4-AMINOINDAN

4-AMINOINDAN Property

Melting point:

9℃

Boiling point:

90-92 °C (lit.)

Density 

1.102 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.592(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

liquid

pka

4.49±0.20(Predicted)

color 

Yellow (material may darken on storage)

InChI

InChI=1S/C9H11N/c10-9-6-2-4-7-3-1-5-8(7)9/h2,4,6H,1,3,5,10H2

InChIKey

RXTJLDXSGNEJIT-UHFFFAOYSA-N

SMILES

C1C2=C(C(N)=CC=C2)CC1

CAS DataBase Reference

32202-61-2

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2921490090

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.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

4-AMINOINDAN Chemical Properties,Usage,Production

Uses

4-Aminoindan was used in the synthesis of 4,5-dihydro-N-(2,3-dihydro-1H-inden-4-yl)oxazol-2-amine and 1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-4-yl)urea.

General Description

4-Aminoindan undergoes nucleophlic addition reaction with 2-chloroacetylisocyanate to yield 1-(2-chloroacetyl)-3-(2,3-dihydro-1H-inden-4-yl)-urea.

Synthesis

General procedure for the synthesis of 4-aminoindan from 4-nitro-2,3-dihydro-1H-indene: 4-nitroindan (10 g, 61 mmol) was dissolved in 50 mL of ethanol in a 500 mL Parr shaker vessel. A 10% Pd/C (1 g) ethanol slurry was added. The mixture was subjected to a hydrogen atmosphere (50 psi) and reacted on a Parr oscillator for 1 h. The progress of the reaction was monitored by thin-layer chromatography (TLC, unfolding agent was a hexane solution of 20% ethyl acetate) to confirm that the feedstock was completely consumed. Upon completion of the reaction, the mixture was filtered twice through a diatomaceous earth pad and washed with a large amount of ethanol and filtered once more through filter paper. The ethanol was removed by evaporation under reduced pressure and the resulting crude product was purified by fast column chromatography on silica gel (eluent was a hexane solution of 10% ethyl acetate) to afford the target compound 4-aminoindan (8) as a viscous colored oil (7.04 g, 86% yield). Its 1H NMR (400 MHz, DMSO-d6) data were as follows: δ 1.95 (m, 2H), 2.61 (t, J = 7.3 Hz, 2H), 2.76 (t, J = 7.5 Hz, 2H), 4.77 (s, 2H), 6.36 (d, J = 7.8 Hz, 1H), 6.42 (d, J = 6.8 Hz, 1H), 6.80 (t, J = 7.6 Hz, 1H).

References

[1] Patent: US2005/101569, 2005, A1. Location in patent: Page/Page column 17
[2] Patent: US2008/125454, 2008, A1. Location in patent: Page/Page column 17
[3] Patent: WO2006/21544, 2006, A1. Location in patent: Page/Page column 35-36
[4] Monatshefte fuer Chemie, 1974, vol. 105, p. 1362 - 1373
[5] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 461 - 465