1H-indol-2-ylmethanol

• ChemBase ID: 141400
• Molecular Formular: C9H9NO
• Molecular Mass: 147.17386
• Monoisotopic Mass: 147.06841391
• SMILES: c1ccc2c(c1)cc([nH]2)CO
• Canonical SMILES: OCc1cc2c([nH]1)cccc2
• InChI: InChI=1S/C9H9NO/c11-6-8-5-7-3-1-2-4-9(7)10-8/h1-5,10-11H,6H2
• InChIKey: XEEANGGQJOWRTG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indol-2-ylmethanol
• IUPAC Traditional name: 1H-indol-2-ylmethanol
• Synonyms: (1H-Indol-2-yl)methanol; NSC 165230; 2-(Hydroxymethyl)indole; 1H-Indole-2-methanol; 2-羟甲基吲哚; 1H-吲哚-2-甲醇

Database IDs

• CAS Number: 24621-70-3
• MDL Number: MFCD00030195
• PubChem SID: 162235634
• PubChem CID: 98783

CALCULATED PROPERTIES

• Acid pKa: 14.6297035
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 1.2246592
• LogD (pH = 7.4): 1.2246591
• Log P: 1.2246592
• Molar Refractivity: 43.8379 cm^3
• Polarizability: 18.035334 Å^3
• Polar Surface Area: 36.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 72-78 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 90%; 95+%
• Empirical Formula (Hill Notation): C9H9NO

DETAILS

Sigma Aldrich - 687227

Application
Useful starter in indole chemistry.5
Reactant for the synthesis of:
• Oxazino[4,3-a]indoles1
• 2-arylsulfonylmethyl-3-piperazinylmethylindole derivatives as 5-HT6 receptor ligands2
• SR13668 designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signaling3
• Azido- and isothiocyanato-substituted indoles as melatoninergic agents4
Packaging
1, 5 g in glass bottle