eth-1-ene-1,1,2,2-tetracarbonitrile

• ChemBase编号: 79610
• 分子式: C6N4
• 平均质量: 128.091
• 单一同位素质量: 128.01229602
• SMILES: N#CC(=C(C#N)C#N)C#N
• Canonical SMILES: N#CC(=C(C#N)C#N)C#N
• InChI: InChI=1S/C6N4/c7-1-5(2-8)6(3-9)4-10
• InChIKey: NLDYACGHTUPAQU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: eth-1-ene-1,1,2,2-tetracarbonitrile
• IUPAC传统名: tetracyanoethylene
• 别名: 四氰基乙烯; 四氰基乙烯; 四氰基代乙烯; 四氰乙烯; TETRACYANOETHYLENE; Tetracyanoethylene; 2,3-Dicyanobut-2-ene-1,4-dinitrile; Ethene-1,1,2,2-tetracarbonitrile; eth-1-ene-1,1,2,2-tetracarbonitrile; TCNE; NSC 24833; Ethylenetetracarbonitrile; Percyanoethylene; Tetracyanoethylene

登记号

• CAS号: 670-54-2
• EC号: 211-578-0
• MDL号: MFCD00001850
• Beilstein号: 1679885
• 默克索引号: 149195
• PubChem SID: 24888858; 162044373; 24900563
• PubChem CID: 12635
• Chemspider ID: 12114
• 维基百科标题: Tetracyanoethylene

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 0.03203398
• LogD (pH = 7.4): 0.03203398
• Log P: 0.03203398
• 摩尔折射率: 32.6728 cm^3
• 极化性: 11.009124 Å^3
• 极化表面积: 95.16 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

• 熔点: 197 - 199°C; 197-199 °C(lit.); 197-199°C; 197-200 °C; 197-200°C; 199 °C
• 沸点: 130-140 °C, 0.1 mm Hg (sublimes); 223°C; 223°C
• 密度: 1.348; g/cm^3
• 疏水性(logP): -1.88

安全信息

• 保存注意事项: Moisture Sensitive; Very Toxic/Moisture Sensitive/Store under Argon/Keep Cold
• RTECS编号: KM7300000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811; UN3439
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 1; II
• 危险公开号: 20/21-28; 24-28-36/37/38; R:22
• 安全公开号: 20-26-27/28-36/37-45; 28-36/37-45; S:36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H310-H315-H319-H335; H300-H312-H332
• GHS警示性声明: P261-P301+P310-P305+P351+P338-P361-P405-P501A; P264-P280-P301 + P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97.0% (N); 95%; 95+%; 98%
• 级别: purum
• 线性分子式: (NC)2C=C(CN)2

详细说明

MP Biomedicals - 05219182

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T8809

包装
5, 25 g in glass bottle
Application
Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability1Reactant for:
• Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 and TCBD derivatives3
• Thermal addition reaction with alkynes4
• One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds5
• Synthesis of cobalt tetracyanoethylene films6
• Biotransformation by Botrytis cinerea7

Sigma Aldrich - 87120

Other Notes
用于环加成反应的强效亲二烯体?，综述8,9
Application
Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability1Reactant for:
• Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 and TCBD derivatives3
• Thermal addition reaction with alkynes4
• One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds5
• Synthesis of cobalt tetracyanoethylene films6
• Biotransformation by Botrytis cinerea7

参考文献

• Versatile reagent and reactive dienophile. Reviews: Miscellaneous chemistry: Chem. Rev., 67, 611 (1967); Synthesis, 249 (1986); Addition and cycloaddition reactions: Synthesis, 749 (1987); Organometallic chemistry: Synthesis, 959 (1987).
• π-Acid catalyst, compare DDQ (2,3-Dichloro-5,6-dicyanobenzoquinone, A11879) for the rearrangement of epoxides to ketones, formation of acetonides (1,3-dioxolanes) by reaction of epoxides with acetone: Chem. Lett., 17 (1993), formation of epoxides with hydrogen peroxide: Chem. Pharm. Bull., 43, 686 (1995), and for stereospecific alcoholysis of epoxides under mild conditions: Synlett, 847 (1993). In the presence of pyridine, carboxylic acids are converted to anhydrides: Tetrahedron Lett., 26, 1503 (1985). In an alcohol as solvent, catalyzes esterification and transesterification reactions: Chem. Lett., 55 (1997).
• Also catalyzes the carbon-carbon bond formation reactions of aldehydes, ketones and acetals with silylated nucleophiles including Trimethylsilyl cyanide, A19598, allyltrimethylsilane, silyl enol ethers and triethylsilane: J. Chem. Soc., Perkin 1, 2155 (1995).