2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile

• ChemBase编号: 77700
• 分子式: C12H4N4
• 平均质量: 204.18696
• 单一同位素质量: 204.04359615
• SMILES: N#CC(=c1ccc(=C(C#N)C#N)cc1)C#N
• Canonical SMILES: N#CC(=c1ccc(=C(C#N)C#N)cc1)C#N
• InChI: InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
• InChIKey: PCCVSPMFGIFTHU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
• IUPAC传统名: tetracyanoquinodimethane
• 别名: 2,2'-(2,5-环己二烯-1,4-二基)丙二腈; 7,7,8,8-四氰基对苯二醌二甲烷; 7,7,8,8-四氰基对醌二甲烷; (2,5-Cyclohexadiene-1,4-diylidene)-dimalononitrile; 7,7,8,8-Tetracyanoquinodimethane; 2,2'-(Cyclohexa-2,5-diene-1,4-diylidene)dipropane-1,3-dinitrile; TCNQ; Tetracyanoquinodimethane; (2,5-Cyclohexadiene-1,4-diylidene); -dimalononitrile, 7,7,8,8-Tetracyanoquinodimethane

登记号

• CAS号: 1518-16-7
• EC号: 216-174-8
• MDL号: MFCD00011664
• Beilstein号: 611604; 1427366
• PubChem SID: 162042571; 24849689
• PubChem CID: 73697
• CHEBI ID: 52445
• Chemspider ID: 66342
• 维基百科标题: Tetracyanoquinodimethane

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 0.7475403
• LogD (pH = 7.4): 0.7475403
• Log P: 0.7475403
• 摩尔折射率: 61.1884 cm^3
• 极化性: 20.516354 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

• 外观: green-coloured crystals
• 熔点: 287-289 °C (dec.)(lit.); 287-289(dec.)°C; 293.5–296 °C; ca 288°C dec.
• 沸点: sublimes
• 轨道能量: LUMO 4.6 eV
• 半导体性质: N-type (mobility=10-5 cm2/V·s)

安全信息

• 保存注意事项: Harmful/Irritant
• RTECS编号: GU4850000
• 欧盟危险性物质标志: 有毒(Toxic) (T); X
• 联合国危险货物编号: 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): III
• 危险公开号: 20/21/22; 23/24/25
• 安全公开号: 36/37; 36/37-45
• TSCA收录: 是
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301 + H311 + H331; H331-H302-H312
• GHS警示性声明: P261-P280-P301 + P310-P311; P261-P280-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 相关基因信息: human ... CAPN1(823)rat ... Capn1(29153), Nos1(24598)

产品相关信息

• 纯度: ≥98.0% (N); 98%
• 级别: purum
• Empirical Formula (Hill Notation): C12H4N4

详细说明

Sigma Aldrich - 157635

包装
10 g in poly bottle
5 g in glass bottle
Application
用于形成电荷转移超导体的电子受体分子。1

Sigma Aldrich - 87126

Other Notes
形成电荷转移复合物1

参考文献

• Effective catalyst for the ɑ-chlorination of carboxylic acids using chlorosulfonic acid; the presence of TCNQ suppresses competing free-radical chlorination: J. Org. Chem., 48, 1364 (1983).
• Electron-acceptor, forming stable radical anions: J. Am. Chem. Soc., 82, 6408 (1960); 84, 3370, 3374 (1962).
• Forms charge-transfer complexes with electron-rich donors: J. Am. Chem. Soc., 95, 948 (1973).
• For a review of the differences between "metallic" and "non-metallic" salts of TCNQ, see: Acc. Chem. Res., 12, 79 (1979).