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

• ChemBase ID: 35452
• Molecular Formular: C9H6BrNO2
• Molecular Mass: 240.05344
• Monoisotopic Mass: 238.95819044
• SMILES: c1([nH]c2c(c1)cc(cc2)Br)C(=O)O
• Canonical SMILES: Brc1ccc2c(c1)cc([nH]2)C(=O)O
• InChI: InChI=1S/C9H6BrNO2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,(H,12,13)
• InChIKey: YAULOOYNCJDPPU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromo-1H-indole-2-carboxylic acid
• IUPAC Traditional name: 5-bromo-1H-indole-2-carboxylic acid
• Synonyms: NSC 73384; 5-Bromoindole-2-carboxylic acid; 5-Bromo-1H-indole-2-carboxylic acid; 5-溴吲哚-2-羧酸

Database IDs

• CAS Number: 7254-19-5
• MDL Number: MFCD00022705
• PubChem SID: 160998759; 24891672
• PubChem CID: 252137

CALCULATED PROPERTIES

• Acid pKa: 3.5998216
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.5228148
• LogD (pH = 7.4): -0.9247544
• Log P: 2.4183445
• Molar Refractivity: 51.901 cm^3
• Polarizability: 20.661715 Å^3
• Polar Surface Area: 53.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 283 - 285°C; 287 - 288 °C; 287-288°C
• Hydrophobicity(logP): 3.075

Safety Information

• Storage Warning: IRRITANT; Irritant/Store at -20°C
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >95%; 95%; 95+%

DETAILS

Sigma Aldrich - B2761

包装
1 g in poly bottle
Application
Reactant involved in studies of biologically active molecules including:
• Discovery of indole inhibitors of MMP-13 for treatment of arthritic diseases1
• Synthesis of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors2
• cis-Diaminocyclohexane derivatives prepared for use as factor Xa inhibitors3
• Synthesis of tubulin polymerization inhibitors and cancer cell growth inhibitors4
• Preparation of dual PPARγ/δ agonists5
• Synthesis of chemical probes to examine the role of hFPRL1 receptor in inflammation6