134155

1-Methylindole-2-carboxylic acid

98%

• Synonym(s): NSC 68357
• Empirical Formula (Hill Notation): C₁₀H₉NO₂
• CAS Number: 16136-58-6
• Molecular Weight: 175.18
• MDL number: MFCD00005801
• UNSPSC Code: 12352100
• PubChem Substance ID: 24848134
• NACRES: NA.22

Properties

• assay: 98%
• form: powder
• 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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H315,H319,H335
• pcodes: P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves