Skip to Content
Merck
All Photos(2)

Documents

138924

Sigma-Aldrich

Cyclooctatetraene

98%

Synonym(s):

[8]Annulene

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C8H8
CAS Number:
629-20-9
Molecular Weight:
104.15
Beilstein:
2496800
MDL number:
MFCD00004161
UNSPSC Code:
12352103
PubChem Substance ID:
24848370
NACRES:
NA.23

Assay

98%

form

liquid

contains

0.1% hydroquinone as inhibitor

refractive index

n20/D 1.537 (lit.)

bp

142-143 °C (lit.)

mp

−5-−3 °C (lit.)

density

0.925 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

C1=CC=CC=CC=C1

InChI

1S/C8H8/c1-2-4-6-8-7-5-3-1/h1-8H/b2-1-,3-1-,4-2-,5-3-,6-4-,7-5-,8-6-,8-7-

InChI key

KDUIUFJBNGTBMD-BONZMOEMSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Cyclooctatetraene (COT) is a nonaromatic 4n π-conjugated system with a non-planar tub-shaped geometry and potential energy surfaces at the ground state.
Cyclooctatetraene is an 8p electron system and has a triplet ground state if the p electrons are delocalized. It is antiaromatic hence highly unstable and reactive. It adopts a non-planar boat conformation to attain stability with alternating single and double bonds and hence behaves like a polyolefin.

Application

  • Used in the synthesis of highly organic film for silicon surfaces to improve its chemical and physical properties.
  • Used in liquid state organic dye lasers.
  • Used as triplet state quencher to reduce dye blinking.
COT may be functionalized by two side groups which can be used as active anode materials for rechargeable batteries. High capacity and voltage organic cathodes may be developed by using COT that can be fused with carbon molecules.

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

71.6 °F - closed cup

Flash Point(C)

22 °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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Evaluation of Cyclooctatetraene-Based Aliphatic Polymers as Battery Materials: Synthesis, Electrochemical, and Thermal Characterization Supported by DFT Calculations.
Speer ME.
ChemPlusChem, 82(10), 1274-1281 (2017)
Superposed Redox Chemistry of Fused Carbon Rings in Cyclooctatetraene-Based Organic Molecules for High-Voltage and High-Capacity Cathodes.
Zhao X, et al.
ACS Applied Materials & Interfaces, 10(3), 2496-2503 (2018)
Sarah Schols et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 10(7), 1071-1076 (2009-04-18)
Phosphorescence and delayed fluorescence of polyfluorene polymer films doped with cyclooctatetraene (COT) and anthracene are studied by means of time-resolved photoluminescence (PL) measurements. The occurrence of an anomalous nonvertical triplet energy transfer in solid conjugated polymer films is demonstrated for
About the Antiaromaticity of Planar Cyclooctatetraene I thank Jens Panitzky for the additional DFT calculations, and Professor Jay Siegel, La Jolla, CA, and Professor Otto Ermer, Cologne, for helpful comments.
Frank-Gerrit Klärner
Angewandte Chemie (International ed. in English), 40(21), 3977-3981 (2002-10-31)
Lauryn E Sass et al.
Biochemistry, 49(14), 3174-3190 (2010-02-26)
The first step in DNA mismatch repair (MMR) is the recognition of DNA mismatches or nucleotide insertions/deletions (IDLs) by MutS and MutS homologues. To investigate the conformational properties of MutS-mismatch complexes, we used single-molecule fluorescence resonance energy transfer (smFRET) to
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service