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I3408

Sigma-Aldrich

Indole

≥99%

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Synonym(s):
1H-Benzo[b]pyrrole
Empirical Formula (Hill Notation):
C8H7N
CAS Number:
Molecular Weight:
117.15
Beilstein:
107693
EC Number:
MDL number:
UNSPSC Code:
12352100
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.

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Irrit. 2

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Synthesis and nonlinear optical properties of novel conjugated small molecules based on indole donor
Liu J, et al.
Journal of Molecular Structure, 1165(30), 223-227 (2018)
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)
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)
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)

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