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134155 Sigma-Aldrich

1-Methylindole-2-carboxylic acid

98%

Synonym: NSC 68357

  • CAS Number 16136-58-6

  • Empirical Formula (Hill Notation) C10H9NO2

  • Molecular Weight 175.18

  •  MDL number MFCD00005801

  •  PubChem Substance ID 24848134

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C10, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
assay   98%
mp   212-213 °C (dec.) (lit.)
SMILES string   Cn1c(cc2ccccc12)C(O)=O
InChI   1S/C10H9NO2/c1-11-8-5-3-2-4-7(8)6-9(11)10(12)13/h2-6H,1H3,(H,12,13)
InChI key   MAHAMBLNIDMREX-UHFFFAOYSA-N

Description

General description

1-Methylindole-2-carboxylic acid reacts with thionyl chloride to yield sulfinyl chlorides.

Application

• Reactant for preparation of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors
• Reactant for synthesis of fenbufen and ethacrynic acid derivatives as potential antitumor agents via amide coupling reactions
• Reactant for diastereoselective synthesis of vinylated heterocycles via ruthenium-catalyzed oxidative vinylation with alkenes
• Reactant for synthesis of 2,3-dihalo indoles via hypervalent iodine mediated decarboxylative halogenation
• Reactant for preparation of α-ketoamides as cathepsin S inhibitors with potential applications against tumor invasion and angiogenesis
• Reactant for preparation of anthranilic acid mimics as bacterial translation inhibitors

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
NL6012400

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Protocols & Articles

Articles

Indoles

Sigma-Aldrich is proud to offer a new series of ChemFiles—called Privileged Structures, to our Drug Discovery and Organic Synthesis customers. Each piece will highlight a specific motif, selected app...
Chemfiles Volume 4 Article 8
Keywords: Building blocks, Cardiovascular, Diabetes, Diseases, Drug discovery, Medicinal chemistry, Organic synthesis, Respiratory

Peer-Reviewed Papers
15

References

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