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1-Phenyl-1H-pyrrol-2,5-dion

N-Phenylmaleimide

HCID 13662
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Grundinformationen

CAS
941-69-5
Standard-SMILES
O=C1C=CC(=O)N1c1ccccc1
InChIKey
HIDBROSJWZYGSZ-UHFFFAOYSA-N
Summenformel
C10H7NO2
Durchschnittliche Molmasse
173,17 g/mol
Monoisotopische Masse
173,04767847

Überblick

N-phenylmaleimide appears as yellow needles. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
N-Phenylmaleimide
IUPAC
1-phenylpyrrole-2,5-dione
Lokaler Name
1-Phenyl-1H-pyrrol-2,5-dion
Englischer Name
N-Phenylmaleimide
Summenformel
C10H7NO2
Molmasse
173.17

Namen und Synonyme

N-Phenylmaleimide941-69-5Maleanil1-Phenyl-1H-pyrrole-2,5-dioneMaleimidobenzene1H-Pyrrole-2,5-dione, 1-phenyl-MALEIMIDE, N-PHENYL-DTXSID00412749U9KT462VWNSC-8183DTXCID8021274RefChem:830997
Weitere Namen anzeigen
N-PMIphenylmaleimideN-PhenylmaleimidN-Phenylmaleinimide1-PHENYL-PYRROLE-2,5-DIONEPMICASImilexP
213-382-01-phenylpyrrole-2,5-dioneMaleinanil1-phenyl-2,5-dihydro-1H-pyrrole-2,5-dioneN-phenyl maleimideN-Fenylimid kyseliny maleinoveNSC 8183MFCD00005502

Datenbank-Bezeichner

CAS
941-69-5
PubChem CID
13662
DTXSID
DTXSID0041274
ChEMBL
CHEMBL76012
ChEBI
CHEBI:230728
UNII
9U9KT462VW
EC Number
213-382-0

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,1
Polarare Oberfläche (TPSA)
37,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
13
Formalladung
0
Komplexität
246

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesChemical shift
LogP1.09
SolubilitySparingly soluble (NTP, 1992)
Boiling Point324 °F at 12 mmHg (NTP, 1992)
Melting Point192 to 194 °F (NTP, 1992)
Physical Description · 2 Einträge

N-phenylmaleimide appears as yellow needles. (NTP, 1992)

Other Solid

Collision Cross Section135.3 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0041274]

Physikochemische Eigenschaften

Schmelzpunkt
85 · 85-87 °C (lit.)
Siedepunkt
162 · 162-163 °C/12 mmHg (lit.)

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 · 6 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 137 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 1H-Pyrrole-2,5-dione, 1-phenyl-

1H-Pyrrole-2,5-dione, 1-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Pyrrole-2,5-dione, 1-phenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: N-phenylmaleimide (EC: 213-382-0)

1H-Pyrrole-2,5-dione, 1-phenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation.
Reactive GroupAmides and Imides

Chemie und Industrie

Verwendung und Herstellung

U.S. Production2023: 250,000 - <550,000 lb
Industry UsesMonomers
General Manufacturing Information · 2 Einträge

Plastics Material and Resin Manufacturing

1H-Pyrrole-2,5-dione, 1-phenyl-: ACTIVE

Anwendungen

VerwendenN-phenylmaleimide can be used as cross-linking agent in rubber vulcanization, can improve the heat resistance, impact resistance, hot melt processability. Also be used to produce heat-resistant polymers.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

2 3-DICHLORO-N-PHENYLMALEIMIDE3-bromo-1-phenyl-1H-pyrrole-2,5-dione5-Benzyl-2-phenyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Zugehörige Reaktionen

37
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 25355
HRID 25355als Produktuspto-grants-2005_02
Reaktionsgleichung von HRID 65605
HRID 65605als Produktuspto-grants-1978_12
Reaktionsgleichung von HRID 247614
HRID 247614als Eduktuspto-grants-1987_11
Reaktionsgleichung von HRID 257550
HRID 257550als Eduktuspto-grants-1993_11
Reaktionsgleichung von HRID 262421
HRID 262421als Produktuspto-grants-1979_05
Reaktionsgleichung von HRID 263096
HRID 263096als Eduktuspto-grants-1979_05
Reaktionsgleichung von HRID 274986
HRID 274986als Eduktuspto-grants-1995_02
Reaktionsgleichung von HRID 296768
HRID 296768als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
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Nikkaji
J7.180C
Dichte
1.2427 · 1.2427 (rough estimate)
Dampfdruck
0.021 Pa · 0.021Pa at 25℃
Brechungsindex
1.52 · 1.5200 (estimate)
Flammpunkt
162 · 162-163°C/12mm
storage temp.
Sealed in dry,Room Temperature
Löslichkeit
815 g/l · 815g/l insoluble
pka
-0.81 · -0.81±0.20(Predicted)
Aggregatzustand
Crystalline Powder or Flakes
Farbe
Yellow
Wasserlöslichkeit
Soluble in water (slightly ), methanol, ethanol, and benzene.
Merck
14 · 14,7299
BRN
125098 · 125098
InChI
1S/C10H7NO2/c12-9-6-7-10(13)11(9)8-4-2-1-3-5-8/h1-7H
InChIKey
HIDBROSJWZYGSZ-UHFFFAOYSA-N
SMILES
O=C1C=CC(=O)N1c2ccccc2
LogP
1.16 at · 1.16 at 25℃
CAS Datenbank
941 · 941-69-5(CAS DataBase Reference)
NIST chemische Informationen
N-Phenylmaleimide(941-69-5)
EPA chemische Informationen
N-Phenylmaleimide (941-69-5)
Reactivity Profile · 1 Eintrag

N-PHENYLMALEIMIDE is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Air and Water ReactionsSparingly water soluble (NTP, 1992).
Hazard Classes and Categories · 3 Einträge

Acute Tox. 3 (100%)

Acute toxicity (Oral) - Category 3

Acute toxicity (Oral) - Category 3

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 Eintrag

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Sicherheitsdaten

F
10-21
wgk
3
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 3
hs_code
29251995
RTECS-Nr.
ON5950000
risk_code
25-36/37/38-23/24/25-50-43-41-38
hazard_code
T,Xi,N
hazard_note
Irritant
safety_code
45-24/25-36/37/39-26-61-39-36/37
hazard_class
6.1
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1