m-Dinitrobenzene（DNB） - ≥99%(GC) , CAS No.99-65-0

CAS: 99-65-0 Cat. No.: D137764 Formula: C₆H₄N₂O₄ Peso molecolare: 168.11 Beilstein Registry Number: 1105654 Numero EC: 202-776-8

GRADE & PURITY ≥99%(GC)

Synonyms

D87507 | 1,3-Dinitrobenzene, 97% anhydrous basis | 1,3 Dinitrobenzene | 1,3-Dinitrobenzene 10 microg/mL in Methanol | NSC 7189 | CCRIS 1802 | 1,3-Dinitrobenzene | 1,3-Dinitro-benzene | 1,3-DINITROBENZENE [HSDB] | EN300-19976 | ghl.PD_Mitscher_leg0.916 | C

Storage

Store at 2-8°C

Shipped In

Wet ice,FedEx DG Service

Panoramica

1,3-Dinitrobenzene can undergo reductive degradation by alkaline ascorbic acid to produce 1,3-phenylenediamine.
Purpose
1,3-Dinitrobenzene can be used as a reactant to synthesize:      
2′,6′- dinitrobiphenyl-4-ol and 1-nitrodibenzofuran via copper-catalyzed regioselective cross-coupling reaction with 4-iodophenol and 2-iodophenol respectively.
1H-indazole derivatives by reacting with various N-tosylhydrazones in the presence of a base catalyst.    
3-(1H-Tetrazol-1-yl)benzenamine by reacting with triethyl orthoformate and NaN3 in the presence of a three-functional redox catalytic system

Specifications

Sinonimi

D87507 | 1,3-Dinitrobenzene, 97% anhydrous basis | 1,3 Dinitrobenzene | 1,3-Dinitrobenzene 10 microg/mL in Methanol | NSC 7189 | CCRIS 1802 | 1,3-Dinitrobenzene | 1,3-Dinitro-benzene | 1,3-DINITROBENZENE [HSDB] | EN300-19976 | ghl.PD_Mitscher_leg0.916 | C

Specifiche e purezza

≥99%(GC)

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice,FedEx DG Service

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Purezza

≥99%(GC)

Nomi e identificatori

• Pubchem Sid: 488180438
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180438
• Sorrisi canonici: C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]
• IUPAC Name: 1,3-dinitrobenzene
• InChIKey: WDCYWAQPCXBPJA-UHFFFAOYSA-N
• INCHI: 1S/C6H4N2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H
• Isomeri SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]
• WGK Germania: 2
• RTECS: CZ7350000
• Numero UN: 1597
• Gruppo di imballaggio: II
• Peso molecolare: 168.11
• Beilstein: 1105654
• Reaxy-Rn: 1105654
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1105654&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Nitrobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrobenzenes
• Alternative Parents: Nitroaromatic compounds Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Nitrobenzene - Nitroaromatic compound - Organic nitro compound - C-nitro compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic oxoazanium - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
• External Descriptors: a small molecule

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

Obiettivi associati (umani)

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

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Lymphoblastoid cell (5959 Activities)

Explore this target

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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LMNA Tbio Prelamin-A/C (36751 Activities)

Discover Target: LMNA

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

Discover Target: PMP22

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Obiettivi associati (non umani)

Salmonella typhimurium (15756 Activities)

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lef Anthrax lethal factor (7585 Activities)

Discover Target: lef

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Sensibilità: Moisture sensitive.
• Punto di infiammabilità (°F): 302 °F
• Punto di infiammabilità (°C): 150 °C
• Punto di ebollizione (°C): 291°C
• Punto di fusione (°C): 89°C
• Peso molecolare: 168.110 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 168.017 Da
• Monoisotopic Mass: 168.017 Da
• Topological Polar Surface Area: 91.600 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 175.000
• 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

Riferimenti

1. Haotian Wu, Guangfa Wang, Zhenzhen Cai, Dezhong Li, Fangfang Xiao, Da Lei, Zhuohua Dai, Xincun Dou.  (2022)  Polyethyleneimine-capped copper nanoclusters for detection and discrimination of 2,4,6-trinitrotoluene and 2,4,6-trinitrophenol.  Analytical Methods,  14  (44): (4485-4494).  [PMID:36317750] [10.1039/D2AY01311H]

2. Lihua Zhu, Huan Zhang, Huaze Zhu, Huan Fu, Anna Kroner, Zhiqing Yang, Hengqiang Ye, Bing Hui Chen, Rafael Luque.  (2022)  Controlling nanostructures of PtNiCo/C trimetallic nanocatalysts and relationship of structure-catalytic performance for selective hydrogenation of nitroarenes.  JOURNAL OF CATALYSIS,      [PMID:] [10.1016/j.jcat.2022.08.012]

3. Chaorui Xue, Qian Zhang, Yang Shen, Shengliang Hu, Qing Chang, Huiqi Wang, Ning Li, Jinlong Yang.  (2022)  Laser thermal synthesis of reduced graphene oxide/CuS nanocomposites for efficient solar-driven water purification.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2022.121168]

4. Hanxing Yang, Zhongguang Ji, Yanbo Zeng, Jian Zhang, Lifen Chen, Hailong Wang, Yiwen Yang, Longhua Guo, Lei Li.  (2022)  Aggregation-induced emission monomer-based fluorescent molecularly imprinted poly(ionic liquid) synthesized by a one-pot method for sensitively detecting 4-nitrophenol.  Analytical Methods,  14  (10): (1023-1030).  [PMID:35188146] [10.1039/D1AY02132J]

5. Wenli Peng, Li Gan, Weihan Li, Shixiong Deng.  (2021)  Carbon Dot Functionalized Papers for the Selective Detection of 2,4,6-Trinitrophenol in Aqueous Solutions.  Advances in Materials Science and Engineering,      [PMID:] [10.1155/2021/4867869]

6. Xiaonan Duan, Jiabin Yin, Mengmeng Huang, Aoxing Feng, Weisong Fu, Huaxiang Chen, Zhenfu Huang, Yagang Ding, Jisong Zhang.  (2021)  Hydrogenation kinetics of m-dinitrobenzene in a continuous micro-packed bed reactor.  CHEMICAL ENGINEERING SCIENCE,      [PMID:] [10.1016/j.ces.2021.117113]

7. Deyi Zhan, Abdul Saeed, Zixuan Li, Chengming Wang, Zhiwu Yu, Junfeng Wang, Nanjing Zhao, Weihong Xu, Jinhuai Liu.  (2020)  Highly fluorescent scandium-tetracarboxylate frameworks: selective detection of nitro-aromatic compounds, sensing mechanism, and their application.  DALTON TRANSACTIONS,  49  (48): (17737-17744).  [PMID:33237063] [10.1039/D0DT03781H]

8. Qian Liu, Feifei Zhao, Bingfeng Shi, Changli Lü.  (2020)  Mussel-inspired polydopamine-encapsulated carbon dots with dual emission for detection of 4-nitrophenol and Fe3+.  LUMINESCENCE,  36  (2): (431-442).  [PMID:33043598] [10.1002/bio.3961]

9. Xinfeng Chen, Congming Sun, Yang Liu, Long Yu, Kui Zhang, Abdullah M. Asiri, Hadi M. Marwani, Hua Tan, Yuejie Ai, Xiangke Wang, Suhua Wang.  (2019)  All-inorganic perovskite quantum dots CsPbX3 (Br/I) for highly sensitive and selective detection of explosive picric acid.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2019.122360]

10. Lamaocao Ma, Hengchang Ma.  (2019)  Synthesis of π-conjugated network polymers based on triphenylamine (TPA) and tetraphenylethylene (TPE) as building blocks via direct Pd-catalyzed reactions and their application in CO2 capture and explosive detection.  RSC Advances,  9  (32): (18098-18105).  [PMID:35515247] [10.1039/C9RA02469G]

11. Jie Ma, Lei Bian, Lei Zhao, Xiaotong Feng, Lizhi Zhao, Zhaoyan Wang, Qiaosheng Pu.  (2019)  Dialysed caramel as an effective fluorophore for the simultaneous detection of three nitrophenols.  TALANTA,      [PMID:30771918] [10.1016/j.talanta.2019.01.006]

12. Yulian Li, Lingyun Feng, Wei Yan, Irshad Hussain, Li Su, Bien Tan.  (2018)  PVP-templated highly luminescent copper nanoclusters for sensing trinitrophenol and living cell imaging.  Nanoscale,  11  (3): (1286-1294).  [PMID:30603761] [10.1039/C8NR07142J]

13. Ju Yan Jun, Li Na, Liu Shi Gang, Fan Yu Zhu, Ling Yu, Xiao Na, Luo Hong Qun, Li Nian Bing.  (2018)  Green Synthesis of Blue Fluorescent P-doped Carbon Dots for the Selective Determination of Picric Acid in an Aqueous Medium.  ANALYTICAL SCIENCES,  35  (2): (147-152).  [PMID:30249931] [10.2116/analsci.18P372]

14. Wen Jie Zhang, Shi Gang Liu, Lei Han, Yu Ling, Liu Li Liao, Shi Mo, Hong Qun Luo, Nian Bing Li.  (2018)  Copper nanoclusters with strong fluorescence emission as a sensing platform for sensitive and selective detection of picric acid.  Analytical Methods,  10  (35): (4251-4256).  [PMID:] [10.1039/C8AY01357H]

15. Jinxia Xu, Zhangjun Bai, Fanlin Zu, Fanyong Yan, Junfu Wei, Saihui Zhang, Yunmei Luo.  (2018)  A dual spectroscopic fluorescence probe based on carbon dots for detection of 2,4,6-trinitrophenol/Fe (III) ion by fluorescence and frequency doubling scattering spectra and its analytical applications.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:29679931] [10.1016/j.saa.2018.03.080]

16. Na Xiao, Shi Gang Liu, Shi Mo, Na Li, Yan Jun Ju, Yu Ling, Nian Bing Li, Hong Qun Luo.  (2018)  Highly selective detection of p-nitrophenol using fluorescence assay based on boron, nitrogen co-doped carbon dots.  TALANTA,      [PMID:29674031] [10.1016/j.talanta.2018.02.114]

17. Yu Zhu Fan, Ying Zhang, Na Li, Shi Gang Liu, Ting Liu, Nian Bing Li, Hong Qun Luo.  (2016)  A facile synthesis of water-soluble carbon dots as a label-free fluorescent probe for rapid, selective and sensitive detection of picric acid.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2016.09.063]

18. Meng Li Liu, Bin Bin Chen, Ze Xi Liu, Cheng Zhi Huang.  (2016)  Highly selective and sensitive detection of 2,4,6-trinitrophenol by using newly developed blue–green photoluminescent carbon nanodots.  TALANTA,      [PMID:27769497] [10.1016/j.talanta.2016.08.046]

19. Tao Lu, Yuan Yuan, Yan Jiao, Zhining Wen, Lu Wang, Yihuan Zhao, Yuxiang Zhang, Menglong Li, Xuemei Pu, Tao Xu.  (2016)  Simultaneous spectrophotometric quantification of dinitrobenzene isomers in water samples using multivariate calibration methods.  CHEMOMETRICS AND INTELLIGENT LABORATORY SYSTEMS,      [PMID:] [10.1016/j.chemolab.2016.03.022]

20. Bin Bin Chen, Ze Xi Liu, Hong Yan Zou, Cheng Zhi Huang.  (2016)  Highly selective detection of 2,4,6-trinitrophenol by using newly developed terbium-doped blue carbon dots.  ANALYST,  141  (9): (2676-2681).  [PMID:27109163] [10.1039/C5AN02569A]

21. Haiyang Cheng, Weiwei Lin, Xiaoru Li, Chao Zhang, Fengyu Zhao.  (2014)  Selective Hydrogenation of m-Dinitrobenzene to m-Nitroaniline over Ru-SnOx/Al2O3 Catalyst.  Catalysts,  4  (3): (276-288).  [PMID:] [10.3390/catal4030276]

22. Ruiqi Qiao, Yingxing Li, Rongchao Zhu, Huazangnaowu Bai, Chuanfang Zhao, Baiyi Zu, Zhenzhen Cai.  (2025)  Carbonized polymer dots for discrimination of 2,4,6-trinitrotoluene and 2,4,6-trinitrophenol.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:40112434] [10.1016/j.jhazmat.2025.137944]

23. Yongli Liu, Guobei Ge, Huanjia Liu, Yuxin Wang, Penghui Zhou, Bin Li, Guifen Zhu.  (2024)  Fast and eco-friendly synthesis of carbon dots from pinecone for highly effective detection of 2,4,6-trinitrophenol in environmental samples.  ENVIRONMENTAL TECHNOLOGY,      [PMID:38887014] [10.1080/09593330.2024.2367725]

24. Kefa Sheng, Hongyu Xia, Jianping Ge.  (2024)  Highly dispersed Pd nanoparticles supported by magnetically separable Fe3O4@ SiO2 nanotube for catalytic hydrogenation of nitroaromatics.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:39059282] [10.1016/j.jcis.2024.07.156]

25. Zitao Shen, Zhuo Wang, Pengfei Ye, Lihong Guo, Sheng Peng, Yuefan Liu, Yongsheng Cui, Juan Zheng, Gangfeng Ouyang.  (2025)  Highly hydrophobic calixarene polymers for efficient enrichment of polar nitrobenzene compounds.  TALANTA,      [PMID:39778492] [10.1016/j.talanta.2025.127555]

26. Zhiang Hou, Huachun Lan, Xiaoqiang An, Ruijuan Liu, Lan Yang, Lie Liu, Huijuan Liu, Jiuhui Qu.  (2024)  Nitrogen-doped hierarchical porous carbon with enhanced interfacial affinity for the efficient adsorption of antibiotic micropollutants from water.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.155055]

27. Zhuohua Dai, Guangfa Wang, Fangfang Xiao, Da Lei, Xincun Dou.  (2023)  Amorphous Copper-Based Nanoparticles with Clusterization-Triggered Phosphorescence for Ultrasensing 2,4,6-Trinitrotoluene.  ADVANCED MATERIALS,  35  (24): (2300526).  [PMID:36929680] [10.1002/adma.202300526]

28. Zhijun Li, Mingyang Zhang, Xiuli Dong, Siqi Ji, Lili Zhang, Leipeng Leng, Honghong Li, J. Hugh Horton, Qian Xu, Junfa Zhu.  (2022)  Strong electronic interaction of indium oxide with palladium single atoms induced by quenching toward enhanced hydrogenation of nitrobenzene.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2022.121462]

29. Yihong Zhou, Yang Xu, Peng Wang, Jing Zhang, Shangxing Chen, Dayong Peng, Zongde Wang, Yuling Yang, Hai Luo, Ji Zhang.  (2025)  Modification of Pickering emulsions using zein-tannic acid particles: enhancement of antioxidant and thermal stability properties of citral.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2025.117761]

Domande frequenti

What is the purity of this product, and how is it determined?

This product is supplied at ≥99% purity, determined by gas chromatography (GC). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 99-65-0, the molecular formula is C6H4N2O4, and the molecular weight is 168.11 g/mol. InChIKey WDCYWAQPCXBPJA-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.