N-Methylmaleimide supplier

Name
N-Methylmaleimide
EINECS 213-226-1
CAS No. 930-88-1
Article Data33
CAS DataBase
Density 1.29 g/cm³
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
Hazard Symbols C
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;
PSA 37.38000
LogP -0.52090

Synthetic route

: 108-31-6
maleic anhydride

: 74-89-5
methylamine

: 930-88-1
N-methylmaleimide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium acetate; acetic acid at 110℃; for 4h;	30%

: 6936-48-7
N-methylmaleamic acid

: 930-88-1
N-methylmaleimide

Conditions

Conditions	Yield
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

Conditions	Yield
With tetrabutylammomium bromide; bromine In diethyl ether; dichloromethane at 0℃; Yield given;

acidic malate methylamine: acidic malate methylamine

: 930-88-1
N-methylmaleimide

Conditions

Conditions	Yield
at 200℃;

: 96-54-8
N-Methylpyrrole

: 64-19-7
acetic acid

chromium (VI)-oxide: chromium (VI)-oxide

: 930-88-1
N-methylmaleimide

...Expand

: 1121-07-9
N-methylsuccinimide

: 930-88-1
N-methylmaleimide

Conditions

Conditions	Yield
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

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

...Expand

: C5H7NO3

: 930-88-1
N-methylmaleimide

Conditions

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;

: C12H13NO5

A: 930-88-1
N-methylmaleimide

B: 623-17-6
furfurylacetate

Conditions

Conditions	Yield
In dichloromethane at 60℃; Equilibrium constant; Temperature;

: 2,4-dimethyl-3a,4,7,7a-tetrahydro-4,7-epioxido-isoindole-1,3-dione

A: 534-22-5
2-methylfuran

B: 930-88-1
N-methylmaleimide

Conditions

Conditions	Yield
at 140℃;

: 930-88-1
N-methylmaleimide

: 100-64-1
Cyclohexanone oxime

: 5535-48-8
PVS

: 135583-71-0
2,2-spiropentamethylene-3-(2'-phenylsulphonylethyl)-7-methyl-3,7-diaza-4-oxabicyclo<3.3.0>octane-6,8-dione

Conditions

Conditions	Yield
In [D3]acetonitrile for 720h; Ambient temperature;	100%

...Expand

: 930-88-1
N-methylmaleimide

: 1705-82-4
10-diazo-10H-anthracen-9-one

: 118494-66-9
4-Hydroxy-2-methyl-3a,4,9,9a-tetrahydro-4,9<1',2'>benzeno-1H-benzisoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In pyridine	100%

: 930-88-1
N-methylmaleimide

: 90-44-8
anthracen-9(10H)-one

: 118494-66-9
4-Hydroxy-2-methyl-3a,4,9,9a-tetrahydro-4,9<1',2'>benzeno-1H-benzisoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 0.25h; Ambient temperature; other anthrones, other dienophiles;	100%
In N,N-dimethyl-formamide at 25℃; Product distribution; other related phenols, hydroquinones, and naphthacene analogues, other dienophiles, var. solvents and temperatures; solvent-dependent diene reactivity, base-catalyzed Diels-Alder reaction;	100%
With triethylamine In tetrahydrofuran at 24℃; for 0.25h;	100%
dihydroquinidine 9-O-(4-chlorobenzoate) In chloroform

: 930-88-1
N-methylmaleimide

: 4392-73-8
10-imino-9(10H)-anthracenone

: 118494-71-6, 132206-06-5
4-Amino-4,9<1',2'>-benzeno-3a,4,9,9a-tetrahydro-9-hydroxy-2-methyl-1H-benzisoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In pyridine for 2h;	100%

: 930-88-1
N-methylmaleimide

: 57402-97-8
N-<(trimethylsilyl)methyl>benzaldimine

: 2-Methyl-4-phenyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione

Conditions

Conditions	Yield
With water; acetic acid In N,N,N,N,N,N-hexamethylphosphoric triamide for 24h; Ambient temperature;	100%
With N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetic acid	100%

: 930-88-1
N-methylmaleimide

: 28539-14-2
N,N-bis(benzotriazol-1-ylmethyl)hydroxylamine

A: 3-(2H-benzotriazol-2-yl)-1-methylpyrrolidine-2,5-dione

B: 132287-03-7
N-methyl-3-benzotriazol-1-ylsuccinimide

: 132286-97-6
cis-2-(benzotriazol-1-ylmethyl)-5-methyl-2,3,3a,6a-tetrahydropyrrolo<3,4-d>isoxazole-4,6-dione

Conditions

Conditions	Yield
In toluene for 24h; Heating; Title compound not separated from byproducts;	A n/a B n/a C 100%
In toluene for 24h; Heating;	A n/a B n/a C 100%

...Expand

: 930-88-1
N-methylmaleimide

: 16883-69-5
N-phenacylpyridinium bromide

: 88089-38-7
(3aS,4S,9aR,9bR)-4-Benzoyl-2-methyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione

Conditions

Conditions	Yield
With triethylamine In chloroform for 0.166667h; Ambient temperature;	100%
With triethylamine In dimethyl sulfoxide at 20℃; for 0.0833333h;	n/a

: 930-88-1
N-methylmaleimide

: 946-07-6
1-(2-(furan-2-yl)-2-oxoethyl)pyridinium bromide

: 88089-36-5
(3aS,4S,9aR,9bR)-4-(Furan-2-carbonyl)-2-methyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione

Conditions

Conditions	Yield
With triethylamine In chloroform for 0.166667h; Mechanism; Ambient temperature; other compounds;	100%
With triethylamine In chloroform for 0.166667h; Ambient temperature;	100%
With triethylamine In dichloromethane for 0.166667h; Ambient temperature;	100%

: 930-88-1
N-methylmaleimide

: 76212-02-7
1-pyridinium-bromid

: 88089-42-3
(3aR,9aS,9bS)-2-Methyl-1,3-dioxo-1,2,3,3a,9a,9b-hexahydro-pyrrolo[3,4-a]indolizine-4,4-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With triethylamine In chloroform for 4h; Heating;	100%

: 930-88-1
N-methylmaleimide

: 34039-84-4
α-(benzylideneamino)acetonitrile

: 102845-50-1, 103530-39-8
(1R,3R,3aS,6aR)-5-Methyl-4,6-dioxo-3-phenyl-octahydro-pyrrolo[3,4-c]pyrrole-1-carbonitrile

Conditions

Conditions	Yield
In toluene for 6.5h; Product distribution; Mechanism; Heating; reactions with var. olefinic dipolarrophiles;	100%
In toluene for 6.5h; Heating;	100%

: 930-88-1
N-methylmaleimide

: 126134-14-3
2-Methyl-4,5,6,7-tetramethyl-2H-isoindolen

: 137003-84-0
endo-1,2,3,4-Tetrahydro-5,6,7,8,9,N'-hexamethyl-1,4-iminonaphthalin-2,3-dicarboximid

Conditions

Conditions	Yield
In diethyl ether for 2h; Product distribution; Ambient temperature; with N-4-methylphenyl-maleinimde; 2-tert-butyl-4,5,6,7-tetramethyl-2H-isoindolene;	100%
In diethyl ether for 2h; Ambient temperature;	100%

: 930-88-1
N-methylmaleimide

: 36377-40-9
pyridinium benzoylmethylide

: 88089-38-7
(3aS,4S,9aR,9bR)-4-Benzoyl-2-methyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione

Conditions

Conditions	Yield
In chloroform for 0.166667h; Ambient temperature;	100%
Yield given;

: 930-88-1
N-methylmaleimide

: 100-52-7
benzaldehyde

: 616-34-2
methoxycarbonylmethylamine

: 111098-98-7, 111187-10-1, 113349-48-7
(1RS,3SR,3aRS,6aSR)-methyl 5-methyl-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Conditions

Conditions	Yield
In toluene for 24h; Heating;	100%

...Expand

: 930-88-1
N-methylmaleimide

: 93969-61-0
1-Acetoxy-1,4-dihydro-8-methoxy-1,4-epoxynaphthalene

: 93969-67-6
(3aα,4β,9α,9aα)-4-acetoxy-5-methoxy-2-methyl-3a,4,9,9a-tetrahydro-4,9-epoxy-1H-benzisoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In chloroform at 60℃; for 0.5h;	100%

: 930-88-1
N-methylmaleimide

: 78158-11-9
1-(1-methylene-2-propenyl)-Cyclopentanol

: 91790-82-8
5-(1-Hydroxy-cyclopentyl)-2-methyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
In toluene for 20h; Heating;	100%

: 930-88-1
N-methylmaleimide

: 97204-09-6, 105017-19-4
((1R,2R,3R,10bR)-2,3-Dibenzoyl-1,2,3,10b-tetrahydro-pyrrolo[2,1-a]isoquinolin-1-yl)-phenyl-methanone

: 97204-10-9
8-benzoyl-10-methyl-11a,11b-dihydro-8H-pyrrolo[3',4':3,4]pyrrolo[2,1-a]isoquinoline-9,11(8aH,10H)-dione

B: 959-28-4
1,4-diphenylbut-2-ene-1,4-dione

Conditions

Conditions	Yield
In dimethylsulfoxide-d6 at 50 - 60℃; for 24h;	A 100% B n/a

...Expand

: 930-88-1
N-methylmaleimide

: 88089-46-7
N-(2-furoylmethyl)thiazolium bromide

: 88089-44-5
(5S,5aS,8aS,8bR)-5-(Furan-2-carbonyl)-7-methyl-5,5a,8a,8b-tetrahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]thiazole-6,8-dione

Conditions

Conditions	Yield
With triethylamine In chloroform for 0.166667h; Ambient temperature;	100%
With triethylamine In dimethyl sulfoxide for 0.166667h; Ambient temperature;	100%

: 930-88-1
N-methylmaleimide

: 1074-12-0
phenylglyoxal hydrate

: 616-34-2
methoxycarbonylmethylamine

: 111120-70-8
methyl (1S*,3R*,3aS*,6aR*)-3-benzoyl-5-methyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Conditions

Conditions	Yield
In chloroform for 16h; Heating;	100%
In chloroform for 16h; Heating; Yield given;

...Expand

: 930-88-1
N-methylmaleimide

: 1121-07-9
N-methylsuccinimide

Conditions

Conditions	Yield
With acetic anhydride; zinc In toluene at 40 - 86℃; for 48h; Inert atmosphere; chemoselective reaction;	100%
With Aeroxide (Evonik) P25 TiO2, consisting of a 3:1 anatase/rutile mixture In methanol; acetonitrile for 17h; Inert atmosphere; UV-irradiation;	90%
With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); ethyl 3-([1,1'-biphenyl]-2-yl)-3-oxopropanoate; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere;	86%

: 930-88-1
N-methylmaleimide

: 35946-59-9
2,5-dimethyl-tetrahydro-cyclobuta[1,2-c;3,4-c']dipyrrole-1,3,4,6-tetraone

Conditions

Conditions	Yield
In acetonitrile for 9h; UV-irradiation;	100%
In tetrachloromethane Product distribution; Quantum yield; Ambient temperature; Irradiation; Effect of concentration on quantum yield is studied;	95%
In 1,1,2-Trichloro-1,2,2-trifluoroethane Product distribution; Quantum yield; Ambient temperature; Irradiation;	95%

: 930-88-1
N-methylmaleimide

: 107554-38-1
(E)-2-(benzylideneamino)acetonitrile

: (1S,3S,3aS,6aR)-5-Methyl-4,6-dioxo-3-phenyl-octahydro-pyrrolo[3,4-c]pyrrole-1-carbonitrile

Conditions

Conditions	Yield
In toluene for 6.5h; Heating;	100%

: 930-88-1
N-methylmaleimide

: ethyl 3-[1-[(1-methylethyl)amino]ethyl]-1H-indole-2-acetate

: (3aS,4S,10R,10aS)-2,10-Dimethyl-1,3-dioxo-1,2,3,3a,4,5,10,10a-octahydro-pyrrolo[3,4-b]carbazole-4-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In toluene Addition; elimination; Heating;	100%

: 930-88-1
N-methylmaleimide

: 428855-45-2
2-(thiobenzoylmethyl)-1,3-butadiene

: thiobenzoic acid S-[1-(2-methyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-5-yl)-ethyl] ester

Conditions

Conditions	Yield
In benzene for 30h; Heating;	100%

: 930-88-1
N-methylmaleimide

: 118888-09-8
3,4-Di-tert-butylthiophene S-oxide

: (1R,2R,6S,7S)-8,9-Di-tert-butyl-4-methyl-10-oxo-10λ4-thia-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Diels-Alder reaction;	100%

: 930-88-1
N-methylmaleimide

: 609771-80-4
(E)-1-(4-ethoxypenta-2,4-dienyl)toluene

: (3aR,7aS)-6-Ethoxy-2-methyl-4-(2-methyl-benzyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
Diels-Alder reaction;	100%

: 930-88-1
N-methylmaleimide

: 380377-18-4
C32H24F6N2O6

: C37H29F6N3O8

Conditions

Conditions	Yield
for 0.0333333h; Diels-Alder reaction;	100%

: 930-88-1
N-methylmaleimide

: (2-aminoethanethiolato-N,S)bis(1,2-diaminoethane)cobalt(III) perchlorate

: [(en)2Co(S(CHCON(CH3)COCH2)CH2CH2NH2)](ClO4)3

Conditions

Conditions	Yield
With H(1+) In perchloric acid aq. HClO4; to the soln. of Co-compd. in aq. HClO4 was added an org. compd.; after 1-2 h the soln. was dild. with H2O; the react. mixt. was absorbed onto an ion-exchange column; washing with aq. HClO4, elution with NaClO4 (pH 2);; Ba(NO3)2 and K2SO4 were added; KClO4 and BaSO4 were removed by fitration; the soln. was condensed by rotoevapn. at 30°C and was filtered; addn. of HClO4, standing overnight at 8°C; recrystn. from HClO4, cooling for 4 h at the same temp.;;	100%

Yield

With H(1+) In perchloric acid aq. HClO4; to the soln. of Co-compd. in aq. HClO4 was added an org. compd.; after 1-2 h the soln. was dild. with H2O; the react. mixt. was absorbed onto an ion-exchange column; washing with aq. HClO4, elution with NaClO4 (pH 2);; Ba(NO3)2 and K2SO4 were added; KClO4 and BaSO4 were removed by fitration; the soln. was condensed by rotoevapn. at 30°C and was filtered; addn. of HClO4, standing overnight at 8°C; recrystn. from HClO4, cooling for 4 h at the same temp.;;

100%

: 930-88-1
N-methylmaleimide

: 93102-05-7
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

: 5-benzyl-2-methyl-tetrahydropyrrolo[3,4-c]pyrrole-1,3-dione

Conditions

Conditions	Yield
Stage #1: N-methylmaleimide With trifluoroacetic acid In dichloromethane at 0℃; Stage #2: N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine In dichloromethane at 5℃; for 24h;	100%

: 930-88-1
N-methylmaleimide

: 65060-93-7
N-methyl bromomaleimide

Conditions

Conditions	Yield
Stage #1: N-methylmaleimide With bromine In diethyl ether for 1h; Reflux; Stage #2: With triethylamine In diethyl ether at 0 - 18℃;	100%
Stage #1: N-methylmaleimide With bromine In methanol at 20℃; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 24h;	89%
Stage #1: N-methylmaleimide With bromine In methanol at 20℃; for 24h; Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 24h; Time;	89%

: 930-88-1
N-methylmaleimide

: 2,3-dimethyl-N-(quinolin-8-yl)benzamide

: 2,3-dimethyl-6-(1-methyl-2,5-dioxopyrrolidin-3-yl)-N-(quinolin-8-yl)benzamide

Conditions

Conditions	Yield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In toluene at 160℃; for 12h; regioselective reaction;	100%

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.

Product Name

N-Methylmaleimide

Synthetic route

N-Methylmaleimide Specification

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