Product Name

  • Name

    Monoethyl fumarate

  • EINECS 219-544-7
  • CAS No. 2459-05-4
  • Article Data44
  • CAS DataBase
  • Density 1.208 g/cm3
  • Solubility Soluble in water.
  • Melting Point 66-68 °C(lit.)
  • Formula C6H8 O4
  • Boiling Point 261.6 °C at 760 mmHg
  • Molecular Weight 144.127
  • Flash Point 109.6 °C
  • Transport Information
  • Appearance almost white to beige cryatalline power
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2459-05-4 (Monoethyl fumarate)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Butenedioicacid (2E)-, monoethyl ester (9CI);2-Butenedioic acid (E)-, monoethyl ester;Fumaric acid, ethyl ester (6CI,7CI);Fumaric acid, monoethyl ester (8CI);(E)-4-Ethoxy-4-oxo-2-butenoic acid;Ethyl hydrogen fumarate;Monoethylfumarate;Monoethyl trans-2-butenedioate;
  • PSA 63.60000
  • LogP 0.19030

Synthetic route

diethyl Fumarate
623-91-6

diethyl Fumarate

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 8h; Ambient temperature;89%
With Candida antarctica lipase; water In 1,4-dioxane for 144h;78%
ethyl acetate
141-78-6

ethyl acetate

maleic acid
110-16-7

maleic acid

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With iron(III) perchlorate for 2h; Ambient temperature;87%
carbon dioxide
124-38-9

carbon dioxide

3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-acrylic acid ethyl ester
1263187-14-9

3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-acrylic acid ethyl ester

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With potassium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 70℃; under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;76%
ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate
1009307-13-4

ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate

carbon dioxide
124-38-9

carbon dioxide

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With potassium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 70℃; for 24h; Sealed tube; Schlenk technique;76%
malonic acid monoethyl ester
2459-05-4, 3249-53-4, 3990-03-2

malonic acid monoethyl ester

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With aluminum (III) chloride at 70℃; for 2h;58%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethyl 2-diazo-3-methyl-3-butenoate
126580-11-8

ethyl 2-diazo-3-methyl-3-butenoate

A

malonic acid monoethyl ester
2459-05-4, 3249-53-4, 3990-03-2

malonic acid monoethyl ester

B

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

C

diethyl 2-methylcyclobutene-1,3-dicarboxylate
1198173-63-5

diethyl 2-methylcyclobutene-1,3-dicarboxylate

Conditions
ConditionsYield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate In dichloromethane at 20℃; for 2h; Inert atmosphere;A n/a
B n/a
C 33%
...Expand
maleic anhydride
108-31-6

maleic anhydride

ethanol
64-17-5

ethanol

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With thionyl chloride
With TEA
Stage #1: maleic anhydride; ethanol at 60℃; for 3h;
Stage #2: With aluminum (III) chloride at 20 - 90℃; for 2h;
ethanol
64-17-5

ethanol

malic acid
617-48-1

malic acid

A

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

B

diethyl Fumarate
623-91-6

diethyl Fumarate

Conditions
ConditionsYield
With hydrogenchloride
...Expand
ethanol
64-17-5

ethanol

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
at 120℃;
With hydrogenchloride
ethanol
64-17-5

ethanol

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

A

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

B

diethyl Fumarate
623-91-6

diethyl Fumarate

Conditions
ConditionsYield
With sulfuric acid
at 120℃;
...Expand
Diethyl maleate
141-05-9

Diethyl maleate

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With potassium hydroxide; ethanol Schuetteln, Filtrieren, Verdunsten des Filtrats, Loesen des Rueckstands in Wasser und Schuetteln mit Aether aus; der waessr.Loesung mit Salzsaeure Uebersaettigen und mit Aether Ausschuetteln;
1,3,5,7,9,10-hexahydro-3,7,10-trimethylpyrimido<5,4-g>pteridine-2,4,6,8-tetrone
82639-48-3

1,3,5,7,9,10-hexahydro-3,7,10-trimethylpyrimido<5,4-g>pteridine-2,4,6,8-tetrone

diethyl Fumarate
623-91-6

diethyl Fumarate

A

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

B

3,7,10-trimethyl-(1H,3H,7H,10H)-pyrimido<5-4-g>pteridine-2,4,6,8-tetrone
82639-46-1

3,7,10-trimethyl-(1H,3H,7H,10H)-pyrimido<5-4-g>pteridine-2,4,6,8-tetrone

C

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

D

succinic acid diethyl ester
123-25-1

succinic acid diethyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 30℃; for 12h; Rate constant; pH=7.00;A 19 % Spectr.
B n/a
C 10 % Spectr.
D 32 % Chromat.
...Expand
selenium(IV) oxide
7446-08-4

selenium(IV) oxide

succinic acid diethyl ester
123-25-1

succinic acid diethyl ester

A

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

B

diethyl Fumarate
623-91-6

diethyl Fumarate

Conditions
ConditionsYield
at 170℃;
...Expand
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

diethylphosphonoacetic acid
3095-95-2

diethylphosphonoacetic acid

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
Stage #1: diethylphosphonoacetic acid With sodium hydride In 1,2-dimethoxyethane at 20℃;
Stage #2: glyoxylic acid ethyl ester In 1,2-dimethoxyethane at 20℃; Further stages.;
maleic anhydride
108-31-6

maleic anhydride

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
iodine In ethanol
but-2-enedioic acid tert-butyl ester ethyl ester
107679-25-4

but-2-enedioic acid tert-butyl ester ethyl ester

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With water Alkaline conditions;
malonic acid monoethyl ester
2459-05-4, 3249-53-4, 3990-03-2

malonic acid monoethyl ester

thiourea
17356-08-0

thiourea

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Conditions
ConditionsYield
In water at 80 - 85℃; for 4h;112 g
[(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester
121-75-5

[(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester

A

malathion alpha-dicarboxylic acid
1190-28-9

malathion alpha-dicarboxylic acid

B

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

C

S-(1,2-dicarboethoxyethyl)O,S-dimethyl phosphorodithioate
3344-12-5

S-(1,2-dicarboethoxyethyl)O,S-dimethyl phosphorodithioate

D

malathion monocarboxylic acid
1190-29-0

malathion monocarboxylic acid

E

oxallic acid isobutyle nonyl ester

oxallic acid isobutyle nonyl ester

F

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
ConditionsYield
With carboxylesterase from Escherichia coli IES-02 In aq. phosphate buffer at 37℃; for 1h; pH=7.5; Catalytic behavior; Enzymatic reaction;
...Expand
Sorbyl alcohol
17102-64-6

Sorbyl alcohol

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

ethyl (2E,4E)-hexa-2,4-dien-1-yl fumarate
160386-62-9

ethyl (2E,4E)-hexa-2,4-dien-1-yl fumarate

Conditions
ConditionsYield
With dmap; 2`,3`-dideoxycytidine In dichloromethane Ambient temperature;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3.5h;90%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

octa-4t,6t-dien-3-ol
186417-99-2

octa-4t,6t-dien-3-ol

(E)-But-2-enedioic acid ethyl ester (2E,4E)-1-ethyl-hexa-2,4-dienyl ester
186418-00-8

(E)-But-2-enedioic acid ethyl ester (2E,4E)-1-ethyl-hexa-2,4-dienyl ester

Conditions
ConditionsYield
With dmap; 2`,3`-dideoxycytidine In dichloromethane Ambient temperature;100%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

4-methoxy-aniline
104-94-9

4-methoxy-aniline

(E)–4-((4-methoxyphenyl)amino)-4-oxobut-2-enoic acid
37904-20-4

(E)–4-((4-methoxyphenyl)amino)-4-oxobut-2-enoic acid

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With oxalyl dichloride; N,N-dimethyl-formamide In benzene at 20℃; for 4h; Inert atmosphere;
Stage #2: 4-methoxy-aniline With caesium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: With potassium hydroxide; water In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;		100%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

4-nitro-aniline
100-01-6

4-nitro-aniline

fumaric acid mono-N-(4-nitrophenyl)amide
37904-21-5

fumaric acid mono-N-(4-nitrophenyl)amide

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With oxalyl dichloride; N,N-dimethyl-formamide In benzene at 20℃; for 4h; Inert atmosphere;
Stage #2: 4-nitro-aniline With caesium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: With potassium hydroxide; water In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;		100%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

(-)-(4E,6Z)-(1'R,2R,3S)-1,2,3-trihydroxy-1,3-O-ethylidene-4,6-octadiene
937172-42-4

(-)-(4E,6Z)-(1'R,2R,3S)-1,2,3-trihydroxy-1,3-O-ethylidene-4,6-octadiene

(-)-(4E,6Z)-(1'R,2R,3S)-1,3-dihydroxy-1,3-O-ethylidene-4,6-octadien-2-yl ethyl fumarate
937172-48-0

(-)-(4E,6Z)-(1'R,2R,3S)-1,3-dihydroxy-1,3-O-ethylidene-4,6-octadien-2-yl ethyl fumarate

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With dmap In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #3: (-)-(4E,6Z)-(1'R,2R,3S)-1,2,3-trihydroxy-1,3-O-ethylidene-4,6-octadiene In dichloromethane for 1h; Inert atmosphere; Reflux;		100%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-hydroxy-1-naphthaldehyde
7770-45-8

4-hydroxy-1-naphthaldehyde

4-aminomethylphenol
696-60-6

4-aminomethylphenol

C29H32N2O6

C29H32N2O6

Conditions
ConditionsYield
With lithium chloride; sodium hydroxide In water at 50℃; under 7500.75 Torr; for 1h; pH=7; Inert atmosphere; Microwave irradiation;100%
...Expand
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-hydroxy-1-naphthaldehyde
7770-45-8

4-hydroxy-1-naphthaldehyde

benzylamine
100-46-9

benzylamine

C29H32N2O5

C29H32N2O5

Conditions
ConditionsYield
With lithium chloride; sodium hydroxide In water at 50℃; under 7500.75 Torr; for 1h; pH=7; Inert atmosphere; Microwave irradiation;100%
...Expand
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

N-methyl-1-naphthalenemethylamine hydrochloride
65473-13-4

N-methyl-1-naphthalenemethylamine hydrochloride

trans-3-(N-methyl-1-naphthylmethylcarbamoyl)propenoic acid ethyl ester

trans-3-(N-methyl-1-naphthylmethylcarbamoyl)propenoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane
Stage #2: N-methyl-1-naphthalenemethylamine hydrochloride In dichloromethane Further stages.;		99%
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -20℃; for 0.5h;
Stage #2: N-methyl-1-naphthalenemethylamine hydrochloride In dichloromethane at 20℃; for 4h; Further stages.;		99%
piperidine
110-89-4

piperidine

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

trans-3-(1-piperidylcarbonyl)propenoic acid ethyl ester
92912-62-4

trans-3-(1-piperidylcarbonyl)propenoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -20℃; for 0.5h;
Stage #2: piperidine In dichloromethane at 20℃; for 4h; Further stages.;		99%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

N-methylaniline
100-61-8

N-methylaniline

(E)-4-(methylphenylamino)-4-oxo-2-butenoic acid ethyl ester
1027101-46-7

(E)-4-(methylphenylamino)-4-oxo-2-butenoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -20℃; for 0.5h;
Stage #2: N-methylaniline In dichloromethane at 20℃; for 4h; Further stages.;		99%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

(E)-4-[methyl(phenylmethyl)amino]-4-oxo-2-butenoic acid ethyl ester
945379-56-6

(E)-4-[methyl(phenylmethyl)amino]-4-oxo-2-butenoic acid ethyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃;98%
76%
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane
Stage #2: benzyl-methyl-amine In dichloromethane Further stages.;		76%
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -20℃; for 0.5h;
Stage #2: benzyl-methyl-amine In dichloromethane at 20℃; for 4h; Further stages.;		76%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

fumaric acid ethyl ester mono chloride
26367-48-6

fumaric acid ethyl ester mono chloride

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 24h;97%
With oxalyl dichloride In N,N-dimethyl-formamide93%
With dmap; oxalyl dichloride In dichloromethane at 20℃; for 1.5h;93%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

(+/-)-2-(Bromomethyl)-1-butanol
40893-97-8

(+/-)-2-(Bromomethyl)-1-butanol

(+/-)-Ethyl (E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoate
155529-26-3

(+/-)-Ethyl (E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide97%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature;97%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Di(tert-butyl)-N-(3-aminopropyl)-N,N'-(ethan-1,2-diyl)bis
142039-01-8

Di(tert-butyl)-N-(3-aminopropyl)-N,N'-(ethan-1,2-diyl)bis

3-{3-[BOC-(2-BOC-Aminoethyl)-amino]-propylcarbamoyl}-acrylic acid ethyl ester

3-{3-[BOC-(2-BOC-Aminoethyl)-amino]-propylcarbamoyl}-acrylic acid ethyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;97%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

(2E)-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)prop-2-en-1-ol
610768-33-7

(2E)-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)prop-2-en-1-ol

(2E)-2-butenedioic acid (2E)-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl ester ethyl ester
610768-45-1

(2E)-2-butenedioic acid (2E)-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl ester ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -78 - 20℃; for 4h;97%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

pivalaldehyde
630-19-3

pivalaldehyde

benzylamine
100-46-9

benzylamine

(E)-ethyl 4-(benzyl(1-(benzylamino)-3,3-dimethyl-1-oxobutan-2-yl)amino)-4-oxobut-2-enoate

(E)-ethyl 4-(benzyl(1-(benzylamino)-3,3-dimethyl-1-oxobutan-2-yl)amino)-4-oxobut-2-enoate

Conditions
ConditionsYield
In dichloromethane at 200℃; under 13501.4 Torr; for 0.333333h; Ugi reaction; microwave irradiation;97%
...Expand
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

C8H13N3O3S
220378-49-4

C8H13N3O3S

(2E)-2-butenedioic acid (2E)-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl ester ethyl ester
610768-45-1

(2E)-2-butenedioic acid (2E)-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl ester ethyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;97%
N-(2-pyrimidyl)indole
221044-05-9

N-(2-pyrimidyl)indole

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

(E)-3-(1-pyrimidin-2-yl-1H-indol-2-yl)-acrylic acid ethyl ester

(E)-3-(1-pyrimidin-2-yl-1H-indol-2-yl)-acrylic acid ethyl ester

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; 2,2-dimethylpropanoic anhydride In toluene at 140℃; for 1h; Inert atmosphere; stereoselective reaction;97%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-4-ethyl-(2E)-but-2-endioate

1-benzyl-4-ethyl-(2E)-but-2-endioate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;97%
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 16h;42.9 g
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

(-)-(E)-(1'R,2R,3S)-1,2,3-trihydroxy-1,3-O-ethylidene-5-methyl-4,6-heptadiene
1310682-99-5

(-)-(E)-(1'R,2R,3S)-1,2,3-trihydroxy-1,3-O-ethylidene-5-methyl-4,6-heptadiene

(-)-(E)-(1'R,2R,3S)-1,3-dihydroxy-1,3-O-ethylidene-5-methyl-4,6-heptadien-2-yl ethyl fumarate
1310683-04-5

(-)-(E)-(1'R,2R,3S)-1,3-dihydroxy-1,3-O-ethylidene-5-methyl-4,6-heptadien-2-yl ethyl fumarate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 1h; Inert atmosphere; Reflux;96%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

pivaloyl chloride
3282-30-2

pivaloyl chloride

C11H16O5

C11H16O5

Conditions
ConditionsYield
With triethylamine In dichloromethane at -25 - 20℃; Solvent; Temperature; Time; Cooling with acetone-dry ice;96%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

β-naphthaldehyde
66-99-9

β-naphthaldehyde

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

(E)-ethyl 4-((2-(benzylamino)-1-(naphthalen-2-yl)-2-oxoethyl)(4-methoxybenzyl)amino)-4-oxobut-2-enoate

(E)-ethyl 4-((2-(benzylamino)-1-(naphthalen-2-yl)-2-oxoethyl)(4-methoxybenzyl)amino)-4-oxobut-2-enoate

Conditions
ConditionsYield
In dichloromethane at 200℃; under 13501.4 Torr; for 0.333333h; Ugi reaction; microwave irradiation;95%
...Expand
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

α-methyl-p-hydroxybenzylamine
134855-87-1

α-methyl-p-hydroxybenzylamine

pivalaldehyde
630-19-3

pivalaldehyde

C24H36N2O5

C24H36N2O5

Conditions
ConditionsYield
In water at 200℃; under 13501.4 Torr; microwave irradiation;95%
...Expand
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

N-benzyl-1-(4-fluorophenyl)methanamine
55096-88-3

N-benzyl-1-(4-fluorophenyl)methanamine

trans-3-(benzyl-4-fluorobenzyl)carbamoylpropenoic acid ethyl ester
1027101-48-9

trans-3-(benzyl-4-fluorobenzyl)carbamoylpropenoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -20℃; for 0.5h;
Stage #2: N-benzyl-1-(4-fluorophenyl)methanamine In dichloromethane at 20℃; for 4h; Further stages.;		95%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

dibutylamine
111-92-2

dibutylamine

trans-3-dibutylcarbamoylpropenoic acid ethyl ester
109447-28-1

trans-3-dibutylcarbamoylpropenoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -20℃; for 0.5h;
Stage #2: dibutylamine In dichloromethane at 20℃; for 4h; Further stages.;		95%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

diethylamine
109-89-7

diethylamine

trans-3-diethylcarbamoylpropenoic acid ethyl ester
110793-11-8

trans-3-diethylcarbamoylpropenoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (E)-4-ethoxy-4-oxobut-2-enoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -20℃; for 0.5h;
Stage #2: diethylamine In dichloromethane at 20℃; for 4h; Further stages.;		95%
morpholine
110-91-8

morpholine

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

(E)-4-(4-morpholinyl)-4-oxo-2-butenoic acid ethyl ester
92912-63-5

(E)-4-(4-morpholinyl)-4-oxo-2-butenoic acid ethyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃;95%
(S)-3-amino-2-(tert-butyldiphenylsilanyloxy)propylcarbamic acid tert-butyl ester
1007217-08-4

(S)-3-amino-2-(tert-butyldiphenylsilanyloxy)propylcarbamic acid tert-butyl ester

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

C30H42N2O6Si
1373889-07-6

C30H42N2O6Si

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;94%
isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

(E)-4-ethoxy-4-oxobut-2-enoic anhydride
675876-18-3

(E)-4-ethoxy-4-oxobut-2-enoic anhydride

Conditions
ConditionsYield
With triethylamine In dichloromethane at -25 - 10℃; for 6.5h; Solvent; Temperature; Time; Cooling with acetone-dry ice;94%
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

2,2-Diphenylethylamine
3963-62-0

2,2-Diphenylethylamine

fumaric acid mono-2,2-diphenylethylamide monoethyl ester
573986-11-5

fumaric acid mono-2,2-diphenylethylamide monoethyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 20h;93%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane85%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h;85%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;71%

Monoethyl fumarate Chemical Properties

The molecular structure of Ethyl fumarate (CAS NO.2459-05-4):

IUPAC Name: (E)-4-Ethoxy-4-oxobut-2-enoic acid 
Molecular Formula: C6H8 O4
Molecular Weight: 144.1253 g/mol
Density: 1.208 g/cm3
Melting Point: 66-68 °C(lit.)
Boiling Point: 261.6 °C at 760 mmHg
Flash Point: 109.6 °C
Index of Refraction: 1.469
Molar Refractivity: 33.24 cm3
Molar Volume: 119.2 cm3
Polarizability: 13.17 ×10-24 cm3
Surface Tension: 42.4 dyne/cm 
Enthalpy of Vaporization: 54.97 kJ/mol
Vapour Pressure: 0.0034 mmHg at 25 °C 
XLogP3-AA: 0.2
H-Bond Donor: 1
H-Bond Acceptor: 4
Rotatable Bond Count: 4
Exact Mass: 144.042259
MonoIsotopic Mass: 144.042259
Topological Polar Surface Area: 63.6
Heavy Atom Count: 10 
Canonical SMILES: CCOC(=O)C=CC(=O)O
Isomeric SMILES: CCOC(=O)/C=C/C(=O)O
InChI: InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3+
InChIKey: XLYMOEINVGRTEX-ONEGZZNKSA-N
EINECS: 219-544-7
Classification Code: dermatologic agents

Monoethyl fumarate Uses

 Ethyl fumarate (CAS NO.2459-05-4) is used as preservative, polymer aggregation agent and  food additive.

Monoethyl fumarate Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany: 1
HazardClass: IRRITANT

Monoethyl fumarate Specification

 Ethyl fumarate (CAS NO.2459-05-4) is also named as Ethyl hydrogen fumarate ; Fumaric acid, monoethyl ester ; Monoethyl fumarate ; Monoethyl trans-2-butenedioate ; NSC 524101 ; 2-Butenedioic acid (E)-, monoethyl ester (9CI) ; Fumaric acid, ethyl ester . Ethyl fumarate (CAS NO.2459-05-4) is almost white to beige cryatalline power.

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