Maleimid
Maleimide
Grundinformationen
- CAS
541-59-3- Standard-SMILES
O=C1C=CC(=O)N1- InChIKey
PEEHTFAAVSWFBL-UHFFFAOYSA-N- Summenformel
- C4H3NO2
- Durchschnittliche Molmasse
- 97,07 g/mol
- Monoisotopische Masse
- 97,01637834
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Maleimide
- IUPAC
- pyrrole-2,5-dione
- Lokaler Name
- Maleimid
- Englischer Name
- Maleimide
- Summenformel
- C4H3NO2
- Molmasse
- 97.07
Namen und Synonyme
MALEIMIDE541-59-31H-Pyrrole-2,5-dionePyrrole-2,5-dione2,5-PyrroledioneMaleic imideDTXSID30494172519R1UGP8NSC-13684DTXCID2029377CHEBI:16072RefChem:800776
Weitere Namen anzeigen
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;
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,3
- Polarare Oberfläche (TPSA)
- 46,2 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 132
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 91 · 91-93 °C (lit.)
- Siedepunkt
- 97 · 97-103°C 5mm
- Dichte
- 1 · 1,2493 g/cm3
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
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%)
Toxikologische Informationen
Adverse EffectsDermatotoxin - Skin burns.
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2923 8/PG 2
- hs_code
- 29251995
- RTECS-Nr.
- ON4800000
Chemie und Industrie
Verwendung und Herstellung
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information1H-Pyrrole-2,5-dione: ACTIVE
Anwendungen
VerwendenReacts 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.
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