6-Aminoindanone

6-Aminoindanone Property

Melting point:

167-171 °C(Solv: methanol (67-56-1))

Boiling point:

330.3±31.0 °C(Predicted)

Density 

1.254±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

Solution

pka

3.85±0.20(Predicted)

color 

Light brown to black

InChI

InChI=1S/C9H9NO/c10-7-3-1-6-2-4-9(11)8(6)5-7/h1,3,5H,2,4,10H2

InChIKey

UOJCPAAEKXNPQT-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC(N)=C2)CC1

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

2811

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29223900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H227Combustible liquid

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P284Wear respiratory protection.

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

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

6-Aminoindanone Chemical Properties,Usage,Production

Uses

6-Amino-1-indanone is a synthetic compound belonging to the indanone class. It is an ethylene oxide synthesized via a multi-step process involving the dehydration and reductive amination of an amine. In organic chemistry, it is used as an intermediate in the synthesis of various other compounds, such as serotonin. This compound exhibits an affinity for palladium catalysts during reductive amination, which can be used for sequence optimization experiments.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 46, p. 399, 2003 DOI: 10.1021/jm020067s

Synthesis

The general procedure for the synthesis of 6-amino-1-indanone from 6-nitro-1-indanone was as follows: a mixed suspension of 6-nitroindan-1-one (10 g, 56 mmol) with 10% Pd/C catalyst (2.0 g) in methanol (200 mL) was subjected to stirring in a hydrogenation reactor for 3 hr at room temperature under a hydrogen pressure of 30 psi. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford 6-aminoindan-1-one (7.2 g, 87% yield).

References

[1] Chemistry - A European Journal, 2015, vol. 21, # 37, p. 13052 - 13057
[2] Patent: WO2006/71940, 2006, A2. Location in patent: Page/Page column 396
[3] Patent: WO2007/148808, 2007, A1. Location in patent: Page/Page column 126-127
[4] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 399 - 408
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 20, p. 5665 - 5670