Diethyl maleate supplier | CasNO.141-05-9

Name
Diethyl maleate
EINECS 205-451-9
CAS No. 141-05-9
Article Data201
CAS DataBase
Density 1.068 g/cm³
Solubility insoluble in water
Melting Point -10 °C
Formula C₈H₁₂O₄
Boiling Point 214 °C at 760 mmHg
Molecular Weight 172.181
Flash Point 93.3 °C
Transport Information
Appearance colourless liquid
Safety 26-36/37-37-24
Risk Codes 36-43
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Butenedioicacid (2Z)-, diethyl ester (9CI);2-Butenedioic acid (Z)-, diethyl ester;Maleicacid, diethyl ester (6CI,8CI);(2Z)-2-Butenedioic acid diethyl ester;Diethyl(Z)-2-butenedioate;2-Butenedioicacid (2Z)-, 1,4-diethyl ester;Ethyl maleate;Staflex DEM;
PSA 52.60000
LogP 0.66880

Synthetic route

: 763-51-9
diethyl 2-bromosuccinate

: 327-62-8
potassium propionate

: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 20h;	100%

: 327-62-8
potassium propionate

: 99967-60-9
2-(Methylsulfonyloxy)-diethylester

: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 20h;	100%

: 608-82-2, 1114-30-3, 1114-31-4, 40205-59-2
diethyl dl-dibromosuccinate

A: 623-91-6
diethyl Fumarate

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With N-benzyl-1,4-dihydronicotinamide In acetonitrile at 49.9℃; for 7h;	A 100% B n/a

: 623-73-4
diazoacetic acid ethyl ester

: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With trans-IICl2(pyboxip)(=CHSiMe3)> Ambient temperature;	98%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 15h;	95%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃;	95%

: 623-73-4
diazoacetic acid ethyl ester

: 104575-54-4
N-(2-naphthalenylmethylene)butane-1-amine

: (2R,3S)-1-Butyl-3-naphthalen-2-yl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 96% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 172367-39-4
N-(2-naphthalenylmethylene)hexane-1-amine

: (2R,3S)-1-Hexyl-3-naphthalen-2-yl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 96% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 627463-17-6
4-bromo-2-fluoro-1-vinylbenzene

A: 934995-82-1
C12H12BrFO2

: C12H12BrFO2

C: 623-91-6
diethyl Fumarate

D: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With aluminum oxide; potassium carbonate; copper(I) trifluoromethanesulfonate benzene; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] In chloroform at 0 - 20℃; for 24 - 25h; Product distribution / selectivity;	A n/a B 96% C n/a D n/a
copper(I) trifluoromethanesulfonate benzene; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] In ethyl acetate at 0 - 20℃; for 24 - 25h; Product distribution / selectivity;	A n/a B n/a C n/a D n/a
copper(I) trifluoromethanesulfonate benzene; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] In toluene at 0 - 20℃; for 24 - 25h; Product distribution / selectivity; Molecular sieve;	A n/a B n/a C n/a D n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 3910-55-2
N-(p-methoxybenzylidene)butylamine

: (2R,3S)-1-Butyl-3-(4-methoxy-phenyl)-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 94% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 53054-00-5
N-hexyl-1-(4-methoxyphenyl)methanimine

: (2R,3S)-1-Hexyl-3-(4-methoxy-phenyl)-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 94% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 19340-96-6
N-benzylidenehexylamine

: (2R,3S)-1-Hexyl-3-phenyl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 93% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 7020-93-1
butyl-(4-methyl-benzyliden)-amine

: (2R,3S)-1-Butyl-3-p-tolyl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 93% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 53053-99-9
N-hexyl-1-(4-methylphenyl)methanimine

: (2R,3S)-1-Hexyl-3-p-tolyl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 93% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 836-41-9
p-methoxybenzylidene-phenylamine

: (2S,3R)-3-(4-Methoxy-phenyl)-1-phenyl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 92% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 1077-18-5
N-benzylidenebutan-1-amine

: trans 1-butyl-3-phenylaziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 92% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 172367-38-3
N-(4-nitrobenzylidene)hexan-1-amine

: (2R,3S)-1-Hexyl-3-(4-nitro-phenyl)-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 92% B n/a

...Expand

: 762-42-5
dimethyl acetylenedicarboxylate

: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With {(Rh[((1S,1'S,2R,2’R)-1,1’-di-tert-butyl-(2,2’)-diphospholane)]H)3(μ2-H)3(μ3-H)}(BF4)2; hydrogen In methanol at 30℃; under 757.576 Torr; for 1.83333h; Inert atmosphere; Schlenk technique;	92%

: 623-73-4
diazoacetic acid ethyl ester

: 89414-89-1
3α,7β-diacetoxy-24-nor-5β-chol-22-ene

A: 89414-90-4, 89495-32-9, 89495-33-0, 89495-34-1, 91423-34-6
(E)-ethyl 3α,7β-diacetoxy-22,23-methylene-5β-cholan-24-oate

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With dirhodium tetraacetate In dichloromethane	A 91.6% B 0.52 g

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 764-13-6
2,5-Dimethyl-2,4-hexadiene

A: 97-41-6
ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

B: 623-91-6
diethyl Fumarate

C: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
hexarhodium hexadecacarbonyl at 60℃; for 7h;	A 91% B n/a C n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 25105-94-6
N-(4-nitrophenylmethylidene)-n-butylamine

: (2R,3S)-1-Butyl-3-(4-nitro-phenyl)-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 91% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 131559-05-2
N-tert-butyliminoaniline

A: 3-tert-Butyl-1-phenyl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
copper(II) bis(trifluoromethanesulfonate) In dichloromethane at -25℃;	A 90% B n/a

...Expand

: 108-31-6
maleic anhydride

: 64-17-5
ethanol

: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate at 120℃; for 1h; Reagent/catalyst; Microwave irradiation;	88.39%
With sulfuric acid
With sulfuric acid; benzene

: 623-73-4
diazoacetic acid ethyl ester

: 110-83-8
cyclohexene

A: 52917-64-3
ethyl 7-norcaranecarboxylate

B: 623-91-6
diethyl Fumarate

C: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
hexarhodium hexadecacarbonyl at 25℃; for 7h;	A 88% B n/a C n/a
ruthenacarborane 3 at 60℃; for 4h;	A 79 % Chromat. B n/a C n/a

...Expand

: 292638-84-7
styrene

: 623-73-4
diazoacetic acid ethyl ester

A: 946-38-3, 946-39-4, 34702-96-0, 34702-97-1, 34703-00-9, 34716-60-4, 63038-62-0, 63038-63-1, 97-71-2
ethyl 2-phenylcyclopropylcarboxylate

B: 623-91-6
diethyl Fumarate

C: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
hexarhodium hexadecacarbonyl at 25℃; for 7h;	A 87% B n/a C n/a
ruthenacarborane 3 at 60℃; for 4h;	A 93 % Chromat. B n/a C n/a
With palladium(II) trimethylacetate In toluene at 30℃; for 0.65h; stereoselective reaction;	A 83.16 %Chromat. B n/a C n/a
With phenol In dichloromethane at 20℃; Inert atmosphere;	A 72 %Spectr. B n/a C n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 111-34-2
-butyl vinyl ether

A: 78932-45-3
ethyl 2-butoxycyclopropanecarboxylate

B: 623-91-6
diethyl Fumarate

C: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
hexarhodium hexadecacarbonyl at 25℃; for 7h;	A 87% B n/a C n/a
ruthenacarborane 1 at 60℃; for 4h;	A 93 % Chromat. B n/a C n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 538-51-2
benzylidene phenylamine

: 20414-50-0, 20414-52-2, 49790-76-3
ethyl trans-1,3-diphenylaziridine-2-carboxylate

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 87% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 91-78-1
1,3,5-triphenylhexahydro-1,3,5-triazine

A: 147454-97-5
ethyl 1-phenylaziridine-2-carboxylate

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 0℃; for 4h;	A 85% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 4784-77-4, 29576-14-5, 39616-19-8
(E/Z)-crotyl bromide

A: 79357-22-5
Ethyl 2-bromo-3-methyl-4-pentenoate

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With [Ru(CO)(ttppp)] In dichloromethane at 20℃; Inert atmosphere; optical yield given as %de;	A 84% B n/a

...Expand

: 110-87-2
3,4-dihydro-2H-pyran

: 623-73-4
diazoacetic acid ethyl ester

A: 72229-08-4
ethyl 2-oxabicyclo<4.1.0>heptane-7-carboxylate

B: 623-91-6
diethyl Fumarate

C: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
hexarhodium hexadecacarbonyl at 25℃; for 1.5h;	A 82% B n/a C n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 928-49-4
hex-3-yne

A: 623-91-6
diethyl Fumarate

B: Ethyl 2,3-diethylcycloprop-1-enecarboxylate

C: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
copper(I) hydrotris(3,5-dimethylpyrazol-1-yl)borate In 1,2-dichloro-ethane at 20℃;	A n/a B 82% C n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 1458-98-6
2-methyl-3-bromo-1-propene

A: ethyl 2-bromo-4-methyl-4-pentenoate

B: 623-91-6
diethyl Fumarate

C: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With [Ru(CO)(ttppp)] In dichloromethane at 20℃; Inert atmosphere; optical yield given as %de;	A 81% B n/a C n/a
With (5,10,15,20-tetramesitylporphyrinato)ruthenium(II) carbonyl In dichloromethane at 20℃; Inert atmosphere; optical yield given as %de;	A 6% B n/a C n/a

...Expand

: 107-15-3
ethylenediamine

: 141-05-9
Diethyl maleate

: 33422-35-4
ethyl 2-(3-oxopiperazin-2-yl)acetate

Conditions

Conditions	Yield
In propan-1-ol at 55℃; for 16h;	100%
In isopropyl alcohol at 55℃; for 18h;	76%
In isopropyl alcohol at 55℃; for 6h;	60.8%

: 124-13-0
Octanal

: 141-05-9
Diethyl maleate

: 73642-72-5
2-Octanoylbutandisaeure-diethylester

Conditions

Conditions	Yield
With 4-cyanobenzaldehyde In Petroleum ether at 20℃; for 16h; Reagent/catalyst; Sealed tube; Irradiation;	100%
With dibenzoyl peroxide
With dibenzoyl peroxide

: 156-41-2
4-chlorophenylethylamine

: 141-05-9
Diethyl maleate

: 1,4-diethyl 2-{[2-(4-chlorophenyl)ethyl]amino}butanedioate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 1.5h;	100%
In acetonitrile at 20℃; for 1.5h;	100%

: 141-05-9
Diethyl maleate

: 623-91-6
diethyl Fumarate

Conditions

Conditions	Yield
With diphenyldisulfane In hexane for 24h; Isomerization; Irradiation; reflux;	99%
With C16H25N3O2S In acetonitrile at 80℃; for 16h;	99%
With triphenylphosphine In water at 120℃; for 30h; Product distribution; Mechanism; other phosphines;	80%

aqueous hydroxylamine sulfate: aqueous hydroxylamine sulfate

: 141-05-9
Diethyl maleate

: 146328-23-6
diethyl N-hydroxyaspartate

Conditions

Conditions	Yield
With sodium hydroxide; sodium sulfate In ethanol	99%

: 623-73-4
diazoacetic acid ethyl ester

: 586-96-9
Nitrosobenzene

: 141-05-9
Diethyl maleate

: triethyl 2-phenylisoxazolidine-3,4,5-tricarboxylate

Conditions

Conditions	Yield
With potassium acetate In 1,2-dichloro-ethane at 50℃; for 24h;	99%
With C50H40N4O2Ru In dichloromethane at 20℃; for 4h; diastereoselective reaction;	95%
With trifluorormethanesulfonic acid In dichloromethane at 23℃; diastereoselective reaction;	77%

...Expand

: 30433-91-1
[2-(2-thyenyl)ethyl]amine

: 141-05-9
Diethyl maleate

: 1,4-diethyl 2-{[2-(thiophen-2-yl)ethyl]amino}butanedioate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 16h;	99%
In acetonitrile at 20℃; for 16h;	99%

: methyl 2-(1-naphthalenemethyleneamino)acetate

: 141-05-9
Diethyl maleate

: 3,4-diethyl 2-methyl 5-(naphthalen-1-yl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With 2-(diphenylphosphino)-N-((S)-3-methyl-1-oxo-1-(((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; Inert atmosphere; enantioselective reaction;	99%

: (S)-2-{[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-amino}-propionic acid methyl ester

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 5-(4-fluorophenyl)-2-methylpyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With 2-(diphenylphosphino)-N-((S)-3-methyl-1-oxo-1-(((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; for 48h; Inert atmosphere; enantioselective reaction;	99%

: 66646-88-6
methyl 2-(benzylideneamino)acetate

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 5-phenylpyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With N-((S)-3,3-dimethyl-1-oxo-1-(((S)-1-phenylethyl)amino)butan-2-yl)-2-(diphenylphosphino)benzamide; triethylamine; silver carbonate In toluene at 20℃; for 3h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;	99%
With 2-(diphenylphosphino)-N-((S)-3-methyl-1-oxo-1-(((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; enantioselective reaction;	96%
With 2-(diphenylphosphino)-N-((S)-2-(((1S,2S)-2-(isobutylamino)-1,2-diphenylethyl)amino)-2-oxo-1-phenylethyl)benzamide; silver carbonate In toluene at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere;	94%
With N-((S)-2-(((S)-2-(dimethylamino)-1-phenylethyl)amino)-2-oxo-1-phenylethyl)-2-(diphenylphosphino)benzamide; silver carbonate In toluene at 20℃; for 3h; Inert atmosphere; Darkness; enantioselective reaction;	93%
With (S)-2-(diphenylphosphino)-N-(1-((2-(isobutylamino)benzyl)amino)-3,3-dimethyl-1-oxobutan-2-yl)benzamide; silver(l) oxide In toluene at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; Temperature; stereoselective reaction;	90%

: [(4-methyl-benzylidene)-amino]-acetic acid methyl ester

: 141-05-9
Diethyl maleate

: (2R,3S,4R,5S)-3,4-diethyl 2-methyl 5-(p-tolyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With N-((R)-2-(((S)-2-(dimethylamino)-1-phenylethyl)amino)-2-oxo-1-phenylethyl)-2-(diphenylphosphino)benzamide; silver carbonate In toluene at 20℃; for 3h; Inert atmosphere; Darkness; enantioselective reaction;	99%
With 2-(diphenylphosphino)-N-((R)-3-methyl-1-oxo-1-(((R)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; Inert atmosphere; enantioselective reaction;	91%

: 479499-37-1
(4-fluorobenzylideneamino)acetic acid methyl ester

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 5-(4-fluorophenyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With N-((S)-3,3-dimethyl-1-oxo-1-(((S)-1-phenylethyl)amino)butan-2-yl)-2-(diphenylphosphino)benzamide; triethylamine; silver carbonate In toluene at 20℃; for 18h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;	99%
With 2-(diphenylphosphino)-N-((S)-2-(((1S,2S)-2-(isobutylamino)-1,2-diphenylethyl)amino)-2-oxo-1-phenylethyl)benzamide; silver carbonate In toluene at 20℃; for 2h; Inert atmosphere;	95%
With 2-(diphenylphosphino)-N-((S)-3-methyl-1-oxo-1-(((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; Inert atmosphere; enantioselective reaction;	93%
With (S)-2-(diphenylphosphino)-N-(1-((2-(isobutylamino)benzyl)amino)-3,3-dimethyl-1-oxobutan-2-yl)benzamide; silver(l) oxide In toluene at 20℃; for 2h; stereoselective reaction;	90%
With N-((S)-2-(((S)-2-(dimethylamino)-1-phenylethyl)amino)-2-oxo-1-phenylethyl)-2-(diphenylphosphino)benzamide; silver carbonate In toluene at 20℃; for 2.5h; Inert atmosphere; Darkness; enantioselective reaction;	84%

: 479499-37-1
(4-fluorobenzylideneamino)acetic acid methyl ester

: 141-05-9
Diethyl maleate

: (2R,3S,4R,5S)-3,4-diethyl 2-methyl 5-(4-fluorophenyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With 2-(diphenylphosphino)-N-((R)-3-methyl-1-oxo-1-(((R)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; Inert atmosphere; enantioselective reaction;	99%
With N-((R)-2-(((S)-2-(dimethylamino)-1-phenylethyl)amino)-2-oxo-1-phenylethyl)-2-(diphenylphosphino)benzamide; silver carbonate In toluene at 20℃; for 3h; Inert atmosphere; Darkness; enantioselective reaction;	82%

: 76862-09-4
methyl N-(4-chlorobenzylidene)glycinate

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 5-(4-chlorophenyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With 2-(diphenylphosphino)-N-((S)-3-methyl-1-oxo-1-(((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; Inert atmosphere; enantioselective reaction;	99%
With N-((S)-3,3-dimethyl-1-oxo-1-(((S)-1-phenylethyl)amino)butan-2-yl)-2-(diphenylphosphino)benzamide; triethylamine; silver carbonate In toluene at 20℃; for 5h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;	99%
With 2-(diphenylphosphino)-N-((S)-2-(((1S,2S)-2-(isobutylamino)-1,2-diphenylethyl)amino)-2-oxo-1-phenylethyl)benzamide; silver carbonate In toluene at 20℃; for 2h; Inert atmosphere;	99%
With (S)-2-(diphenylphosphino)-N-(1-((2-(isobutylamino)benzyl)amino)-3,3-dimethyl-1-oxobutan-2-yl)benzamide; silver(l) oxide In toluene at 20℃; for 2h; stereoselective reaction;	88%

: 76862-09-4
methyl N-(4-chlorobenzylidene)glycinate

: 141-05-9
Diethyl maleate

: (2R,3S,4R,5S)-3,4-diethyl 2-methyl 5-(4-chlorophenyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With N-((R)-2-(((S)-2-(dimethylamino)-1-phenylethyl)amino)-2-oxo-1-phenylethyl)-2-(diphenylphosphino)benzamide; silver carbonate In toluene at 20℃; for 2h; Inert atmosphere; Darkness; enantioselective reaction;	99%
With 2-(diphenylphosphino)-N-((R)-3-methyl-1-oxo-1-(((R)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; Inert atmosphere; enantioselective reaction;	96%

: 126079-18-3
(4-cyanobenzylideneamino)acetic acid methyl ester

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 5-(4-cyanophenyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With 2-(diphenylphosphino)-N-((S)-3-methyl-1-oxo-1-(((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; Inert atmosphere; enantioselective reaction;	99%
With 2-(diphenylphosphino)-N-((S)-2-(((1S,2S)-2-(isobutylamino)-1,2-diphenylethyl)amino)-2-oxo-1-phenylethyl)benzamide; silver carbonate In toluene at 20℃; for 1h; Inert atmosphere;	85%

: 40216-71-5
methyl 2-(benzylideneamino)propanoate

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 2-methyl-5-phenylpyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With N-((S)-3,3-dimethyl-1-oxo-1-(((S)-1-phenylethyl)amino)butan-2-yl)-2-(diphenylphosphino)benzamide; triethylamine; silver carbonate In toluene at 20℃; for 18h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;	99%
With 2-(diphenylphosphino)-N-((S)-2-(((1S,2S)-2-(isobutylamino)-1,2-diphenylethyl)amino)-2-oxo-1-phenylethyl)benzamide; silver carbonate In toluene at 20℃; for 40h; Inert atmosphere;	91%
With (S)-2-(diphenylphosphino)-N-(1-((2-(isobutylamino)benzyl)amino)-3,3-dimethyl-1-oxobutan-2-yl)benzamide; silver(l) oxide In toluene at 20℃; for 48h; stereoselective reaction;	67%

: 68870-85-9
methyl 2-(benzylideneamino)-3-phenylpropionate

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 2-benzyl-5-phenylpyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With N-((S)-3,3-dimethyl-1-oxo-1-(((S)-1-phenylethyl)amino)butan-2-yl)-2-(diphenylphosphino)benzamide; triethylamine; silver carbonate In toluene at 20℃; for 24h; Inert atmosphere; enantioselective reaction;	99%
With 2-(diphenylphosphino)-N-((S)-2-(((1S,2S)-2-(isobutylamino)-1,2-diphenylethyl)amino)-2-oxo-1-phenylethyl)benzamide; silver carbonate In toluene at 20℃; for 56h; Inert atmosphere;	80%

: 104-88-1
4-chlorobenzaldehyde

: 616-34-2
methoxycarbonylmethylamine

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 5-(4-chlorophenyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
Stage #1: 4-chlorobenzaldehyde; methoxycarbonylmethylamine With diisopropyl-carbodiimide In toluene for 3h; Inert atmosphere; Stage #2: Diethyl maleate With 2-(diphenylphosphino)-N-((S)-2-(((1S,2S)-2-(isobutylamino)-1,2-diphenylethyl)amino)-2-oxo-1-phenylethyl)benzamide; silver carbonate In toluene at 20℃; for 3h; Inert atmosphere;	99%

...Expand

: 756-80-9
O,O-dimethyl phosphorodithioic acid

: 141-05-9
Diethyl maleate

: 121-75-5
[(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester

Conditions

Conditions	Yield
With hydrogenchloride In water at 10 - 40℃; for 8h; Reagent/catalyst; Green chemistry;	98%
With triethylamine; hydroquinone
With hydroquinone In water at 53℃; for 8h;
at -30 - -25℃; Inert atmosphere;
With triethylamine; hydroquinone

: 114050-31-6
3-Phenyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester

: 141-05-9
Diethyl maleate

: 146352-28-5
2-Phenethyl-3-(pyridin-2-ylsulfanyl)-succinic acid diethyl ester

Conditions

Conditions	Yield
In dichloromethane at 0 - 5℃; Irradiation;	98%

: 141-05-9
Diethyl maleate

: 123-25-1
succinic acid diethyl ester

Conditions

Conditions	Yield
With acetic acid; zinc for 2h; Ambient temperature; sonication;	98%
With Decaborane; palladium on activated charcoal In methanol at 25℃; for 0.3h; Reduction;	98%
With 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-7-methylbenzo-[d]imidazole; [Zr(2,6-bis(5-methyl-3-phenyl-1H-pyrrol-2-yl)pyridine)2] In benzene-d6 for 8h; UV-irradiation;	98%

: 29601-98-7
N-benzylhydroxylamine hydrochloride

: 141-05-9
Diethyl maleate

: (+/-)-cis-diethyl 2-benzylisoxazolidine-4,5-dicarboxylate

Conditions

Conditions	Yield
Stage #1: formaldehyd; N-benzylhydroxylamine hydrochloride In ethanol; water at 20℃; for 1h; Stage #2: Diethyl maleate In ethanol; water for 3h; Heating / reflux;	98%

dodecane+O,O-dimethyl-dithiophosphoric acid: dodecane+O,O-dimethyl-dithiophosphoric acid

: 756-80-9
O,O-dimethyl phosphorodithioic acid

: 141-05-9
Diethyl maleate

: 121-75-5
[(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dodecane	98%

...Expand

: 1386380-13-7
C32H47NO

: 141-05-9
Diethyl maleate

: 1386381-12-9
C40H57NO5

Conditions

Conditions	Yield
With palladium(II) trimethylacetate; silver pivalate In 1,2-dichloro-ethane at 90℃; sealed tube; optical yield given as %de; stereoselective reaction;	98%

: [(4-methyl-benzylidene)-amino]-acetic acid methyl ester

: 141-05-9
Diethyl maleate

: (2S,3R,4S,5R)-3,4-diethyl 2-methyl 5-(p-tolyl)pyrrolidine-2,3,4-tricarboxylate

Conditions

Conditions	Yield
With 2-(diphenylphosphino)-N-((S)-2-(((1S,2S)-2-(isobutylamino)-1,2-diphenylethyl)amino)-2-oxo-1-phenylethyl)benzamide; silver carbonate In toluene at 20℃; for 4.5h; Inert atmosphere;	98%
With 2-(diphenylphosphino)-N-((S)-3-methyl-1-oxo-1-(((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)butan-2-yl)benzamide; silver carbonate In toluene at 20℃; Inert atmosphere; enantioselective reaction;	95%
With N-((S)-2-(((S)-2-(dimethylamino)-1-phenylethyl)amino)-2-oxo-1-phenylethyl)-2-(diphenylphosphino)benzamide; silver carbonate In toluene at 20℃; for 3h; Inert atmosphere; Darkness; enantioselective reaction;	94%
With N-((S)-3,3-dimethyl-1-oxo-1-(((S)-1-phenylethyl)amino)butan-2-yl)-2-(diphenylphosphino)benzamide; triethylamine; silver carbonate In toluene at 20℃; for 6h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;	85%

Diethyl maleate Chemical Properties

Structure of Diethyl maleate (CAS NO.141-05-9):

IUPAC Name: diethyl (Z)-but-2-enedioate
Empirical Formula: C₈H₁₂O₄
Molecular Weight: 172.1785
EINECS: 205-451-9
Index of Refraction: 1.442
Molar Refractivity: 42.71 cm³
Molar Volume: 161.1 cm³
Polarizability: 16.93×10^-24cm³
Surface Tension: 33.2 dyne/cm
Density: 1.068 g/cm³
Flash Point: 93.3 °C
Enthalpy of Vaporization: 45.03 kJ/mol
Melting point: -10 ºC
Boiling Point: 214 °C at 760 mmHg
Vapour Pressure: 0.159 mmHg at 25°C
Water Solubility: insoluble
Physical Appearance: colourless liquid
Stability: Stable. Combustible. Incompatible with oxidizing agents, bases, acids, reducing agents.
Product Categories: Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer
Synonyms of Diethyl maleate (CAS NO.141-05-9): 2-Butenedioic acid (Z)-, diethyl ester ; 4-02-00-02207 (Beilstein Handbook Reference) ; Diethylester kyseliny maleinove ; Ethyl maleate
Canonical SMILES: CCOC(=O)C=CC(=O)OCC
Isomeric SMILES: CCOC(=O)/C=C\C(=O)OCC
InChI: InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
InChIKey: IEPRKVQEAMIZSS-WAYWQWQTSA-N

Diethyl maleate Toxicity Data With Reference

1.	skn-rbt 10 mg/24H open MLD	JIHTAB Journal of Industrial Hygiene and Toxicology. 31 (1949),60.
2.	skn-rbt 530 mg open MLD	UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 10/29 ,1957.
3.	eye-rbt 500 mg open	JIHTAB Journal of Industrial Hygiene and Toxicology. 31 (1949),60.
4.	orl-rat LD50:3200 mg/kg	JIHTAB Journal of Industrial Hygiene and Toxicology. 31 (1949),60.
5.	ipr-rat LD50:3070 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 52 (1980),422.
6.	skn-rbt LD50:4000 mg/kg	UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 10/29 ,1957.

Diethyl maleate Consensus Reports

Reported in EPA TSCA Inventory.

Diethyl maleate Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36-43
R36:Irritating to eyes.
R43:May cause sensitization by skin contact.
Safety Statements: 26-36/37-37-24
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S37:Wear suitable gloves.
S24:Avoid contact with skin.
RIDADR: 3334
WGK Germany: 2
RTECS: ON1225000
HS Code: 29171990
Moderately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO₂, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Diethyl maleate Specification

Diethyl maleate's Handling and Storage
Storage: Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Avoid contact with heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.

Product Name

Diethyl maleate

Synthetic route

Diethyl maleate Chemical Properties

Diethyl maleate Toxicity Data With Reference

Diethyl maleate Consensus Reports

Diethyl maleate Safety Profile

Diethyl maleate Specification

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