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29580

Sigma-Aldrich

cis,cis-1,5-Cyclooctadiene

≥98.0% (GC)

Synonym(s):

COD

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About This Item

Empirical Formula (Hill Notation):
C8H12
CAS Number:
1552-12-1
Molecular Weight:
108.18
Beilstein:
1209288
EC Number:
216-291-4
MDL number:
MFCD00001752
UNSPSC Code:
12352100
PubChem Substance ID:
57648379

Assay

≥98.0% (GC)

refractive index

n20/D 1.493

solubility

water: soluble 0.05 g/L

density

0.880 g/mL at 20 °C (lit.)

SMILES string

C1CC=CCCC=C1

InChI

1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7-

InChI key

VYXHVRARDIDEHS-QGTKBVGQSA-N

General description

Surface grafting of cis,cis-1,5-cyclooctadiene (cyclic olefin) with low strain energy was explored using ring-opening metathesis polymerization in the vapor phase. The inclusion complex of cis,cis-1,5-cyclooctadiene with β-cyclodextrin (β-CD) was studied by using proton NMR spectroscopy.

Application

cis,cis-1,5-Cyclooctadiene (COD) has been employed as ligand:
  • during regio- and stereoselective synthesis of (Z)-1,2-dihaloalkenes
  • in the preparation of metal complexes, e.g. bis-COD-nickel, a versatile reagent for preparing (PI)-allylnickel halides

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 2 - Asp. Tox. 1 - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

89.6 °F - closed cup

Flash Point(C)

32 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBL2155V
1369462V
1369462
429961/1
368430/1

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Maria Felisa Z Lerum et al.
Langmuir : the ACS journal of surfaces and colloids, 27(9), 5403-5409 (2011-04-08)
Surface grafting of cyclic olefins with low strain energies, including cyclopentene (CP), 1,4-cyclohexadiene (CHD), cycloheptene (CHP), cis-cyclooctene (CO), cis,cis-1,5-cyclooctadiene (COD), 1,3,5,7-cyclooctatetraene (COT), cyclododecene (CD), and trans,trans,cis-1,5,9-cyclododecatriene (CDT), was explored using ring-opening metathesis polymerization in the vapor phase. These monomers do
Ting Ma et al.
Science advances, 6(1), eaau3798-eaau3798 (2020-01-11)
Increased human activity threatens inland water quality in China. Major efforts have been made to alleviate water pollution since 2001. Understanding how water quality responds to these forces can help to guide future efforts to maintain water security and sustainability.
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Org. React., 19, 115-115 (1972)
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