324906

4,5,6,7-Tetrahydroindole

98%

• Synonym(s): 2,3-Tetramethylenepyrrole, Cyclohex[b]pyrrole, NSC 122455
• Empirical Formula (Hill Notation): C₈H₁₁N
• CAS Number: 13618-91-2
• Molecular Weight: 121.18
• Beilstein/REAXYS Number: 108853
• MDL number: MFCD00012134
• UNSPSC Code: 12352100
• PubChem Substance ID: 24859477
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 98%
• form: solid
• mp: 53-57 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: C1CCc2[nH]ccc2C1
• InChI: 1S/C8H11N/c1-2-4-8-7(3-1)5-6-9-8/h5-6,9H,1-4H2
• InChI key: KQBVVLOYXDVATK-UHFFFAOYSA-N

Description

General description

4,5,6,7-Tetrahydroindoles, due to their easy aromatization, are good intermediates to synthesize indoles. 4,5,6,7-Tetrahydroindole on condensation with cyanoacetate leads to 1-ethylthio-2-cyano-4,5,6,7-tetrahydrocyclohexa-[c]-3H-pyrrolizin-3-one.

Application

4,5,6,7-Tetrahydroindole was used as reactant in:

• synthesis of ethyl 3-(4,5,6,7-tetrahydroindol-2-yl)-2-propynoate
• preparation of BODIPY dyes
• N-alkylation with chloromethyloxirane
• preparation of hydroindolepropynoate by chemo- and regioselective solvent-free ethynylation
• palladium- and copper-free cross-coupling of halopropynoates
• preparation of carbonylalkenyl indoles via coupling with dicarbonyl compounds
• 1:2 annelation of 4,5,6,7-tetrahydroindole with 1-benzoyl-2-phenylacetylene

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves