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CAS No.: | 930-88-1 |
---|---|
Name: | N-Methylmaleimide |
Article Data: | 33 |
Molecular Structure: | |
Formula: | C5H5NO2 |
Molecular Weight: | 111.1 |
Synonyms: | Maleimide,N-methyl- (6CI,7CI,8CI);1-Methyl-1H-pyrrole-2,5-dione;N-Methylmaleimide;N-Methylmaleinimide;N-Methylpyrrole-2,5-dione;NSC 57594; |
EINECS: | 213-226-1 |
Density: | 1.29 g/cm3 |
Melting Point: | 94-96 °C(lit.) |
Boiling Point: | 194.1 °C at 760 mmHg |
Flash Point: | 84.4 °C |
Solubility: | Slightly soluble in water. |
Appearance: | pale yellow crystals |
Hazard Symbols: | C |
Risk Codes: | R22-34-43-25-20/21 |
Safety: | S26-36/37/39-45 |
Transport Information: | UN 1759 |
PSA: | 37.38000 |
LogP: | -0.52090 |
Conditions | Yield |
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With sulfuric acid; copper(II) sulfate; sodium sulfate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; | 90% |
Stage #1: maleic anhydride; methylamine In dichloromethane at 20℃; for 1h; Stage #2: With sodium acetate; acetic anhydride at 90℃; for 16h; | |
Stage #1: maleic anhydride; methylamine In diethyl ether at 20℃; for 1.5h; Stage #2: With sodium acetate; acetic anhydride Heating; |
Conditions | Yield |
---|---|
With niobium(V) oxide In hexane; water for 30h; Inert atmosphere; Reflux; | 81% |
Conditions | Yield |
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With potassium acetate; acetic acid at 110℃; for 4h; | 30% |
Conditions | Yield |
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at 160℃; | |
With sodium acetate; acetic anhydride for 1h; Heating; Yield given; | |
With sodium acetate; acetic anhydride at 90 - 100℃; for 0.5h; |
2,5-Bis((trimethylsilyl)oxy)-N-methylpyrrole
N-methylmaleimide
Conditions | Yield |
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With tetrabutylammomium bromide; bromine In diethyl ether; dichloromethane at 0℃; Yield given; |
N-methylmaleimide
Conditions | Yield |
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at 200℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / diethyl ether 2: n-Bu4NBr, Br2 / diethyl ether; CH2Cl2 / 0 °C View Scheme |
rhodamine B
A
N-methylmaleimide
B
N-Ethylmaleimide
E
benzene-1,2-dicarboxylic acid
F
benzoic acid
G
N,N-diethylaniline
Conditions | Yield |
---|---|
With oxygen In water pH=2; Kinetics; pH-value; Irradiation; Green chemistry; |
N-methylmaleimide
Conditions | Yield |
---|---|
With sodium acetate; acetic anhydride at 110℃; for 4h; | |
With 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide In tetrahydrofuran at 40 - 70℃; for 4.5h; Inert atmosphere; | |
With sodium acetate; acetic anhydride for 0.5h; | |
With sodium acetate In acetic anhydride at 120℃; for 0.5h; Microwave irradiation; |
N-Methylmaleimide , its cas register number is 930-88-1. The IPUAC name about this chemicals is 1-Methylpyrrole-2,5-dione .The index of refraction about it is 1.53, molar refractivity is 26.58 cm3, molar volume is 86 cm3 and surface tension is 46.6 dyne/cm, also, it have other chemical properties, for example, the enthalpy of vaporization about this chemicals is 43.03 kJ/mol, vapour pressure is 0.449 mmHg at 25 °C, refractive index is 1.5180 and so on. It belongs to the following product categories, such as N-Substituted Maleimides, N-Substituted Maleimides, Succinimides & Phthalimides, Carbonyl Compounds, Cyclic Imides and Organic Building Blocks.
N-Methylmaleimide is a light yellow crystals, we can store it at 2-8 °C. If you want to use it, you shoulde be more careful, because it is harmful and toxic if swallowed or inhalation and in contact with skin, also it may causes burns and may cause sensitization by skin contact. In the use process, you need to wear suitable protective clothing, gloves and eye/face protection and in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, also in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). However it should be kept under argon, and it is sensitive to humidity, so storge must be carful. Expect these measures, it also have some importent sfety imformations, RIDADR about it is UN 1759 8/PG 2, WGK Germany is 3, RTECS number is ON5600000, its HazardClass is 6.1, and its PackingGroup is II.
This chemicals can be described computed from structure:
1) Canonical SMILES: CN1C(=O)C=CC1=O
2) InChI: InChI=1S/C5H5NO2/c1-6-4(7)2-3-5(6)8/h2-3H,1H3
The most important thing about N-Methylmaleimide is the toxicity, following is the form:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LDLo | intraperitoneal | 15600ug/kg (15.6mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 9, Pg. 344, 1957. |