cycloocta-1,5-diene

• ChemBase ID: 109472
• Molecular Formular: C8H12
• Molecular Mass: 108.18088
• Monoisotopic Mass: 108.09390038
• SMILES: C1CC=CCCC=C1
• Canonical SMILES: C1CC=CCCC=C1
• InChI: InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2
• InChIKey: VYXHVRARDIDEHS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cycloocta-1,5-diene; (1Z,5Z)-cycloocta-1,5-diene
• IUPAC Systematic name: Cycloocta-1,5-diene
• IUPAC Traditional name: 1,5-cyclooctadiene; 1,5-cyclooctadiene, (Z,Z)-
• Synonyms: 1,5-CYCLOOCTADIENE; COD; cis,cis-1,5-Cyclooctadiene; 1,5-Cyclooctadiene; 顺,顺-1,5-环辛二烯; 1,5-环辛二烯

Database IDs

• CAS Number: 1552-12-1; 111-78-4
• EC Number: 203-907-1; 216-291-4
• MDL Number: MFCD00001752
• Beilstein Number: 1209288; 2036542; 1209288 (1Z,5Z)-1,5-diene; 2036542
• PubChem SID: 162095296; 24892340; 24854773; 24857812; 24846334
• PubChem CID: 8135; 82916
• Chemspider ID: 7843
• MeSH Name: 1,5-cyclooctadiene
• Wikipedia Title: 1,5-Cyclooctadiene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.832706
• LogD (pH = 7.4): 2.832706
• Log P: 2.832706
• Molar Refractivity: 39.0412 cm^3
• Polarizability: 14.319889 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless liquid
• Melting Point: -69 °C(lit.); -69.15°C (204K); -70°C
• Boiling Point: 149.85°C (423K); 149-150 °C(lit.); 151-152°C
• Flash Point: 100.4 °F; 32 °C; 32°C(89°F); 32–38 °C; 38 °C; 89.6 °F
• Auto Ignition Point: 222 °C; 431 °F
• Density: 0.880; 0.880 g/mL at 20 °C(lit.); 0.882 g/mL at 25 °C(lit.); 882 mg cm^-3
• Refractive Index: 1.493; 1.4940; n20/D 1.493; n20/D 1.493(lit.); n20/D 1.494
• Vapor Pressure: 25.8 mmHg ( 37.7 °C); 6.8 mmHg ( 25 °C); 910 Pa
• Heat Capacity: 198.9 J K^-1 mol^-1
• Std enthalpy of combustion: -4.890--4.884 MJ mol^-1
• Std enthalpy of formation: 21-27 kJ mol^-1
• Std molar entropy: 250.0 J K^-1 mol^-1

Safety Information

• RTECS: GX9560000; GX9560000; GX9620000 (1Z,5Z)-1,5-diene; GX9620000
• European Hazard Symbols: Nature polluting (N); X; Irritant (Xi); Harmful (Xn)
• UN Number: 2520; UN2520
• German water hazard class: 2; 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-19-36/38-43; 10-20/22-36/37/38-43-51/53; 10-36/38-42/43-65; R:36/37/38; R10, R36/38, R42/43, R65
• Safety Statements: 23-26-36/37-62; 24-26-36/37-61; 26-36; S:20-25-26-37/39; S23, S26, S36/37, S62
• TSCA Listed: 是
• GHS Pictograms: GHS flame; GHS health hazard; GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: DANGER; Danger; Warning
• GHS Hazard statements: 226, 304, 315, 317, 319, 334; H226-H302-H332-H315-H319-H317-H335-H411-H401; H226-H304-H315-H317-H319-H334; H226-H315-H317-H319-H332
• GHS Precautionary statements: 261, 280, 301+310, 305+351+338, 331, 342+311; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P280-P301 + P310-P305 + P351 + P338-P331-P342 + P311; P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2520 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); ≥99%; ≥99.0% (GC); 99%; 99%, stab. with 50-200ppm Irganox 1076
• Grade: puriss.
• Contains: stabilizer
• Purified By: redistillation
• Does not contain: stabilizer
• Empirical Formula (Hill Notation): C8H12

DETAILS

MP Biomedicals - 05211179

MP Biomedicals Rare Chemical collection

Sigma Aldrich - C109207

Packaging
1, 4 L in glass bottle
100, 500 mL in glass bottle

Sigma Aldrich - 246050

Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - 29580

Other Notes
Ligand for the preparation of metal complexes, e.g. bis-COD-nickel, a versatile reagent for preparing (PI)-allylnickel halides1
Packaging
1 L in glass bottle
250 mL in glass bottle

REFERENCES

• Undergoes many interesting transannular reactions to give bicyclic derivatives. Reaction with chloroform under free-radical conditions gives 2-(trichloromethyl)bicyclo[3.3.0]octane: Org. Synth. Coll., 5, 93 (1973); J. Am. Chem. Soc., 86, 946, 1885 (1964); Tetrahedron, 20, 1843 (1964). With Iodosobenzene diacetate, B24531, gives 2,6-diacetoxybicyclo[3.3.0]octane: Org. Synth. Coll., 8, 43 (1993). Addition of borane gives the important hydroborating agent 9-borabicyclo[3.3.1]nonane (9-BBN): J. Am. Chem. Soc., 90, 5280, 5281 (1968); J. Org. Chem., 46, 3978, 4599 (1981). Sulfur dichloride gives 2,6-dichloro-9-thiabicyclo[3.3.1]nonane: J. Org. Chem., 31, 1663, 1669 (1966); Org. Synth. Coll., 9, 692 (1998).
• Allylic monobromination (NBS) followed by dehydrobromination gives 1,3,5-cyclooctatriene: Org. Synth. Coll., 9,191 (1998). Addition of elemental bromine to the diene double bonds followed by dehydrobromination of the resulting tetrabromides with KO-t-Bu/18-crown-6 in THF gives the highly-reactive 1,5-cyclooctadiiyne. On prolonged base treatment, or in DMSO, conversion to cyclooctatetraene occurs: Chem. Ber., 127, 1529 (1994).
• Useful bidentate ligand in transition metal chemistry. For examples, see Chloro(1,5-cyclooctadiene)iridium(I) dimer, 12749 and Chloro(1,5-cyclooctadiene)rhodium(I) dimer, 10466.