2-Hydroxy-3-cyanopyridine Chemical Properties

Melting point:

90-94

Boiling point:

352.3±35.0 °C(Predicted)

Density 

1.27±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in dimethyl sulfoxide.

form 

Solid

pka

8.93±0.10(Predicted)

InChI

InChI=1S/C6H4N2O/c7-4-5-2-1-3-8-6(5)9/h1-3H,(H,8,9)

InChIKey

DYUMBFTYRJMAFK-UHFFFAOYSA-N

SMILES

C1(=O)NC=CC=C1C#N

CAS DataBase Reference

20577-27-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

22-41

Safety Statements 

26-39

RIDADR 

UN3439

Hazard Note 

Irritant/Keep Cold

HazardClass 

6.1

HS Code 

2933399990

2-Hydroxy-3-cyanopyridine Usage And Synthesis

Chemical Properties

Dark Yellow Solid

Uses

2-Hydroxy-3-cyanopyridine (cas# 20577-27-9) is a compound useful in organic synthesis.

Definition

ChEBI: 3-cyano-2-pyridone is a member of pyridines and a nitrile.

Synthesis

The general procedure for the synthesis of 2-oxo-1,2-dihydropyridine-3-carbonitrile from 2-chloro-3-cyanopyridine was as follows: acetic acid (826 mL) was slowly added to 2-chloro-3-cyanopyridine (250 g), and the mixture was subsequently heated to reflux and held for 48 hours. Upon completion of the reaction, the reaction mixture was quenched by careful pouring into an ice-water mixture. The resulting precipitate was collected by filtration, washed well with deionized water and dried under appropriate conditions to give the target product 2-hydroxy-3-cyanopyridine. The yield of this step was 95%. The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 12.57 (s, 1H), 8.16 (dd, J = 3.6 Hz, 1H), 7.80 (dd, J = 3.6 Hz, 1H), 6.37 (t, 1H); the mass spectrum (ES) showed m/z of 121.

References

[1] Tetrahedron Letters, 2004, vol. 45, # 35, p. 6633 - 6636
[2] Patent: WO2014/207508, 2014, A1. Location in patent: Page/Page column 55
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7624 - 7643
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5738 - 5746
[5] Synthetic Communications, 2011, vol. 41, # 19, p. 2859 - 2869

2-Hydroxy-3-cyanopyridine(20577-27-9)Related Product Information

• 1H-INDOL-3-OL
• CHLOROPHOSPHONAZO III
• 2-Chloro-3-hydroxypyridine
• 3-Hydroxypyridine
• 3-Cyanopyridine
• Protocatechuic acid
• 2-Hydroxypyridine
• 3-Aminopyridine
• 3-Cyano-4,6-dimethyl-2-hydroxypyridine
• 2-HYDROXY-4-METHOXYMETHYL-6-METHYLNICOTINONITRILE
• Milrinone
• RICININE
• 7'-METHYL-5'-OXO-3',5'-DIHYDRO-2'H-SPIRO[[1,3]DIOXOLANE-2,1'-INDOLIZINE]-6'-CARBONITRILE
• 3-Cyano-6-methyl-2(1H)-pyridinone
• 1,4-Dimethyl-3-cyano-6-hydroxypyrid-2-one
• 1-Ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• 2-Hydroxy-3-cyanopyridine
• ETHYL 2-(6'-CYANO-5'-OXO-3',5'-DIHYDRO-2'H-SPIRO[[1,3]DIOXOLANE-2,1'-INDOLIZINE]-7'-YL)ACETATE