3-NITRO-4-QUINOLINOL Chemical Properties

Melting point:

>3000C

Boiling point:

334.7±22.0 °C(Predicted)

Density 

1.496±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMF (Slightly), DMSO (Slightly)

form 

Solid

pka

-0.02±0.50(Predicted)

color 

Light Beige

Stability:

<-200C

InChI

InChI=1S/C9H6N2O3/c12-9-6-3-1-2-4-7(6)10-5-8(9)11(13)14/h1-5H,(H,10,12)

InChIKey

ZWISCKSGNCMAQO-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C(O)=C([N+]([O-])=O)C=1

CAS DataBase Reference

50332-66-6(CAS DataBase Reference)

Safety Information

Risk Statements 

25-37-38-41

Safety Statements 

26-36/37/39

RIDADR 

2811

HazardClass 

IRRITANT

HS Code 

29334900

3-NITRO-4-QUINOLINOL Usage And Synthesis

Chemical Properties

Tan Solid

Uses

3-Nitro-4-hydroxyquinoline (cas# 50332-66-6) is a compound useful in organic synthesis.

Definition

ChEBI: 3-nitro-1H-quinolin-4-one is a nitro compound and a member of quinolines.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 365, 1947 DOI: 10.1021/ja01194a060

Synthesis

Step 1: 5 g of 4-hydroxyquinoline (34.48 mmol, purchased from Jiuding Chemical) was dissolved in 40 mL of propionic acid (purity ≥99.5%) and heated to 120 °C. Subsequently, 3.5 mL of concentrated nitric acid (41.38 mmol, concentration 65-68%) was diluted with propionic acid and slowly added dropwise to the reaction system over 1.5 hours. After about 15 minutes of dropwise addition, a yellow precipitate appeared in the reaction solution. 20 mL of propionic acid was added and the reaction was continued at reflux for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm that the 4-hydroxyquinoline was completely consumed. The heating was stopped and the reaction solution was cooled to room temperature. The reaction mixture was filtered, the filter cake was washed with petroleum ether and dried under vacuum to give 4-hydroxy-3-nitroquinoline as a yellow solid (5.28 g, 80.7% yield).

References

[1] Patent: US5367076, 1994, A
[2] Patent: US5175296, 1992, A
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3481 - 3491
[4] Patent: CN108003153, 2018, A. Location in patent: Paragraph 0063; 0068
[5] Patent: US2011/136801, 2011, A1. Location in patent: Page/Page column 21

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