5-Nitro-1-tetralone Chemical Properties

Melting point:

103-104 °C

Boiling point:

349.9±31.0 °C(Predicted)

Density 

1.322±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to light yellow Solid

5-Nitro-1-tetralone Usage And Synthesis

Synthesis Reference(s)

Journal of Medicinal Chemistry, 19, p. 472, 1976 DOI: 10.1021/jm00226a004

Synthesis

The general procedure for the synthesis of 5-nitro-α-tetralone from 4-(2-nitrophenyl)butyric acid was as follows: first, 1 g of 4-(2-nitrophenyl)butyric acid (NPBS, 4.78 mmol) and 18 g of trifluoromethanesulfonic acid (TFMS) were added to a 100 mL two-necked flask fitted with a reflux condenser and magnetic stirrer at 20 °C. Under stirring, the reaction mixture was placed in an oil bath preheated to 130 °C and stirred continuously at this temperature for 45 min. Upon completion of the reaction, the mixture was cooled and transferred to a microdistillation unit. Most of the excess TFMS was removed by distillation at 52 °C and 0.5 mbar.After distillation, the bottom residue contained 0.914 g of 5-nitro-3,4-dihydro-1(2H)-naphthalenone and 3.44 g of TFMS (as determined by the GC-ISTD/internal standard method) in 99.3% yield, with 100% conversion to NPBS and 99.3% selectivity.

References

[1] Patent: EP1369412, 2003, A1. Location in patent: Page 6
[2] Patent: EP1369412, 2003, A1. Location in patent: Page 6
[3] Patent: US2003/176722, 2003, A1

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