Maleimide
Basic information
- CAS
541-59-3- Standard SMILES
O=C1C=CC(=O)N1- InChIKey
PEEHTFAAVSWFBL-UHFFFAOYSA-N- Molecular formula
- C4H3NO2
- Average molar mass
- 97.07 g/mol
- Monoisotopic mass
- 97.01637834
Overview
Maleimide is a cyclic dicarboximide in which the two carboacyl groups on nitrogen together with the nitogen itself form a 1H-pyrrole-2,5-dione structure. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a dicarboximide and a member of maleimides. It is functionally related to a maleic acid. It derives from a hydride of a 1H-pyrrole.
Names & identifiers
- Preferred name
- Maleimide
- IUPAC
- pyrrole-2,5-dione
- English name
- Maleimide
- Molecular formula
- C4H3NO2
- Molecular weight
- 97.07
Names & synonyms
MALEIMIDE541-59-31H-Pyrrole-2,5-dionePyrrole-2,5-dione2,5-PyrroledioneMaleic imideDTXSID30494172519R1UGP8NSC-13684DTXCID2029377CHEBI:16072RefChem:800776
Show more names
MaleiMide, 98% 10GRNSC 13684maleicimideMaleimide>
208-787-4Maleinimide3-Pyrroline-2,5-dione2,5-dihydro-1H-pyrrole-2,5-dionemaleic acid imideMFCD000054945-hydroxy-2H-pyrrol-2-one2,5-Dioxo-2,5-dihydropyrrole; 3-Pyrroline-2,5-dione; Maleic Imide; NSC 13684;
Database identifiers
- CAS
541-59-3- PubChem CID
- 10935
- DTXSID
DTXSID3049417- ChEMBL
CHEMBL201511、CHEMBL387762- ChEBI
CHEBI:16072- UNII
- 2519R1UGP8
- EC Number
- 208-787-4
- Nikkaji
- J6.395I
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 46.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 132
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
SpringerMaterials PropertiesSchoenflies notation
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP-0.29
Solubility9 [ug/mL] (The mean of the results at pH 7.4)
Vapor Pressure0.00000277 [mmHg]
Physical DescriptionWhite crystalline powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 91 · 91-93 °C (lit.)
- Boiling point
- 97 · 97-103°C 5mm
- Density
- 1 · 1,2493 g/cm3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (98%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P264, P270, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P333+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationMaleimide: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses burns; May cause skin sensitization; Toxic by ingestion; [Alfa Aesar MSDS] Search for (541-59-3[EC/RN Number]) AND (allergic OR dermatitis OR sensitizer OR sensitization): no reported allergic contact dermatitis; [PubMed]
Hazard Classes and CategoriesAcute Tox. 3 (98%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- ON4800000
- ridadr
- UN 2923 8/PG 2
Chemistry & industry
Uses & manufacturing
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information1H-Pyrrole-2,5-dione: ACTIVE
Applications
UsesReacts quantitatively with sulfhydryl groups.Maleimide is used to immobilize the bovine serum albumin-boronic acid conjugates in association with silica beads. Its nanoparticle surface favors the conjugation with cell penetration peptides. It is involved in Rhodium-catalyzed conjugate arylation with arylboronic acids. It is actively involved in Michael additions and Diels-Alder reactions by the addition across the double bond. It acts as crosslinking reagents in polymer chemistry.
UsesRhodium-catalyzed conjugate arylation with arylboronic acids.1
General DescriptionMaleimide (2,5-Pyrroledione) is a new nanoparticle surface functional group which favors easy conjugation with cell penetration peptides. The conjugation is enabled via click chemistry to preserve its biofunctions.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
201 records
Compound notes
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