methyl 1H-indole-6-carboxylate

• ChemBase ID: 15102
• Molecular Formular: C10H9NO2
• Molecular Mass: 175.18396
• Monoisotopic Mass: 175.06332853
• SMILES: [nH]1ccc2ccc(cc12)C(=O)OC
• Canonical SMILES: COC(=O)c1ccc2c(c1)[nH]cc2
• InChI: InChI=1S/C10H9NO2/c1-13-10(12)8-3-2-7-4-5-11-9(7)6-8/h2-6,11H,1H3
• InChIKey: AYYOZKHMSABVRP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 1H-indole-6-carboxylate
• IUPAC Traditional name: methyl 1H-indole-6-carboxylate
• Synonyms: Methyl indole-6-carboxylate; Methyl indole-6-carboxylate 98%; 1H-Indole-6-carboxylic Acid Methyl Ester; 6-Methoxycarbonylindole; Methyl 1H-Iindole-6-carboxylate; Indole-6-carboxylic acid methyl ester; Methyl indole-6-carboxylate; 吲哚-6-羧酸甲酯; 吲哚-6-甲酸甲酯

Database IDs

• CAS Number: 50820-65-0
• EC Number: 000-000-0
• MDL Number: MFCD00211063
• Beilstein Number: 141837
• PubChem SID: 160978409; 24880929
• PubChem CID: 639844

CALCULATED PROPERTIES

• Acid pKa: 14.54734
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.0754848
• LogD (pH = 7.4): 2.0754848
• Log P: 2.0754848
• Molar Refractivity: 49.1698 cm^3
• Polarizability: 19.96302 Å^3
• Polar Surface Area: 42.09 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 76-80 °C(lit.); 78-80°C; 78-80°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C10H9NO2

DETAILS

Sigma Aldrich - 578495

Packaging
5 g in glass bottle
Application
Reactant for preparation of:Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1Inhibitor of botulinum neurotoxin2ITK inhibitors3Antibacterial agents4CB2 cannabinoid receptor ligands5Inhibitors of hepatitis C virus NS5B polymerase6Inhibitors with histamine H1-blocking activity7

Toronto Research Chemicals - M313480

An indole compound for treating pain, inflammation and other conditions.

REFERENCES

• Leclerc, S., et al.: J. Biol. Chem., 276, 251 (2001)
• Meijer, L., et al.: Chem. Biol., 10, 1255 (2001)
• Juhaszova, M., et al.: J. Clin. Invest., 113, 1535 (2001)
• Noble, M., et al.: Science, 303, 1800 (2004)