2-Indanone Property

Melting point:

51-54 °C (lit.)

Boiling point:

218°C

Density 

1.0712

refractive index 

1.5380 (estimate)

Flash point:

212 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Crystals or Powder

color 

Light yellow to yellow-brown

Specific Gravity

1.07 (liquid)

Odor

moderately tenacious odor

Odor Threshold

0.00036ppm

Water Solubility 

insoluble

Sensitive 

Hygroscopic

BRN 

636550

InChIKey

UMJJFEIKYGFCAT-UHFFFAOYSA-N

LogP

1.230 (est)

CAS DataBase Reference

615-13-4(CAS DataBase Reference)

NIST Chemistry Reference

2H-inden-2-one, 1,3-dihydro-(615-13-4)

EPA Substance Registry System

2-Indanone (615-13-4)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

NK7535500

F 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29145090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

2-Indanone Chemical Properties,Usage,Production

Chemical Properties

Wet crystalline aggregates or needle-like crystals (formed by ethanol or ether) evaporate when in contact with water vapor. These crystals have a melting point range of 58-61 ℃ and a flash point of 100 ℃. Indene compounds are commonly found in numerous natural products, exhibiting diverse physiological activities and serving as crucial intermediates in organic synthesis processes.

Uses

2-Indanone undergoes TiCl4-Mg mediated coupling with CHBr3 to yield dibromomethyl carbinol. It reacts with 5,5-dimethyl-3-pyrazolidinone to yield 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone. On photolysis by 266-nm one-photon excitation yields o-xylylene. It was used as starting reagent in the synthesis of indene-fused porphyrins.

Preparation

2-Indanone is prepared by using acetic acid as solvent, acetic anhydride as catalyst and through hydrogen peroxide oxidation into 1, 2-indenediol, which reacted with dilute sulfuric acid solution in order to obtain crude 2-indanone. Finally, vacuum sublimation to obtain 2-indanone with high-purity, the total yield is 89%.

Definition

ChEBI: 2-Indanone is an indanone with an oxo substituent at position 2. It is a metabolite of indane. It has a role as a xenobiotic metabolite. 2-Indanone is an intermediate for the preparation of aprindine hydrochloride and ceforanide. It is an important intermediate in organic synthesis.

Application

2-Indanone is mentioned mainly for the completion and illustration of the series in which dpila- and be{u-Hydrindone have been emphasized as having potential interest in the perfume industry. It is the author's impression that the two materials are not used in perfumes or flavors.

Synthesis Reference(s)

Chemistry Letters, 11, p. 325, 1982
Organic Syntheses, Coll. Vol. 5, p. 647, 1973
Tetrahedron Letters, 15, p. 3789, 1974 DOI: 10.1016/S0040-4039(01)92010-6

General Description

2-Indanone undergoes TiCl₄-Mg mediated coupling with CHBr₃ to yield dibromomethyl carbinol. It reacts with 5,5-dimethyl-3-pyrazolidinone to yield 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone. 2-Indanone on photolysis by 266-nm one-photon excitation yields o-xylylene.