1H-indol-5-ylmethanamine

• ChemBase ID: 140903
• Molecular Formular: C9H10N2
• Molecular Mass: 146.1891
• Monoisotopic Mass: 146.08439833
• SMILES: c1cc2c(cc[nH]2)cc1CN
• Canonical SMILES: NCc1ccc2c(c1)cc[nH]2
• InChI: InChI=1S/C9H10N2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-5,11H,6,10H2
• InChIKey: UAYYSAPJTRVEQA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indol-5-ylmethanamine; (1H-indol-5-yl)methanamine
• IUPAC Traditional name: 1H-indol-5-ylmethanamine
• Synonyms: 1H-Indole-5-methanamine; ((Indol-5-yl)methyl)amine; (1H-Indol-5-ylmethyl)amine; 1-(1H-Indol-5-yl)methanamine; 5-(Aminomethyl)indole; Indole-5-methanamine; 5-(Aminomethyl)indole; C-(1H-INDOL-5-YL)-METHYLAMINE; 5-(氨基甲基)吲哚

Database IDs

• CAS Number: 81881-74-5
• MDL Number: MFCD01719220
• PubChem SID: 162235141; 24884128
• PubChem CID: 54791

CALCULATED PROPERTIES

• Acid pKa: 16.408659
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): -1.7805681
• LogD (pH = 7.4): -0.77186704
• Log P: 1.1977762
• Molar Refractivity: 45.6179 cm^3
• Polarizability: 19.00787 Å^3
• Polar Surface Area: 41.81 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 114-122 °C

Safety Information

• RTECS: NL4461500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 98%
• Empirical Formula (Hill Notation): C9H10N2

DETAILS

Sigma Aldrich - 655864

Packaging
1, 5 g in glass bottle
Application
Reactant for preparation of:
• HIV-1 integrase inhibitors targeting the catalytic domain and its ability for interaction with LEDGF/p751
• Inhibitors of Gli1-mediated transcription in the Hedgehog pathway2
• SCIO-469-like compounds for the inhibition of p38 MAP kinase3
• 4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles as protein kinase c theta (PKC θ) inhibitors4
• Non-covalent thrombin inhibitors5

Toronto Research Chemicals - A616825

5-(Aminomethyl)indole is used in the synthesis of Vigabatrin (V253000) bioisosteres as inhibitors of γ-aminobutyric acid aminotransferase (GABA-AT) inhibitors.

REFERENCES

• Yuan, H., et al.: Bioorg. Med. Chem., 14, 1331 (2006)