I3408

Sigma-Aldrich

Indole

≥99%

Synonym(s):
1H-Benzo[b]pyrrole
Empirical Formula (Hill Notation):
C8H7N
CAS Number:
Molecular Weight:
117.15
Beilstein/REAXYS Number:
107693
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥99%

bp

253-254 °C (lit.)

mp

51-54 °C (lit.)

SMILES string

c1ccc2[nH]ccc2c1

InChI

1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

InChI key

SIKJAQJRHWYJAI-UHFFFAOYSA-N

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Application

  • Indole is a nitrogen-containing heterocycle used in the total synthesis of compounds such as goniomitine, (−)-isatisine A, and (±)-aspidospermidine.
  • It is used as an electron donor moiety in synthesizing dyes for organic photovoltaics.
  • It can also be used in the preparation of indole based conjugated small molecules for nonlinear optics applications.

Packaging

25, 100, 500 g in glass bottle

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all

WGK Germany

WGK 1

Flash Point(F)

249.8 °F

Flash Point(C)

121 °C

Catalytic selective cyclizations of aminocyclopropanes: formal synthesis of aspidospermidine and total synthesis of goniomitine
De Simone F, et al.
Angewandte Chemie (International ed. in English), 122(33), 5903-5906 (2010)
Regioselective Inter-and Intramolecular Formal [4+ 2] Cycloaddition of Cyclobutanones with Indoles and Total Synthesis of (?)-Aspidospermidine
Kawano M, et al.
Angewandte Chemie (International ed. in English), 125(3), 940-944 (2013)
Synthesis of double D-A branched organic dyes employing indole and phenoxazine as donors for efficient DSSCs
Hong Y, et al.
Tetrahedron, 70(36), 6296-6302 (2014)
Total Synthesis of (−)-Isatisine A
Zhang X, et al.
Angewandte Chemie (International ed. in English), 50(27), 6164-6166 (2011)
Impact of Thermal Annealing on Organic Photovoltaic Cells Using Regioisomeric Donor-Acceptor-Acceptor Molecules
Zhang T, et al.
ACS Applied Materials & Interfaces, 9(30), 25418-25425 (2017)

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