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324906

Sigma-Aldrich

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:
13618-91-2
Molecular Weight:
121.18
Beilstein:
108853
MDL number:
MFCD00012134
UNSPSC Code:
12352100
PubChem Substance ID:
24859477
NACRES:
NA.22

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

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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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBJ2630V
06307CE
02622BD
19814HA
10018PF

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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)
Markova, M., V.; et al.
ARKIVOC (Gainesville, FL, United States), 57-57 (2008)
Chemo-and regioselective ethynylation of 4, 5, 6, 7-tetrahydroindoles with ethyl 3-halo-2-propynoates.
Trofimov, B., A.; et al.
Tetrahedron Letters, 49, 3946-3946 (2008)
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