4-Nitrophthalonitrile - ≥98%(GC) , CAS No.31643-49-9

CAS: 31643-49-9 Cat. No.: N130031 Molecular Weight: 173.13 Beilstein Registry Number: 1877554 EC Number: 250-748-9

GRADE & PURITY ≥98%(GC)

Synonyms

5-Nitrobenzene-1,2-dicarbonitrile | 4-Nitro-phthalonitrile | 1,2-Benzenedicarbonitrile | 1,2-Dicyano-4-nitrobenzene | 4-nitrobenzene-1,2-dicarbonitrile | 4-Nitro-1,2-benzenedicarbonitrile | 3,4-Dicyanonitrobenzene

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

5-Nitrobenzene-1, 2-dicarbonitrile | 4-Nitro-phthalonitrile | 1, 2-Benzenedicarbonitrile | 1, 2-Dicyano-4-nitrobenzene | 4-nitrobenzene-1, 2-dicarbonitrile | 4-Nitro-1, 2-benzenedicarbonitrile | 3, 4-Dicyanonitrobenzene

Specifications & Purity

≥98%(GC)

Storage

Room temperature

Shipped In

Normal

Purity

≥98%(GC)

Names and Identifiers

• Pubchem Sid: 488187053
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187053
• Canonical Smiles: C1=CC(=C(C=C1[N+](=O)[O-])C#N)C#N
• IUPAC Name: 4-nitrobenzene-1,2-dicarbonitrile
• InChIKey: NTZMSBAAHBICLE-UHFFFAOYSA-N
• INCHI: 1S/C8H3N3O2/c9-4-6-1-2-8(11(12)13)3-7(6)5-10/h1-3H
• Isomeric SMILES: C1=CC(=C(C=C1[N+](=O)[O-])C#N)C#N
• WGK Germany: 3
• RTECS: TI8576000
• Molecular Weight: 173.13
• Beilstein: 1877554
• Reaxy-Rn: 1877554
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1877554&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrobenzenes
• Alternative Parents: Nitroaromatic compounds Benzonitriles Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Nitriles Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Nitrobenzene - Benzonitrile - Nitroaromatic compound - C-nitro compound - Organic nitro compound - Carbonitrile - Nitrile - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organonitrogen compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: 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: 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

Chemical and Physical Properties

• Solubility: Insoluble in water.
• Melt Point(°C): 142-145°C
• Molecular Weight: 173.130 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 173.023 Da
• Monoisotopic Mass: 173.023 Da
• Topological Polar Surface Area: 93.400 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 302.000
• 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

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63. Kaikai Xu, Lulu Kong, Kebin Ye, Beibei Xu, Yongming Deng, Yicheng Wang, Shaohua Wei.  (2025)  NiPc-Cu 2D MOF: Facile and scalable synthesis of an antimicrobial agent rivaling clinical antibiotics.  INORGANIC CHEMISTRY COMMUNICATIONS,      [PMID:] [10.1016/j.inoche.2025.114343]

64. Haonan Xu, Yuping Han, Danying Zhao, Zheng Liu, Guibin Wang, Yunhe Zhang.  (2025)  Novel axial fullerenol-substituted hyperbranched phthalocyanines:Synthesis, photophysical and nonlinear optical properties.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2025.112642]

65. Zhiyi Guo, Qiufei Chen, Zhicheng Wang, Athar Ali Khan Gorar, Jun Wang, Wenbin Liu.  (2024)  Novel bio-based propylene-derived phthalonitrile compounds: Synthesis, curing behavior and thermal properties.  REACTIVE & FUNCTIONAL POLYMERS,      [PMID:] [10.1016/j.reactfunctpolym.2024.106058]

66. Min He, Yidong Bin, Lixian Huang, Caiying Li, Yuzhen Ma, Yan-Ni Luo, Shulin Zhao, Jinzhe Liang.  (2025)  Novel zinc(II) phthalocyanine nanoparticles as diagnosis-treatment nanoprobe for photoacoustic imaging-guided synergistic photothermal/photodynamic-enhanced cancer therapy.  Inorganic Chemistry Frontiers,      [PMID:] [10.1039/D4QI02898H]

67. Muyao Gao, Qian Wu, Tianhao Li, Li Liu, Bing Li, Yujie Song, Ming Liu.  (2024)  Rediscovering phthalonitrile resins: a novel liquid monomer towards high-performance resins.  Polymer Chemistry,  15  (21): (2157-2166).  [PMID:] [10.1039/D4PY00100A]

68. Shuna Jia, Zhijiang Dong, Zhiqiang Wang, Boxiong Shen, Honghong Lyu.  (2024)  Tailoring the local catalytic microenvironment of metal centers NH2 groups to enhance the CO2RR performance of Ni based catalysts.  Journal of Environmental Chemical Engineering,      [PMID:] [10.1016/j.jece.2024.114130]

69. Jianjun Zhao, Jun Chen, Miaomiao Zhou, Qian Zhang, Xiaocheng Li, Junqing Pan.  (2024)  Ultra-firm phthalocyanine-based tetragonal covalent organic framework layer @ nano silicon anode for high durability Li-ion battery.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.151110]

70. Yabin Zhang, Wenguang Zhang, Houxiang Yin, Yanlin Wang, Bingbing Wang, Lishuai Zong, Jinyan Wang, Xigao Jian.  (2024)  Wave-transparent and eco-friendly flame-retardant phosphorus-based phthalonitrile/quartz composites by a synchronized self-curing strategy with cyano and alkynyl groups.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.156885]

71. Kebin Ye, Xinlu Bao, Zhikang Song, Mingzhu Zhang, Shaohua Wei, Jishuang Zhang, Lin Zhou.  (2025)  A mono-substituted aluminum phthalocyanine photosensitizer with high phototoxicity index for effective bladder cancer treatment.  BIOORGANIC CHEMISTRY,      [PMID:40644816] [10.1016/j.bioorg.2025.108730]

72. Zhu Guanglai, Xu Chao, Xu Ziyi, Yu Yitao, Sun Cuicui, Zhuang Haihua, Ma Baichang, Hou Yantao, Li Bing, Wang Zhenhua, Dai Caifeng.  (2025)  A novel naphthyl amine curing agent and its effect on curing performance of AF-type phthalonitrile resin.  IRANIAN POLYMER JOURNAL,      [PMID:] [10.1007/s13726-025-01524-9]

73. Yuhang Liu, Cong Peng, Ruoxi Fan, Zhanjun Wu.  (2025)  Trifluoromethyl-containing phthalonitrile modified epoxy thermoset with improved flame retardancy and thermal stability.  POLYMER DEGRADATION AND STABILITY,      [PMID:] [10.1016/j.polymdegradstab.2025.111591]

74. Xinru Dong, Yang Li, Xuejun Zhang, Nan Liu, Peng Gao.  (2025)  Construction of Broad-Spectrum-Responsive D–A Type COF Photocatalysts with Mechanistic Insights into Visible-Light-Driven Tetracycline Degradation.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2025.143986]

75. Xinlu Bao, Kebin Ye, Zhikang Song, Mingzhu Zhang, Shaohua Wei, Lin Zhou.  (2025)  From cell membrane to lysosome: Arginine modification boosts the phototoxic index of zinc phthalocyanine for efficient bladder cancer treatment.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2025.113219]

76. Jiaojiao Xu, Qiuxuan Ren, Yuqi Liu, Yan Yang, Gai Zhang.  (2025)  Bio-inspired photocatalytic desulfurization performance of TiO2 wrapped spherical metallophthalocyanine.  INORGANICA CHIMICA ACTA,      [PMID:] [10.1016/j.ica.2025.122929]

77. Hailong Wang, Lele Zhao, Xueqiang Liu, Jing Xu, Wenlong Hou, Jianmin Wang, Enfang He, Ruijun Zhang, Haiquan Zhang.  (2016)  Novel hydrogen bonding composite based on copper phthalocyanine/perylene diimide derivatives p-n heterojunction with improved photocatalytic activity.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2016.11.014]

78. Rongxiang Hu, Fenghua Zhang, Lan Luo, Linlin Wang, Yanju Liu, Jinsong Leng.  (2024)  An end-capping strategy for shape memory phthalonitrile resins via annealing enables conductivity and wave-absorption.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.150956]

79. Zichun Ding, Jianjian Jiao, Yuhang Wang, Runze Liu, Qing Wang, Jianing Guo, Siying Wang, Lishuai Zong, Xigao Jian, Jinyan Wang.  (2025)  Synergistic improvement of toughness and thermal properties of phthalonitrile resin based on the multiple curing mechanism of amino-carborane.  COMPOSITES PART A-APPLIED SCIENCE AND MANUFACTURING,      [PMID:] [10.1016/j.compositesa.2025.108903]

80. Rongxiang Hu, Fenghua Zhang, Lan Luo, Linlin Wang, Yanju Liu, Jinsong Leng.  (2025)  Reconfigurable high-temperature thermal protection shape memory aerogel based on phthalonitrile resin with facile template method.  CARBON,      [PMID:] [10.1016/j.carbon.2025.120378]

81. Yanbing Yin, Chunxin Li, Zhou Wang, Yongming Feng, Bei Jiang, Yifei Li, Wei Yang.  (2025)  A type of binary composite catalyst CuTNPc/ZnO for synergistic photocatalytic degradation of dyes.  JOURNAL OF COORDINATION CHEMISTRY,      [PMID:] [10.1080/00958972.2025.2497838]

82. Kaikai Xu, Lulu Kong, Zhikang Song, Xingchen Mu, Dongxin Wang, Zhou Lin, Wei Wang, Shaohua Wei.  (2025)  L-Glucose-Modified Mirror-Image Zinc Phthalocyanine Photosensitizers for Enhanced Tumor-Targeted Photodynamic Therapy.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2025.143095]

83. Yunlong Wang, Suqian Meng, Nian Li, Tianyu Pan, Xu Ma, Xingrui Qi, Tao Jin.  (2025)  Photodynamic inactivation of bacteria by aluminum tetraaminophthalocyanine and nitrogen doped graphene quantum dots nanoconjugates.  JOURNAL OF ALLOYS AND COMPOUNDS,      [PMID:] [10.1016/j.jallcom.2025.185499]

84. Xuhui Li, Menghan Zhang, Mengyang Yin, Xingming Ning, Zhongwei An, Xinbing Chen, Pei Chen.  (2025)  Weak d–d coupling in iron‑cobalt tetranitro-phthalocyanine boosting oxygen electrocatalysis for high-performance flexible zinc-air batteries.  Journal of Energy Storage,      [PMID:] [10.1016/j.est.2025.119485]

85. Ren Qiuxuan, Xu Jiaojiao, Liu Yuqi, Ma Aijie, Zhang Gai.  (2026)  Enhanced activity for oxygen reduction reaction of π-π self-assembled Co2Pc2(EP)4/RGO catalysts.  RESEARCH ON CHEMICAL INTERMEDIATES,      [PMID:] [10.1007/s11164-025-05872-2]

86. Xiaolu Sun, Shilin Wang, Siyuan Dong, Xi Chen, Xinbo Dong, Yang Wang, Xigao Jian, Cheng Liu.  (2026)  Synthesis and Degradation Mechanisms of Schiff-base-containing Phthalonitrile Resins: Thermal Stability and Bond Reconfiguration.  POLYMER DEGRADATION AND STABILITY,      [PMID:] [10.1016/j.polymdegradstab.2026.111945]

87. Jiawei Liu, Yingqing Zhan, Penglun Zheng, Pan Wang, Ying Li, Kui Li, Wei Feng, Xulin Yang.  (2026)  Molecularly designed bio-based phthalonitrile for simultaneous mechanical and thermal reinforcement of bismaleimide resin.  Materials Today Chemistry,      [PMID:] [10.1016/j.mtchem.2026.103380]

88. Hao Zeng, Xiangbing Zou, Shuo Yang, Sizhe Tang, Shanshan Luo, Meiyue Cheng, Haiping Xu, Yujie Song, Ming Liu, Yang Liu, Ming Yang, Bing Li.  (2026)  Functional group engineering for boosting catalytic activity: high turnover frequency in electrocatalytic CO2 reduction and Zn-CO2 batteries.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:41621356] [10.1016/j.jcis.2026.139983]

89. Xin Qu, Liwei Yang, Yidi Liu, Fangzheng Jia, Jingcheng Liu, Xiaojie Li, Wei Wei.  (2026)  Phthalonitrile-Schiff base epoxy resin: unique gas-condensed phase synergy endows excellent flame retardancy.  POLYMER,      [PMID:] [10.1016/j.polymer.2026.129849]