2,5-Thiophenedicarboxylic acid - ≥98% , CAS No.4282-31-9

CAS: 4282-31-9 Cat. No.: T107116 Molecular Weight: 172.16 Beilstein Registry Number: 18(5)7,49 EC Number: 224-284-2 PubChem CID: 20273

GRADE & PURITY ≥98%

Synonyms

AB01326194-02 | Maybridge4_002021 | YSWG415 | Z56855146 | Q27262737 | DTXSID7063392 | SY005216 | AKOS000592865 | 5Q8A2G9Y8A | SCHEMBL70493 | THIOPHENE-2,5-DICARBOXYLIC ACID | PS-3266 | 2,5-Thiophenedicarboxylic acid, 99% | 2,5-Thiophene dicarboxylic acid

Storage

Room temperature

Shipped In

Normal

Overview

2,5-Thiophenedicarboxylic acid (2,5-TDCA, H2TDC) is an important building block in the preparation of fluorescent brightening agent, fungicides and anti-cancer drug. It has been generated by chlorination of adipic acid using thionyl chloride.Due to its diverse coordination modes, it is an excellent choice as an aromatic linker to generate coordination networks. The enthalpies of combustion and sublimation of 2,5-thiophenedicarboxylic acid have been evaluated by rotary-bomb combustion calorimetry.

Specifications

Synonyms

AB01326194-02 | Maybridge4_002021 | YSWG415 | Z56855146 | Q27262737 | DTXSID7063392 | SY005216 | AKOS000592865 | 5Q8A2G9Y8A | SCHEMBL70493 | THIOPHENE-2, 5-DICARBOXYLIC ACID | PS-3266 | 2, 5-Thiophenedicarboxylic acid, 99% | 2, 5-Thiophene dicarboxylic acid

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488182603
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488182603
• Canonical Smiles: C1=C(SC(=C1)C(=O)O)C(=O)O
• IUPAC Name: thiophene-2,5-dicarboxylic acid
• InChIKey: YCGAZNXXGKTASZ-UHFFFAOYSA-N
• INCHI: 1S/C6H4O4S/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)
• Isomeric SMILES: C1=C(SC(=C1)C(=O)O)C(=O)O
• WGK Germany: 3
• PubChem CID: 20273
• Molecular Weight: 172.16
• Beilstein: 18(5)7,49
• Reaxy-Rn: 136781

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Thiophenes
      • Subclass Thiophene carboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Thiophenes
• Subclass: Thiophene carboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Thiophene carboxylic acids
• Alternative Parents: 2,5-disubstituted thiophenes Dicarboxylic acids and derivatives Heteroaromatic compounds Carboxylic acids Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Thiophene carboxylic acid - 2,5-disubstituted thiophene - Dicarboxylic acid or derivatives - Heteroaromatic compound - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as thiophene carboxylic acids. These are compounds containing a thiophene ring which bears a carboxylic acid 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: Very soluble in water. Solubility in Methanolalmost transparency
• Melt Point(°C): 300°C
• Molecular Weight: 172.160 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 171.983 Da
• Monoisotopic Mass: 171.983 Da
• Topological Polar Surface Area: 103.000 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 171.000
• 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

References

1. Jin Lin, Hong Wang, Chao Wang, Li Guo, Yanzhong Wang.  (2023)  Ru-modulated morphology and electronic structure of nickel organic framework bifunctional electrocatalyst for efficient overall water splitting.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2023.143300]

2. Hong-Yan Wu, Qiao-Wei Gao, Hao-Hong Li, Wen-Zhong Lai, Ting Hu, Jian-Han Zhang.  (2023)  Constructing stable uranyl-copper(II) bimetallic organic frameworks using rigid thiophenedicarboxylic acid.  POLYHEDRON,      [PMID:] [10.1016/j.poly.2023.116570]

3. Xiaoqin Wei, Hao Guo, Zongyan Lu, Lei Sun, Zhilan Pan, Bingqing Liu, Liping Peng, Wu Yang.  (2023)  A novel electrochemical sensor based on DUT-67/ZnCo2O4-MWCNTs modified glassy carbon electrode for the simultaneous sensitive detection of dopamine and uric acid.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2023.131921]

4. Sunan Tian, Kaihuan Shi, Jun Xu, Baohua Guo.  (2023)  Synthesis and Structure–Property Relationships of Novel High Molecular Weight Fully Biobased 2,5-Thiophenedicarboxylic Acid-Based Polyesters.  BIOMACROMOLECULES,      [PMID:37272822] [10.1021/acs.biomac.3c00001]

5. Qianqian Wang, Xiaoyan Ma, Pengcheng Ma, Ran Bi, Senyang Song.  (2023)  Defect-Rich, Rose-Shaped Fe2Ni1-Metal–Organic Framework Nanoarrays for Efficient Oxygen Evolution Reaction.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.3c00962]

6. Lesly Dasilva Wandji Djouonkep, Christian Tatchum Tamo, Belle Elda Simo, Nasiru Issah, Marc Nivic Tchouagtie, Naomie Beolle Songwe Selabi, Ingo Doench, Arnaud Kamdem Tamo, Binqiang Xie, Anayancy Osorio-Madrazo.  (2023)  Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties.  MOLECULES,  28  (4): (1825).  [PMID:36838821] [10.3390/molecules28041825]

7. Siegu William Mawuko Kodzo, Djouonkep Lesly Dasilva Wandji, Selabi Naomie Beolle Songwe, Bonku Emmanuel Mintah, Cheng Zhengzai, Gauthier Mario.  (2022)  Synergistic Effect and Structure–Property of Bio-based 1,6-Hexanediol on Thermal, Mechanical and Degradation Properties of Biopolymers.  JOURNAL OF POLYMERS AND THE ENVIRONMENT,  31  (3): (1144-1159).  [PMID:] [10.1007/s10924-022-02666-0]

8. Jing Shi, Xiaozhan Yang, Hui Pan, Wenlin Feng.  (2022)  Photoluminescent terbium-metal-organic framework and its trace bismuth-ion sensing performance.  JOURNAL OF SOLID STATE CHEMISTRY,      [PMID:] [10.1016/j.jssc.2022.123652]

9. Yan Guan, Peng-Bin Si, Tong Yang, Yuan Wu, Yun-Hui Yang, Rong Hu.  (2022)  A novel method for detection of ochratoxin A in foods—Co-MOFs based dual signal ratiometric electrochemical aptamer sensor coupled with DNA walker.  FOOD CHEMISTRY,      [PMID:36162265] [10.1016/j.foodchem.2022.134316]

10. Qiuju Fu, Dandan Liu, Weijing Niu, Shuo Zhang, Ruihua Chen, Yujia Wang, Pengze Zhao, Huimin Jiang, Yanchao Zhao, Lingzhi Yang, Liting Yan, Haiyan Wang, Xuebo Zhao.  (2022)  Defect-engineered MOF-808 with highly exposed Zr sites as highly efficient catalysts for catalytic transfer hydrogenation of furfural.  FUEL,      [PMID:] [10.1016/j.fuel.2022.125085]

11. Bin-Cheng Wang, Zhi-Ying Feng, Biao-Biao Hao, Chen-Xi Zhang, Qing-Lun Wang.  (2021)  Promotion of Proton Conductivity by Encapsulation of Metal-Organic Polyhedra in Metal-Organic Frameworks.  CHEMISTRY-A EUROPEAN JOURNAL,  27  (47): (12137-12143).  [PMID:34164856] [10.1002/chem.202101213]

12. Chongliang Li, Feng Zhang, Xing Li, Gaowei Zhang, Yangyi Yang.  (2018)  A luminescent Ln-MOF thin film for highly selective detection of nitroimidazoles in aqueous solutions based on inner filter effect.  JOURNAL OF LUMINESCENCE,      [PMID:] [10.1016/j.jlumin.2018.08.069]

13. Xiao Yang, Lian Duan, Xiaoqi Ran.  (2018)  Photocatalytic degradation of organic dyes by a donor–acceptor type conjugated polymer: poly(thiophene-1,3,4-oxadiazole) and its photocatalytic mechanism.  POLYMER INTERNATIONAL,  67  (9): (1282-1290).  [PMID:] [10.1002/pi.5652]

14. Shengwen Liu, Xian Zhang, Guozhong Wang, Yunxia Zhang, Haimin Zhang.  (2017)  High-Efficiency Co/CoxSy@S,N-Codoped Porous Carbon Electrocatalysts Fabricated from Controllably Grown Sulfur- and Nitrogen-Including Cobalt-Based MOFs for Rechargeable Zinc–Air Batteries.  ACS Applied Materials & Interfaces,      [PMID:28895723] [10.1021/acsami.7b11101]

15. Yang Yang, Qi Zhang, Cuicui Cao, Limin Cheng, Ying Shi, Wenge Yang, Yonghong Hu.  (2014)  Solubility and solution thermodynamics of 2,5-thiophenedicarboxylic acid in (water + ethanol) binary solvent mixtures.  THERMOCHIMICA ACTA,      [PMID:] [10.1016/j.tca.2014.08.002]

16. Pengyi Guo, Yu-e Shi, Song Shen, Chengyan Zhou, Jingjing Jiang, Zhenguang Wang.  (2024)  Achieving Efficient Room-Temperature Phosphorescence in the Host–Guest System through Covalent-Bond-Strengthened Hydrogen Bonding.  Journal of Physical Chemistry C,      [PMID:] [10.1021/acs.jpcc.4c00285]

17. Yulong Xiang, Xinbin Ji, Xiaoli Dong, Yu Wang, Nan Zheng, Chundong Liu, Menglin Wang, Chumin Yan.  (2025)  Construction of direct Z-scheme DUT-67/Fe2O3 heterostructures for efficient photoreduction of Cr(VI).  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.161196]

18. Yuzhen Zhang, Huajun Zhou, Peihua Zhao, Kai Yuan, Rui Zhou, Yongping Qu, Yanzhong Wang.  (2024)  Facile synthesis of amorphous/crystalline Ni-Fe thiophenedicarboxylate coordination polymer nanobelts for efficient water oxidation.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:38531279] [10.1016/j.jcis.2024.03.148]

19. Hong-Yi Tan, Bing-Hao Wang, Meng-Yi Xu, Zhi-Yong Peng, Wen-Juan Wu, Sheng Shen, Shuangfeng Yin.  (2024)  Heteroatom-Based Ligand Engineering of Metal Organic Frameworks for Efficient and Robust Electrochemical Water Oxidation.  ChemSusChem,      [PMID:39670688] [10.1002/cssc.202402112]

20. Hong Wang, Shuai Wu, Peihua Zhao, Chao Wang, Li Guo, Yanzhong Wang.  (2024)  Modulation of morphology and electronic structure of cobalt thiophenedicarboxylic coordination polymer via ligand exchange for high-performance oxygen evolution reaction and supercapacitor.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:38996701] [10.1016/j.jcis.2024.07.071]

21. Chenglong Ji, Yuncai Gao, Yulu Wang, Ran Li, Yu-e Shi, Zhenguang Wang, Yongqing Zhai.  (2024)  Regulating Room-Temperature Phosphorescence of Organic Luminophores Through Stepwise Stabilization by Coordination and In-Situ Precipitation Reaction.  CHEMISTRY-A EUROPEAN JOURNAL,      [PMID:39567256] [10.1002/chem.202403829]

22. Huijuan Han, Yalei Zhang, Chunrui Zhou, Haixin Yun, Yiwen Kang, Kexin Du, Jianying Wang, Shujun Chao, Jichao Wang.  (2025)  S- and N-Co-Doped Carbon-Nanoplate-Encased Ni Nanoparticles Derived from Dual-Ligand-Assembled Ni-MOFs as Efficient Electrocatalysts for the Oxygen Evolution Reaction.  MOLECULES,  30  (4): (820).  [PMID:40005132] [10.3390/molecules30040820]

23. Liu Jie, Ye Qiu, Wu Yi, Chen Junliang, Ge Yongjie, Zhang Linjie, Abazari Reza, Qian Jinjie.  (2025)  Short-range electronic engineering by coupling Fe phthalocyanines with MOF-derived N,S-doped carbon nanorods for oxygen reduction.  Science China-Chemistry,      [PMID:] [10.1007/s11426-024-2349-x]

24. Xiaojun Ma, Hongji Wang, Ziqing Wang, Yin Lv, Zhong Wei.  (2024)  Synthesis and properties of biodegradable thiophene-based aliphatic polycarbonate/polyester copolymer: Potential substitutes for terephthalic acid-based polymer.  EUROPEAN POLYMER JOURNAL,      [PMID:] [10.1016/j.eurpolymj.2024.112972]

25. Qian Liu, Liying Wang, Guohua Chen, Gaoqi Wu, Jingjing Wang, Zhiwei Liu, Zhenzhu Cao, Yongfeng Zhang.  (2024)  The heterogeneous structure facilitates the rapid transport of lithium ions in novel single-crystal CoMn-MOF derivatives.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2024.10.142]

26. Chaoji Xiong, Kejie Li, Chunzhi Peng, Xingmao Zhang, Kun Liang, Wei Wu, Qian Chen.  (2024)  Thiophene network polyamides (TPPA) with tri(4-aminophenyl)benzene: Synthesis and removal of Hg2+ from aqueous solution.  EUROPEAN POLYMER JOURNAL,      [PMID:] [10.1016/j.eurpolymj.2024.113152]

27. Xin Miao, Yunxin Shi, Liying Wang, Zhenzhu Cao, Yongfeng Zhang, Shaohua Luo.  (2025)  Enhancing electrochemical performance of lithium-ion battery anodes using hollow nanospheres with rich oxygen vacancies.  JOURNAL OF POWER SOURCES,      [PMID:] [10.1016/j.jpowsour.2025.238092]

28. Xinqi Luan, Xuehui Jia, Syed Jalil Shah, Jingyu Bao, Xin Yu, Ruimeng Wang, Zhongfeng Shi, Qi Pan, Liqin Zhou, Zhongxing Zhao, Zhenxia Zhao.  (2025)  3D high-positive-potential spatial strategy enhanced the performance of U66N-FT/COF composites for synergistic adsorption of toluene and formaldehyde: An experimental and theoretical study.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.168884]

29. Yang Kang, Li Ming, Gao Tianqi, Xu Guoliang, Li Di, Zheng Yao, Li Qiang, Duan Jingjing.  (2024)  An acid-tolerant metal-organic framework for industrial CO2 electrolysis using a proton exchange membrane.  Nature Communications,  15  (1): (1-12).  [PMID:39152107] [10.1038/s41467-024-51475-7]

30. Yanan Liu, Shuaishuai Lu, Siqi Wang, Zhelin Tang, Janina Bahnemann, Yun Liu, Huan Chen, Fang Jiang.  (2025)  Conductive polymer/sulfur-doped graphitic carbon nitride with π-π conjugated structure for photocatalytic degradation of tetracycline in high and low salinity aquatic systems: Unveiling switching between free radical and non-radical pathways.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:40220639] [10.1016/j.jcis.2025.137548]

31. Hongxu Tao, Chenkai Gu, Rujing Hou, Shengui Ju, Yichang Pan.  (2025)  Designing pore size and pore electronegativity environment in aluminum-based MOF membranes for efficient cyclohexanone/cyclohexanol separation.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2025.124157]

32. Xiaoxiao Xia, Kunfeng Li, Guobing Chen, Song Li.  (2025)  Relationship between Water Adsorption Kinetics and Structure Property of Metal-Organic Frameworks for Adsorption Cooling.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2025.137168]

33. Weibiao Guo, Zhikuan Wang, Yu Liang, Shujun Liu, Xuejun Xu, Huixia Chao, ChongXiong Duan, Hongxia Xi.  (2025)  Carbon nanotube-regulated growth of metal–organic framework nanosheets for enhanced electrochemical energy storage.  Journal of Materials Chemistry C,      [PMID:] [10.1039/D5TC00963D]

34. Zhao-Hao Li, Ke Zheng, Yuan-Meng Yue, Ya-Meng Li, Bang-Tun Zhao.  (2025)  Synthesis, crystal structure, photochromism and photo-regulated luminescence of a viologen-functionalized material.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2025.142818]

35. Zhichao Li, Yuhong Du, Gaoshuang Zuo, Jin Wang, Chao Wang, Li Guo, Yanzhong Wang.  (2025)  Modulation of morphology and electronic structure of nickel thiophenedicarboxylic framework microrod arrays with Ni3S2 for efficient water oxidation.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:40543314] [10.1016/j.jcis.2025.138209]

36. Qianqian Wang, Xiaoyan Ma, Ran Bi, Xiangpan Hu, Senyang Song, Pengcheng Ma, Fang Chen.  (2025)  In situ formation of heterojunction of thiophene-based metal–organic frameworks with carbon dots for efficient overall water splitting and supercapacitor applications.  Journal of Materials Chemistry A,  13  (20): (14873-14883).  [PMID:] [10.1039/D4TA08523J]

37. Junling Chen, Heng Zhang, Qiang Liu, Qiaonan Yu, Qianxiang Zhao, Hanqing Lin, Rong Liang, Keliang Wu, Tiexin Zhang.  (2025)  Ru-engineered bimetallic Co-MOF as bifunctional catalyst for ultra-efficient hydrogen and oxygen evolution reactions.  CHEMICAL ENGINEERING SCIENCE,      [PMID:] [10.1016/j.ces.2025.123087]

38. Jie Liu, Qiu Ye, Hui Liu, Junliang Chen, Yi Wu, Haoran Wang, Yunan Ye, Lei Zhang, Qipeng Li, Jinjie Qian.  (2025)  Facile Synthesis of Thiophene-Based MOF-Derived Bimetallic ZnM Sulfides (M═Fe, Co, Ni) for Electrocatalytic Oxygen Reduction and Zinc Air Batteries.  Small,      [PMID:41451563] [10.1002/smll.202511568]

39. Xiang Yulong, Ji Xinbin, Dong Xiaoli, Wang Yu, Zheng Nan, Luo Yang, Zhao Honglin, Yan Chumin.  (2026)  Ag nanoparticles anchored on oxygen vacancy-rich DUT-67 for highly efficient photocatalytic reduction of Cr(VI).  RESEARCH ON CHEMICAL INTERMEDIATES,      [PMID:] [10.1007/s11164-026-05988-z]