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

Melting point:

135-136 °C

alpha 

60 º (c=2, CH3OH)

Boiling point:

153 °C11 mm Hg(lit.)

Density 

1.067 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.623(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)

form 

Liquid

pka

9.26±0.40(Predicted)

Specific Gravity

1.07

color 

brown

optical activity

[α]20/D +55°, c = 2 in ethanol

Water Solubility 

Soluble in water (<10/l).

Sensitive 

Air Sensitive

BRN 

2208025

Stability:

Stable. Air-sensitive. Incompatible with acids, oxidizing agents, acid anhydrides, chloroformates, acid chlorides.

InChIKey

RTCUCQWIICFPOD-SECBINFHSA-N

CAS DataBase Reference

3886-70-2(CAS DataBase Reference)

EPA Substance Registry System

1-Naphthalenemethanamine, .alpha.-methyl-, (.alpha.R)- (3886-70-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

2735

WGK Germany 

3

RTECS 

QJ6963000

F 

10-34

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29211990

MSDS

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

Description

(R)-(+)-1-(1-Naphthyl)ethylamine is a reagent used in the formation of isolated acids via salt formation. It is also a raw material for the synthesis of (R)-1-(1-Naphthyl)ethyl isocyanate. In materials research, the use of Reflectance Absorption Infrared Spectroscopy (RAIRS) can be used to study the structure, bonding and orientation of R-1- nea and (S)-(-)-1-(2-naphthyl)ethylamine (S-2- nea) on Pd(1 1 1).

Chemical Properties

Colorless to light yellow liqui

Uses

It is used in chiral synthesis in organic reactions including the synthesis of β-amino acids and the enantioselective of ketones to nitroolefins. Also used as absolute configuration of primary amines determined using chiral (2-nitrophenyl)proline amides and H NMR.

Uses

(R)-(+)-1-(1-Naphthyl)ethylamine is a key intermediate in the synthesis of the chiral drug cinacalcet (trade name: Sensipar) and also an important intermediate in the synthesis of a coronavirus PLpro protease inhibitor. (R)-(+)-1-(1-Naphthyl)ethylamine and (S)-(-)-1-(1-naphthyl)ethylamine both belong to the class of chiral aromatic amine separators and have broad application prospects in fields such as chiral drugs and chiral pesticides.

Application

Absolute configuration of primary amines determined using chiral (2-nitrophenyl)proline amides and 1H NMR.

Preparation

There are three main methods for preparing (R)-(+)-1-(1-Naphthyl)ethylamine: (1) Enzymatic separation method; (2) Chemical separation method, with the following separation agents used: chiral aspartic acid, chiral α-hydroxy naphthoic acid, protective chiral glycerol derivatives, and chiral tartaric acid; (3) Dissymmetric synthesis, etc. Using dissymmetric synthesis as an example, obtain Chiral Amine to prochiral ketone oxime through asymmetric catalytic hydrogenation reduction, method adopts ammonium formiate to reduce by 1-(1-naphthyl) acetophenone oxime, at chlorine { [(1R, 2R)-(-)-2-ammonia-1,2-Diphenethyl] (4-tolylsulfonyl) ammonia (p-isopropyl toluene) ruthenium (II)) catalyzer exist under, adopt polar solvent as dimethyl formamide, methyl alcohol, ethanol, n-propyl alcohol, Virahol, butanols, the one in the trimethyl carbinol.Catalytic asymmetric reduction single step reaction preparation (R)-(+)-1-(1-naphthyl) ethamine is carried out to 1-(1-naphthyl) acetophenone oxime.

General Description

(R)-(+)-1-(1-Naphthyl)ethylamine is a chiral derivatization reagent useful for all gas chromatography (GC) applications in the chiral field. It is specially selected to meet the requirements for derivatization reagents for enantiomeric excess determinations.

Solubility in organics

(R)-(+)-1-(1-Naphthyl)ethylamine is soluble in chloroform and ethanol. Insoluble in water.

Purification Methods

Purify the amine by distillation in a good vacuum. [Mori et al. Tetrahedron 37 1343 1981, cf Wilson in Topics Stereochem (Allinger and Eliel eds) v o l 6 135 1971, Fredga et al. Acta Chem Scand 11 1609 1957.] The hydrochlorides crystallise from H2O [] D 18 ±3.9o (c 3, H2O), and the sulfates recrystallise from H2O as tetrahydrates m 230-232o. The RS-amine has b 153o/11mm, 156o/15mm, 183.5o/41mm [Blicke & Maxwell J Am Chem Soc 6 1 1780 1939]. [Beilstein 12 III 3111.]

(R)-(+)-1-(1-Naphthyl)ethylamine(3886-70-2)Related Product Information

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