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I3408

Sigma-Aldrich

Indole

≥99%

Synonym(s):

1H-Benzo[b]pyrrole

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About This Item

Empirical Formula (Hill Notation):
C8H7N
CAS Number:
120-72-9
Molecular Weight:
117.15
Beilstein:
107693
EC Number:
204-420-7
MDL number:
MFCD00005607
UNSPSC Code:
12352100
PubChem Substance ID:
24896037
NACRES:
NA.22

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
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H302,H311,H319,H400

Hazard Classifications

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

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

249.8 °F - closed cup

Flash Point(C)

121 °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)
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)
Total Synthesis of (−)-Isatisine A
Zhang X, et al.
Angewandte Chemie (International ed. in English), 50(27), 6164-6166 (2011)
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