1-NAPHTHHYDRAZIDE

1-NAPHTHHYDRAZIDE Property

Melting point:

166-168°C

Density 

1.232±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

12.65±0.30(Predicted)

color 

White to Light yellow

BRN 

2966714

InChI

InChI=1S/C11H10N2O/c12-13-11(14)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,12H2,(H,13,14)

InChIKey

VMFUMDXVTKTZQY-UHFFFAOYSA-N

SMILES

C1(C(NN)=O)=C2C(C=CC=C2)=CC=C1

CAS DataBase Reference

43038-45-5(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

2928.00.2500

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

1-NAPHTHHYDRAZIDE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 1-naphthylhydrazine from methyl 1-naphthalenecarboxylate: Methyl 1-naphthalenecarboxylate (0.52 g, 2.8 mmol) was dissolved in 15 mL of 98% hydrazine hydrate, fitted with an air condenser tube, and the reaction was stirred for 8 h at 110 °C. The reaction was carried out in the presence of an air condenser tube. Upon completion of the reaction, the mixture was cooled to room temperature and the precipitated crystalline solid was collected by filtration. The resulting solid was dissolved in ethyl acetate (EtOAc), and the organic phase was washed sequentially with water, saturated sodium bicarbonate (NaHCO3) solution and brine, and then concentrated under reduced pressure to remove the solvent. The product was purified by column chromatography (elution gradient: hexane/ethyl acetate 1:1; hexane/ethyl acetate 1:2) to give 0.38 g (73% yield) of white crystalline solid. Thin layer chromatography (TLC) Rf = 0.53 (unfolding agent: chloroform/methanol 10:1). Melting point 166-169 °C (literature value 166 °C).IR (KBr, cm-1): νmax 3280 (N-H), 1658 (C=O), 1606, 1588, 1524, 1261, 955.1H NMR (300 MHz, DMSO-d6): δ 9.69 (s, 1H, NH), 8.35-8.10 (m. 1H, Ar-H), 8.05-7.88 (m, 2H, Ar-H), 7.63-7.26 (m, 4H, Ar-H), 4.60 (s, 2H, NH2).13C NMR (75 MHz, DMSO-d6): δ 168.2 (C=O), 133.6, 133.3, 130.2, 130.1, 128.4, 128.4 126.8, 126.4, 125.6, 125.6, 125.2 (Ar-C).

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 97 - 110
[2] Journal of the American Chemical Society, 2010, vol. 132, # 20, p. 6900 - 6901
[3] Chemistry - A European Journal, 2011, vol. 17, # 30, p. 8294 - 8298
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3615 - 3621
[5] RSC Advances, 2015, vol. 5, # 37, p. 28996 - 29001