4,5,6,7-tetrahydro-1H-indole

• ChemBase ID: 137727
• Molecular Formular: C8H11N
• Molecular Mass: 121.17964
• Monoisotopic Mass: 121.08914936
• SMILES: c1c[nH]c2c1CCCC2
• Canonical SMILES: C1CCc2c(C1)[nH]cc2
• InChI: InChI=1S/C8H11N/c1-2-4-8-7(3-1)5-6-9-8/h5-6,9H,1-4H2
• InChIKey: KQBVVLOYXDVATK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5,6,7-tetrahydro-1H-indole
• IUPAC Traditional name: 4,5,6,7-tetrahydro-1H-indole
• Synonyms: 2,3-Tetramethylenepyrrole; Cyclohex[b]pyrrole; NSC 122455; 4,5,6,7-Tetrahydroindole; 4,5,6,7-四氢吲哚

Database IDs

• CAS Number: 13618-91-2
• MDL Number: MFCD00012134
• Beilstein Number: 108853
• PubChem SID: 24859477; 162231988
• PubChem CID: 97429

CALCULATED PROPERTIES

• Acid pKa: 18.04986
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 2.2694778
• LogD (pH = 7.4): 2.2694778
• Log P: 2.2694778
• Molar Refractivity: 38.3305 cm^3
• Polarizability: 14.52657 Å^3
• Polar Surface Area: 15.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 53-57 °C; 53-57 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C8H11N

DETAILS

Sigma Aldrich - 324906

Packaging
1 g in glass bottle
Application

• Reactant in preparation of BODIPY dyes1
• Reactant in N-alkylation with chloromethyloxirane2
• Reactant in preparation of hydroindolepropynoate by chemo- and regioselective solvent-free ethynylation3
• Reactant in palladium- and copper-free cross-coupling of halopropynoates4
• Reactant in preparation of carbonylalkenyl indoles via coupling with dicarbonyl compounds5
• Reactant in 1:2 annelation of 4,5,6,7-tetrahydroindole with 1-benzoyl-2-phenylacetylene6

Sigma Aldrich - 87427

Caution
may discolor to red-brown on storage