1,5-Cyclooctadiene

1,5-Cyclooctadiene Basic information
Chemical Properties Uses
Product Name:1,5-Cyclooctadiene
Synonyms:Cycloocta-1,5-diene;COD;CIS,CIS-1,5-CYCLOOCTADIENE;1,5-CYCLOOCTADIENE;1,5-CYCLOOCTADIENE, REDISTILLED, 99+%;1,5-Cyclooctadiene, stabilized, 97%;1,5-COD;CIS,CIS-1,5-CYCLOOCTADIENE , STABILIZED WITH 50-200PPM IRGANOX 1076
CAS:111-78-4
MF:C8H12
MW:108.18
EINECS:203-907-1
Product Categories:Alkenes;Cyclic;Organic Building Blocks
Mol File:111-78-4.mol
1,5-Cyclooctadiene Structure
1,5-Cyclooctadiene Chemical Properties
Melting point -69 °C (lit.)
Boiling point 149-150 °C (lit.)
density 0.882 g/mL at 25 °C (lit.)
vapor pressure 25.8 mm Hg ( 37.7 °C)
refractive index n20/D 1.493
Fp 89 °F
storage temp. 2-8°C
solubility soluble in Chloroform
form Liquid
color Clear colorless
Odor Threshold0.00084ppm
Water Solubility 780 mg/L (20 ºC)
BRN 2036542
Stability:Stable. Flammable.
LogP3.16 at 20℃
CAS DataBase Reference111-78-4(CAS DataBase Reference)
NIST Chemistry Reference1,5-Cyclooctadiene(111-78-4)
EPA Substance Registry System1,5-Cyclooctadiene (111-78-4)
Safety Information
Hazard Codes Xn,N,Xi
Risk Statements 10-36/38-42/43-65-50/53-22-43-19-20/22-52/53-36/37/38
Safety Statements 26-36-61-60-16-37/39
RIDADR UN 2520 3/PG 3
WGK Germany 3
RTECS GX9620000
10-23
Autoignition Temperature431 °F
HazardClass 3.2
PackingGroup III
HS Code 29021990
Hazardous Substances Data111-78-4(Hazardous Substances Data)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
1,5-Cyclooctadiene Usage And Synthesis
Chemical Properties

1,5-Cyclooctadiene is the organic compound with the chemical formula C8H12.It is a colorless liquid with a strong odor. COD has a boiling point of 151°C and a vapor pressure of 6.8mm at 25°C.

Uses

1,5-Cyclooctadiene is generally abbreviated COD, this diene is a useful precursor to other organic compounds and serves as a ligand in organometallic chemistry. 1,5-Cyclooctadiene can be prepared by dimerization of butadiene in the presence of a nickel catalyst, a coproduct being vinylcyclohexene. It is also a chemical intermediate in the production of Nylon.

Chemical Propertiescolourless liquid
UsesCycloocta-1,5-diene is produced from petroleum distillation fractions and is used as an intermediate in the plastics industry, as a synthetic lubricant, and in numerous other applications.
Synthesis Reference(s)Tetrahedron Letters, 24, p. 3913, 1983 DOI: 10.1016/S0040-4039(00)94312-0
CarcinogenicityNone of the components present in this material at concentrations of 0.1% are listed by IARC, NTP, or OSHA as a carcinogen.
Purification MethodsPurify it by GLC. It has been purified via the AgNO3 salt. This is prepared by shaking with a solution of 50% aqueous AgNO3 w/w several times (e.g. 3 x 50mLand4x50mL) at 70ofor ca 20minutes to get a good separation of layers. The upper layers are combined and further extracted with AgNO3 at 40o (2 x 20 mL). The upper layer (19 mL) of original hydrocarbon mixture gives colourless needles of the AgNO3 complex on cooling. The adduct is recrystallised from MeOH (and cooling to 0o). The hydrocarbon is recovered by steam distilling the salt. The distillate is extracted with Et2O, dried (MgSO4), filtered, evaporated and distilled. [Jones J Chem Soc 312 1954,[Beilstein 5 H 116, 5 IV 403.]
1,5-Cyclooctadiene Preparation Products And Raw materials
Preparation Products(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one-->Chloro(1,5-cyclooctadiene)iridium(I) dimer-->Dichloro(cycloocta-1,5-diene)ruthenium(II)-->Bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate-->Chloro(1,5-cyclooctadiene)rhodium(I) dimer-->Dichloro(1,5-cyclooctadiene)platinum(II)-->Dichloro(1,5-cyclooctadiene)palladium(II)-->9-Oxabicyclo[6.1.0]nonan-4-one(8CI,9CI)-->1,3,6-Hexanetricarboxylic acid triethyl ester
1,3-CYCLOOCTADIENE fordine BIONET-BB 8F-915 RARECHEM AQ BC 9125 (1,5-CYCLOOCTADIENE)(HEXAFLUOROACETYLACETONATO)SILVER(I) 1,7-Octadiene [1,4-BIS(DIPHENYLPHOSPHINO)BUTANE](1,5-CYCLOOCTADIENE)RHODIUM(I) TETRA-FLUOROBORATE chloro(1,5-cyclooctadiene)iridium(i ((1,2,5,6-eta)-1,5-cyclooctadiene)(2,4-pentanedionato-o,o’)-rhodi Dichloro(cycloocta-1,5-diene)ruthenium(II) dichloro[(1,2,5,6-eta)-1,5-cyclooctadiene]-palladi Bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate TETRAMETHYL 2,6-DIHYDROXYBICYCLO[3.3.1]NONA-2,6-DIENE-1,3,5,7-TETRACARBOXYLATE BIS(1,5-CYCLOOCTADIENE)RHODIUM(I) TETRAFLUOROBORATE HYDRATE 1,5-Cyclooctadiene dichloro[(1,2,5,6-eta)-1,5-cyclooctadiene]-platin (1,5-CYCLOOCTADIENE)DIMETHYLPLATINUM(II) bis(1,5-cyclooctadiene)-nick

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