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Basic Information
CAS No.: 629-20-9
Name: 1,3,5,7-Cyclooctatetraene
Article Data: 90
Molecular Structure:
Molecular Structure of 629-20-9 (1,3,5,7-Cyclooctatetraene)
Formula: C8H8
Molecular Weight: 104.152
Synonyms: Cyclooctatetraene;NSC 5093;[8]Annulene;
EINECS: 211-080-3
Density: 0.904 g/cm3
Melting Point: -5 - -3 °C(lit.)
Boiling Point: 140.5 °C at 760 mmHg
Flash Point: 22.2 °C
Solubility: Not miscible or difficult to mix in water.
Appearance: colourless to light yellow liquid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 10-36/37/38-65
Safety: 26-62
Transport Information: UN 2358
PSA: 0.00000
LogP: 2.22480
Related products
Synthetic route
34733-74-9

bicyclo[4.2.1]nona-2,4,7-trien-9-one

629-20-9

1,3,5,7-cyclooctatetraene

Conditions
ConditionsYield
In benzene-d6 at 100℃; Kinetics; Rate constant; 125 deg C;100%
153943-48-7

4-Thia-2,6-diazahexacyclo<5.4.02,6.08,11.09,13.010,12>tridecane-3,5-dione

A

629-20-9

1,3,5,7-cyclooctatetraene

B

24046-80-8

Diazabasketene

Conditions
ConditionsYield
In [D3]acetonitrile for 0.5h; Ambient temperature; Irradiation;A 5 % Spectr.
B 80%
In [D3]acetonitrile for 0.5h; Product distribution; Ambient temperature; Irradiation; other solvents; different reaction conditions;A 5 % Spectr.
B 80%
1552-12-1, 111-78-4

1,5-cis,cis-cyclooctadiene

629-20-9

1,3,5,7-cyclooctatetraene

Conditions
ConditionsYield
Stage #1: 1,5-cis,cis-cyclooctadiene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; pentane for 24h;
Stage #2: With di-tert-butyl peroxide In hexane; pentane for 4h; Heating; Further stages.;		65%
Multi-step reaction with 2 steps
1: K / 120 h / 108 °C
2: azobenzene / tetrahydrofuran / 1.) -78 deg C, 2.) room temp., 3 h further oxidizing agents
View Scheme
3194-57-8

1,2,5,6-tetrabromocyclooctane

629-20-9

1,3,5,7-cyclooctatetraene

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In water; pentane61%
69530-46-7, 69576-52-9

(1R,7S,8R)-8-Chloro-bicyclo[5.1.0]octa-2,4-diene

A

292638-84-7

styrene

B

629-20-9

1,3,5,7-cyclooctatetraene

Conditions
ConditionsYield
With potassium tert-butylate at 25℃;A n/a
B 56%
With potassium tert-butylate at 25℃; Product distribution; Mechanism; other temperature: 90 deg C; other cond.: solvent: tetraglyme, temp: 90 deg C, pressure: 1 Torr;A n/a
B 56%
With potassium tert-butylate at 90℃;A 8%
B 8%
74-86-2

acetylene

A

629-20-9

1,3,5,7-cyclooctatetraene

B

108-88-3

toluene

C

123-54-6

acetylacetone

D

71-43-2

benzene

Conditions
ConditionsYield
bis(acetylacetonate)nickel(II); calcium carbide In tetrahydrofuran at 85 - 90℃; Further byproducts given;A 56%
B n/a
C n/a
D 33%
...Expand
74-86-2

acetylene

A

629-20-9

1,3,5,7-cyclooctatetraene

B

71-43-2

benzene

Conditions
ConditionsYield
With calcium carbide; tetrabutylammonium tetrafluoroborate; nickel In tetrahydrofuran at 80℃; under 12751 Torr; for 42h; electrolysis;A 55%
B n/a
With tetrabutylammonium tetrafluoroborate; nickel In tetrahydrofuran at 80℃; under 11250.9 Torr; Product distribution; Mechanism; electrolysis, further solvents, further catalysts, different temperatures;
68344-46-7

1,5-Cyclooctadien-3-in

A

292638-84-7

styrene

B

629-20-9

1,3,5,7-cyclooctatetraene

Conditions
ConditionsYield
at 500℃; under 0.1 Torr;A 51%
B 49%
6909-37-1

semibullvalene

629-20-9

1,3,5,7-cyclooctatetraene

Conditions
ConditionsYield
at 300℃; under 2 Torr; for 0.000555556h; Product distribution; the effect of temperature was investigated;50%
at 370℃; under 2 Torr; for 0.000555556h; Yield given;
20380-30-7

syn-tricyclo{4.2.0.0(2.5)}octa-3,7-diene

629-20-9

1,3,5,7-cyclooctatetraene

Conditions
ConditionsYield
With 1,2,3,5-Tetracyanobenzol In acetonitrile at -40℃; for 10h; Irradiation;46%
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Specification

The Cyclooctatetraene, also known as [8]Annulene, is an unsaturated derivative of cyclooctane with the formula C8H8. It belongs to the product categories of Alkanes; Cyclic; Organic Building Blocks. Its EINECS registry number is 211-080-3. With the CAS registry number 629-20-9, its IUPAC name is 1,3,5,7-cyclooctatetraene(COT). This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature.

Physical properties of Cyclooctatetraene: (1)ACD/LogP: 2.55; (2)ACD/LogD (pH 5.5): 2.55; (3)ACD/LogD (pH 7.4): 2.55; (4)ACD/BCF (pH 5.5): 51.13; (5)ACD/BCF (pH 7.4): 51.13; (6)ACD/KOC (pH 5.5): 581.68; (7)ACD/KOC (pH 7.4): 581.68; (8)Index of Refraction: 1.525; (9)Molar Refractivity: 35.3 cm3; (10)Molar Volume: 115.1 cm3; (11)Surface Tension: 38 dyne/cm; (12)Density: 0.904 g/cm3; (13)Flash Point: 22.2 °C; (14)Enthalpy of Vaporization: 36.21 kJ/mol; (15)Boiling Point: 140.5 °C at 760 mmHg; (16)Vapour Pressure: 7.64 mmHg at 25°C.

Preparation: Reppe's synthesis of cyclooctatetraene, which involves treating acetylene at high pressure with a warm mixture of nickel cyanide and calcium carbide, was much better, with chemical yields near 90%:

Cyclooctatetraene can be synthetized by acetylene at high pressure with a warm mixture of nickel cyanide and calcium carbide

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health and may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In addition, it may cause lung damage if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=CC=CC=C1
(2)Isomeric SMILES: C\1=C\C=C/C=C\C=C1
(3)InChI: 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-
(4)InChIKey: KDUIUFJBNGTBMD-DLMDZQPMSA-N