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391743

Sigma-Aldrich

2-Methyl-1-indanone

99%

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About This Item

Empirical Formula (Hill Notation):
C10H10O
CAS Number:
Molecular Weight:
146.19
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

liquid

refractive index

n20/D 1.555 (lit.)

bp

93-95 °C/4 mmHg (lit.)

density

1.064 g/mL at 25 °C (lit.)

SMILES string

CC1Cc2ccccc2C1=O

InChI

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

InChI key

BEKNOGMQVKBMQN-UHFFFAOYSA-N

General description

2-Methyl-1-indanone, a α-benzocycloalkenone, is a derivative of 1-indanone. Its synthesis has been reported. The enzymatic dynamic kinetic resolution (DKR) of racemic 2-methyl-1-indanone has been studied. The asymmetric α-arylation and hydroxymethylation of 2-methyl-1-indanone has been reported. It participated in the synthesis of 2-methyl-6-carboxyazulene.

Application

2-Methyl-1-indanone may be used as a starting material in the synthesis of β-benzocycloalkenone. It may be used in the synthesis of the following:
  • cyclohex-2-en-1-yl 2-methyl-1H-inden-3-yl carbonate
  • 2-hydroxy-2-methyl-1-indanone
  • O-alkoxycarbonylation of lithium enolates

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Amino alcohol-mediated enantioselective syntheses of α-substituted indanones and tetralones, ammonium enolates as key intermediates.
Muzart J.
Tetrahedron Asymmetry, 25(9), 697-704 (2014)
Structural effects in the Pd-induced enantioselective deprotection-decarboxylation of β-ketoesters.
Kukula P, et al.
Tetrahedron Asymmetry, 18(24), 2859-2868 (2007)
Selective and easy preparation of enol carbonates of α-disubstituted aryl ketones from their lithium enolates.
Aboulhoda SJ, et al.
Tetrahedron Letters, 36(27), 4795-4796 (1995)
Michał Rachwalski et al.
Chemical Society reviews, 42(24), 9268-9282 (2013-09-26)
Deracemisation of racemic compounds is still the most important strategy to produce optically pure compounds despite many recent advances in asymmetric synthesis. Especially deracemisation approaches that give rise to single enantiomers are preferred, which can be achieved either by invoking
Cyclophanes. 9. anti-[2.2](2, 6) Azulenophane. Synthesis and charge-transfer interaction.
Luhowy R and Keehn PM.
Journal of the American Chemical Society, 99(11), 3797-3805 (1977)

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