6-NITROQUINOLINE Chemical Properties

Melting point:

151-153 °C(lit.)

Boiling point:

305.12°C (rough estimate)

Density 

1.2190 (estimate)

refractive index 

1.6820 (rough estimate)

storage temp. 

Sealed in dry,Room Temperature

Water Solubility 

Slightly soluble in water

form 

powder to crystal

pka

3.24±0.10(Predicted)

color 

Needles from water or alc

BRN 

136138

InChI

InChI=1S/C9H6N2O2/c12-11(13)8-3-4-9-7(6-8)2-1-5-10-9/h1-6H

InChIKey

SMHPLBXIVNQFBA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

613-50-3(CAS DataBase Reference)

EPA Substance Registry System

6-Nitroquinoline (613-50-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-40

Safety Statements 

7-22-36-45

WGK Germany 

3

RTECS 

VC1900000

HS Code 

29339900

Toxicity

mma-sat 100 mmol/plate MUREAV 58,11,78

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-NITROQUINOLINE Usage And Synthesis

Chemical Properties

beige to light brown powder

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx. Seealso other nitroquinoline entries.

Synthesis

GENERAL STEPS: 6-bromoquinoline (0.5 mmol), copper(II) trifluoromethanesulfonate (45 mg, 0.125 mmol), potassium nitrite (KNO2, 128 mg, 1.5 mmol), and anhydrous dimethylsulfoxide (DMSO, 0.6 mL) were sequentially added to a pre-dried oven-dried pressure tube under nitrogen protection. The pressure tube was sealed with a PTFE screw cap with a micro-valve and purged by nitrogen for 5 min to remove air. Subsequently, the reaction mixture was stirred at room temperature for 10 minutes and then gradually warmed up to 130°C and the reaction was continued at this temperature for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature, washed with excess ice water and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography on silica gel (for entries 1-18 in Table 2) or basic alumina (for entries 19-23 in Table 2), using a solvent mixture of ethyl acetate and hexane as eluent, and the target product, 6-nitroquinoline, was finally obtained in good yield.

References

[1] Tetrahedron Letters, 2012, vol. 53, # 12, p. 1511 - 1513
[2] Tetrahedron, 2013, vol. 69, # 31, p. 6409 - 6414

6-NITROQUINOLINE(613-50-3)Related Product Information

• 2-METHYL-6-NITROQUINOLINE
• 6-NITROQUINOLINE
• 5-NITRO-1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID
• 4-HYDROXY-6-NITROQUINOLINE
• 5-Nitro-1,10-phenanthroline
• 5-Amino-6-nitroquinoline
• 6-BROMO-5-NITROQUINOLINE
• 2-METHYL-8-NITROQUINOLINE
• 2-NITROQUINOLINE
• 1,2,3,4-TETRAHYDRO-7-NITROQUINOLINE
• 6-CHLORO-5-NITROQUINOLINE
• 2-BROMO-4-NITROQUINOLINE
• 2-CHLORO-3-NITROQUINOLINE
• 6-Methoxy-8-nitroquinoline, GC 99%
• 5-NITROQUINOLINE 98+%
• 2-CHLORO-6-NITROQUINOLINE
• 4-NITROQUINOLINE N-OXIDE POWDER,4-NITROQUINOLINE N-OXIDE 98+%,4-Nitroquinoline-N-oxide, HPLC 98%
• 8-HYDROXY-6-NITROQUINOLINE