(S)-(-)-1-(2-Naphthyl)ethylamine Chemical Properties

Melting point:

47-50 °C

Boiling point:

90°C 0,15mm

alpha 

-21 º (C=1%, IN MEOH)

Density 

1.064±0.06 g/cm3(Predicted)

refractive index 

-20 ° (C=1, MeOH)

Flash point:

90°C/0.15mm

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

9.36±0.40(Predicted)

color 

White to Light yellow

optical activity

[α]20/D 21±1°, c = 1% in methanol

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

3195949

InChI

1S/C12H13N/c1-9(13)11-7-6-10-4-2-3-5-12(10)8-11/h2-9H,13H2,1H3/t9-/m0/s1

InChIKey

KHSYYLCXQKCYQX-VIFPVBQESA-N

SMILES

C[C@H](N)c1ccc2ccccc2c1

CAS DataBase Reference

3082-62-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-51/53

Safety Statements 

26-36-61

RIDADR 

2923

WGK Germany 

3

F 

10-34

HazardClass 

8

PackingGroup 

III

HS Code 

2921490090

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Chronic 2
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(S)-(-)-1-(2-Naphthyl)ethylamine Usage And Synthesis

Uses

(S)-(-)-1-(2-Naphthyl)ethylamine is used in asymmetric synthesis. It is also used in the preparation of thiourea compounds using chiral amine, which is used as a bifunctional catalyst for the Strecker and nitro-Michael reactions. Further, it acts as a chiral building block and chiral resolution reagent.

Synthesis

GENERAL METHODS: N-acylation reactions were carried out in cyclohexane in the presence or absence of TIPS-β-CD with racemic 1-(naphthalen-2-yl)ethylamine (1), (S)-(-)-1-(2-naphthalenyl)ethylamine (2), and 1-(naphthalen-2-yl)ethylamine (3) as the substrates, benzoyl chloride (4a-j) as the acylation reagent, and triethylamine as the base. First, racemic 1, 2, and 3 (6.0 × 10^-4 mmol) were mixed with 6-O-methylsilylated β-CD in cyclohexane (600 μL) and stirred for 1 h to reach complexation equilibrium. Subsequently, 6-O-methylsilylated β-CD, triethylamine (6.0 x 10^-4 mmol) and chloroyl chloride 4a-j were added at 10 °C. The reaction mixture was continued to be stirred for 6 h at 10 °C. Upon completion of the reaction, the product was analyzed by high performance liquid chromatography (HPLC) using a Diacel Chiralcel OD-H chiral column (250 mm × 4.6 mm I.D.) with hexane/2-propanol (80:20 or 95:5) as eluent at a flow rate of 0.5 or 1.5 mL/min and a UV detector (254 nm). The HPLC profiles of the N-acylation reaction products of 1, 2, and 3 with chloroyl chloride 4a-j (3.3 × 10^-4 mmol) in cyclohexane (600 μL), including triethylamine (6.0 × 10^-4 mmol), in the absence and presence of TIPS-β-CD (3.0 × 10^-3 mmol) are shown in Figures 1 and 2, and S18-26, respectively in.

References

[1] Tetrahedron, 2014, vol. 70, # 2, p. 197 - 203

(S)-(-)-1-(2-Naphthyl)ethylamine(3082-62-0)Related Product Information

• Etamsylate
• Ethambutol
• Ethylamine
• Triethylamine hydrochloride
• L-1-Phenylethylamine
• Diethylamine
• 1-(1-NAPHTHYL)-2-THIOUREA
• 3-(3-Trifluoromethyl-phenyl)-prop-2-en-1-ol
• 4-NITROPHENYL PHENYL SULFIDE
• Ethanone, 1-(1-naphthalenyl)-, oxiMe
• Benzenemethanol, 3-(trifluoromethyl)-, 1-(4-methylbenzenesulfonate)
• SEVZPXQQXHZTBG-JKSUJKDBSA-N
• Benzenepropanol, 3-methyl-, 1-(4-methylbenzenesulfonate)
• 3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL
• 1-(NAPHTHALEN-1-YL)ETHANONE OXIME
• 3-Phenylpropionic acid methyl ester
• Triethylamine
• 3-(3-Trifluoromethylphenyl)propionic acid