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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[1].

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[2]
  • 1-methylindane-2-carboxylic acid via reduction with sodium amalgam[3]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
STBC7029V
S12669
20326DU
18105CA
11301CY

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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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