Dimethyl maleate supplier | CasNO.624-48-6

Name
Dimethyl maleate
EINECS 210-848-5
CAS No. 624-48-6
Article Data150
CAS DataBase
Density 1.124 g/cm³
Solubility Miscible with water.
Melting Point -19 °C
Formula C₆H₈O₄
Boiling Point 193 °C at 760 mmHg
Molecular Weight 144.127
Flash Point 91.1 °C
Transport Information UN 2810 6.1/PG 3
Appearance colourless liquid
Safety 26-36/37-23
Risk Codes 21/22-36/37/38-43
Molecular Structure
Hazard Symbols Xn
Synonyms 2-Butenedioicacid (2Z)-, dimethyl ester (9CI);2-Butenedioic acid (Z)-, dimethyl ester;Maleic acid, dimethyl ester (6CI,8CI);(2Z)-2-Butenedioic acid dimethyl ester;(Z)-Dimethyl 2-butenedioate;Dimethyl (Z)-butenedioate;Dimethylcis-butenedioate;Dimethyl cis-ethenedicarboxylate;Dimethylcis-ethylenedicarboxylate;Methyl maleate;Sipomer DMM;
PSA 52.60000
LogP -0.11140

Synthetic route

: 67-56-1
methanol

: 110-16-7
maleic acid

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With boron trifluoride at 65℃; for 0.333333h;	100%
With sulfuric acid at 75℃; for 16h;	97%
With sulfuric acid at 75℃; for 16h; Reflux;	97%

: 762-42-5
dimethyl acetylenedicarboxylate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With hydrogen; montmorillonit-bipyridinpalladium(II)-acetate In tetrahydrofuran Ambient temperature;	98%
With isocyanate de chlorosulfonyle; hydrogen; palladium diacetate; borohydride exchange resin In ethanol for 2h;	98%
With borohydride exchange resin; hydrogen; nickel diacetate In methanol at -15℃; under 760 Torr; for 2h;	96%

: 108-31-6
maleic anhydride

: 1634-04-4
tert-butyl methyl ether

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With sulfuric acid at 10 - 20℃; regioselective reaction;	95%

: 108-31-6
maleic anhydride

: 67-56-1
methanol

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate at 120℃; for 1h; Catalytic behavior; Reagent/catalyst; Microwave irradiation;	94.59%
With acetyl chloride unter Lichtausschluss;

: dimethyl 2-(p-toluenesulfonamido)-3-(triphenylphosphoranylidene)butanedioate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 1058-14-6
N-p-tolylsulfonylphosphine imide

C: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
In toluene for 14h; Heating;	A n/a B 93% C n/a

...Expand

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 74-86-2
acetylene

A: 692-91-1, 692-92-2, 1119-43-3, 1733-37-5
cis,cis-dimethyl muconate

B: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

C: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
PdI2-KI at 60℃; under 19000 Torr; for 15h;	A 7% B 89% C 3%

...Expand

: dimethyl meso-tartrate cyclic sulfate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With magnesium iodide In acetonitrile for 0.5h; Ambient temperature;	88%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 74-86-2
acetylene

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
With hydrogenchloride; oxygen; copper dichloride; palladium dichloride under 1 Torr; for 2h;	A 86% B 14%

...Expand

: 6832-16-2
methyl diazoacetate

: 55261-56-8
3-morpholino-but-2-enoic acid methyl ester

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

: (1R,2R)-3-Methyl-3-morpholin-4-yl-cyclopropane-1,2-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
copper acetylacetonate In ethyl acetate Heating;	A n/a B n/a C 86%

...Expand

: 762-42-5
dimethyl acetylenedicarboxylate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 106-65-0
Dimethyl succinate

Conditions

Conditions	Yield
palladium anchored polystyrene In diethyl ether at 25℃; under 1551.4 Torr; for 18h;	A 84% B 4%
With hydrogen; ethylenediamine; Pd on pumice In tetrahydrofuran for 0.5h;	A 94 % Chromat. B 6 % Chromat.
With [Pd(p-benzoquinone)(1,3-dimesitylimidazol-2-ylidene)]2; hydrogen In tetrahydrofuran at 20℃; under 750.06 Torr;

: 23652-59-7
4-(pyrrolidin-1-yl)pent-3-en-2-one

: 6832-16-2
methyl diazoacetate

A: 85392-47-8
methyl 2-acetyl-4-oxovalerate

B: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

C: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
copper(I) triflate In dichloromethane at 20℃; for 24h;	A 84% B n/a C n/a

...Expand

: 6832-16-2
methyl diazoacetate

: 137201-66-2
E-methyl β-morpholino-cinnamate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

: (1R,2R)-3-Morpholin-4-yl-3-phenyl-cyclopropane-1,2-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
copper acetylacetonate In ethyl acetate Heating;	A n/a B n/a C 84%

...Expand

: 6832-16-2
methyl diazoacetate

: (E)-3-Morpholin-4-yl-3,N-diphenyl-acrylamide

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

: (1R,3R)-2-Morpholin-4-yl-2-phenyl-3-phenylcarbamoyl-cyclopropanecarboxylic acid methyl ester

Conditions

Conditions	Yield
copper acetylacetonate In ethyl acetate Heating;	A n/a B n/a C 83%

...Expand

: 80306-63-4
dimethyl acetylenedicarboxylate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 106-65-0
Dimethyl succinate

Conditions

Conditions	Yield
With 1,1,3,3-Tetramethyldisiloxane In dichloromethane at 25℃; for 24h;	A 82% B n/a

: 3277-26-7
1,1,3,3-Tetramethyldisiloxane

: 762-42-5
dimethyl acetylenedicarboxylate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 106-65-0
Dimethyl succinate

Conditions

Conditions	Yield
With gold on titanium oxide In dichloromethane at 25℃; for 24h;	A 82% B n/a

...Expand

: 762-42-5
dimethyl acetylenedicarboxylate

A: 89330-93-8
dimethyl phenylmaleate

B: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

C: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
With cyclopentadienylchromiumtricarbonyl hydride In benzene Inert atmosphere;	A 76% B 17% C 5%

...Expand

: 70008-80-9
3-morpholin-4-yl-1-phenyl-but-2-en-1-one

: 6832-16-2
methyl diazoacetate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 75519-84-5
3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid methyl ester

C: 624-49-7
dimethylfumarate

D: 3-Methyl-5-phenyl-furan-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
copper(I) triflate In dichloromethane at 20℃;	A n/a B 73% C n/a D 4%

...Expand

: 1634-04-4
tert-butyl methyl ether

: 110-16-7
maleic acid

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With sulfuric acid Reflux; regioselective reaction;	73%

: 489-84-9
7-isopropyl-1,4-dimethyl-azulene

: 762-42-5
dimethyl acetylenedicarboxylate

A: 98525-07-6, 72898-39-6, 98525-12-3, 98525-13-4
dimethyl 1,6-dimethyl-9-(1-methylethyl)heptalene-4,5-dicarboxylate

B: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

C: 145948-88-5
dimethyl (E)-1-(5'-isopropyl-3',8'-dimethylazulen-1-yl)-ethene-1,2-dicarboxylate

D: 145948-89-6
dimethyl (Z)-1-(5-isopropyl-3,8-dimethylazulen-1-yl)ethene-1,2-dicarboxylate

E: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
In acetonitrile at 100℃; for 4h; Mechanism; other solvents, other substrates;	A 71% B 1% C 15% D 11% E 1%

...Expand

: 70008-81-0
(E)-3-morpholin-4-yl-1,3-diphenylpropenone

: 6832-16-2
methyl diazoacetate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 90904-37-3
methyl α,β-dibenzoyl-propionate

C: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
copper(I) triflate In dichloromethane at 20℃;	A n/a B 70% C n/a

...Expand

: 67-56-1
methanol

: 141-05-9
Diethyl maleate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With Merrifield resin-supported N3=P(MeNCH2CH2)3N at 23 - 25℃; for 2.5h; Inert atmosphere;	70%

: 762-42-5
dimethyl acetylenedicarboxylate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
With formic acid; dihydridotetrakis(triphenylphosphine)ruthenium In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; optical yield given as %de; stereoselective reaction;	A 23% B 68%
With 1-n-butyronitrile-2,3-dimethylimidazolium bis(trifluoromethanesulfonimide); nickel; hydrogen In cyclohexane at 30℃; under 3000.3 Torr; for 6h; Autoclave; Glovebox;	A 26% B n/a
palladium at 100℃; for 160h; Yield given. Yields of byproduct given;

: 513-37-1
2-methylprop-1-enyl chloride

: 6832-16-2
methyl diazoacetate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

: methyl 3-chloro-2,2-dimethylcyclopropane-1-carboxylate

: methyl 3-chloro-2,2-dimethylcyclopropane-1-carboxylate

Conditions

Conditions	Yield
[Ru2(CO)4(OAc)2]n In dichloromethane Title compound not separated from byproducts;	A 55% B 19% C n/a D n/a

...Expand

: 67-56-1
methanol

: 140-98-7
N-carbamoyl-maleamic acid butyl ester

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
Amberlyst sulfonic acid resin Heating / reflux;	50%

: 55667-43-1
1,1-dichloro-4-methyl-penta-1,3-diene

: 6832-16-2
methyl diazoacetate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 61976-30-5
methyl 2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane-1-carboxylate

: 59897-93-7, 59897-94-8, 61898-95-1, 61976-30-5, 61976-31-6, 63805-74-3, 74561-29-8, 84984-65-6, 84984-66-7
methyl trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

D: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
[Ru2(CO)4(OAc)2]n In dichloromethane Title compound not separated from byproducts;	A 48% B n/a C n/a D 18%

...Expand

: 563-79-1
2,3-Dimethyl-2-butene

: 6832-16-2
methyl diazoacetate

A: 2415-95-4
ethyl 2,2,3,3-tetramethylcyclopropanecarboxylate

B: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

C: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 16h;	A 47% B 36% C 15%

...Expand

: 463-49-0
1,2-propanediene

: 6832-16-2
methyl diazoacetate

A: 88787-23-9
2-methoxycarbonyl-1-methylenecyclopropane

B: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With copper(II) oxide at 150℃; further temperatures and catalysts;	A 46.5% B 15%

...Expand

: 5176-27-2
N-tert-butyloxycarbonyl-pyrrole

: 6832-16-2
methyl diazoacetate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

: (+/-)-(1R,5R,6R)-2-tert-butyl 6-methyl 2-azabicyclo[3.1.0]hex-3-ene-2,6-dicarboxylate

: 5-azatricyclo[4.1.0.02,4]heptane-3,5,7-tricarboxylic acid 5-tert-butyl ester 3,7-dimethyl ester

Conditions

Conditions	Yield
copper(II) bis(trifluoromethanesulfonate); phenylhydrazine In dichloromethane at 20℃; for 18h;	A n/a B n/a C 39% D 3%

...Expand

: 617-90-3
2-furancarbonitrile

: 6832-16-2
methyl diazoacetate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 121262-23-5
3-cyano-6-methoxycarbonyl-2-oxabicyclo<3.1.0>hex-3-ene

C: 121262-24-6
2-Furan-2-yl-5-methoxy-oxazole

Conditions

Conditions	Yield
With rhodium(II) acetate	A n/a B 12% C 36%

...Expand

: 89141-08-2
Methyl thioglyoxylate

: 21204-67-1
methyl (triphenylphosphoranylidene)acetate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
In toluene Heating;	35%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
With 1-hexylimidazolium DL-lactate at 70℃; for 24h; Kinetics; Product distribution; Further Variations:; Reagents; Temperatures;	100%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane Heating;	100%
With bromine In dichloromethane at 50℃; for 5h; Irradiation;	98%

: 542-92-7
cyclopenta-1,3-diene

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 39589-98-5
endo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic dimethyl ester

Conditions

Conditions	Yield
at 20℃; for 8h; Diels-Alder cycloaddition;	100%
With 3-(n-butoxycarbonyl)-1-methylpyridinium bis(trifluoromethanesulfonyl)imide at 20℃; for 18h; Diels-Alder reaction; optical yield given as %de; diastereoselective reaction;	95%

: 7467-00-7
3-(2-oxo-2-phenylethyl)-1,3-benzothiazol-3-ium bromide

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 78113-54-9, 78184-05-1
(1S,2S,3S,3aR)-1-Benzoyl-1,2,3,3a-tetrahydro-benzo[d]pyrrolo[2,1-b]thiazole-2,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With triethylamine In chloroform for 0.333333h;	100%

: 39595-94-3
2-(cyanomethyl)isoquinolin-2-ium bromide

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: (1S,2R,3R,10bR)-3-Cyano-1,2,3,10b-tetrahydro-pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylic acid dimethyl ester

Conditions

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

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 90330-49-7
3-(methoxymethylene)-2,4-bis(trimethylsilyloxy)-1,4-pentadiene

: 3-Methoxy-5-trimethylsilanyloxy-4-(1-trimethylsilanyloxy-vinyl)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
In benzene for 72h; Heating;	100%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 106-65-0
Dimethyl succinate

Conditions

Conditions	Yield
With silica gel-supported amine In water Electrochemical reaction;	100%
With ammonium formate; silica gel; palladium dichloride In formic acid; water for 0.133333h; microwave irradiation;	81%
With E. coli BL21(DE3) at 37℃; for 12h; Sealed tube; Microbiological reaction; stereoselective reaction;	78%

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

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 82959-82-8, 82959-83-9, 82959-84-0, 82959-85-1
(3R,4R)-2-Phenyl-pyrrolidine-3,4-dicarboxylic acid dimethyl ester

Conditions

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

: 28663-68-5
ethyl chloro(2-phenylhydrazono)acetate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: (4S,5R)-1-Phenyl-4,5-dihydro-1H-pyrazole-3,4,5-tricarboxylic acid 3-ethyl ester 4,5-dimethyl ester

Conditions

Conditions	Yield
With triethylamine In chloroform for 2h; Heating;	100%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 108303-84-0
[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-trimethylsilanylmethyl-amine

: 2-({[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-methyl)-succinic acid dimethyl ester

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; water In tetrahydrofuran at 0℃; for 0.5h;	100%

: 107554-42-7
benzylidene(cyano)benzylamine

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 19054-95-6, 41414-08-8, 41414-09-9, 41414-10-2, 41414-11-3
3,4-dimethoxycarbonyl-2,5-diphenyl-1-pyrrolidine

Conditions

Conditions	Yield
In benzene for 15h; Heating;	100%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: Trifluoro-methanesulfonate2,5-diphenyl-3-trimethylsilanylmethyl-[1,3,4]oxadiazol-3-ium;

: 1-Benzoylamino-5-phenyl-2,3-dihydro-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With cesium fluoride In dichloromethane at -60℃; for 120h;	100%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: C14H34O2Si4

: C20H42O6Si4

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 80℃; for 3h; Addition;	100%

: 41078-15-3
3-aminothieno<3,4:3',4'>benzopyran-4-one

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: dimethyl 4-aminobenzocoumarin-2,3-dicarboxylate

Conditions

Conditions	Yield
Heating;	100%

: 20433-10-7
5-(4-methoxyphenyl)-2-phenyl-2H-tetrazole

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: (4SR,5SR)-dimethyl 3-(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole-4,5-dicarboxylate

Conditions

Conditions	Yield
In ethyl acetate for 2h; UV-irradiation;	100%

: 117753-93-2
(P(CH2CH2P(C6H5)2)3)Co(H2)(1+)*PF6(1-) = (P(CH2CH2P(C6H5)2)3)CoH2PF6

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
In tetrahydrofuran	100%

: 111-81-9
Methyl 10-undecenoate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

A: 70086-90-7
dimethyl dodec-2-en-1,12-dioate

B: 292638-85-8
acrylic acid methyl ester

Conditions

Conditions	Yield
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In toluene at 50℃; for 3h; Reagent/catalyst; Temperature;	A 100% B n/a

...Expand

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 109-89-7
diethylamine

: 17459-44-8
dimethyl (diethylamino)ethylene-1,2-dicarboxylate

Conditions

Conditions	Yield
With Kuganak montmorillonite at 20℃; for 1.5h; Michael addition;	99%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: (1R,4S)-1,7,7-Trimethyl-3-[1-phenyl-meth-(E)-ylidene]-bicyclo[2.2.1]heptane-2-thione

: (1R,4S,5S,6S,8S)-1,11,11-Trimethyl-6-phenyl-3-thia-tricyclo[6.2.1.02,7]undec-2(7)-ene-4,5-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at 20℃; for 0.166667h; Cycloaddition;	99%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: (1R,4S)-1,7,7-Trimethyl-3-[1-p-tolyl-meth-(E)-ylidene]-bicyclo[2.2.1]heptane-2-thione

: (1R,4S,5S,6S,8S)-1,11,11-Trimethyl-6-p-tolyl-3-thia-tricyclo[6.2.1.02,7]undec-2(7)-ene-4,5-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at 20℃; for 0.166667h; Cycloaddition;	99%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: (1R,4S)-3-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2-thione

: (1R,4S,5S,6S,8S)-6-(4-Methoxy-phenyl)-1,11,11-trimethyl-3-thia-tricyclo[6.2.1.02,7]undec-2(7)-ene-4,5-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at 20℃; for 0.166667h; Cycloaddition;	99%

: 542-92-7
cyclopenta-1,3-diene

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 5826-73-3
dimethyl carbate

Conditions

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; for 6h; Cycloaddition; Diels-Alder reaction;	99%
With C8H17OH; acetic anhydride; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; for 12h; Diels-Alder reaction;	94%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 76862-10-7
(E)-[(4-methyl-benzylidene)-amino]-acetic acid methyl ester

: trimethyl (2S,3R,4S,5R)-5-(4-methylphenyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With chiral ferrocenyloxazoline-based ligand; silver(I) acetate In diethyl ether at -25℃; for 3h;	99%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 76862-09-4
(E)-methyl 2-((4-chlorobenzylidene)amino)acetate

: trimethyl (2S,3R,4S,5R)-5-(4-chlorophenyl)pyrroli-dine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With chiral ferrocenyloxazoline-based ligand; silver(I) acetate In diethyl ether at -25℃; for 3h;	99%

: CpRuCl(.sigam.,σ-N,N`-1,4-di-i-propyl-1,4-diaza-1,3-butadiene)

: 2923-28-6
silver trifluoromethanesulfonate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: cyclopentadienyl(1,4-diisopropyl-1,3-diazabutadiene)(η2-dimethyl maleate)ruthenium trifluoromethanesulfonate

Conditions

Conditions	Yield
In tetrahydrofuran under N2; approx. equimolar amts. Ru-complex and Ag salt dissolved in THF, mixt. stirred (room temp., 15 min), formation of intermediate, suspn. filtered, red-brown soln. cooled to 0°C, addn. of the maleate, pptn. within 15 min; filtered, elem. anal.;	99%

...Expand

: [Pt(η(3)-CH3CHC6H5)(Bu(t)2P(CH2)3PBu(t)2)][BF4]

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 198825-64-8
Pt(CH(CO2CH3)CH2COOCH3)(((CH3)3C)2P(CH2)3P(C(CH3)3)2)(1+)*BF4(1-)=[Pt(CH(CO2CH3)CH2CO2CH3)((C4H9)2P(CH2)3P(C4H9)2)]BF4

Conditions

Conditions	Yield
In dichloromethane byproducts: CH2=CHC6H5; absence of air and moisture; excess alkene, 0.5 h; solvent removal (vac.), washing (hexane), drying (vac.), recrystn. (CH2Cl2/Et2O); elem. anal.;	99%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 60-34-4
methylhydrazine

: methyl 2-methyl-5-oxopyrazolidine-3-carboxylate hydrobromide

Conditions

Conditions	Yield
Stage #1: methylhydrazine With potassium hydroxide In isopropyl alcohol at 60 - 65℃; Inert atmosphere; Stage #2: dimethyl cis-but-2-ene-1,4-dioate In isopropyl alcohol at 5 - 25℃; for 16h; Inert atmosphere; Stage #3: With Acetyl bromide In isopropyl alcohol at 20 - 25℃; for 0.2h; Inert atmosphere;	99%

: 104-87-0
4-methyl-benzaldehyde

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: dimethyl 2-(4-methylbenzoyl)butanedioate

Conditions

Conditions	Yield
With [Ir(dF(CF3)ppy)2(dtbbpy)]Cl In benzene for 16h; Sealed tube; Irradiation; Heating; Inert atmosphere;	99%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: dimethyl 2-(2-(triphenyl phosphaneylidene)acetyl)succinate

Conditions

Conditions	Yield
With [Ir(dF(CF3)ppy)2(dtbbpy)]Cl In benzene for 16h; Sealed tube; Irradiation; Heating; Inert atmosphere;	99%

: 623-73-4
diazoacetic acid ethyl ester

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 586-96-9
Nitrosobenzene

: 3-ethyl 4,5-dimethyl 2-phenylisoxazolidine-3,4,5-tricarboxylate

Conditions

Conditions	Yield
With potassium acetate In 1,2-dichloro-ethane at 50℃; for 24h;	99%

...Expand

Dimethyl maleate Chemical Properties

Molecular Structure:

Molecular Formula: C₆H₈O₄
Molecular Weight: 144.1253
IUPAC Name: Dimethyl (Z)-but-2-enedioate
Synonyms of Dimethyl maleate (CAS NO.624-48-6): 2-Butenedioic acid, dimethyl ester, (Z)- ; 4-02-00-02204 (Beilstein Handbook Reference) ; AI3-07869 ; BRN 0471705 ; Dimethyl cis-butenedioate ; Dimethyl cis-ethylenedicarboxylate ; Dimethylester kyseliny maleinove ; Dimethylester kyseliny maleinove [Czech] ; EINECS 210-848-5 ; Maleic acid, dimethyl ester ; Methyl maleate ; NSC 5161 ; Sipomer DMM ; 2-Butenedioic acid (2Z)-, 1,4-dimethyl ester ; 2-Butenedioic acid (2Z)-, dimethyl ester ; 2-Butenedioic acid (Z)-, dimethyl ester ; Maleic acid, dimethyl ester (8CI)
CAS NO: 624-48-6
Classification Code: Skin / Eye Irritant
Melting point: -19°C
Index of Refraction: 1.435
Molar Refractivity: 33.45 cm³
Molar Volume: 128.1 cm³
Surface Tension: 33.1 dyne/cm
Density: 1.124 g/cm³
Flash Point: 91.1 °C
Enthalpy of Vaporization: 42.92 kJ/mol
Boiling Point: 193 °C at 760 mmHg
Vapour Pressure: 0.475 mmHg at 25°C

Dimethyl maleate Uses

Dimethyl maleate (CAS NO.624-48-6) is used in many organic syntheses as a dienophile for diene synthesis. It is used as an additive and intermediate for plastics, pigments, pharmaceuticals, and agricultural products. It is also an intermediate for the production of paints, adhesives, and copolymers. It has also found use in applications where improvements in the hardness and toughness of polymer films are desired. This includes, in particular, the improvement of anti-blocking properties of copolymers of vinyl acetate with DMM. It is also used as an internal modifier to increase the glass transition temperature of styrene or vinyl chloride polymers.

Dimethyl maleate Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LC	inhalation	> 1500mg/m3/10 (1500mg/m3)	National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. Aug, 1942.
rabbit	LD50	skin	530uL/kg (0.53mL/kg)	American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
rat	LD50	oral	1410mg/kg (1410mg/kg)	American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.

Dimethyl maleate Consensus Reports

Reported in EPA TSCA Inventory.

Dimethyl maleate Safety Profile

Moderately toxic by ingestion and skin contact. An eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO₂, dry chemical. Safety Information of Dimethyl maleate (CAS NO.624-48-6):
Hazard Codes : Xn
Xn : Harmful
Risk Statements :21/22-36/37/38-43 ( Harmful in contact with skin and if swallowed ; Irritating to eyes, respiratory system and skin ;May cause sensitization by skin contact )
Safety Statements: 26-36/37-23 ( In case of contact with eyes, rinse immediately with plenty of water and seek medical advice ; Wear suitable protective clothing and gloves ;Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) )
RIDADR UN 2810 6.1/PG 3
WGK Germany 1
RTECS EM6300000
HazardClass 6.1(b)
PackingGroup III
HS Code 29171990

Product Name

Dimethyl maleate

Synthetic route

Dimethyl maleate Chemical Properties

Dimethyl maleate Uses

Dimethyl maleate Toxicity Data With Reference

Dimethyl maleate Consensus Reports

Dimethyl maleate Safety Profile

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