7-Nitro-1-tetralone Chemical Properties

Melting point:

108-109°C

Boiling point:

349.1±31.0 °C(Predicted)

Density 

1.322±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

BRN 

1570515

CAS DataBase Reference

40353-34-2(CAS DataBase Reference)

NIST Chemistry Reference

1(2H)-naphthalenone, 3,4-dihydro-7-nitro-(40353-34-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-52

Safety Statements 

22-24/25

RTECS 

QK5025000

HS Code 

2914790090

Toxicity

mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00954,

MSDS

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7-Nitro-1-tetralone Usage And Synthesis

Application

7-Nitro-3,4-Dihydro-2H-1-naphthone is a ketone derivative that can be used as a pharmaceutical intermediate.

Chemical Properties

earthy yellow powder

Synthesis

General procedure for the synthesis of 7-nitro-3,4-dihydro-2H-1-naphthalenone from 1-tetralone: Concentrated sulfuric acid (60 mL) was cooled to 0 °C in an ice bath. 1-Tetrahydronaphthalenone (8 g, 54.7 mmol) was added with stirring, and then potassium nitrate (6 g, 59.3 mmol, 1.08 eq.) dissolved in concentrated sulfuric acid (18 mL) was slowly added dropwise through a dropping funnel, controlling the reaction temperature to no more than 15 °C. The reaction was carried out at a controlled temperature of 15 °C. The reaction was completed with the addition of potassium nitrate (6 g, 59.3 mmol, 1.08 eq.). After the dropwise addition was completed, the reaction mixture was continued to be stirred for 1 hour. The reaction was quenched by pouring the reaction solution into crushed ice, the precipitate was collected by filtration and washed with distilled water. After drying, recrystallization was carried out through a solvent mixture of ethanol/water (1:1) to give 7-nitro-3,4-dihydro-2H-1-naphthalenone (8.5 g, 81% yield) as a light yellow solid with a melting point of 104-106 °C. The product was analyzed by infrared spectroscopy (IR, film) showing characteristic absorption peaks located at 1675 cm?1, 1500 cm?1 and 1340 cm?1. The nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, CDCl3) data are as follows: δ 2.18-2.25 (2H, m, CH2), 2.75 (2H, t, J = 6.8 Hz, CH2), and 3.10 (2H, t, J = 6.1 Hz, CH2), 7.45 (1H, d, J = 8.4 Hz, ArH), 8.30 (1H, dd, J = 2.4 Hz, 8.4 Hz, ArH), 8.86 (1H, d, J = 2.4 Hz, ArH).

References

[1] Patent: WO2004/87124, 2004, A1. Location in patent: Page/Page column 47-48
[2] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 237 - 249
[3] Tetrahedron Letters, 1994, vol. 35, # 38, p. 7061 - 7064
[4] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
[5] Journal of the Chemical Society. Perkin transactions 1, 1969, vol. 10, p. 1376 - 1378

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