2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 2,3-二氯-5,6-二氰基-1,4-苯醌

CAS 84-58-2 MFCD00001593

化学结构图

84-58-2
SMILES: N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O

化学属性

Mol. FormulaC8Cl2N2O2
Mol. Weight227.00
Density1.7
Melting Point210-215
TSCAYes
SolubilitySoluble in water (slightly), ethanol, acetic acid, ethyl acetate, and chloroform (slightly)
Stability对湿度,热及空气敏感

别名和识别编码

Chemical Name2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
CAS Number84-58-2
Synonym 2,3-Dichloro-5,6-dicyano-p-benzoquinone 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile 二氨二氰基苯醌 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- {uni_hamburg} {Chemical 2,3-Dichloro-5,6-Dicyano-1,4-benzenoquinone 2,3-Dicyano-5,6-dichloro-1,4-benzoquinone 1,2-Dichloro-4,5-dicyanobenzoquinone 2,3-Dicyano-5,6-dichlorobenzoquinone 4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE-1,2-CARBONITRILE 2,3-Dichloro-5 4-Cyclohexadiene-1,2-dic 4,5-Dichloro-3,6-dioxo-1,2-benzenedicarbonitrile 2,3 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE 2,3-二氯-5, DDQ 2,3-Dichloro-5,6-dicyano-p-benzoquinone DDQ (oxidizing agent) 2,3-二氯-5,6-二氰-1,4-苯醌 2,3-​Dichloro-​5,6-​dicyano-p-benzoquinone
EC Number201-542-2
Beilstein Registry Number10,902
MDL NumberMFCD00001593
PubChem Substance ID87567635
Merck Number3063
Reaxys-RN747939
Chemical Name Translation2,3-二氯-5,6-二氰基-1,4-苯醌
Wiswesser Line NotationL6V DVJ BCN CCN EG FG
LabNetwork Molecule IDLN00192891
信息真实价格透明    资金保障    专业采购外包团队在线服务   
信息真实价格透明    资金保障    专业采购外包团队在线服务   
品牌质保精细包装    现货库存    一流品牌服务   

分类

  • {SNA} Chemical Synthesis, Others, Oxidizing Agents, Synthetic Reagents
  • Aromatics
  • {SNA} Chemical Synthesis, Other Oxidizing Agents, Oxidizing Agents, Synthetic Reagents
  • Intermediates
  • {uni_hamburg} no charge; carbocycle; aromatic; 6RingOnly; 6ring; ketone; 1fragment

产品应用

  • 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。

相关文献及参考

  • For a brief feature on uses of the reagent in synthesis, see: Synlett, 196 (2006).
  • Merck: 14,3063 Beilstein:10,902
  • 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).
  • 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 c
  • Short: III/20b
  • Short: IV/4
  • Short: EINECS
  • 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):
  • 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).
  • Merck: 14,3063

安全信息

Signal word
GHS Symbol
WGK Germany3
Safety Statements
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S20 When using do not eat or drink 使用时，不得进食，饮水；
  • S7/8 Keep container tightly closed and dry 保存在严格密闭容器中，保持干燥；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
Risk Statements
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P310
  • P301+P310+P330
  • P302+P352+P312+P361+P364
  • P304+P340+P311
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P332+P313
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H301 Toxic if swallowed 吞食有毒
  • H301+H311+H331
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
RTECSGU4825000
Packing GroupIII
UN Number 3439
Storage condition 0-10 0-10°C 0-6°C Moisture Sensitive 储存温度 2-8°C 储存温度2-8°C, 充氩保存
Hazard Codes T
Hazard Class6.1
Warnings 危化品目录(2015) 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 31 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CHTHBK Chemotherapy (Basel).  (S. Karger Pub., Inc., 79 Fifth Ave., New
   York, NY 10003) V.13-    1968-  Volume(issue)/page/year: 16,371,1971

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 13 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems
   Laboratory, NIOSH Exchange Chemicals.  (Aberdeen Proving Ground, MD 21010)
   Volume(issue)/page/year: NX#07894

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 180 nmol/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 347,37,1995

Restrict 危险品

其他信息

  • Sigma Aldrich:84-58-2(sigmaaldrich)
  • MOL 文件:84-58-2.mol
  • 储运特性:库房通风低温干燥; 与氧化剂、食品化工添加剂、酸类分开存放
  • 上游原料:四氯化碳 --> 3,6-二羟基邻苯二甲腈
  • 类别:有毒物品
  • 毒性分级:剧毒
  • Alfa Aesar:2,3-二氯-5,6-二氰基苯醌,98+% 2,3-Dichloro-5,6-dicyanobenzoquinone, 98+%(84-58-2)
  • 下游产品:1-苯并呋喃-5-甲醛 --> 异补骨脂素 --> 2,6-二叔丁基苯醌
  • 海关编码:29269095
  • 用途二:合成甾族化合物的氧化剂，用于计划生育用药氯地孕酮、三烯高诺酮的生产。
  • An oxidizing agent, especially in steroid synthesis
  • 2,3-二氯-5,6-二氰基-1,4-苯醌价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 xw010218 2,3-二氯-5,6-二氰对苯醌 100g 600元 2011/08/23 AD6040002 2,3-二氯-5,6-二氰基-1,4-苯醌 10g 470元 2011/08/23 K3568001 2.3-二氯-5.6-二氰对苯醌purum95.0％ 10g 257.4元
  • 用途一:用作医药中间体，专门作为甾体类激素化合物的脱氢剂
  • 急性毒性:腹腔-小鼠 LD50: 31 毫克/公斤;静脉-小鼠 LD50: 13 毫克/公斤
  • TCI Shanghai:二氯二氰基苯醌 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone,>;97.0%(T)(84-58-2)
  • 检测方法:HPLC
  • Acros Organics:2,3-二氯-5,6-二氰基-1,4-苯醌 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 98%(84-58-2)
  • 能溶于苯、二氧六环、乙酸、微溶于氯仿、二氯甲烷，遇水迅速分解，把露于 85% 以上相对湿度空气中，局部很快变黑后分解。
  • F:21
  • 方法一:将2,3-二氰基氢醌和盐酸搅成浆状物，在35℃左右慢慢加入70%硝酸、继续搅拌反应1h。过滤，用四氯化碳洗涤，干燥，得DDQ，产率90%。
  • 存储注意事项:湿度敏感
  • 外观性质:黄橙色固体。
  • 图谱信息:2,3-二氯-5,6-二氰基-1,4-苯醌(84-58-2)核磁图( 13 CNMR) 2,3-二氯-5,6-二氰基-1,4-苯醌(84-58-2)红外图谱(IR1) 2,3-二氯-5,6-二氰基-1,4-苯醌(84-58-2)质谱(MS) 2,3-二氯-5,6-二氰基-1,4-苯醌(84-58-2)红外图谱(IR2)
  • 敏感性:Moisture Sensitive
  • 灭火剂:干石粉、二氧化碳、砂土。
  • MSDS 信息:2,3-二氰-5,6-二氯苯醌(84-58-2).msds
  • 可燃性危险特性:明火可燃; 高热分解放出氮氧化物和氯化物气体

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Others 其他杂环
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Others 其他杂环
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Oxidation - Synthetic Reagents
  4. Osmium - Oxidation
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Oxidation - Synthetic Reagents
  4. Others - Oxidation
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Halogenated Hydrocarbons 卤代烃
  5. Aryl 芳基卤代烃
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Chemicals by Class 化学分类法
  4. Benzoquinones
  1. Materials Science 材料科学
  2. Charge Transfer Complexes for Organic Metals