2-Chloro-4-hydroxypyridine Chemical Properties

Melting point:

169-172°C

Boiling point:

401.8±25.0 °C(Predicted)

Density 

1.392±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

7.94±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

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

InChIKey

VBEHFOMFHUQAOW-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(O)=C1

CAS DataBase Reference

17368-12-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36

HS Code 

2933399990

2-Chloro-4-hydroxypyridine Usage And Synthesis

Chemical Properties

White crystal

Uses

2-Chloro-4-hydroxypyridine is a chemical that is used as a building block for various organic synthesis reactions. 

Preparation

2-Chloro-4-hydroxypyridine can be produced by the reaction of chloroform and pyridine, which results in the formation of 2-chloro-4-hydroxypyridine.

Reactions

2-Chloro-4-hydroxypyridine has been shown to react with copper metal under dehydrogenative conditions to form monochloropyridine. It also reacts with tribromide to form tribromopyridine and with graphene oxide to form hydroxypyridinium bromide. Lastly, it reacts with an organic solvent such as acet.

Synthesis

The general procedure for the synthesis of 2-chloro-4-hydroxypyridine from 2-chloro-4-aminopyridine is as follows: in a round-bottomed flask, 2-chloro-4-aminopyridine (3.0 g, 23.3 mmol) was dissolved in 40% sulfuric acid solution (50 g). The solution was stirred at 0 °C and sodium nitrite (1.93 g, 28.0 mmol) was added slowly. After addition, the reaction mixture was stirred continuously at room temperature for 24 hours. Upon completion of the reaction, the reaction solution was neutralized by dropwise addition of aqueous sodium hydroxide and aqueous sodium bicarbonate. Subsequently, the organic phase was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, distilled to remove the solvent and dried under reduced pressure to give 2-chloro-4-hydroxypyridine (light brown solid, 2.78 g, 92% yield). The product was characterized by 1H-NMR (270 MHz, DMSO-d6): δ 11.20 (s, 1H, -OH), 8.09 (d, 1H, J = 5.4 Hz, ArH), 6.81 (s, 1H, ArH), 6.77 (d, 1H, J = 2.2 Hz, ArH).

References

[1] Patent: WO2009/11447, 2009, A2. Location in patent: Page/Page column 37-38

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