1,5-Cyclooctadiene

1,5-Cyclooctadiene
Names
	Preferred IUPAC name Cycloocta-1,5-diene
Identifiers
CAS Number	111-78-4 ; 1552-12-1 (Z,Z) ; 5259-71-2 (Z,E) ; 17612-50-9 (E,E) ;
3D model (JSmol)	Interactive image;
Abbreviations	1,5-COD
Beilstein Reference	2036542; 1209288 (Z,Z)
ChemSpider	7843 ; 74815 (Z,Z) ; 18520443 (Z,E) ; 19971660 (E,E) ;
ECHA InfoCard	100.003.552
EC Number	203-907-1;
MeSH	1,5-cyclooctadiene
PubChem CID	8135; 82916 (Z,Z); 5364364 (Z,E); 5702534 (E,E);
RTECS number	GX9560000; GX9620000 (Z,Z);
UNII	1E1VVD385Z ;
UN number	2520
CompTox Dashboard (EPA)	DTXSID0026888 ;
	InChI InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7- Key: VYXHVRARDIDEHS-QGTKBVGQSA-N ; InChI=1/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7- Key: VYXHVRARDIDEHS-QGTKBVGQBM;
	SMILES C1CC=CCCC=C1;
Properties
Chemical formula	C8H12
Molar mass	108.184 g·mol−1
Appearance	Colorless liquid
Density	0.882 g/mL
Melting point	−69 °C; −92 °F; 204 K
Boiling point	150 °C; 302 °F; 423 K
Vapor pressure	910 Pa
Refractive index (nD)	1.493
Thermochemistry
Heat capacity (C)	198.9 J K−1 mol−1
Std molar; entropy (S⦵298)	250.0 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	21–27 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−4.890 – −4.884 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H304, H315, H317, H319, H334
Precautionary statements	P261, P280, P301+P310, P305+P351+P338, P331, P342+P311
Flash point	32 to 38 °C (90 to 100 °F; 305 to 311 K)
Autoignition; temperature	222 °C (432 °F; 495 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cycloocta-1,5-diene is a cyclic hydrocarbon with the chemical formula C₈H₁₂, specifically [−(CH₂)₂−CH=CH−]₂.

There are three configurational isomers with this structure, that differ by the arrangement of the four C–C single bonds adjacent to the double bonds. Each pair of single bonds can be on the same side (cis,Z) or on opposite sides (trans,E) of the double bond's plane; the three possibilities are denoted cis,cis, trans,trans, and cis,trans; or (Z,Z), (E,E), and (Z,E). (Because of overall symmetry, trans,cis is the same configuration as cis,trans.)

Generally abbreviated COD, the cis,cis isomer of this diene is a useful precursor to other organic compounds and serves as a ligand in organometallic chemistry. It is a colorless liquid with a strong odor. 1,5-Cyclooctadiene can be prepared by dimerization of butadiene in the presence of a nickel catalyst, a coproduct being vinylcyclohexene. Approximately 10,000 tons were produced in 2005.

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