6-nitrocoumarin Chemical Properties

Melting point:

186 °C

Boiling point:

326.87°C (rough estimate)

Density 

1.4625 (rough estimate)

refractive index 

1.4500 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

BRN 

166079

CAS DataBase Reference

2725-81-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

40-22

Safety Statements 

22-24/25-36-37/39-26

HS Code 

2932.20.4500

MSDS

• Language:English Provider:ALFA

6-nitrocoumarin Usage And Synthesis

Synthesis

The method was carried out with reference to the literature (Roy et al., 2011). In a 250 mL three-necked flask equipped with a condenser tube, thermometer and dropping funnel, coumarin (10 g, 68.5 mmol) and 50 mL of concentrated sulfuric acid (0.935 mol) were added. After cooling the reaction system to -10 °C, a mixture consisting of concentrated sulfuric acid (15 mL, 0.28 mol) and fuming nitric acid (5 mL, 0.12 mol) was added slowly and dropwise over a period of 1 hour, during which the reaction temperature was kept below -5 °C. Upon completion of the reaction, the mixture was decanted into ice water, the precipitate was collected by filtration and recrystallized from acetic acid. A white solid 11.26 g of 6-nitro-2H-benzopyran-2-one was obtained in 86% yield with a melting point of 191-192.5 °C (literature value 188-190 °C). The structure of the product was confirmed by 1H NMR and 13C NMR: 1H NMR (400.13 MHz, CDCl3) δ 6.60 (d, J = 9.5 Hz, 1H), 7.48 (d, J = 9.0 Hz, 1H), 7.83 (d, J = 9.5 Hz, 1H), 8.42 (dd, J = 9.0 Hz, 2.5 Hz, 1H). 8.46 (d, J = 2.5 Hz, 1H); 13C NMR (100.62 MHz, CDCl3) δ 118.1, 118.8, 118.8, 123.7, 126.6, 142.2, 144.0, 157.5, 158.8.

References

[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 5894 - 5901
[2] Synthetic Communications, 2001, vol. 31, # 2, p. 301 - 309
[3] Molecular Pharmacology, 1995, vol. 48, # 6, p. 1063 - 1067
[4] Polyhedron, 2011, vol. 30, # 6, p. 913 - 922
[5] Journal of Inorganic Biochemistry, 2011, vol. 105, # 4, p. 577 - 588

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