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188425

Sigma-Aldrich

3-Methylindene-2-carboxylic acid

98%

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About This Item

Empirical Formula (Hill Notation):
C11H10O2
CAS Number:
34225-81-5
Molecular Weight:
174.20
EC Number:
251-888-3
MDL number:
MFCD00044428
UNSPSC Code:
12352100
PubChem Substance ID:
24851160
NACRES:
NA.22

Assay

98%

form

powder

mp

201-203 °C (lit.)

SMILES string

CC1=C(Cc2ccccc12)C(O)=O

InChI

1S/C11H10O2/c1-7-9-5-3-2-4-8(9)6-10(7)11(12)13/h2-5H,6H2,1H3,(H,12,13)

InChI key

RONBYWGSEXDEKC-UHFFFAOYSA-N

General description

3-Methylindene-2-carboxylic acid undergoes asymmetric hydrogenation over Pd/Al2O3 in the presence of cinchonidine as a chiral modifier.

Application

3-Methylindene-2-carboxylic acid was used in the synthesis of:
  • LKS01-B650, an imaging probe that selectively binds the catalytically active LMP7 subunit of immunoproteasome in living cells
  • 1-methylindane-2-carboxylic acid via reduction with sodium amalgam

Storage Class Code

13 - Non Combustible Solids

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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cis-and trans-2-Substituted 1-methylindanes.
Shadbolt, RS.
J. Chem. Soc. Sect. C, 7, 920-922 (1970)
Asymmetric hydrogenation of indene carboxylic acids: stereochemistry of hydrogen addition.
Borszeky K, et al.
Tetrahedron Asymmetry, 10(24), 4781-4789 (1999)
Lalit Kumar Sharma et al.
Chembiochem : a European journal of chemical biology, 13(13), 1899-1903 (2012-07-19)
Probing the unknown: The immunoproteasome, an alternative form of the constitutive proteasome, has been implicated in a number of pathological states such as cancer and autoimmune diseases. In an effort to understand the role of the immunoproteasome in cells, the

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