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Merck

T8809

Sigma-Aldrich

四氰乙烯

96%

别名:

NSC 24833, TCNE, 四氰基乙烯, 四氰基代乙烯

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About This Item

线性分子式:
(NC)2C=C(CN)2
CAS号:
分子量:
128.09
Beilstein:
1679885
EC號碼:
MDL號碼:
分類程式碼代碼:
12352117
PubChem物質ID:
NACRES:
NA.22

品質等級

化驗

96%

反應適用性

reagent type: oxidant

mp

197-199 °C (lit.)

儲存溫度

2-8°C

SMILES 字串

N#CC(C#N)=C(C#N)C#N

InChI

1S/C6N4/c7-1-5(2-8)6(3-9)4-10

InChI 密鑰

NLDYACGHTUPAQU-UHFFFAOYSA-N

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應用

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:
  • 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

象形圖

Skull and crossbones

訊號詞

Danger

危險聲明

危險分類

Acute Tox. 1 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation

儲存類別代碼

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Milan Kivala et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(25), 7638-7647 (2008-07-22)
A series of monomeric and oligomeric donor-substituted 1,1,4,4-tetracyanobuta-1,3-dienes (TCBDs) with various topologies have been synthesized by means of thermal [2+2] cycloaddition between tetracyanoethylene (TCNE) and donor-substituted alkynes, followed by retro-electrocyclization. One-electron-reduced and -oxidized stages of the donor-substituted TCBDs were generated
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
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)

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