MilliporeSigma
All Photos(2)

324906

Sigma-Aldrich

4,5,6,7-Tetrahydroindole

98%

Synonym(s):
NSC 122455, Cyclohex[b]pyrrole, 2,3-Tetramethylenepyrrole
Empirical Formula (Hill Notation):
C8H11N
CAS Number:
Molecular Weight:
121.18
Beilstein:
108853
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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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

Packaging

1 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Arcadi, A.; et al.
Advanced Synthesis & Catalysis, 348, 331-331 (2006)
Pyrrole-2-dithiocarboxylates: Synthesis of 2-(1-Alkylthio-2-cyanoethenyl) pyrroles.
Sobenina LN, et al.
Tetrahedron, 51(14), 4223-4230 (1995)
Markova, M., V.; et al.
ARKIVOC (Gainesville, FL, United States), 57-57 (2008)
Sobenina, L. N.; et al.
Khim. Geterotsikl. Soedin., 39, 1113-1113 (2003)
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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