T8809
四氰乙烯
96%
别名:
NSC 24833, TCNE, 四氰基乙烯, 四氰基代乙烯
质量水平
方案
96%
反应适用性
reagent type: oxidant
mp
197-199 °C (lit.)
储存温度
2-8°C
SMILES字符串
N#CC(C#N)=C(C#N)C#N
InChI
1S/C6N4/c7-1-5(2-8)6(3-9)4-10
InChI key
NLDYACGHTUPAQU-UHFFFAOYSA-N
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应用
用于聚苯乙炔衍生物的后官能化加成，以改变透氧性
作为以下反应的反应物：
作为以下反应的反应物：
- 区域选择性[2+2]环加成反应，用于生产BODIPY染料 和TCBD衍生物
- 与炔的热力加成反应
- 与亲核试剂的一锅法反应，形成芳香族氰基乙烯基化合物
- 合成四氰乙烯钴薄膜
- 通过灰霉菌（Botrytis cinerea）进行生物转化
警示用语：
Danger
危险声明
危险分类
Acute Tox. 1 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation
储存分类代码
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
法规信息
危险化学品
Dane Tomasino et al.
The Journal of chemical physics, 138(9), 094506-094506 (2013-03-15)
We have studied the pressure-induced physical and chemical transformations of tetracyanoethylene (TCNE or C6N4) in diamond anvil cells using micro-Raman spectroscopy, laser-heating, emission spectroscopy, and synchrotron x-ray diffraction. The results indicate that TCNE in a quasi-hydrostatic condition undergoes a shear-induced
Mathieu Auzias et al.
Organic letters, 13(3), 474-477 (2010-12-22)
Complex tetracyclic ring systems were assembled by a photoinduced rearrangement of 3,3'-bis(arylbenzofurans). Irradiation of 1 under N(2) atmosphere yielded the benzonaphthofurans 2 in 75-90% yield. When the reaction was conducted under an O(2) atmosphere in the presence of tetracyanoethylene (TCNE)
Click-type reaction of aromatic polyamines for improvement of thermal and optoelectronic properties.
Tsuyoshi Michinobu
Journal of the American Chemical Society, 130(43), 14074-14075 (2008-10-07)
A quantitative addition reaction between aromatic amino-substituted alkynes and tetracyanoethylene (TCNE), yielding donor-substituted tetracyanobutadiene chromophores, was for the first time employed as a click-type reaction to improve the thermal and optoelectronic properties of aromatic polyamines. The first reduction potentials or
Siham Y Alqaradawi et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 71(4), 1594-1598 (2008-08-12)
The solid charge-transfer complexes formed in the reaction of the electron donor 1,4,7-trimethyl-1,4,7-triazacyclononane (TMTACN) with the acceptors iodine, tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) have been isolated. These were characterized through electronic and infrared spectra as well as thermal and elemental
Styliana I Mirallai et al.
The Journal of organic chemistry, 78(17), 8655-8668 (2013-07-31)
Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared in four steps from N'-arylbenzamidines 11 and tetracyanoethylene (TCNE) in ~70-90% yields. The transformation involves the initial formation of N-aryl-N'-(1,2,2-tricyanovinyl)benzamidines 12 in 87-99% yields, which in MeCN undergo a 5-exodig cyclization to give the 2-[1-aryl-5-imino-2-phenyl-1H-imidazol-4(5H)-ylidene]malononitriles
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