, dipyrrolylmethane 28, and 2-isopropoxy-4-dimethylamino-5H-1,3-diazepine 25b were determined by X-ray crystallography. In the latter case, this represents the first reported X-ray crystal structure of a 5H-1,3-diazepine.

Demethylation of methoxypyridines with sodium trimethylsilanethiolate

Demethylation of methoxypyridines was accomplished in 55-87percent yield by use of ca. 1.5-2.5 equivalents of NaSSiMe3 in 1,3-dimethyl-2-imidazolidinone at 120-180 deg C.This method was found applicable to a methoxyquinoline and methoxypyridines containing a second substituent, such as Cl, OMe, and COOMe.

EQUILIBRE LACTIME-LACTAME DES HYDROXY-PYRIDINES ET DES HYDROXY-PYRIMIDINES (URACILES) EN MILIEU APOLAIRE: ETUDE INFRA-ROUGE

In contrast to what observed with mono hydroxy-pyridines and -pyrimidines the lactim-lactam equilibrium of uracils is not found to be markedly influenced by solvent polarity.

Displacement of Protomeric Equilibria by Self-Association: Hydroxypyridine-Pyridone and Mercaptopyridine-Thiopyridone Isomer Pairs

Values of both self-association and protomeric equilibrium constants are reported for 2-hydroxypyridine-2-pyridone, 4-hydroxypyridine-4-pyridone, and 2-mercaptopyridine-2-thiopyridone isomer pairs in different solvents.These results provide quantitative evidence for significant differences in the positions of protomeric equilibria for self-associated and monomeric species.The 2-substituted isomers are associated as well-known dimers while the 4-substituted systems form oligomers.In polar and hydrogen-bonding solvents self-association is substantially reduced.Sterically hindered 2- and 4-pyridones are less associated than unhindered systems.The implication of these results, that determinations and interpretations of protomeric equilibrium should take into account the possible dominance of self-association, is discussed.

Influence of Carboxylic Acid Association upon the Lactim-Lactam Tautomeric Equilibrium of 2-Hydroxypyridines

I.r. and u.v. absorption spectroscopy in CCl4 at room temperature provides evidence for lactim-acid and lactam-acid heterodimer formation in 6-chloro-2-hydroxypyridine-acetic acid mixtures.Measurements of association constants for two types of 1:1 hydrogen bonded complexes reveal preferential association with the lactam tautomer, leading to a shift in the apparent tautomeric equilibrium constant.These results suggest that specific interactions are of great importance in understanding solvent effects on protomeric equilibria.