(+/-)1-(1-Naphthyl)ethylamine Chemical Properties

Boiling point:

156 °C15 mm Hg(lit.)

Density 

1.063 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.621(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in alcohol, ether; insoluble in H2O

form 

clear liquid

pka

9.26±0.40(Predicted)

color 

Colorless to Yellow to Green

optical activity

Consistent with structure

Sensitive 

Air Sensitive

BRN 

3197375

InChI

InChI=1S/C12H13N/c1-9(13)11-8-4-6-10-5-2-3-7-12(10)11/h2-9H,13H2,1H3

InChIKey

RTCUCQWIICFPOD-UHFFFAOYSA-N

SMILES

C12C=CC=CC1=CC=CC=2C(N)C

CAS DataBase Reference

42882-31-5(CAS DataBase Reference)

EPA Substance Registry System

1-Naphthalenemethanamine, .alpha.-methyl- (42882-31-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-34-25

Safety Statements 

26-36-45-36/37/39

RIDADR 

2735

WGK Germany 

3

F 

10-34

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29214990

MSDS

• Language:English Provider:(+/-)1-(1-Naphthyl)ethylamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(+/-)1-(1-Naphthyl)ethylamine Usage And Synthesis

Chemical Properties

Colorless or yellow liquidcrystalline

Uses

1-(1-Naphthyl)ethylamine is used in the enzymic resolution of amines. A chirality modifier.

General Description

The adsorption of 1-(1-naphthyl)ethylamine on platinum surfaces has been characterized by reflection-absorption infrared spectroscopy and temperature-programmed desorption both under ultrahigh vacuum and in situ from liquid solutions.

Synthesis

General procedure for the synthesis of 1-naphthylethylamine from 1-naphthylethanone: The corresponding ketone (10 mmol, specifically 1.14 g of 1a, 0.98 g of 1b, 1.48 g of 1c, 1.46 g of 1d, 1.46 g of 1e, 1.32 g of 1f, 1.20 g of 1g, 1.70 g of 1h, 1.70 g of 1i) was mixed with hydroxylamine hydrochloride ( 15 mmol, 1.04 g), ammonium formate (60 mmol, 3.78 g) and zinc powder (30 mmol, 1.96 g) in methanol (30 mL) and the reaction was stirred under reflux conditions. After completion of the reaction, the reaction mixture was filtered through Celite. The filtrate was subjected to vacuum rotary evaporation to remove the solvent. The residue was treated with concentrated hydrochloric acid followed by the addition of 4 mL of HCl solution and 30 mL of water and extracted with ether (2 x 20 mL) to remove organic impurities. The aqueous phase was adjusted to pH=10 with ammonia and extracted with dichloromethane (4 x 25 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, and finally the solvent was removed in vacuum to obtain the target product 1-naphthylethylamine.

References

[1] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1310 - 1312
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6197 - 6208
[3] Patent: WO2008/58235, 2008, A2. Location in patent: Page/Page column 23-24
[4] Synthetic Communications, 2011, vol. 41, # 3, p. 341 - 346
[5] Molecules, 2014, vol. 19, # 12, p. 21386 - 21397

(+/-)1-(1-Naphthyl)ethylamine(42882-31-5)Related Product Information

• Ethambutol
• Bensulfuron methyl
• METSULFURON METHYL
• Triethylamine
• L-1-Phenylethylamine
• Ethylamine
• Kresoxim-methyl
• Triethylamine hydrochloride
• Etamsylate
• Methylparaben
• 1-(1-NAPHTHYL)-2-THIOUREA
• Diethylamine
• Methyl acrylate
• Methyl acetate
• 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
• Thiophanate-methyl
• Methyl
• (R)-(+)-1-(1-Naphthyl)ethylamine