1-Naphthylhydrazine hydrochloride Chemical Properties

Melting point:

119 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

color 

White to Light gray to Light orange

CAS DataBase Reference

2243-56-3(CAS DataBase Reference)

EPA Substance Registry System

1-Naphthylhydrazine hydrochloride (2243-56-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-51-22

Safety Statements 

22-36/37/39

WGK Germany 

3

HS Code 

2928.00.2500

1-Naphthylhydrazine hydrochloride Usage And Synthesis

Synthesis

2.1 Synthesis of 2-naphthylhydrazine hydrochloride To a hydrochloric acid solution of 2-naphthylamine (800 mg, 5.59 mmol), a solution of sodium peroxide (Na?O?, 578 mg, 8.38 mmol) in water (1.2 mL) was slowly added under water-ice bath cooling conditions (addition time: 2 min). Subsequently, 6.0 M hydrochloric acid (6 mL) was added to the reaction system. The resulting solution was stirred in a water-ice bath for 1 h. Stannous chloride (SnCl?, 3.71 g, 19.56 mmol) was then slowly added (addition time: 5 min). The resulting suspension was continued to be stirred in a water-ice bath for 3.5 h, after which it was filtered. The filter cake was washed sequentially with water at 0 °C (4 × 8 mL), water at room temperature (1 × 8 mL), ether at 0 °C (Et?O, 2 × 4 mL), ether/hexane (1:1, 2 × 4 mL) and hexane (2 × 5 mL). The solid was dried to give 690 mg of the target product (Rf = 0.7, 40% ethyl acetate/hexane unfolding agent, milky white solid, 63% yield). 1H NMR (DMSO-d6, 250 MHz, δ): 7.81 (m, 2H, ArH), 7.71 (d, J=7.5 Hz, 1H, ArH), 7.49-7.19 (m, 4H, ArH). MS-EI+ m/z: 159.1 ([M-HCl]+).

References

[1] Patent: WO2011/147910, 2011, A1. Location in patent: Page/Page column 29-30; 36-37

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