CAS 13676-54-5 1,1'-(Methylenedi-p-phenylene)bismaleimide (HCID 83648)

Names & identifiers

Preferred name: 1,1'-(Methylenedi-p-phenylene)bismaleimide
IUPAC: 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione
English name: Bismaleimide
Molecular formula: C21H14N2O4
Molecular weight: 358.35

Names & synonyms

1,1'-(Methylenedi-p-phenylene)bismaleimideRefChem:409135Bismaleimide13676-54-54,4'-BismaleimidodiphenylmethaneBismaleimide S1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis-4,4'-Methylenebis(N-phenylmaleimide)p,p'-DimaleimidodiphenylmethaneBis(4-maleimidophenyl)methaneDiphenylmethanebismaleimide1,1'-(Methylenedi-4,1-phenylene)bismaleimide

Show more names

BMIbismaleimidesBismaleimide, 4,4'-diphenylmethane1,1’-(methylenedi-1,4-phenylene)bis-1H-pyrrole-2,5-dione1-(4-[4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzyl]phenyl)-1H-pyrrole-2,5-dionexu292amb-3000

p,p'-Methylenebis(N-phenylmaleimide)Bis(p-maleimidophenyl)methane1,1'-(Methylenebis(4,1-phenylene))bis(1H-pyrrole-2,5-dione)4,4'-Dimaleimidodiphenylmethane4,4'-Diphenylmethanedimaleimide4,4'-Biphenylmethanebismaleimide4,4'-DiphenylmethanebismaleimideN,N'-Bismaleimido-4,4'-diphenylmethane

Database identifiers

CAS: 13676-54-5
PubChem CID: 83648
DTXSID: DTXSID8044381
ChEMBL: CHEMBL478304
UNII: I67AL345KM
EC Number: 237-163-4
Nikkaji: J208.092C

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 74.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 27
Formal charge: 0
Complexity: 614

Experimental & physicochemical properties

Physical DescriptionDry Powder; Other Solid

Collision Cross Section · 1 item

174.3 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID8044381]；182.7 Å² [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID8044381]；197.5 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID8044381]

Physicochemical properties

Melting point: 156 · 156-158 °C(lit.)
Boiling point: 490.79 °C · 490.79°C (rough estimate)
Density: 1.336 · 1.3360 (rough estimate)
vapor pressure: 0 Pa · 0Pa at 25℃
refractive index: 1.68 · 1.6800 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: Water (Slightly)
form: powder to crystal
pka: -0.4 · -0.40±0.20(Predicted)
color: Light yellow to Amber to Dark green
Water Solubility: Insoluble in water.
BRN: 333986 · 333986
InChI: 1S/C21H14N2O4/c24-18-9-10-19(25)22(18)16-5-1-14(2-6-16)13-15-3-7-17(8-4-15)23-20(26)11-12-21(23)27/h1-12H,13H2
InChIKey: XQUPVDVFXZDTLT-UHFFFAOYSA-N
SMILES: O=C1C=CC(=O)N1c2ccc(Cc3ccc(cc3)N4C(=O)C=CC4=O)cc2
LogP: 1.5 at · 1.5 at 25℃
CAS DataBase Reference: 13676 · 13676-54-5(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
NCI Dictionary of Cancer Terms: BMI
FDA UNII: 67 AL345KM · I67AL345KM
NIST Chemistry Reference: p,p'-Bis(N-maleimidophenyl)methane(13676-54-5)
EPA Substance Registry System: 1 H-Pyrrole-2,5-dione, · 1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis- (13676-54-5)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 315 · H315-H319-H330-H335
Precautionary statements: 260 · P260-P264-P271-P302+P352-P304+P340+P310-P305+P351+P338
target organs: Respiratory system
PPE: 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes: T
Risk Statements: 23 · 23-36/37/38
Safety Statements: 26 · 26-45-37/39
RIDADR: 2811 · UN 2811 6.1/PG 2
WGK Germany: 2 · 2
RTECS: 5670000 · ON5670000
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29251900 · 29251900
Storage Class: 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 2 InhalationEye · Acute Tox. 2 InhalationEye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H315 (78.7%): Causes skin irritation [Warning Skin corrosion/irritation]；H317 (12%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H319 (76.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H330 (87.8%): Fatal if inhaled [Danger Acute toxicity, inhalation]；H335 (76.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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

Aggregated GHS information provided per 648 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 4 items

Chemical: 1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis-

1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis- 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)

Status: Active Update: 13-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11119

1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis-: 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.

Hazard Classes and CategoriesSkin Irrit. 2 (78.7%)；Skin Sens. 1A (12%)；Eye Irrit. 2 (76.4%)；Acute Tox. 2 (87.8%)；STOT SE 3 (76.2%)

Regulatory information

Regulatory Information · 4 items

Chemical: 1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis-

1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis- 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)

Status: Active Update: 13-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11119

1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis-: 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.

Safety data

PPE: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk: 2
tsca: TSCA listed
rtecs: ON5670000
ridadr: UN 2811 6.1/PG 2
hs_code: 29251900
risk_code: 23-36/37/38
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T
safety_code: 26-45-37/39
hazard_class: 6.1
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group: III
target organs: Respiratory system
Hazard statements: H315-H319-H330-H335
REACH Registrations: Active
Hazard Classifications: Acute Tox. 2 InhalationEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P260-P264-P271-P302+P352-P304+P340+P310-P305+P351+P338

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 313,612 lb；2022: 130,706 lb；2021: 163,633 lb；2020: 164,398 lb

Consumer UsesOther

Industry UsesIntermediate；Monomers

General Manufacturing Information · 2 items

Rubber Product Manufacturing；Plastics Material and Resin Manufacturing

1H-Pyrrole-2,5-dione, 1,1'-(methylenedi-4,1-phenylene)bis-: ACTIVE

Applications · 3 items

Uses1,1′-(Methylenedi-4,1-phenylene)bismaleimide was used to cure glycidyl ester of eleostearic acid (GEEA).

UsesBismaleimide products can be used to make bismaleimide resins, modified phenolic resins, modified epoxy thermosetting resins such as heat resistance and PP, PVC, PBT, PMMA and other plastics, as well as high-grade rubber products.

General DescriptionThe thermal and mechanical properties of GEEA cured by 1,1′-(methylenedi-4,1-phenylene)bismaleimide were studied.