CAS 941-69-5 N-Phenylmaleimide (HCID 13662)

Names & identifiers

Preferred name: N-Phenylmaleimide
IUPAC: 1-phenylpyrrole-2,5-dione
English name: N-Phenylmaleimide
Molecular formula: C10H7NO2
Molecular weight: 173.17

Names & synonyms

N-Phenylmaleimide941-69-5Maleanil1-Phenyl-1H-pyrrole-2,5-dioneMaleimidobenzene1H-Pyrrole-2,5-dione, 1-phenyl-MALEIMIDE, N-PHENYL-DTXSID00412749U9KT462VWNSC-8183DTXCID8021274RefChem:830997

Show more names

N-PMIphenylmaleimideN-PhenylmaleimidN-PhenylmaleinimidePMICASImilexP

213-382-01-phenylpyrrole-2,5-dioneMaleinanil1-phenyl-2,5-dihydro-1H-pyrrole-2,5-dioneN-phenyl maleimideNSC 8183MFCD000055021-Phenyl-pyrrole-2,5-dione

Database identifiers

CAS: 941-69-5
PubChem CID: 13662
DTXSID: DTXSID0041274
ChEMBL: CHEMBL76012
ChEBI: CHEBI:230728
UNII: 9U9KT462VW
EC Number: 213-382-0
Nikkaji: J7.180C

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 37.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 13
Formal charge: 0
Complexity: 246

Physicochemical properties

Melting point: 85 · 85-87 °C (lit.)
Boiling point: 162 · 162-163 °C/12 mmHg (lit.)
Density: 1.2427 · 1.2427 (rough estimate)
vapor pressure: 0.021 Pa · 0.021Pa at 25℃
refractive index: 1.52 · 1.5200 (estimate)
Flash point: 162 · 162-163°C/12mm
storage temp.: Sealed in dry,Room Temperature
solubility: 815 g/l · 815g/l insoluble
pka: -0.81 · -0.81±0.20(Predicted)
form: Crystalline Powder or Flakes
color: Yellow
Water Solubility: 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 DataBase Reference: 941 · 941-69-5(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 9 U9KT462VW · 9U9KT462VW
NIST Chemistry Reference: N-Phenylmaleimide(941-69-5)
EPA Substance Registry System: N-Phenylmaleimide (941-69-5)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 6 · GHS06,GHS09
Signal word: Danger
Hazard statements: 301 · H301-H400
Precautionary statements: 273 · P273-P301+P310+P330
PPE: 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes: T,Xi,N
Risk Statements: 25 · 25-36/37/38-23/24/25-50-43-41-38
Safety Statements: 45 · 45-24/25-36/37/39-26-61-39-36/37
RIDADR: 2811 · UN 2811 6.1/PG 3
WGK Germany: 3 · 3
RTECS: 5950000 · ON5950000
F: 10 · 10-21
Hazard Note: Irritant
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29251995 · 29251995
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 3 OralAquatic · Acute Tox. 3 OralAquatic Acute 1
REACH Registrations: Active
Limited Quantities: 5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

Safety data

F: 10-21
PPE: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk: 3
tsca: TSCA listed
rtecs: ON5950000
ridadr: UN 2811 6.1/PG 3
hs_code: 29251995
risk_code: 25-36/37/38-23/24/25-50-43-41-38
Signal word: Danger
Symbol(GHS): GHS06,GHS09
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
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group: III
Hazard statements: H301-H400
Limited Quantities: 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations: Active
Hazard Classifications: Acute Tox. 3 OralAquatic Acute 1
Precautionary statements: P273-P301+P310+P330

Chemistry & industry

Applications · 4 items

UsesN-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.

UsesN-Phenylmaleimide is used as a dipolarophile in 1,3-cycloaddition reaction with a nitrone, useful for the preparation of crystalline adducts of dienes. It is used as a plastic modifier.

UsesDienophile in the Diels-Alder reaction. Usually gives cryst adducts.

General DescriptionYellow needles.

Preparation methods · 1 item

PreparationN-phenylmaleimide can be prepared by reacting maleic anhydride with aniline. The reaction involves the formation of an amide acid in the first stage and iminolation in the second stage. Previously, iminolation was prone to side reactions that reduced yield and purity. Now, a catalytic method is used, avoiding side reactions and improving both yield and purity.