4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile

• ChemBase编号: 77210
• 分子式: C8Cl2N2O2
• 平均质量: 227.0038
• 单一同位素质量: 225.93368261
• SMILES: ClC1=C(C(=O)C(=C(C1=O)C#N)C#N)Cl
• Canonical SMILES: N#CC1=C(C#N)C(=O)C(=C(C1=O)Cl)Cl
• InChI: InChI=1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13
• InChIKey: HZNVUJQVZSTENZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
• IUPAC传统名: 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
• 别名: 4,5-二氯-3,6-二氧-1,4-环己二烯-1,2-二甲腈; 2,3-二氯-5,6-二氰基对苯醌; 2,3-二氯-5,6-二氰基苯醌; * 2,3-Dichloro-5,6-dicyano-p-benzoquinone* 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile* Dichlorodicyanobenzoquinone; 2,3-DICHLORO-5,6-DICYANOQUINONE; 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone; 1,2-Dichloro-4,5-dicyano-3,6-dioxocyclohexa-1,4-diene; 4,5-Dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile; 2,3-Dichloro-5,6-dicyanobenzoquinone; 1,2-Dichloro-4,5-dicyano-p-benzoquinone; 2,3-Chloro-5,6-dicyanoquinone; 2,3-Dichloro-5,6-dicyano-p-quinone; Dichlorodicyano-p-benzoquinone; Dicyanodichloroquinone; NSC 401087; 2,3-Dichloro-5,6-dicyano-p-benzoquinone; DDQ; 2,3-Dichloro-5,6-dicyano-p-benzoquinone; 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile; 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE; 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

登记号

• CAS号: 84-58-2
• EC号: 201-542-2
• MDL号: MFCD00001593
• Beilstein号: 747939
• 默克索引号: 143063
• PubChem SID: 162042083; 24893996; 24861867
• PubChem CID: 6775
• Chemspider ID: 6517
• 维基百科标题: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 1.4257357
• LogD (pH = 7.4): 1.4257357
• Log P: 1.4257357
• 摩尔折射率: 50.7186 cm^3
• 极化性: 18.073162 Å^3
• 极化表面积: 81.72 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

• 溶解度: Benzene; Ethyl Acetate; reacts in water
• 外观: Yellow Solid; yellow to orange powder
• 熔点: 210-215 °C (dec.); 210-215 °C (dec.)(lit.); 210-215°C; 214-218°C; 219-221°C
• 沸点: 301.8°C @ 760mmHg
• 闪点: 136.3°C
• 密度: 1.7g/cm3

安全信息

• 保存条件: 0°C; -20°C Freezer
• 保存注意事项: Moisture Sensitive; Toxic/Moisture Sensitive/Store under Argon
• RTECS编号: GU4825000
• 欧盟危险性物质标志: 有毒(Toxic) (T); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3439; 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): 3; II
• 危险公开号: 25-29; R:36/37/38; R25 R29
• 安全公开号: 22-24/25-37-45; 7/8-20-36-45; S:20-25-26-37/39; S22 S24/25 S37 S45
• TSCA收录: 是
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P264-P270-P301+P310-P321-P405-P501A; P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3439 6.1/PG 3
• 欧盟补充危害声明: Contact with water liberates toxic gas.
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0% (RT); 98%; 98+%
• 级别: purum
• Empirical Formula (Hill Notation): C8Cl2N2O2

详细说明

MP Biomedicals - 05209966

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150864

Orange-yellow crystals.
Dehydrogenation reagent. Also used as a spray reagent for carbazoles.

Sigma Aldrich - D60400

Application
多种化合物（例如硫缩醛、缩醛和缩酮）的通用脱保护试剂。可用于通过亚胺和炔烃或烯烃合成喹啉的电子转移试剂。
用于与 Ph3P 高效合成 1 2-苯并异噁唑类化合物。1
包装
5, 10, 100 g in glass bottle

Sigma Aldrich - 35680

Other Notes
用于氢化芳族化合物脱氢的试剂1；用于温和断裂醚类保护基团的试剂2,3,4

Toronto Research Chemicals - D434110

An oxidizing agent, especially in steroid synthesis.

参考文献

• Silyl and THP ethers are deprotected: J. Chem. Soc., Perkin 1, 2997 (1992); Synth. Commun., 25, 2373 (1995), respectively. Ethers of benzylic or allylic alcohols are oxidized to aldehydes, permitting the use of the methoxymethyl group as a masked aldehyde: Can. J. Chem., 67, 699 (1989). For cleavage of thioacetals to carbonyl groups, see: J. Org. Chem., 58, 7576 (1993); Chem. Lett., 965 (1994).
• Widely used dehydrogenation reagent, e.g. in aromatization reactions; review: Chem. Rev., 67, 153 (1967); 78, 317 (1978). For an example, see: Org. Synth. Coll., 6, 731 (1988). Dehydrogenation of chromanones to chromones and flavanones to flavones: Synthesis, 310 (1983); spirocyclohexenones to the corresponding cross-conjugated dienones: Org. Synth. Coll., 7, 473 (1990).
• Catalyzes formation of THP ethers from alcohols: Bull. Chem. Soc. Jpn., 65, 304 (1992), the isopropylidenation of carbohydrates with 2,2-Dimethoxypropane, A13810: Acta Chem. Scand., 47, 843 (1993); and C-N bond formation e.g. imines from arylamines and aldehydes (see also 1,2-Dianilinoethane, B23098), and, with 1 mole of DDQ, benzimidazole formation: Tetrahedron, 51, 5813 (1995):
  
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 196 (2006).