5-Nitro-2-indanone Chemical Properties

Boiling point:

340.6±42.0 °C(Predicted)

Density 

1.396±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Light brown to brown Solid

InChI

InChI=1S/C9H7NO3/c11-9-4-6-1-2-8(10(12)13)3-7(6)5-9/h1-3H,4-5H2

InChIKey

VSEBFWRYDORZJI-UHFFFAOYSA-N

SMILES

C1C2=C(C=C([N+]([O-])=O)C=C2)CC1=O

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2914790090

5-Nitro-2-indanone Usage And Synthesis

Application

5-Nitro-2-indanone is a pharmaceutical intermediate that can be prepared from 2-indanol in four steps or from indanol by nitration followed by oxidation.

Synthesis

Add 5.6 g of 2-indanone and 40 mL of chloroform to a 250 mL single neck flask. Measure 13 mL of 95% fuming nitric acid. Both were cooled in a cryogenic bath at a temperature below -20°C. The cooled 2-indanone was slowly added to the cooled fuming nitric acid. The dropwise addition process was continued for 40 minutes under vigorous stirring. The progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent: chloroform:methanol=100:1, product Rf=0.64, 2-indanone Rf=0.79). After dropwise addition was complete, the reaction was continued at -20°C for 20 min to ensure complete reaction. The reaction was quenched with 60 mL of 10% sodium hydroxide solution mixed with ice water. The reaction mixture was layered in a dispensing funnel. The upper aqueous phase was extracted with chloroform (3 x 30 mL). The organic phases were combined and washed with saturated saline until neutral. The organic solvent was evaporated using a rotary evaporator to give a yellow solid. Recrystallized by ethyl acetate and cyclohexane and cooled to give reddish brown crystals. Upon filtration, 3.8 g of 5-nitro-2-indanone was obtained in 49.5% yield with a melting point of 141-143°C. The crystals were purified by filtration.

References

[1] Journal of the American Chemical Society, 1997, vol. 119, # 52, p. 12722 - 12726
[2] Patent: CN105315204, 2016, A. Location in patent: Paragraph 0028; 0032; 0033
[3] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 738 - 747
[4] Chemische Berichte, 1899, vol. 32, p. 28,31

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