2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) - ≥98% , CAS No.84-58-2

CAS: 84-58-2 Cat. No.: D109444 Peso molecular: 227 Beilstein Registry Number: 747939 Número EC: 201-542-2

GRADE & PURITY ≥98%

Synonyms

DDQ | 2,3-dichloro-5,6-dicyano- 1,4-benzoquinone | 2,3-dichloro-5,6-dicyano -1,4-benzoquinone | 2,3-dichloro 5,6-dicyanobenzoquinone | SCHEMBL2952 | 5,6-Dichloro-2,3-dicyano-p-benzoquinone | 5,6-Dicyano-2,3-dichloro-p-benzoquinone | 2,3,-dichloro-5,6-dicy

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice,FedEx DG Service

Descripción general

An oxidizing agent, especially in steroid synthesis
Versatile deprotection reagent for a variety of compounds, such as thioacetals, acetals, and ketals. Useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes. Used with Ph3P in an efficient synthesis of 1,2-benzisoxazoles Used with Ph3P in an efficient synthesis of 1,2-benzisoxazoles

Specifications

Sinónimos

DDQ | 2, 3-dichloro-5, 6-dicyano- 1, 4-benzoquinone | 2, 3-dichloro-5, 6-dicyano -1, 4-benzoquinone | 2, 3-dichloro 5, 6-dicyanobenzoquinone | SCHEMBL2952 | 5, 6-Dichloro-2, 3-dicyano-p-benzoquinone | 5, 6-Dicyano-2, 3-dichloro-p-benzoquinone | 2, 3, -dichloro-5, 6-dicy

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Argon charged

Enviado en

Wet ice, FedEx DG Service

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N
• IUPAC Name: 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
• InChIKey: HZNVUJQVZSTENZ-UHFFFAOYSA-N
• INCHI: 1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13
• Isómeros SMILES: C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N
• WGK Alemania: 3
• RTECS: GU4825000
• Número ONU: 3439
• Peso molecular: 227
• Beilstein: 747939
• Reaxy-Rn: 747939
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=747939&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Clase Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Cyclic ketones
            • Level7 Quinones
              • Level8 Benzoquinones
                • Level9 P-benzoquinones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Clase: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Cyclic ketones - Quinones - Benzoquinones
• Direct Parent: P-benzoquinones
• Alternative Parents: Vinylogous halides Alpha-chloroketones Vinyl chlorides Nitriles Chloroalkenes Organopnictogen compounds Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: P-benzoquinone - Alpha-haloketone - Alpha-chloroketone - Vinylogous halide - Carbonitrile - Nitrile - Vinyl chloride - Chloroalkene - Haloalkene - Vinyl halide - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organonitrogen compound - Organochloride - Organohalogen compound - Organopnictogen compound - Aliphatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (no humanos)

Plasmodium falciparum (966862 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in water (slightly), ethanol, acetic acid, ethyl acetate, and chloroform (slightly)
• Sensibilidad: Moisture, Heat and Air sensitive
• Punto de fusión (°C): 214℃
• Peso molecular: 227.000 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 225.934 Da
• Monoisotopic Mass: 225.934 Da
• Topological Polar Surface Area: 81.700 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 464.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Quan Shi, Ming-Hui Chen, Ji Xiong, Ting Li, Ya-Qing Feng, Bao Zhang.  (2023)  Porphyrin-Based Two-Dimensional Metal-Organic framework nanosheets for efficient photocatalytic CO2 transformation.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.148301]

2. Min Li, Ziyi Cheng, Heng Liu, Kun Dou, Huan Xiao, Linlu Zhao, Fabiao Yu.  (2023)  Multifunctional protein-based self-assembled nanoplatform: overcoming hypoxic tumor microenvironment for enhanced imaging-guided photodynamic therapy.  Biomaterials Science,      [PMID:37647018] [10.1039/D3BM01130E]

3. Xiaoxiao Zhou, Shouhui Chen, Yi Pan, Yuanfeng Wang, Naifeng Xu, Yanwen Xue, Xinlin Wei, Ying Lu.  (2023)  High-Performance Au@Ag Nanorods Substrate for SERS Detection of Malachite Green in Aquatic Products.  Biosensors-Basel,  13  (8): (766).  [PMID:37622852] [10.3390/bios13080766]

4. Ya-Ting Gao, Shuai Chang, Bin-Bin Chen, Da-Wei Li.  (2023)  Dual-Exciting Central Carbon Nanoclusters for the Dual-Channel Detection of Hemin.  Inorganics,  11  (6): (226).  [PMID:] [10.3390/inorganics11060226]

5. Li Chen, Xiang Li, Mengmeng Xiong, Yimei Zhao, Suyi Liu, Cao Li, Kai Wang.  (2022)  Development of novel nanoporphyrin biomaterials for NIR-II activated photothermal therapy against tumor in vivo.  MATERIALS & DESIGN,      [PMID:] [10.1016/j.matdes.2022.111532]

6. Yuqing Ren, Yao Chen, Qinyu Li, Hexing Li, Zhenfeng Bian.  (2022)  Microwave-Assisted Photocatalytic Degradation of Organic Pollutants via CNTs/TiO2.  Catalysts,  12  (9): (940).  [PMID:] [10.3390/catal12090940]

7. Huiping Dang, Youliang Tian, Quan Cheng, Changchang Teng, Kai Xie, Lifeng Yan.  (2021)  Galactose conjugated boron dipyrromethene and hydrogen bonding promoted J-aggregates for efficiently targeted NIR-II fluorescence assistant photothermal therapy.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:34995865] [10.1016/j.jcis.2021.12.177]

8. Yuqian Liu, Lei Lei, Yeyu Wu, Yuyun Chen, Jun Yan, Weiwei Zhu, Xuecai Tan, Qi Wang.  (2021)  Fabrication of sea urchin-like Au@SiO2 nanoparticles SERS substrate for the determination of malachite green in tilapia.  VIBRATIONAL SPECTROSCOPY,      [PMID:] [10.1016/j.vibspec.2021.103319]

9. Chen Yao, Xu Mengjiao, Wen Jieya, Wan Yu, Zhao Qingfei, Cao Xia, Ding Yong, Wang Zhong Lin, Li Hexing, Bian Zhenfeng.  (2021)  Selective recovery of precious metals through photocatalysis.  Nature Sustainability,  4  (7): (618-626).  [PMID:] [10.1038/s41893-021-00697-4]

10. Xiu Chen, Ying Zhang, Jin Han, Linzhou Zhang, Suoqi Zhao, Chunming Xu, Quan Shi.  (2021)  Direct Nickel Petroporphyrin Analysis through Electrochemical Oxidation in Electrospray Ionization Ultrahigh-Resolution Mass Spectrometry.  ENERGY & FUELS,      [PMID:] [10.1021/acs.energyfuels.0c03785]

11. Xuesong Gu, Shubo Xie, Qiang Chen, Shufeng Chen, Haiying Zhao, Zhanxi Bian.  (2018)  Anti-migration and burning rate catalytic performances of novel ferrocene-based porphyrins and their transition-metal complexes.  NEW JOURNAL OF CHEMISTRY,  42  (16): (13319-13328).  [PMID:] [10.1039/C8NJ02376J]

12. Tingting Zhu, Ji Xiong, Zhongbo Xue, Yu Su, Fengnan Sun, Ran Chai, Jialiang Xu, Yaqing Feng, Shuxian Meng.  (2018)  A novel amphiphilic fluorescent probe BODIPY–O-CMC–cRGD as a biomarker and nanoparticle vector.  RSC Advances,  8  (36): (20087-20094).  [PMID:35541689] [10.1039/C8RA02125B]

13. Lujun Yu, Xiang Li, Qixin Yang, Yaofeng Zhu, Yaqin Fu.  (2018)  Regular helix carbon rods with nitrogen-doped characteristic.  MATERIALS LETTERS,      [PMID:] [10.1016/j.matlet.2018.05.065]

14. Weihan Wang, Xichuan Yang, Jiajia Li, Haoxin Wang, Jincheng An, Li Zhang, Xiao Jiang, Ze Yu, Licheng Sun.  (2017)  Enhancing the Energy-Conversion Efficiency of Solid-State Dye-Sensitized Solar Cells with a Charge-Transfer Complex based on 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone.  Energy Technology,  6  (4): (752-758).  [PMID:] [10.1002/ente.201700633]

15. Yukun Feng, Hui Wang, Qian Wang, Wenlin Huang, Ying Peng, Jiang Zheng.  (2017)  Chemical Interaction of Protein Cysteine Residues with Reactive Metabolites of Methyleugenol.  CHEMICAL RESEARCH IN TOXICOLOGY,      [PMID:28107620] [10.1021/acs.chemrestox.6b00290]

16. Huina Yao, Ying Peng, Jiang Zheng.  (2016)  Identification of glutathione and related cysteine conjugates derived from reactive metabolites of methyleugenol in rats.  CHEMICO-BIOLOGICAL INTERACTIONS,      [PMID:27154494] [10.1016/j.cbi.2016.05.006]

17. Kun Hu, Pei Chen, Qiang Weng, Dingqian Shi, Ran Chen, Xinbing Chen, Zhongwei An.  (2015)  Preparation and properties of lateral monofluoro-substituted benzoxazole-based mesogenic compounds.  LIQUID CRYSTALS,      [PMID:] [10.1080/02678292.2015.1069412]

18. Kun Hu, Pei Chen, Qiang Weng, Dingqian Shi, Ran Chen, Xinbing Chen, Zhongwei An.  (2015)  Improved mesophase stability of benzoxazole derivatives via dipole moment modification.  LIQUID CRYSTALS,      [PMID:] [10.1080/02678292.2015.1084656]

19. Baomei Huang, Xibin Zhou, Jing Chen, Guofan Wu, Xiaoquan Lu.  (2015)  Determination of malachite green in fish based on magnetic molecularly imprinted polymer extraction followed by electrochemiluminescence.  TALANTA,      [PMID:26003716] [10.1016/j.talanta.2015.04.053]

20. Pei Chen, Yiwei Xu, Weisong Du, Guangping Zhang, Xinbing Chen, Zhongwei An.  (2014)  New Mesogenic Compounds Containing a Terminal-Substituted Benzoxazole Unit.  MOLECULAR CRYSTALS AND LIQUID CRYSTALS,      [PMID:] [10.1080/15421406.2013.837997]

21. Guangfei Wu, Fang Zeng, Shuizhu Wu.  (2013)  A water-soluble and specific BODIPY-based fluorescent probe for hypochlorite detection and cell imaging.  Analytical Methods,  5  (20): (5589-5596).  [PMID:] [10.1039/C3AY41268G]

22. Yiwei Xu, Xinbing Chen, Fengqi Zhao, Xuezhong Fan, Pei Chen, Zhongwei An.  (2013)  Synthesis and properties of substituted benzoxazole-terminated liquid crystals.  LIQUID CRYSTALS,      [PMID:] [10.1080/02678292.2012.735709]

23. Lidong Li, Hean Zhang, Lu Han, Ming Qiu, Qianling Cui, Xiaona Qin.  (2025)  A dynamic solvent-modulated single component emissive system for information encryption.  Journal of Materials Chemistry C,      [PMID:] [10.1039/D4TC05410E]

24. Min-Fu Wu, Nuo Xu, Sha Li, Yi-Lan Huang, Min-Hua Wu, Jia-Dong Li, Ri-Sheng Chen, Wen-Ming Xiong, Yong-Jun Li, Hong-Tao Lei, Xin-An Huang, Zhen-Lin Xu.  (2024)  A hapten design strategy to enhance the selectivity of monoclonal antibodies against malachite green.  Frontiers in Sustainable Food Systems,      [PMID:] [10.3389/fsufs.2024.1490750]

25. Shi Quan, Xu Yun-Hao, Chen Ming-Hui, Zhao Peng, Deng Wen-Bo, Xiong Ji, Guo Kai, Feng Ya-Qing, Zhang Bao.  (2025)  A versatile synthetic strategy towards rare earth based metal-organic frameworks.  Science China-Chemistry,      [PMID:] [10.1007/s11426-024-2322-9]

26. Xiao Tu, Jiaxin Hu, Jinghao Peng, Qihan Chen, Yangle Zhao, Zemao Gu.  (2025)  Discovery of thymoquinone analogues with high anthelmintic activity against monogenean infections in goldfish (Carassius auratus).  VETERINARY PARASITOLOGY,      [PMID:39837239] [10.1016/j.vetpar.2025.110401]

27. Lipeng Wang, Meilin Yin, Rui Li, Shaokun Tang.  (2024)  Hydroxyl-functionalized ionic liquid-modified covalent organic frameworks for efficient CO2 cycloaddition conversion.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2024.114331]

28. Junyang Liu, Yanan Wang, Mengping Wang, Xinyi Dong, Xinxin Liu, Mengqi Li, Guangjiu Zhao.  (2025)  In situ ligand passivated organic–inorganic hybrid perovskite quantum dots for photocatalytic antibacterial applications.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:40022785] [10.1016/j.jcis.2025.02.167]

29. Lu Yang, Yanglin Jiang, Ailin Sun, Mingqing Chen, Qiwei Li, Peng Wang, Jianping Zhang.  (2024)  Mechanism of two styryl BODIPYs as fluorescent probes and protective agents in lipid bilayers against aqueous ClO−.  RSC Advances,  14  (39): (28957-28964).  [PMID:39263435] [10.1039/D4RA03433C]

30. Yaqi Duan, Conghao Ku, Yuping Lv, Yantao Wang, Weiran Yang.  (2024)  Synergistic catalytic effect of activated carbon nanomaterial and CaO for highly selective oxidation of levulinic acid to citramalic acid.  FUEL,      [PMID:] [10.1016/j.fuel.2024.131121]

31. Xiao-Yi Tang, Hui-Di Zhang, Zi-Jie Li, Shuai Wang, Si-Yan Liu, Tao-Yuan Xiu, Ji-Pan Yu, Lin Wang, Li-Yong Yuan, Wang-Suo Wu, Wei-Qun Shi.  (2025)  Synthesis of phosphorylated covalent organic frameworks with different linkages–Critical factors controlling the extraction of uranium from highly acidic media.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.160226]

32. Qinhai Xu, Kang Li, Peng Wang.  (2024)  The reaction mechanism of p-hydroxystyryl-substituted BODIPY with ABTS•+ and Fe3+ in solutions and in liposomes.  Arabian Journal of Chemistry,      [PMID:] [10.1016/j.arabjc.2024.106041]

33. Hean Zhang, Ming Qiu, Qianling Cui, Yufeng Luo, Lidong Li.  (2024)  Viscosity-modulated intramolecular excitation energy transfer for mitochondria-targeted sensing and photokilling.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2024.135911]

34. Liu Guangyong, Lu Yumiao, Lu JunFeng, Wang Yanlei, Liang Shijing, He Hongyan, Jiang Lilong.  (2023)  Ionic liquid-trimetallic electrocatalytic system for C-O bond cleavage in lignin model compounds and lignin under ambient conditions.  Nano Research,      [PMID:] [10.1007/s12274-023-6086-z]

35. Jian Song, Hai-Long Qian, Shu-Ting Xu, Cheng Yang, Xiu-Ping Yan.  (2025)  Boronate affinity molecularly imprinted covalent organic framework for highly selective recognition and extraction of zearalenone.  FOOD CHEMISTRY,      [PMID:40339412] [10.1016/j.foodchem.2025.144590]

36. Shibin Zhang, Yan Xu, Danni Zhang, Lishun Bai, Yue Liu, Ying He, Feiyan Yu, Chengjun Liu, Sijie Li, Zhi Chang.  (2025)  Soft glass interphase engineering for ultra-stable aluminum metal batteries.  GREEN CHEMISTRY,      [PMID:] [10.1039/D5GC01118C]

37. Xinyue Yang, Zhixing Gao, Wei Zou, Zhongjie Du, Chen Zhang.  (2025)  Fabrication of cornflower-like PANI via synergistic induction strategy for effective improvement in electromagnetic shielding.  EUROPEAN POLYMER JOURNAL,      [PMID:] [10.1016/j.eurpolymj.2025.114340]

38. Hongda Gui, Ze Wang, Yuliang Cao, Fei Xu.  (2025)  Hybridization-tuned dual-chain conjugated polythioether quinones for high-energy rechargeable magnesium batteries.  Chemical Science,      [PMID:41229920] [10.1039/D5SC07331F]

39. Nan Han, Yu Zhang, Chunyuan Hou, Jun Gu, Jun Luo.  (2025)  Peripheral Tailoring of Pentacene: Developing Next-Generation Organic Sonosensitizers for Cancer Sonodynamic Therapy.  RSC Medicinal Chemistry,      [PMID:41355867] [10.1039/D5MD00851D]

40. Junyu Qu, Yixuan Liu, Wenqiang Fang, Huitao Liu, Zhenbo Liu.  (2025)  A Novel BODIPY-Derived Fluorescent Sensor for Sulfite Monitoring.  SENSORS,  25  (20): (6332).  [PMID:41157386] [10.3390/s25206332]

41. Chuangyu Wei, Meitong Li, Rui Tao, Xinyu Yang, Yuexing Zhang, Xue Cai.  (2026)  Electrochemical sensing platform based on fluorine-containing porphyrin conjugated polymers for simultaneous detection of dopamine and uric acid detection.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2026.116928]