138924

Cyclooctatetraene

98%

• Synonym(s): [8]Annulene
• Empirical Formula (Hill Notation): C₈H₈
• CAS Number: 629-20-9
• Molecular Weight: 104.15
• Beilstein/REAXYS Number: 2496800
• MDL number: MFCD00004161
• UNSPSC Code: 12352103
• PubChem Substance ID: 24848370
• NACRES: NA.23

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02,GHS08,GHS07
• signalword: Danger
• hcodes: H225,H304,H315,H319,H335,H412
• pcodes: P210 - P273 - P301 + P310 - P303 + P361 + P353 - P305 + P351 + P338 - P331
• 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: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 71.6 °F - closed cup
• flash_point_c: 22 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter