cis,cis-1,5-Cyclooctadiene

• Catalog No.: B21196
• CAS Number: 1552-12-1
• M. F.: C8H12
• M. W.: 108.18088
• Purity: 99%, stab. with 50-200ppm Irganox 1076

SYNONYMS

• Title: 顺,顺-1,5-环辛二烯
• IUPAC name: (1Z,5Z)-cycloocta-1,5-diene
• IUPAC Traditional name: 1,5-cyclooctadiene, (Z,Z)-
• Synonyms: COD

DATABASE IDS

• CAS Number: 1552-12-1
• MDL Number: MFCD00001752
• Beilstein Number: 1209288
• EC Number: 216-291-4

PROPERTIES

• Purity: 99%, stab. with 50-200ppm Irganox 1076
• Boiling Point: 151-152°C
• Density: 0.880
• Flash Point: 32°C(89°F)
• Melting Point: -70°C
• Refractive Index: 1.4940
• GHS Hazard statements: H226-H302-H332-H315-H319-H317-H335-H411-H401
• European Hazard Symbols: X
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 10-20/22-36/37/38-43-51/53
• RTECS: GX9620000
• Safety Statements: 24-26-36/37-61
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2520
• Packing Group: III

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.