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246050

Sigma-Aldrich

1,5-Cyclooctadiene

purified by redistillation, ≥99%

Synonym(s):

1,5-COD, cis-1,5-Cyclooctadiene, COD

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About This Item

Empirical Formula (Hill Notation):
C8H12
CAS Number:
111-78-4
Molecular Weight:
108.18
Beilstein:
2036542
EC Number:
203-907-1
MDL number:
MFCD00001752
UNSPSC Code:
12352100
PubChem Substance ID:
24854773
NACRES:
NA.22

vapor pressure

25.8 mmHg ( 37.7 °C)
6.8 mmHg ( 25 °C)

Assay

≥99%

form

liquid

autoignition temp.

431 °F

purified by

redistillation

does not contain

stabilizer

refractive index

n20/D 1.493 (lit.)

bp

149-150 °C (lit.)

mp

−69 °C (lit.)

density

0.882 g/mL at 25 °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

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Application

1,5-Cyclooctadiene was used as a catalyst in the synthesis of aminoindene derivatives by the [3+2] annulation of ketimines with internal and terminal alkynes.

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

100.4 °F - closed cup

Flash Point(C)

38 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL6313
SHBJ2003
SHBF9503V
SHBG0583V
SHBF8903V

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Midori Nagamoto et al.
Chemical communications (Cambridge, England), 50(47), 6274-6277 (2014-05-07)
[3 + 2] Annulation of ketimines with internal and terminal alkynes proceeded via C-H activation to give aminoindene derivatives in high yields, which is catalyzed by a cationic iridium complex coordinated with 1,5-cyclooctadiene (cod).
Eleonora Cavallari et al.
The journal of physical chemistry. B, 119(31), 10035-10041 (2015-07-15)
Hyperpolarization of (13)C carboxylate signals of metabolically relevant molecules, such as acetate and pyruvate, was recently obtained by means of ParaHydrogen Induced Polarization by Side Arm Hydrogenation (PHIP-SAH). This method relies on functionalization of the carboxylic acid with an unsaturated
Adrian Tlahuext-Aca et al.
Dalton transactions (Cambridge, England : 2003), 43(42), 15997-16005 (2014-09-19)
Ni(0)-catalyzed dehydrogenation of benzylic-type imines was performed to yield asymmetrical tetra-substituted imidazoles and 2-imidazolines. This was achieved with a single operational step while maintaining good selectivity and atom economy. The catalytic system shows low to moderate tolerance for fluoro-, trifluoromethyl-

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