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N-Methylmaleimide

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Name

N-Methylmaleimide

EINECS 213-226-1
CAS No. 930-88-1 Density 1.29 g/cm3
PSA 37.38000 LogP -0.52090
Solubility Slightly soluble in water. Melting Point 94-96 °C(lit.)
Formula C5H5NO2 Boiling Point 194.1 °C at 760 mmHg
Molecular Weight 111.1 Flash Point 84.4 °C
Transport Information UN 1759 Appearance pale yellow crystals
Safety S26-36/37/39-45 Risk Codes R22-34-43-25-20/21
Molecular Structure Molecular Structure of 930-88-1 (N-Methylmaleimide) Hazard Symbols CorrosiveC
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;

Article Data 33

N-Methylmaleimide Synthetic route

108-31-6

maleic anhydride

74-89-5

methylamine

930-88-1

N-methylmaleimide

Conditions
ConditionsYield
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;
74-89-5

methylamine

6915-18-0

2-butenedioic acid

930-88-1

N-methylmaleimide

Conditions
ConditionsYield
With niobium(V) oxide In hexane; water for 30h; Inert atmosphere; Reflux;81%
108-31-6

maleic anhydride

593-51-1

methylamine hydrochloride

930-88-1

N-methylmaleimide

Conditions
ConditionsYield
With potassium acetate; acetic acid at 110℃; for 4h;30%
6936-48-7

N-methylmaleamic acid

930-88-1

N-methylmaleimide

Conditions
ConditionsYield
at 160℃;
With sodium acetate; acetic anhydride for 1h; Heating; Yield given;
With sodium acetate; acetic anhydride at 90 - 100℃; for 0.5h;
91210-73-0

2,5-Bis((trimethylsilyl)oxy)-N-methylpyrrole

930-88-1

N-methylmaleimide

Conditions
ConditionsYield
With tetrabutylammomium bromide; bromine In diethyl ether; dichloromethane at 0℃; Yield given;
acidic malate methylamine

acidic malate methylamine

930-88-1

N-methylmaleimide

Conditions
ConditionsYield
at 200℃;
96-54-8

N-Methylpyrrole

64-19-7

acetic acid

chromium (VI)-oxide

chromium (VI)-oxide

930-88-1

N-methylmaleimide

1121-07-9

N-methylsuccinimide

930-88-1

N-methylmaleimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / diethyl ether
2: n-Bu4NBr, Br2 / diethyl ether; CH2Cl2 / 0 °C
View Scheme
81-88-9

rhodamine B

A

930-88-1

N-methylmaleimide

B

128-53-0

N-Ethylmaleimide

C

6-(ethylmethylamino)-3-hydroxyxanthylium

D

6-(diethylamino)-3-hydroxyxanthylium

E

88-99-3

benzene-1,2-dicarboxylic acid

F

65-85-0

benzoic acid

G

91-66-7

N,N-diethylaniline

Conditions
ConditionsYield
With oxygen In water pH=2; Kinetics; pH-value; Irradiation; Green chemistry;

C5H7NO3

930-88-1

N-methylmaleimide

Conditions
ConditionsYield
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 Specification

 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.

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