3345-50-4

Basic information

• Product Name: N-CARBAMOYLMALEIMIDE
• Synonyms: ASISCHEM Y94152;N-CARBAMYL MALEIMIDE;N-CARBAMOYLMALEIMIDE;1-carbamoyl-3-pyrroline-5-dione;2,5-dihydro-2,5-dioxo-1h-pyrrole-1-carboxamid;2,5-dioxo-3-pyrroline-1-carboxamide;2,5-dioxo-3-pyrrolinecarboxamid;2,5-Dioxo-3-pyrroline-1-carboxamide~1H-Pyrrole-2,5-dione-1-carboxamide
• CAS NO: 3345-50-4
• Molecular Formula: C₅H₄N₂O₃
• Molecular Weight: 140.1
• EINECS: 222-097-0
• Product Categories: AMIDE
• Mol File: 3345-50-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 157-160°C
• Boiling Point: 307°Cat760mmHg
• Flash Point: 139.5°C
• Appearance: /
• Density: 1.658g/cm³
• Vapor Pressure: 0.000744mmHg at 25°C
• Refractive Index: 1.628
• PKA: 11.97±0.20(Predicted)
• BRN: 117919
• CAS DataBase Reference: N-CARBAMOYLMALEIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBAMOYLMALEIMIDE(3345-50-4)
• EPA Substance Registry System: N-CARBAMOYLMALEIMIDE(3345-50-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: UY7352700
• Hazardous Substances Data: 3345-50-4(Hazardous Substances Data)

Usage

General Description

N-CARBAMOYLMALEIMIDE is a chemical compound with the molecular formula C6H6N2O3. It is a white to off-white solid that is sparingly soluble in water. N-CARBAMOYLMALEIMIDE is primarily used as a cross-linking agent in the production of polymers, such as nylon, and as a reactant in organic synthesis. It is a versatile compound with applications in the pharmaceutical, agricultural, and industrial sectors. N-CARBAMOYLMALEIMIDE is known for its ability to form stable covalent bonds with a variety of functional groups, making it a valuable tool in chemical research and development. However, it should be handled with care due to its potential health hazards and environmental impact.

InChI:InChI=1/C5H4N2O3/c6-5(10)7-3(8)1-2-4(7)9/h1-2H,(H2,6,10)

Synthetic route

maleuric acid (105-61-3) → N-carbamoylmaleimide (3345-50-4)

Conditions	Yield
With acetic anhydride at 85℃; for 1.5h;	90%
With acetic anhydride; acetic acid
With propionic acid; propionic acid anhydride

C5H6N2O4 → N-carbamoylmaleimide (3345-50-4)

Conditions	Yield
With acetic anhydride at 25 - 85℃; for 2h; Large scale;

N-carbamoylmaleimide (3345-50-4) + allyl alcohol (107-18-6) → maleic acid allyl ester ureide (6951-82-2)

Conditions	Yield
With zinc(II) chloride In acetonitrile for 8h; Heating / reflux;	99%

N-carbamoylmaleimide (3345-50-4) + 1-octadecanol (112-92-5) → maleic acid octadecyl ester ureide

Conditions	Yield
With zinc(II) chloride In 1,4-dioxane for 24h; Heating / reflux;	97%
With zinc(II) chloride

N-carbamoylmaleimide (3345-50-4) + 1-Hexadecanol (36653-82-4) → hexadecyl maleurate (201044-02-2)

Conditions	Yield
With zinc(II) chloride In 1,4-dioxane for 24h; Heating / reflux;	97%

N-carbamoylmaleimide (3345-50-4) + isopropyl alcohol (67-63-0) → maleic acid isopropyl ester ureide (92348-13-5)

Conditions	Yield
With zinc(II) chloride for 4h; Heating / reflux;	95%

N-carbamoylmaleimide (3345-50-4) + 2-Ethylhexyl alcohol (104-76-7) → 2-ethylhexyl maleurate (201044-01-1)

Conditions	Yield
With zinc(II) chloride for 4h; Heating / reflux;	95%

N-carbamoylmaleimide (3345-50-4) + 2-hydroxyethyl acrylate (818-61-1) → 2-hydroxyethylacrylate maleurate (201044-04-4)

Conditions	Yield
With zinc(II) chloride In acetonitrile for 5h; Heating / reflux;	94%

methanol (67-56-1) + N-carbamoylmaleimide (3345-50-4) → maleic acid monoureide methyl ester (105-63-5)

Conditions	Yield
for 6h; Heating / reflux;	93%

N-carbamoylmaleimide (3345-50-4) + butan-1-ol (71-36-3) → N-carbamoyl-maleamic acid butyl ester (140-98-7)

Conditions	Yield
With zinc(II) chloride for 4h; Heating / reflux;	93%
With 1,4-dioxane

N-carbamoylmaleimide (3345-50-4) + 1-Phenyl-4-methyl-3-(2H)isoquinolinone (82255-69-4) → C21H17N3O4 (95849-61-9)

Conditions	Yield
In xylene for 2h; Heating;	85.5%

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + N-carbamoylmaleimide (3345-50-4) → 2-hydroxyethyl metacrylate maleurate (201044-07-7)

Conditions	Yield
With zinc(II) chloride In acetonitrile for 6h; Heating / reflux;	74%

N-carbamoylmaleimide (3345-50-4) + 4-ethyl-5-thioxo-4,5-dihydro-3H-bis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazin-3-one (188535-15-1) → (3aR,6aS)(Z/E)-2-(4-ethyl-3-oxo-6-thioxo-3H,4H-[1,2]-dithiolo[3,4-b][1,4]thiazin-5(6H)-ylidene)-4,6-dioxotetrahydro-5H-[1,3]dithiolo[4,5-c]pyrrole-5-carboxamide (1567324-47-3)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In dichloromethane for 1h; Inert atmosphere; Reflux;	38%

2-pyrrole aldehyde (1003-29-8) + N-carbamoylmaleimide (3345-50-4) + 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine → 1-(3H-imidazol-4-ylmethyl)-4,6-dioxo-3-(1H-pyrrol-2-yl)-octahydro-pyrrolo[3,4-c]pyrrole-1-carboxylic acid

Conditions	Yield
Multistep reaction;	34%

furfural (98-01-1) + N-carbamoylmaleimide (3345-50-4) + 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine → 3-furan-2-yl-1-(3H-imidazol-4-ylmethyl)-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrole-1-carboxylic acid

Conditions	Yield
Multistep reaction;	15%

2-(morpholin-4-yl)ethanol (622-40-2) + N-carbamoylmaleimide (3345-50-4) → N-carbamoyl-maleamic acid 2-morpholin-4-yl-ethyl ester (117862-71-2)

methanol (67-56-1) + N-carbamoylmaleimide (3345-50-4) → fumaric acid methyl ester ureide (116035-54-2)

Conditions	Yield
With aluminium trichloride
With pyridine; water

2-ethoxy-ethanol (110-80-5) + N-carbamoylmaleimide (3345-50-4) → maleic acid-(2-ethoxy-ethyl ester)-ureide

Conditions	Yield
With 1,4-dioxane

N-carbamoylmaleimide (3345-50-4) + formaldehyd (50-00-0) → N,N'-bis-(2,5-dioxo-2,5-dihydro-pyrrole-1-carbonyl)-methylenediamine (6970-97-4)

Conditions	Yield
With sulfuric acid at -5℃;

N-carbamoylmaleimide (3345-50-4) + 1 ,5-pentanediol (111-29-5) → 3,6,14,17-tetraoxo-7,13-dioxa-2,18-diaza-nonadeca-4c,15c-dienedioic acid diamide

Conditions	Yield
With zinc(II) chloride

N-carbamoylmaleimide (3345-50-4) + octanol (111-87-5) → maleic acid octyl ester ureide

Conditions	Yield
With zinc(II) chloride; benzene

N-carbamoylmaleimide (3345-50-4) + ethanol (64-17-5) → N-carbamoyl-maleamic acid ethyl ester (67309-56-2)

N-carbamoylmaleimide (3345-50-4) + 1-dodecyl alcohol (112-53-8) → maleic acid dodecyl ester ureide (6151-04-8)

Conditions	Yield
With 1,4-dioxane

N-carbamoylmaleimide (3345-50-4) + 1-dodecyl alcohol (112-53-8) → fumaric acid dodecyl ester ureide (109815-89-6)

Conditions	Yield
With aluminium trichloride

N-carbamoylmaleimide (3345-50-4) + 2-nitro-1-butanol (609-31-4) → maleic acid-(2-nitro-butyl ester)-ureide (114960-76-8)

Conditions	Yield
With zinc(II) chloride

N-carbamoylmaleimide (3345-50-4) + 2-nitro-1-butanol (609-31-4) → fumaric acid-(2-nitro-butyl ester)-ureide (114698-92-9)

Conditions	Yield
With aluminium trichloride

N-carbamoylmaleimide (3345-50-4) + 4-tert-butyl-2,5-bis(hydroxymethyl)phenol (2203-14-7) → 2,6-Bis-(3-allophanoyl-acryloyloxymethyl)-4-tert-butyl-phenol (123886-22-6)

Conditions	Yield
With 1,4-dioxane

N-carbamoylmaleimide (3345-50-4) + ethylene glycol (107-21-1) → 3,6,11,14-tetraoxo-7,10-dioxa-2,15-diaza-hexadeca-4c,12c-dienedioic acid diamide (99689-21-1)

Conditions	Yield
zinc(II) chloride In acetonitrile for 3h; Heating / reflux;
With 1,4-dioxane; zinc(II) chloride

N-carbamoylmaleimide (3345-50-4) + ethylene glycol (107-21-1) → maleic acid-(2-hydroxy-ethyl ester)-ureide (69796-28-7)

N-carbamoylmaleimide (3345-50-4) + 2-chloro-ethanol (107-07-3) → maleic acid-(2-chloro-ethyl ester)-ureide (6951-81-1)

Conditions	Yield
With zinc(II) chloride

Upstream product

• 105-61-3 maleuric acid 
• 108-31-6 maleic anhydride 
• 57-13-6 urea 
• 15059-25-3 C₅H₆N₂O₄ 

Downstream Products

• 95849-61-9 C₂₁H₁₇N₃O₄ 
• 541-59-3 maleiimide 
• 140-98-7 N-carbamoyl-maleamic acid butyl ester 
• 108749-43-5 N-carbamoyl-malamic acid benzyl ester 
• 6951-81-1 N-Carbamoyl-maleinsaeure-<2-chlor-ethylester>-amid 
• 6951-82-2 N-Carbamoyl-maleinsaeure-allylester-amid 
• 69796-28-7 N-Carbamoyl-maleinsaeure-<2-hydroxy-ethylester>-amid 
• 123886-22-6 2,6-Bis-(3-allophanoyl-acryloyloxymethyl)-4-tert-butyl-phenol 
• 6151-04-8 N-Carbamoyl-maleinsaeure-dodecylester-amid 
• 67309-56-2 N-Carbamoyl-maleinsaeure-ethylester-amid 
• 6970-97-4 N,N'-bis-(2,5-dioxo-2,5-dihydro-pyrrole-1-carbonyl)-methylenediamine 
• 116035-54-2 N-Carbamoyl-fumarsaeure-methylester-amid 
• 105-63-5 maleic acid monoureide methyl ester 

Relevant articles and documents

Aqueous Reversible Addition-Fragmentation Chain Transfer (RAFT) Polymerization: Synthesis, Properties, and Application of an Amphoteric Superplasticizer

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