| Identification | More | [Name]
N-Methylmaleimide | [CAS]
930-88-1 | [Synonyms]
1-METHYL-1H-PYRROLE-2,5-DIONE
N-METHYL-2,5-PYRROLEDIONE
N-METHYLMALEIMID
N-METHYLMALEIMIDE
1H-Pyrrole-2,5-dione, 1-methyl-
1H-Pyrrole-2,5-dione,1-methyl-
1-Methyl-pyrrole-2,5-dione
Maleimide, N-methyl-
Maleimide,N-methyl-
Maleinsαure-N-methylimid
N-Methylmaleinimide
N-Methyl-Malemide
N-Methylmaleimide,98+%
1-Methyl-2,5-dihydro-1H-pyrrole-2,5-dione
1-Methyl-3-pyrroline-2,5-dione | [EINECS(EC#)]
213-226-1 | [Molecular Formula]
C5H5NO2 | [MDL Number]
MFCD00005508 | [Molecular Weight]
111.1 | [MOL File]
930-88-1.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow crystals | [Melting point ]
94-96 °C (lit.) | [Boiling point ]
208.19°C (rough estimate) | [density ]
1.3113 (rough estimate) | [refractive index ]
1.4260 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Crystals | [pka]
-2.18±0.20(Predicted) | [color ]
Light yellow | [Water Solubility ]
Slightly soluble in water. | [BRN ]
108550 | [InChI]
InChI=1S/C5H5NO2/c1-6-4(7)2-3-5(6)8/h2-3H,1H3 | [InChIKey]
SEEYREPSKCQBBF-UHFFFAOYSA-N | [SMILES]
N1(C)C(=O)C=CC1=O | [CAS DataBase Reference]
930-88-1(CAS DataBase Reference) | [NIST Chemistry Reference]
N-Methylmaleimide(930-88-1) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H314-H317 | [Precautionary statements ]
P260-P270-P280-P301+P312-P303+P361+P353-P305+P351+P338 | [Hazard Codes ]
C | [Risk Statements ]
R22:Harmful if swallowed.
R34:Causes burns.
R43:May cause sensitization by skin contact.
R25:Toxic if swallowed.
R20/21:Harmful by inhalation and in contact with skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1759 8/PG 2
| [WGK Germany ]
3
| [RTECS ]
ON5600000
| [F ]
10-21 | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29241990 |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow crystals | [Uses]
N-Methylmaleimide is an electron deficient olefin that acts as a thiol-blocking reagent. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 60, p. 6676, 1995 DOI: 10.1021/jo00126a013 | [Synthesis]
GENERAL METHOD: Methylamine hydrochloride (19.1 g, 0.30 mol) was added to a solution of acetic acid (40 mL) containing maleic anhydride (20 g, 0.20 mol) and potassium acetate (30.0 g, 0.30 mol) and stirred thoroughly. The mixture was heated to reflux temperature (110 °C) and the reaction was maintained for 4 hours. Upon completion of the reaction, the reaction mixture was cooled to 25-30 °C. Subsequently, the reaction mixture was slowly poured into pre-cooled sodium bicarbonate solution (100 mL) and extracted with diethyl ether (3 x 70 mL). The organic layers were combined, washed with brine solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give N-methylmaleimide (6.89 g, 30% yield). | [Purification Methods]
Crystallise the imide three times from diethyl ether. Dry it in vacuo.[Beilstein 21/10 V 5.] | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4577 - 4580 |
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