4-METHYL-1-INDANONE Chemical Properties

Melting point:

94-96 °C (lit.)

Boiling point:

205.81°C (rough estimate)

Density 

0.9071 (rough estimate)

refractive index 

1.5530 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystalline Powder

color 

White to yellow

InChI

InChI=1S/C10H10O/c1-7-3-2-4-9-8(7)5-6-10(9)11/h2-4H,5-6H2,1H3

InChIKey

RUORWXQKVXTQJJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

24644-78-8(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29143990

MSDS

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

4-METHYL-1-INDANONE Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

4-Methyl-2,3-dihydro-1H-inden-1-one acts as a reagent in the synthesis of the following organic compounds: 3,6-dimethylcholanthrene, 3,6-dimethyl-7-methoxycholanthrene and 3-methyl-7-methoxycholanthrene.

Uses

4-Methyl-1-indanone may be used for the following syntheses:

• 3,6-dimethylcholanthrene
• 3,6-dimethyl-7-methoxycholanthrene
• 3-methyl-7-methoxycholanthrene
• methyl 4-methyl-1-fluoroindan-1-carboxylate (4-Me-FICA Me ester)

General Description

4-Methyl-1-indanone on condensation with 2-lithio-N,N-diethyl-1-napthamide and 2-lithio-N,N-diethyl-8-methoxy-1-napthamide, followed by hydrolysis afforded 2-(1-hydroxy-4-methylindan-1-yl)-1-naphthoic acid lactone and 2-(1-hydroxy-4-methylindan-1-yl)-8-methoxy-1-naphthoic acid lactone respectively.

Synthesis

General procedure for the synthesis of 4-methyl-2,3-dihydro-1H-inden-1-one from 3-(2-methylphenyl)propionic acid: trifluoromethanesulfonic acid (3 equiv.) was slowly added to a solution of 3-(2-methylphenyl)propionic acid (0.5 mmol) dissolved in anhydrous dichloromethane (1.0 mL) in a 12 mL Q-tube?pressure tube at 0 °C (provided by QLabtech). The reaction system was then warmed to room temperature. A PTFE septum was placed on top of the reaction tube and sealed using the appropriate cap and pressure adapter. The sealed reaction tube was heated in an oil bath at 80°C. The progress of the reaction was monitored by thin layer chromatography (TLC) and gas chromatography-mass spectrometry (GC/MS) until the feedstock was completely consumed. Upon completion of the reaction, the mixture was poured into ice water and extracted three times with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Finally, the target compound 4-methyl-2,3-dihydro-1H-inden-1-one was purified from the crude product by fast column chromatography.

References

[1] Molecules, 2014, vol. 19, # 5, p. 5599 - 5610
[2] Patent: WO2013/74892, 2013, A1. Location in patent: Page/Page column 39-40
[3] Patent: US9125407, 2015, B2. Location in patent: Page/Page column 27; 28
[4] Chemistry - A European Journal, 2017, vol. 23, # 53, p. 13037 - 13041
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 91, # 1-4, p. 69 - 80

4-METHYL-1-INDANONE(24644-78-8)Related Product Information

• 4-METHYL-1-INDANONE
• 4-(Trifluoromethyl)-1-indanone
• 2,3-dihydro-1-oxo-1H-indene-4-carbonitrile
• 6-METHYL-1-INDANONE,6-METHYL-1-INDANONE,98.0+%(GC)
• 1-OXO-INDAN-4-CARBOXYLIC ACID
• 5,6-Dimethoxy-2-(pyridine-4-yl)methylene-indan-1-one
• 5,6-Dimethoxy-2-[(4-piperidinyl)methyl]-1-indanone
• 5,6-Dimethoxy-2-(4-piperidinylmethyl)-1-indanone hydrochloride
• 5-(Trifluoromethyl)-1-indanone
• 2-Methyl-5-Indanone
• 2-METHYL-1-INDANONE 97%,2-METHYL-1-INDANONE
• 6-FLUORO-2-METHYL-1-INDANONE
• 5-Methyl-1-indanone
• 3-METHYLINDAN-1-ONE
• (Z)-2,3-dihydro-2-[methoxy(methylthio)methylene]-1H-Inden-1-one
• 1-Indanone
• Indan
• 4,7-dimethyl-2,3-dihydroinden-1-one