17368-12-6

Basic information

• Product Name: 2-Chloro-4-hydroxypyridine
• Synonyms: 2-CHLORO-4-HYDROXYPYRIDINE;2-CHLORO-4-PYRIDINOL;2-CHLOROPYRIDIN-4-OL;4-Pyridinol,2-chloro-(7CI,8CI,9CI);2-Chloro-4-hydroxypyridine HCl Salt;2-CHLORO-4-HYDROXYPYRIDINE 99%;2-Chloro-4-hydroxypyridine hydrochloride;2-chloro-1H-pyridin-4-one
• CAS NO: 17368-12-6
• Molecular Formula: C₅H₄ClNO
• Molecular Weight: 129.54
• EINECS: 241-399-3
• Product Categories: PYRIDINE;blocks;Pyridines;CHIRAL CHEMICALS
• Mol File: 17368-12-6.mol

Chemical Properties

• Melting Point: 169-172°C
• Boiling Point: 225.1 °C at 760 mmHg
• Flash Point: 89.9 °C
• Appearance: White crystal
• Density: 1.35 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 7.94±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-4-hydroxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-hydroxypyridine(17368-12-6)
• EPA Substance Registry System: 2-Chloro-4-hydroxypyridine(17368-12-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36
• Hazardous Substances Data: 17368-12-6(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

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

Upstream product

• 17228-67-0 2-chloropyridin-4(1H)-one 
• 14432-12-3 4-Amino-2-chloropyridine 
• 73583-37-6 2-chloro-4-bromopyridine 
• 17228-69-2 2-chloro-4-methoxy-pyridine 
• 23056-36-2 2-chloro-4-nitropyridine 
• 458532-84-8 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine 
• 458532-96-2 2-chloropyridine-4-boronic acid 

Downstream Products

• 17228-67-0 2-chloropyridin-4(1H)-one 
• 159594-99-7 2-(2'-chloropyrid-4'-yloxy)-6-benzyloxypyridine 
• 1620579-59-0 4-((2-chloropyridin-4-yl)oxy)-3,5-difluorobenzaldehyde 

Relevant articles and documents

Chemoselective Demethylation of Methoxypyridine

A chemoselective demethylation method for various methoxypyridine derivatives has been developed. Treatment of 4-methoxypyridine with L-selectride in THF for 2 h at reflux temperature afforded 4-hydroxypyridine in good yield; no reaction to anisole occurred. The utility of our method was demonstrated by the efficient synthesis of the metabolic substances of the antiulcer agent omeprazole. Chemoselective demethylation at the site of 3,5-dimethyl-4-methoxypyridine in the presence of 4-methoxybenzimidazole was achieved.

Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water

A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.

IRIDIUM COMPLEX COMPOUNDS, ORGANIC ELECTROLUMINESCENT DEVICES AND USES THEREOF

Blue-emitting phosphorescent compounds show high solubility in solvents for coating solutions in the production of organic EL devices and have excellent thermal stability. Organic EL devices having the blue-emitting phosphorescent compounds have high luminous efficiency and long life. A blue-emitting phosphorescent compound is an iridium complex compound represented by Formula (1) below: wherein R1 is a C2-30 organic group; R2 to R4 are each independently a hydrogen atom or a C1-10 alkyl group; R5 to R8 are each independently an electron-withdrawing group selected from the group consisting of halogen atoms, C1-10 fluorine-substituted alkyl groups, C1-10 fluorine-substituted alkoxy groups, cyano group, aldehyde group, C2-10 acyl groups, C2-10 alkoxycarbonyl groups, C1-10 aminocarbonyl groups, thiocyanate group and C1-10 sulfonyl groups, a C1-10 organic group optionally having a heteroatom (except the electron-withdrawing groups) or a hydrogen atom; and at least one of R5 to R8 is the electron-withdrawing group.

Tetrabutylammonium salt induced denitration of nitropyridines: Synthesis of fluoro-, hydroxy-, and methoxypyridines

(Chemical Equation Presented) An efficient method for the synthesis of fluoropyridines via the fluorodenitration reaction is reported. The reaction is mediated by tetrabutylammonium fluoride (TBAF) under mild conditions without undue regard to the presence of water. The fluorodenitration is general for 2- or 4-nitro-substituted pyridines, while 3-nitropyridines require attendant electron-withdrawing groups for the reaction to proceed efficiently. Nitropyridines also undergo hydroxy- and methoxydenitration under mild conditions in the presence of the corresponding tetrabutylammonium species.

Efficient synthesis of halohydroxypyridines by hydroxydeboronation

This paper describes a general method for the synthesis of halohydroxypyridines from novel halopyridinylboronic acids and esters recently described by some of us. Halopyridinylboronic acids and esters have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide or meta-chloroperbenzoic acid. These hydroxylations take place regioselectively without other oxidation (N-oxide formation).

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.