N-(2-Hydroxyethyl)maleimide(HEMI) - ≥97% , CAS No.1585-90-6

CAS: 1585-90-6 Cat. No.: N131907 Molecular Weight: 141.12 EC Number: 696-457-4

GRADE & PURITY ≥97%

Synonyms

AKOS016004857 | 1-(2-hydroxyethyl)-2,5-dihydro-1H-pyrrole-2,5-dione | FT-0657724 | InChI=1/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2,8H,3-4H | DTXSID70332522 | AB90352 | EN300-121975 | FD6042 | N-2-Hydroxy-ethymaleimide | 1-(2-hydroxymethyl)-1-H-pyrrole-2,5-di

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Application

Antibody Drug Conjugates(ADC), Drug Delivery, Surface Modification, PEGylation of Protein, Peptide & Oligo

Overview

N-(2-Hydroxyethyl)maleimide may be used to synthesize [2,2-bis(maleimidoethoxy)- propane (BMEP)], a protein cross-linking reagent with potential application in constructing immunotoxins. It may also be used in preparing thermoresponsive self-healing polyurethanes with the shape-memory property.

Specifications

Synonyms

AKOS016004857 | 1-(2-hydroxyethyl)-2, 5-dihydro-1H-pyrrole-2, 5-dione | FT-0657724 | InChI=1/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2, 8H, 3-4H | DTXSID70332522 | AB90352 | EN300-121975 | FD6042 | N-2-Hydroxy-ethymaleimide | 1-(2-hydroxymethyl)-1-H-pyrrole-2, 5-di

Specifications & Purity

≥97%

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 488189891
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189891
• Canonical Smiles: C1=CC(=O)N(C1=O)CCO
• IUPAC Name: 1-(2-hydroxyethyl)pyrrole-2,5-dione
• InChIKey: AXTADRUCVAUCRS-UHFFFAOYSA-N
• INCHI: 1S/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2,8H,3-4H2
• Isomeric SMILES: C1=CC(=O)N(C1=O)CCO
• WGK Germany: 3
• Molecular Weight: 141.12
• Reaxy-Rn: 1210372
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1210372&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrrolidines
      • Subclass Pyrrolidones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrrolidines
• Subclass: Pyrrolidones
• Intermediate Tree Nodes: Not available
• Direct Parent: Maleimides
• Alternative Parents: N-substituted carboxylic acid imides Pyrrolines Dicarboximides Azacyclic compounds Alkanolamines Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Maleimide - Carboxylic acid imide, n-substituted - Carboxylic acid imide - Dicarboximide - Pyrroline - Alkanolamine - Carboxylic acid derivative - Azacycle - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as maleimides. These are compounds containing a 2,5-pyrroledione moiety.
• 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

• Sensitivity: light sensitive
• Boil Point(°C): 130°C
• Melt Point(°C): 66~75℃
• Molecular Weight: 141.120 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 141.043 Da
• Monoisotopic Mass: 141.043 Da
• Topological Polar Surface Area: 57.600 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 179.000
• 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. Xiaosheng Du, Linzhao Jin, Sha Deng, Mi Zhou, Zongliang Du, Xu Cheng, Haibo Wang.  (2021)  Recyclable, Self-Healing, and Flame-Retardant Solid–Solid Phase Change Materials Based on Thermally Reversible Cross-Links for Sustainable Thermal Energy Storage.  ACS Applied Materials & Interfaces,      [PMID:34486880] [10.1021/acsami.1c14862]

2. Sijia Wang, Huifang Xu, Yuanyuan Li, Lingyi Zhang, Shouhong Xu.  (2024)  Aggression to Biomembranes by Hydrophobic Tail Chains under the Stimulus of Reductant.  MOLECULES,  29  (17): (4001).  [PMID:39274849] [10.3390/molecules29174001]

3. Meng Zhou, Xiaowen Xie, Siying An, Ling Zhu, Zhixin Wu, Shuai Chen.  (2024)  PEDOT:PSS based reprocessingly multifunctional dispersions and their optoelectronic films with excellent self-healing capability.  SYNTHETIC METALS,      [PMID:] [10.1016/j.synthmet.2024.117629]

4. Chaoxiang Chen, Xueping Pan, Mengdi Sun, Jialin Wang, Xueqi Su, Tianyu Zhang, Yulei Chen, Daren Wu, Jian Li, Shuqi Wu, Xiaomei Yan.  (2024)  Phospholipid-Anchored Ligand Conjugation on Extracellular Vesicles for Enhanced Cancer Targeting.  Small,      [PMID:38733222] [10.1002/smll.202310712]