5-methoxy-1H-indole-2-carboxylic acid

• ChemBase ID: 33055
• Molecular Formular: C10H9NO3
• Molecular Mass: 191.18336
• Monoisotopic Mass: 191.05824315
• SMILES: c1([nH]c2c(c1)cc(cc2)OC)C(=O)O
• Canonical SMILES: COc1ccc2c(c1)cc([nH]2)C(=O)O
• InChI: InChI=1S/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)
• InChIKey: YEBJVSLNUMZXRJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methoxy-1H-indole-2-carboxylic acid
• IUPAC Traditional name: 5-methoxy-1H-indole-2-carboxylic acid
• Synonyms: NSC 30927; 5-Methoxyindole-2-carboxylic acid; 5-Methoxyindole-2-carboxylic acid; 5-Methoxy-1H-indole-2-carboxylic acid; 5-甲氧基吲哚-2-羧酸; 5-甲氧基吲哚-2-甲酸

Database IDs

• CAS Number: 4382-54-1
• EC Number: 224-487-6
• MDL Number: MFCD00005614
• Beilstein Number: 157478
• PubChem SID: 160996362; 24896653
• PubChem CID: 20401

CALCULATED PROPERTIES

• Acid pKa: 3.6024086
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.40111357
• LogD (pH = 7.4): -1.8502758
• Log P: 1.4919206
• Molar Refractivity: 50.7414 cm^3
• Polarizability: 20.379105 Å^3
• Polar Surface Area: 62.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 199-201 °C(lit.); ca 200°C dec.

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: NL6005000
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ~97%; 97%; 98%
• Empirical Formula (Hill Notation): C10H9NO3
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02102302

Tan crystals
Purity: ~97%

Sigma Aldrich - M14951

Application
Reactant for preparation of:
• Anticancer agents1
• A fluorescent small molecule probe for in vivo lipid imaging2
• Indoleamine 2,3-dioxygenase (IDO) inhibitors3
• Selective Dopamine D3 receptor ligands4
• 5-HT4 receptor ligands5
• Inhibitors of Mycobacterium tuberculosis pantothenate synthetase6
• Hypoxia selective cytotoxins7
• Potent antitumor bifunctional DNA alkylating agents8
Packaging
5, 10 g in glass bottle

REFERENCES

• Starting material for a production scale synthesis of the HIV reverse-transcriptase inhibitor ateviridine: Org. Process Res. Dev., 1, 106 (1997).