≥97% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Room temperature Ships Normal Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 14 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Can be used as the acylating reagent of electron-rich aromatic rings activated acylation. For synthetic organic photoconductor, LCD materials, laser writing and recording material of the electrophotographic photoreceptors intermediate material.
| Canonical Smiles | C1(=C(C(=O)C1=O)O)O |
|---|---|
| IUPAC Name | 3,4-dihydroxycyclobut-3-ene-1,2-dione |
| InChIKey | PWEBUXCTKOWPCW-UHFFFAOYSA-N |
| INCHI | 1S/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H |
| Isomeric SMILES | C1(=C(C(=O)C1=O)O)O |
| WGK Germany | 3 |
| RTECS | GU1800000 |
| PubChem CID | 17913 |
| Molecular Weight | 114.06 |
| Beilstein | 774275 |
| Reaxy-Rn | 774275 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Vinylogous acids |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Vinylogous acids |
| Alternative Parents | Cyclic ketones Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Vinylogous acid - Cyclic ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. |
| External Descriptors | alicyclic ketone - carbon oxoacid |
| Solubility | Soluble in water. |
|---|---|
| Flash Point(°F) | 190 °C |
| Flash Point(°C) | 190°C |
| Melt Point(°C) | 300°C |
| Molecular Weight | 114.060 g/mol |
| XLogP3 | -0.700 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 0 |
| Exact Mass | 113.995 Da |
| Monoisotopic Mass | 113.995 Da |
| Topological Polar Surface Area | 74.600 Ų |
| Heavy Atom Count | 8 |
| Formal Charge | 0 |
| Complexity | 178.000 |
| 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 |
| 1. Jiaqi Liu, Fuyi Sun, Yuanyuan Che, Kaihuan Nie, Zhihao Zhang, Zhen Yang, Liangliang Lin. (2021) Ultrathin rigid UTSA-280/PEI-HPAN hybrid membranes with enhanced organic dye nanofiltration performance. Journal of Environmental Chemical Engineering, [PMID:] [10.1016/j.jece.2021.106842] |
| 2. Rui Xue, Hao Gou, Li Zhang, Yinsheng Liu, Honghong Rao, Guohu Zhao. (2020) A new squaraine-triazine based covalent organic polymer as an electrode material with long life and high performance for supercapacitors. NEW JOURNAL OF CHEMISTRY, 45 (2): (679-684). [PMID:] [10.1039/D0NJ03551C] |
| 3. Yue Gao, Xiaolu Yan, Meng Li, Han Gao, Jing Sun, Shuyun Zhu, Shuang Han, Li-Na Jia, Xian-En Zhao, Hua Wang. (2018) A “turn-on” fluorescence sensor for ascorbic acid based on graphene quantum dots via fluorescence resonance energy transfer. Analytical Methods, 10 (6): (611-616). [PMID:] [10.1039/C7AY02828H] |
| 4. Hongyu Chen, Aijin Fang, Li He, Youyu Zhang, Shouzhuo Yao. (2016) Sensitive fluorescent detection of H2O2 and glucose in human serum based on inner filter effect of squaric acid-iron(III) on the fluorescence of upconversion nanoparticle. TALANTA, [PMID:28107976] [10.1016/j.talanta.2016.10.008] |
| 5. Wenqiang Lai, Dianping Tang, Junyang Zhuang, Guonan Chen, Huanghao Yang. (2014) Magnetic Bead-Based Enzyme-Chromogenic Substrate System for Ultrasensitive Colorimetric Immunoassay Accompanying Cascade Reaction for Enzymatic Formation of Squaric Acid-Iron(III) Chelate. ANALYTICAL CHEMISTRY, [PMID:24785462] [10.1021/ac500738a] |
| 6. Xinghang Duan, Qiaolin Li, Tiantian Cao, Shengxiang Xiong, Gang Chen, Chengjun Dong, Hongtao Guan, Zongyou Yin. (2025) Hollow but perforated C/Co/Mo2C cubes enhance electromagnetic absorption. Journal of Materials Chemistry A, [PMID:] [10.1039/D4TA07459A] |
| 7. Gong Cheng, Chao Sui, Weizhe Hao, Zifu Zang, Yushun Zhao, Yichen Zhou, Chenxi Zhao, Lei Wen, Junjiao Li, Yuna Sang, Xiaodong He, Chao Wang. (2025) Multi-Responsive COF-Enhanced Smart Actuator. ADVANCED FUNCTIONAL MATERIALS, [PMID:] [10.1002/adfm.202420729] |
| 8. Chongxi Zhang, Fengting Li, Dong Wu, Qingmeng Guo, Zhanning Liu, Zhikun Wang, Zixi Kang, Lili Fan, Daofeng Sun. (2025) Oxygen-coordinated MOF membrane facilitated construction of supported Co2P/CoP@C heterostructures for water electrolysis. Inorganic Chemistry Frontiers, [PMID:] [10.1039/D4QI03103B] |
| 9. Li Chen, Cuiyun Zhou, Feng Jiang, Li Zhang, Chuanlai Xu. (2024) Squaraine-Linked Magnetic Covalent Organic Framework as a Solid-Phase Extraction Absorbent to Determine Trace Phenylpyrazoles. Small Methods, [PMID:39225439] [10.1002/smtd.202400777] |
| 10. Zheng Haiying, Liu Guozhen, Dong Xinhe, Chen Feifan, Wang Chao, Yu Hongbo, Zhang Zhihua, Pan Xu. (2025) Self-Regulated Bilateral Anchoring Enables Efficient Charge Transport Pathways for High-Performance Rigid and Flexible Perovskite Solar Cells. Nano-Micro Letters, 17 (1): (1-15). [PMID:40658297] [10.1007/s40820-025-01846-6] |
| 11. Jiabao Lai, Jiao You, Jianhui Zhu, Ming Yang, Yanyi Wang, Shengkui Zhong, Hongwei Mi, Chuanxin He, Dingtao Ma, Peixin Zhang. (2025) A prelithiation pathway with high-release efficiency and self-enhanced interface chemistry to achieve stable Li-ion full cells. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2025.168233] |
| 12. Xiaojie Zhang, Jinchen Zhao, Yan Zhao, Zhumabay Bakenov, Yongguang Zhang. (2021) Engineering zwitterionic barrier by squaraine-based porous organic framework fiber for superior lithium-sulfur batteries. ELECTROCHIMICA ACTA, [PMID:] [10.1016/j.electacta.2021.139276] |
| 13. Shuai Wu, Yincheng Liu, Tianyu Zeng, Tianci Zhou, Yanting Sun, Ying Deng, Juan Zhang, Genxi Li, Yongmei Yin. (2025) Enhanced the Trans-Cleavage Activity of CRISPR-Cas12a Using Metal-Organic Frameworks as Stimulants for Efficient Electrochemical Sensing of Circulating Tumor DNA. Advanced Science, [PMID:40184611] [10.1002/advs.202417206] |
| 14. Chao Ge, Yunlan Gu, Bin He, Yanqing Wang, Yawen Tang, Tongfei Li. (2026) Single-Atom Mn–N4 Sites Engineered in Carbon Nanofiber Networks for AEMFC Oxygen Reduction. LANGMUIR, [PMID:41664502] [10.1021/acs.langmuir.5c06590] |
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