cycloocta-1,5-diene

• ChemBase编号: 109472
• 分子式: C8H12
• 平均质量: 108.18088
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: cycloocta-1,5-diene; (1Z,5Z)-cycloocta-1,5-diene
• IUPAC系统名: Cycloocta-1,5-diene
• IUPAC传统名: 1,5-cyclooctadiene; 1,5-cyclooctadiene, (Z,Z)-
• 别名: 顺,顺-1,5-环辛二烯; 1,5-环辛二烯; 1,5-CYCLOOCTADIENE; COD; cis,cis-1,5-Cyclooctadiene; 1,5-Cyclooctadiene

登记号

• CAS号: 111-78-4; 1552-12-1
• EC号: 203-907-1; 216-291-4
• MDL号: MFCD00001752
• Beilstein号: 1209288; 2036542; 1209288 (1Z,5Z)-1,5-diene; 2036542
• PubChem SID: 24892340; 24854773; 162095296; 24857812; 24846334
• PubChem CID: 82916; 8135
• Chemspider ID: 7843
• 医学主题词(MeSH): 1,5-cyclooctadiene
• 维基百科标题: 1,5-Cyclooctadiene

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.832706
• LogD (pH = 7.4): 2.832706
• Log P: 2.832706
• 摩尔折射率: 39.0412 cm^3
• 极化性: 14.319889 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Colorless liquid
• 熔点: -69 °C(lit.); -69.15°C (204K); -70°C
• 沸点: 149.85°C (423K); 149-150 °C(lit.); 151-152°C
• 闪点: 100.4 °F; 32 °C; 32°C(89°F); 32–38 °C; 38 °C; 89.6 °F
• 自燃点: 222 °C; 431 °F
• 密度: 0.880; 0.880 g/mL at 20 °C(lit.); 0.882 g/mL at 25 °C(lit.); 882 mg cm^-3
• 折射率: 1.493; 1.4940; n20/D 1.493; n20/D 1.493(lit.); n20/D 1.494
• 蒸汽压: 25.8 mmHg ( 37.7 °C); 6.8 mmHg ( 25 °C); 910 Pa
• 热容: 198.9 J K^-1 mol^-1
• 标准摩尔燃烧焓 (ΔcH^o298): -4.890--4.884 MJ mol^-1
• 标准摩尔生成焓 (ΔfH^o298): 21-27 kJ mol^-1
• 标准摩尔熵 (S^o298): 250.0 J K^-1 mol^-1

安全信息

• RTECS编号: GX9560000; GX9560000; GX9620000 (1Z,5Z)-1,5-diene; GX9620000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); X; 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2520; UN2520
• 德国WGK号: 2; 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 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
• 安全公开号: 23-26-36/37-62; 24-26-36/37-61; 26-36; S:20-25-26-37/39; S23, S26, S36/37, S62
• TSCA收录: 是
• GHS危险品标识: GHS flame; GHS health hazard; GHS02; GHS07; GHS08; GHS09
• GHS警示词: DANGER; Danger; Warning
• GHS危险声明: 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警示性声明: 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
• 个人保护装置: 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
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (GC); ≥99%; ≥99.0% (GC); 99%; 99%, stab. with 50-200ppm Irganox 1076
• 级别: puriss.
• 其他组分: stabilizer
• 提纯方法: redistillation
• 不包含成分: stabilizer
• Empirical Formula (Hill Notation): C8H12

详细说明

MP Biomedicals - 05211179

MP Biomedicals Rare Chemical collection

Sigma Aldrich - C109207

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

Sigma Aldrich - 246050

包装
100, 800 mL in Sure/Seal™

Sigma Aldrich - 29580

Other Notes
用作制备金属复合物时的配体，如制备双-COD-镍，这是一种用于制备 (PI)-烯丙基镍卤化物的多功能试剂1
包装
1 L in glass bottle
250 mL in glass bottle

参考文献

• 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.