Determine the necessary mass, volume, or concentration for preparing a solution.
≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C,Argon charged Ships Ice chest + Ice pads 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 209 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Product Application
N,N′-Disuccinimidyl carbonate may be used:
As an activating reagent for the reactive patterning of polymer brushes to couple primary amines via post-functionalization.
As an alkoxycarbonylating reagent for a variety of primary and sterically hindered secondary alcohols, which further allows the synthesis of different structurally diverse carbamates.
As a coupling agent for the synthesis of thiophospholipids, commonly used for anchoring biomembranes to gold surfaces.
It can also be used to prepare a heterobifunctional, cleavable linker-SVEC-(succinimide vinylsufonylethyl carbonate)-for thiol modified-DNA.
| Sonrisas canónicas | C1CC(=O)N(C1=O)OC(=O)ON2C(=O)CCC2=O |
|---|---|
| IUPAC Name | bis(2,5-dioxopyrrolidin-1-yl) carbonate |
| InChIKey | PFYXSUNOLOJMDX-UHFFFAOYSA-N |
| INCHI | 1S/C9H8N2O7/c12-5-1-2-6(13)10(5)17-9(16)18-11-7(14)3-4-8(11)15/h1-4H2 |
| Isómeros SMILES | C1CC(=O)N(C1=O)OC(=O)ON2C(=O)CCC2=O |
| WGK Alemania | 3 |
| Peso molecular | 256.17 |
| Beilstein | 1499137 |
| Reaxy-Rn | 1499137 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1499137&ln= |
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 | Organoheterocyclic compounds |
| Clase | Pyrrolidines |
| Subclass | Pyrrolidones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyrrolidine-2-ones |
| Alternative Parents | Dicarboximides Organic carbonic acids and derivatives Lactams Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | 2-pyrrolidone - Dicarboximide - Carbonic acid derivative - Lactam - Azacycle - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic heteromonocyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring. |
| External Descriptors | Not available |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Fecha | Articulo |
|---|---|---|---|
| Certificate of Analysis | Jan 07, 2026 | D106171 | |
| Certificate of Analysis | Jan 07, 2026 | D106171 | |
| Certificate of Analysis | Jan 07, 2026 | D106171 | |
| Certificate of Analysis | Jan 07, 2026 | D106171 | |
| Certificate of Analysis | Jan 07, 2026 | D106171 | |
| Certificate of Analysis | Sep 09, 2025 | D106171 | |
| Certificate of Analysis | Apr 09, 2025 | D106171 | |
| Certificate of Analysis | Apr 09, 2025 | D106171 | |
| Certificate of Analysis | Apr 09, 2025 | D106171 | |
| Certificate of Analysis | Apr 09, 2025 | D106171 | |
| Certificate of Analysis | Apr 09, 2025 | D106171 | |
| Certificate of Analysis | Jun 14, 2023 | D106171 | |
| Certificate of Analysis | Jun 14, 2023 | D106171 | |
| Certificate of Analysis | Jun 14, 2023 | D106171 | |
| Certificate of Analysis | Jun 14, 2023 | D106171 | |
| Certificate of Analysis | Oct 27, 2022 | D106171 | |
| Certificate of Analysis | Oct 27, 2022 | D106171 | |
| Certificate of Analysis | Oct 27, 2022 | D106171 | |
| Certificate of Analysis | Oct 27, 2022 | D106171 | |
| Certificate of Analysis | Jul 19, 2022 | D106171 | |
| Certificate of Analysis | Jun 09, 2022 | D106171 | |
| Certificate of Analysis | Jun 09, 2022 | D106171 | |
| Certificate of Analysis | Jun 09, 2022 | D106171 |
| Solubilidad | Soluble in DMSO, hot pyridine, acetonitrile, and most organic solvents. Insoluble in water. |
|---|---|
| Sensibilidad | moisture & Heat sensitive |
| Índice de refracción | 1.6 |
| Punto de ebullición (°C) | 383.7℃ |
| Punto de fusión (°C) | 188-191°C |
| Peso molecular | 256.170 g/mol |
| XLogP3 | -1.300 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 4 |
| Exact Mass | 256.033 Da |
| Monoisotopic Mass | 256.033 Da |
| Topological Polar Surface Area | 110.000 Ų |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Complexity | 386.000 |
| 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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| 3. Jie Li, Jiangtao Long, Zheng Zhao, Qianqian Wang, Wang Bo, Liang Ren, Yan Fan, Peng Wang, Yi Cheng, Binbin Liu, Xinkui Cheng, Hongwei Xi. (2023) Procedural Promotion of Multiple Stages in the Wound Healing Process by Graphene-Spiky Silica Heterostructured Nanoparticles. International Journal of Nanomedicine, [PMID:38026527] [10.2147/IJN.S426552] |
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| 5. Zengguang Jia, Jun Zhang, Yawen Wei, Xiuhua Pan, Zongwei Hu, Ruixin Kang, Xiawei Zhou, Qi Shen. (2023) Cascade Bioreactors Based on Host–Guest Molecular Inclusion Complexes for Triple-Negative Breast Cancer Therapy via Inducing Ferroptosis. ADVANCED FUNCTIONAL MATERIALS, [PMID:] [10.1002/adfm.202309727] |
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| 8. Zhaokui Zeng, Jingjing Tian, Zixuan Ren, Ying Yang, Qian Gong, Ruowei Sun, Xun Zhang, Wenfang Liu, Chuanpin Chen. (2023) Digital droplet immunoassay based on a microfluidic chip with magnetic beads for the detection of prostate-specific antigen. JOURNAL OF SEPARATION SCIENCE, 46 (24): (2300471). [PMID:37905470] [10.1002/jssc.202300471] |
| 9. Jiayi Jiang, Bin Wang, Linghuan Luo, Na Ying, Gaofan Shi, Mengmeng Zhang, Haoyuan Su, Dongdong Zeng. (2023) A two-step electrochemical biosensor based on Tetrazyme for the detection of fibrin. BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY, [PMID:37904286] [10.1002/bab.2531] |
| 10. Fang Zhang, Lei Wang, Lutao Yang, Yong Dai, Jun Zhang, Lei He, Juqing Cui, Jian Shen, Zhe Wang. (2023) Recoverable magnetic Fe-MOF immobilized carrier to immobilize two microorganisms for reduction of heavy oil viscosity and oilfield wastewater COD. Journal of Water Process Engineering, [PMID:] [10.1016/j.jwpe.2023.104459] |
| 11. Zhaoxuan Li, Xue Song, Yan Fan, Yuming Bao, Hu Hou. (2023) Physicochemical properties and cell proliferation and adhesive bioactivity of collagen-hyaluronate composite gradient membrane. Frontiers in Bioengineering and Biotechnology, [PMID:37954023] [10.3389/fbioe.2023.1287359] |
| 12. Shweta Pawar, Hamootal Duadi, Moran Friedman Gohas, Yoram Cohen, Dror Fixler. (2023) Bioimaging based on Poly(ethylenimine)-Coated Carbon Dots and Gold Nanoparticles for pH Sensing and Metal Enhanced Fluorescence. ACS Applied Bio Materials, [PMID:37870948] [10.1021/acsabm.3c00639] |
| 13. Shuofeng Li, Fangfang Wang, Bin Zhao, Chun Wang, Zhi Wang, Qiuhua Wu. (2023) MnO2 nanoflowers based colorimetric and fluorescent dual-mode aptasensor for sensitive detection of aflatoxin B1 in milk. ANALYTICA CHIMICA ACTA, [PMID:37827626] [10.1016/j.aca.2023.341844] |
| 14. Xiujun Cao, Yuan Luo, Xueli Liu, Chunqing Shang, Jun Lu, Guoxin Song, Chunhui Deng. (2023) Aptamer-thrombin loaded magnetic microspheres for bio-specific extraction and precise detection of hirudin. TALANTA, [PMID:37757694] [10.1016/j.talanta.2023.125244] |
| 15. Shuheng Wei, Bo Liu, Xiaonan Huang, Yongkang Xi, Shuxin Wang, Like Wang, Shouwei Yin, Xiaoquan Yang. (2023) Sodium Caseinate–Enzyme Conjugates as Biocatalysts for Recyclable Pickering Interfacial Biocatalysis. ACS Sustainable Chemistry & Engineering, [PMID:] [10.1021/acssuschemeng.3c01825] |
| 16. Yuyan Hai, Xin Wen, Rui Ma, Can He, Xue Yang, Rihua Xiong, Jingyun Chen, Qiaoyi Sun. (2023) pH-responsive polyacrylic acid chemical cross-linking for end-of-life reverse osmosis membrane rejuvenation. DESALINATION, [PMID:] [10.1016/j.desal.2023.116932] |
| 17. Yanan Zhao, Xinyu Zu, Ting Wang, Yan Liang, Yingqiu Li, Chenying Wang, Xiangzhong Zhao, Hua Wang. (2023) Chlorella protein hydrogel preparation and its application in loading and slow release of poly(lysine). LWT-FOOD SCIENCE AND TECHNOLOGY, [PMID:] [10.1016/j.lwt.2023.115202] |
| 18. Mo Guichun, Qin Dongmiao, Wu Yusheng, Luo Zhi, Mo Keting, Deng Biyang. (2023) Dual-potential electrochemiluminescence cytosensor based on a metal-organic framework and ABEI-PEI-Au@AgNPs for the simultaneous determination of phosphatidylserine and epidermal growth factor receptors on an apoptotic cell surface. MICROCHIMICA ACTA, 190 (9): (1-14). [PMID:37563470] [10.1007/s00604-023-05934-5] |
| 19. Guangwei Yang, Longxiang Tao, Guijie Kang, Jinhao Yan, Kewu He, Xuefu Wang, Jun Yin. (2023) Construction of Actively Targeted and High Drug Content Polyprodrug Amphiphiles to Perform Synergistic Chemo–Photo-Anti-Tumor Therapy and Immune-Activated Investigation. CHEMISTRY OF MATERIALS, [PMID:] [10.1021/acs.chemmater.3c00820] |
| 20. Xuyan Lu, Zirui Liu, Qirui Jia, Qiusheng Wang, Qi Zhang, Xiaoran Li, Jianyong Yu, Bin Ding. (2023) Flexible Bioactive Glass Nanofiber-Based Self-Expanding Cryogels with Superelasticity and Bioadhesion Enabling Hemostasis and Wound Healing. ACS Nano, [PMID:37278622] [10.1021/acsnano.3c01370] |
| 21. Hu Qing-Di, Jiang Hong-Liu, Lam Kwok-Ho, Hu Zhi-Peng, Liu Zhi-Jie, Wang Hua-Ying, Yang Yong-Yu, Baigenzhenov Omirserik, Hosseini-Bandegharaei Ahmad, He Fu-An. (2023) Polydopamine-modification of a magnetic composite constructed from citric acid–cross-linked cyclodextrin and graphene oxide for dye removal from waters. ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH, 30 (32): (78521-78536). [PMID:37271788] [10.1007/s11356-023-27679-7] |
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| 25. Yue Yu, Yujia Zhang, Yu Chen, Xuekang Wang, Ke Kang, Nanhang Zhu, Yao Wu, Qiangying Yi. (2023) Floating Immunomagnetic Microspheres for Highly Efficient Circulating Tumor Cell Isolation under Facile Magnetic Manipulation. ACS Sensors, [PMID:37067910] [10.1021/acssensors.3c00420] |
| 26. Ping Zhang, Chaoqun Zhang, Jie Song, Shuxin Wang, Qian Li, Feng Su, Suming Li. (2023) Novel fluorescent nanoprobe based on hyaluronic acid and polyethyleneimine functionalized graphene oxide for detecting hyaluronidase as tumor marker. POLYMERS FOR ADVANCED TECHNOLOGIES, 34 (7): (2340-2354). [PMID:] [10.1002/pat.6055] |
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| 30. Xin Sun, Jin Yang, Jie Ma, Tianchang Wang, Xue Zhao, Dan Zhu, Wenjie Jin, Kai Zhang, Xuzhou Sun, Yuling Shen, Neng Xie, Fei Yang, Xiushuai Shang, Shuai Li, Xiaojun Zhou, Chuanglong He, Deteng Zhang, Jinwu Wang. (2023) Three-dimensional bioprinted BMSCs-laden highly adhesive artificial periosteum containing gelatin-dopamine and graphene oxide nanosheets promoting bone defect repair. Biofabrication, 15 (2): (025010). [PMID:36716493] [10.1088/1758-5090/acb73e] |
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| 32. Lei He, Yong Dai, Jingjie Hou, Yanxin Gao, Daishuo Zhang, Juqing Cui, Jun Zhang, Haomiao Zhu, Jian Shen. (2023) MXene based immobilized microorganism for chemical oxygen demand reduction of oilfield wastewater and heavy oil viscosity reduction to enhance recovery. Journal of Environmental Chemical Engineering, [PMID:] [10.1016/j.jece.2023.109376] |
| 33. Xiao Li Li, Peng Liu, Bin Chu, Jin Mei He, Zhen Wang, Song Wang, Chang Sheng Chen, Xiao Hong Ge, Hui Li, Wei Qiang Liu. (2022) Myocardial injection of thermosensitive HADOPA/Ca-FVI/Alg hydrogels improves cardiac repair after myocardial infarction. REACTIVE & FUNCTIONAL POLYMERS, [PMID:] [10.1016/j.reactfunctpolym.2022.105492] |
| 34. Zheng Chen, Jiulong Zhao, Hang Wu, Haibin Wang, Xuhua Lu, Mohammad-Ali Shahbazi, Shige Wang. (2022) A triple-network carboxymethyl chitosan-based hydrogel for hemostasis of incompressible bleeding on wet wound surfaces. CARBOHYDRATE POLYMERS, [PMID:36657832] [10.1016/j.carbpol.2022.120434] |
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| 36. Ding Wang, Yiru Zhao, Shen Zhang, Liping Bao, Huijun Li, Jingcheng Xu, Bin He, Xumin Hou. (2022) Reporter Molecules Embedded Au@Ag Core-Shell Nanospheres as SERS Nanotags for Cardiac Troponin I Detection. Biosensors-Basel, 12 (12): (1108). [PMID:36551074] [10.3390/bios12121108] |
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| 38. Zhiyang Lin, Linhan Li, Kaige Song, Bin Yang, Guoqing Zhou, Gengrong Zhang, Jiang Teng, Erlong Wang, Xiaoqiang Liu, Fei Ling, Gaoxue Wang, Tianqiang Liu. (2022) Boronic acid-modified bacterial cellulose microspheres as packing materials for enveloped virus removal. SCIENCE OF THE TOTAL ENVIRONMENT, [PMID:36414067] [10.1016/j.scitotenv.2022.160341] |
| 39. Juan-Juan Hu, Min Wang, Xiong-Xin Lei, Yan-Lin Jiang, Lei Yuan, Zhong-Jing Pan, Dan Lu, Feng Luo, Jie-Hua Li, Hong Tan. (2022) Scarless Healing of Injured Vocal Folds Using an Injectable Hyaluronic Acid-Waterborne Polyurethane Hybrid Hydrogel to Tune Inflammation and Collagen Deposition. ACS Applied Materials & Interfaces, [PMID:36121932] [10.1021/acsami.2c07225] |
| 40. Wu Leilei, Bao Xueming, Ren Yiwen, Wang Ping, Zhou Man, Yu Yuanyuan, Wang Qiang. (2022) Efficient Regulation of Dyeing Behavior and Physical Properties of Bombyx mori Silks via Graft Polymerization of α-Lipoic Acid. FIBERS AND POLYMERS, 23 (8): (2225-2233). [PMID:] [10.1007/s12221-022-4981-7] |
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| 42. Kaiqing Yun, Juntong Guo, Renfang Zhu, Tianyi Wang, Xiaoyan Zhang, Hao Pan, Weisan Pan. (2022) Design of ROS-Responsive Hyaluronic Acid–Methotrexate Conjugates for Synergistic Chemo-Photothermal Therapy for Cancer. MOLECULAR PHARMACEUTICS, [PMID:35900105] [10.1021/acs.molpharmaceut.2c00472] |
| 43. Junjing Zhou, Xinglian Wu, Chaochen Zhao. (2022) Optimization of decellularized liver matrix-modified chitosan fibrous scaffold for C3A hepatocyte culture. JOURNAL OF BIOMATERIALS APPLICATIONS, [PMID:35834434] [10.1177/08853282221115367] |
| 44. Shuyang Wang, Jieru Li, Yudong Pan, Fengkai Liu, Liangsong Zeng, Yang Gao, Tongqing Lu. (2022) A double-network strategy for the tough tissue adhesion of hydrogels with long-term stability under physiological environment. Soft Matter, 18 (33): (6192-6199). [PMID:35856647] [10.1039/D2SM00688J] |
| 45. Xuanren Shen, Saiqun Li, Xuan Zhao, Jiandong Han, Jiaxin Chen, Zilong Rao, Kexin Zhang, Daping Quan, Jin Yuan, Ying Bai. (2022) Dual-crosslinked regenerative hydrogel for sutureless long-term repair of corneal defect. Bioactive Materials, [PMID:35800407] [10.1016/j.bioactmat.2022.06.006] |
| 46. Shweta Pawar, Hamootal Duadi, Yafit Fleger, Dror Fixler. (2022) Design and Use of a Gold Nanoparticle–Carbon Dot Hybrid for a FLIM-Based IMPLICATION Nano Logic Gate. ACS Omega, [PMID:35811911] [10.1021/acsomega.2c02463] |
| 47. Pandeng Miao, Jie Gan, Jian Zhang, Mingxuan Ma, Xiaoqi Li, Yingxiang Du, Zijie Feng, Liu Zhang. (2022) Carboxymethyl-β-cyclodextrin and histidine-zeolitic imidazolate framework-8 used for enantioseparation of three basic drugs in open-tubular capillary electrochromatography. CHIRALITY, 34 (9): (1209-1218). [PMID:35678370] [10.1002/chir.23480] |
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| 49. Gengrong Zhang, Linhan Li, Guoqing Zhou, Zhiyang Lin, Jun Wang, Gaoxue Wang, Fei Ling, Tianqiang Liu. (2022) Recyclable aminophenylboronic acid modified bacterial cellulose microspheres for tetracycline removal: Kinetic, equilibrium and adsorption performance studies for hoggery sewer. ENVIRONMENTAL POLLUTION, [PMID:35636715] [10.1016/j.envpol.2022.119544] |
| 50. Ziling Chang, Yuxiang Yang, Bo Zhao, Huafei Li, Yuxia Guan, Yi Zhao, Hongming Yuan, Chaoying Ni. (2022) Dual-targeting magnetic fluorescent mesoporous organosilicon hollow nanospheres for gambogic acid loading, sustained release and anti-tumor properties. JOURNAL OF MOLECULAR LIQUIDS, [PMID:] [10.1016/j.molliq.2022.119412] |
| 51. Du Bin, Zheng Mei, Ma Huizhen, Huang Jingshu, Jiao Qingqing, Bai Yimeng, Zhao Mengmeng, Zhou Jie. (2022) Nanozyme-natural enzymes cascade catalyze cholesterol consumption and reverse cancer multidrug resistance. JOURNAL OF NANOBIOTECHNOLOGY, 20 (1): (1-15). [PMID:35501796] [10.1186/s12951-022-01406-9] |
| 52. Lu Tang, Qiaqia Xiao, Yue Yin, Yijun Mei, Jing Li, Lin Xu, Hongbin Gao, Wei Wang. (2022) An enzyme-responsive and NIR-triggered lipid–polymer hybrid nanoplatform for synergistic photothermal/chemo cancer therapy. Biomaterials Science, 10 (9): (2370-2383). [PMID:35383799] [10.1039/D2BM00216G] |
| 53. Wei Ma, Huanli Zhang, Shuying Li, Zhiqiang Wang, Xiaodan Wu, Rui Yan, Fang Geng, Weijie Mu, Yingxue Jin. (2022) A Multifunctional Nanoplatform Based on Fenton-like and Russell Reactions of Cu, Mn Bimetallic Ions Synergistically Enhanced ROS Stress for Improved Chemodynamic Therapy. ACS Biomaterials Science & Engineering, [PMID:35230802] [10.1021/acsbiomaterials.1c01605] |
| 54. Hang Jia, Xuejun Zeng, Rui Cai, Zhouli Wang, Yahong Yuan, Tianli Yue. (2022) Fabrication of Epsilon-Polylysine-Based Magnetic Nanoflowers with Effective Antibacterial Activity against Alicyclobacillus acidoterrestris. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:35040323] [10.1021/acs.jafc.1c06885] |
| 55. Bei-Bei Yan, Chen-Cheng Xue, Meng-Huan Li, Liang Dong, Yang Zhao, Zhong Luo, Shu-Hong Yu. (2022) All-in-one hollow nanoformulations enabled imaging-guided Mn-amplified chemophototherapy against hepatocellular carcinoma. Nano Today, [PMID:] [10.1016/j.nantod.2022.101382] |
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