324906
4,5,6,7-Tetrahydroindole
98%
Synonym(s):
2,3-Tetramethylenepyrrole, Cyclohex[b]pyrrole, NSC 122455
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About This Item
Empirical Formula (Hill Notation):
C8H11N
CAS Number:
Molecular Weight:
121.18
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
108853
Assay:
98%
Form:
solid
InChI
1S/C8H11N/c1-2-4-8-7(3-1)5-6-9-8/h5-6,9H,1-4H2
SMILES string
C1CCc2[nH]ccc2C1
InChI key
KQBVVLOYXDVATK-UHFFFAOYSA-N
assay
98%
form
solid
Quality Level
storage temp.
2-8°C
Related Categories
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Sobenina, L. N.; et al.
Khim. Geterotsikl. Soedin., 39, 1113-1113 (2003)
Pyrrole-2-dithiocarboxylates: Synthesis of 2-(1-Alkylthio-2-cyanoethenyl) pyrroles.
Sobenina LN, et al.
Tetrahedron, 51(14), 4223-4230 (1995)
Arcadi, A.; et al.
Advanced Synthesis & Catalysis, 348, 331-331 (2006)
Trofimov, B. A.; et al.
Tetrahedron Letters, 48, 4661-4661 (2007)
Volker Leen et al.
Chemical communications (Cambridge, England), (30), 4515-4517 (2009-07-21)
A careful choice of the pyrrole building blocks allows the synthesis of a wide range of monohalogenated BODIPY dyes with excellent reactivity in palladium catalyzed coupling reactions.
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