Grundinformationen
- 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-dioneMFCD00005494maleic acid imideSMR000857346CCRIS 3408
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)
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
- Brechungsindex
- 1.4543 · 1.4543 (estimate)
- Flammpunkt
- 97 · 97-103°C/5mm
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- soluble in Methanol
- Aggregatzustand
- Fine Crystalline Powder
- pka
- 8.52 · 8.52±0.20(Predicted)
- Farbe
- White to slightly yellow
- Wasserlöslichkeit
- SOLUBLE
- BRN
- 106910 · 106910
- InChI
- 1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
- InChIKey
- PEEHTFAAVSWFBL-UHFFFAOYSA-N
- SMILES
- O=C1NC(=O)C=C1
- CAS Datenbank
- 541 · 541-59-3(CAS DataBase Reference)
- NIST chemische Informationen
- 1 H-pyrrole-2,5-dione · 1H-pyrrole-2,5-dione(541-59-3)
- EPA chemische Informationen
- 1 H-Pyrrole-2,5-dione · 1H-Pyrrole-2,5-dione (541-59-3)
Sicherheit und Regulatorisches
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
- risk_code
- 25-34-43-36/37/38-36
- hazard_code
- T,C
- safety_code
- 26-36/37/39-45-37/39-28A-7/9
- hazard_class
- 8
- packing_group
- III
- Speicherklasse
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- Acute Tox. 2 OralEye Dam. 1Skin Corr. 1BSkin Sens. 1
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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Ergänzende Hinweise
DefinitionChEBI: A cyclic dicarboximide in which the two carboacyl groups on nitrogen together with the nitogen itself form a 1H-pyrrole-2,5-dione structure.
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