Product Name

  • Name

    diisopropyl maleate

  • EINECS 233-242-2
  • CAS No. 10099-70-4
  • Article Data9
  • CAS DataBase
  • Density 1.027 g/cm3
  • Solubility 9.9g/L at 20℃
  • Melting Point -30.15°C
  • Formula C10H16 O4
  • Boiling Point 225.5 °C at 760 mmHg
  • Molecular Weight 200.235
  • Flash Point 112.3 °C
  • Transport Information
  • Appearance
  • Safety Moderately toxic by ingestion. A skin and eye irritant. See also ESTERS. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Risk Codes
  • Molecular Structure Molecular Structure of 10099-70-4 (diisopropyl maleate)
  • Hazard Symbols
  • Synonyms 2-Butenedioicacid (2Z)-, bis(1-methylethyl) ester (9CI); 2-Butenedioic acid (Z)-,bis(1-methylethyl) ester; Maleic acid, diisopropyl ester (6CI,7CI,8CI);Diisopropyl maleate; Isopropyl maleate
  • PSA 52.60000
  • LogP 1.44580

Synthetic route

isopropyl diazoacetate
22136-61-4

isopropyl diazoacetate

A

diisopropyl maleate
10099-70-4

diisopropyl maleate

B

diisopropyl fumarate
7283-70-7

diisopropyl fumarate

Conditions
ConditionsYield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃;A 95%
B n/a
maleic anhydride
108-31-6

maleic anhydride

isopropyl alcohol
67-63-0

isopropyl alcohol

diisopropyl maleate
10099-70-4

diisopropyl maleate

Conditions
ConditionsYield
for 1.5h; Esterification; Heating;64%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

isopropyl diazoacetate
22136-61-4

isopropyl diazoacetate

A

ethyl isopropyl maleate

ethyl isopropyl maleate

B

diisopropyl maleate
10099-70-4

diisopropyl maleate

C

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
ConditionsYield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃;A 42%
B n/a
C n/a
...Expand
maleic acid
110-16-7

maleic acid

isopropyl alcohol
67-63-0

isopropyl alcohol

diisopropyl maleate
10099-70-4

diisopropyl maleate

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 16h;20%
With sulfuric acid
isopropyl 2-(triphenylphosphoranylidene)acetate
110212-61-8

isopropyl 2-(triphenylphosphoranylidene)acetate

A

diisopropyl maleate
10099-70-4

diisopropyl maleate

B

diisopropyl fumarate
7283-70-7

diisopropyl fumarate

C

triphenylphosphine sulfide
3878-45-3

triphenylphosphine sulfide

Conditions
ConditionsYield
With styrenesulfide In toluene for 48h; Heating; Yield given. Yields of byproduct given;
...Expand
isopropyl diazoacetate
22136-61-4

isopropyl diazoacetate

cyclohexyl diazoacetate
63254-54-6

cyclohexyl diazoacetate

A

C13H20O4

C13H20O4

B

diisopropyl maleate
10099-70-4

diisopropyl maleate

C

dicyclohexyl cis-butenedioate
621-13-6

dicyclohexyl cis-butenedioate

Conditions
ConditionsYield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃;A 52 % Spectr.
B n/a
C n/a
...Expand
isopropyl diazoacetate
22136-61-4

isopropyl diazoacetate

t-butyl diazoacetate
35059-50-8

t-butyl diazoacetate

A

C11H18O4

C11H18O4

B

diisopropyl maleate
10099-70-4

diisopropyl maleate

C

di-tert-butyl maleate
18305-60-7

di-tert-butyl maleate

Conditions
ConditionsYield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃;A 50 % Spectr.
B n/a
C n/a
...Expand
maleic anhydride
108-31-6

maleic anhydride

isopropyl alcohol
67-63-0

isopropyl alcohol

A

diisopropyl maleate
10099-70-4

diisopropyl maleate

B

diisopropyl fumarate
7283-70-7

diisopropyl fumarate

Conditions
ConditionsYield
With 1-(4-diphenylphosphinitebutyl)-3-methylimidazolium chloride In neat (no solvent) at 100℃; for 6h; Reagent/catalyst; Overall yield = 73 %;A n/a
B n/a
...Expand
diisopropyl fumarate
7283-70-7

diisopropyl fumarate

diisopropyl maleate
10099-70-4

diisopropyl maleate

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Inert atmosphere; Sealed tube; Irradiation;
diisopropyl maleate
10099-70-4

diisopropyl maleate

diisopropyl fumarate
7283-70-7

diisopropyl fumarate

Conditions
ConditionsYield
With C16H25N3O2S In acetonitrile at 80℃; for 16h;99%
diisopropyl maleate
10099-70-4

diisopropyl maleate

thiophenol
108-98-5

thiophenol

(S)-(-)-diisopropyl phenylthiosuccinate
97678-37-0

(S)-(-)-diisopropyl phenylthiosuccinate

Conditions
ConditionsYield
With Cinchonin In toluene at 0℃; for 72h; other solvents, other reagents, other temperatures; optical purities, chemical yields;95%
With Cinchonin In toluene at 0℃; for 72h;95%
diisopropyl maleate
10099-70-4

diisopropyl maleate

(3-chloro-2-pyridyl)hydrazine
22841-92-5

(3-chloro-2-pyridyl)hydrazine

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl 2-(3-chloropyridin-2-yl)-5-oxo-pyrazolidine-3-carboxylate

isopropyl 2-(3-chloropyridin-2-yl)-5-oxo-pyrazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: isopropyl alcohol With sodium at 80 - 85℃;
Stage #2: (3-chloro-2-pyridyl)hydrazine With iodotris(triphenylphosphine)silver(I) In isopropyl alcohol at 25℃;
Stage #3: diisopropyl maleate In isopropyl alcohol at 25 - 30℃; Reagent/catalyst;		84%
...Expand
diisopropyl maleate
10099-70-4

diisopropyl maleate

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl 2,2-dimethyl-5-oxotetrahydrofuran-3-carboxylate
34341-66-7

isopropyl 2,2-dimethyl-5-oxotetrahydrofuran-3-carboxylate

Conditions
ConditionsYield
Stage #1: diisopropyl maleate; isopropyl alcohol With Benzoylformic acid for 72h; Irradiation; Green chemistry;
Stage #2: With acetic acid for 24h; Irradiation; Green chemistry;		81%
With 1-hydroxy-pyrrolidine-2,5-dione; dimethylglyoxal at 50℃; for 36h; Sealed tube; Irradiation; Inert atmosphere;80%
diisopropyl maleate
10099-70-4

diisopropyl maleate

(3-chloro-2-pyridyl)hydrazine
22841-92-5

(3-chloro-2-pyridyl)hydrazine

isopropyl 2-(3-chloropyridin-2-yl)-5-oxo-pyrazolidine-3-carboxylate

isopropyl 2-(3-chloropyridin-2-yl)-5-oxo-pyrazolidine-3-carboxylate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium isopropylate; sodium In isopropyl alcohol at 28 - 32℃; for 4h; Temperature; Reagent/catalyst;71%
diisopropyl maleate
10099-70-4

diisopropyl maleate

C10H9F3N2O

C10H9F3N2O

diisopropyl 3,4-cis-2-(2-methylbenzoyl)-5-(trifluoromethyl)pyrazolidine-3,4-dicarboxylate

diisopropyl 3,4-cis-2-(2-methylbenzoyl)-5-(trifluoromethyl)pyrazolidine-3,4-dicarboxylate

diisopropyl 3,4-trans-2-(2-methylbenzoyl)-5-(trifluoromethyl)-pyrazolidine-3,4-dicarboxylate

diisopropyl 3,4-trans-2-(2-methylbenzoyl)-5-(trifluoromethyl)-pyrazolidine-3,4-dicarboxylate

Conditions
ConditionsYield
With potassium carbonate In toluene for 30h; Reflux;A 69%
B 10%
...Expand
diisopropyl maleate
10099-70-4

diisopropyl maleate

(3S)-3-(triisopropylsilyl)oxy-1-pyrroline N-oxide
227954-56-5

(3S)-3-(triisopropylsilyl)oxy-1-pyrroline N-oxide

A

(2R,3S,3aR,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole
227954-57-6

(2R,3S,3aR,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole

B

(2S,3R,3aR,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole

(2S,3R,3aR,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole

C

(2S,3R,3aS,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole

(2S,3R,3aS,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole

Conditions
ConditionsYield
In benzene at 20℃; for 120h; Cycloaddition;A 67%
B 14%
C 12%
...Expand
diisopropyl maleate
10099-70-4

diisopropyl maleate

(4S)-4-tert-butoxy-3,4-dihydro-2H-pyrrole 1-oxide
167971-82-6

(4S)-4-tert-butoxy-3,4-dihydro-2H-pyrrole 1-oxide

A

(2R,3S,3aR,4S)-4-tert-butoxy-2,3-bis(isopropyloxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

(2R,3S,3aR,4S)-4-tert-butoxy-2,3-bis(isopropyloxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

B

(2S,3R,3aR,4S)-4-tert-butoxy-2,3-bis(isopropyloxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

(2S,3R,3aR,4S)-4-tert-butoxy-2,3-bis(isopropyloxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

C

(2S,3R,3aS,4S)-4-tert-butoxy-2,3-bis(isopropyloxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

(2S,3R,3aS,4S)-4-tert-butoxy-2,3-bis(isopropyloxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

Conditions
ConditionsYield
In benzene at 20℃; for 48h; Cycloaddition;A 66%
B 16%
C 15%
...Expand
tetrahydrofuran
109-99-9

tetrahydrofuran

diisopropyl maleate
10099-70-4

diisopropyl maleate

2-(tetrahydro-2-furanyl) butanedioic acid 1,4-diisopropyl ester

2-(tetrahydro-2-furanyl) butanedioic acid 1,4-diisopropyl ester

2-(tetrahydro-2-furanyl) butanedioic acid 1,4-diisopropyl ester

2-(tetrahydro-2-furanyl) butanedioic acid 1,4-diisopropyl ester

Conditions
ConditionsYield
With di-tert-butyl peroxide at 20℃; for 4h; UV-irradiation; Inert atmosphere; Overall yield = 96 percent; diastereoselective reaction;A 60%
B 29%
...Expand
diisopropyl maleate
10099-70-4

diisopropyl maleate

(4-Chloro-benzenesulfonyl)-acetic acid isopropyl ester

(4-Chloro-benzenesulfonyl)-acetic acid isopropyl ester

2-(4-Chloro-benzenesulfonyl)-3-isopropoxycarbonyl-pentanedioic acid diisopropyl ester

2-(4-Chloro-benzenesulfonyl)-3-isopropoxycarbonyl-pentanedioic acid diisopropyl ester

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 40℃; for 4h;56%
diisopropyl maleate
10099-70-4

diisopropyl maleate

2-iodo-succinic acid diisopropyl ester

2-iodo-succinic acid diisopropyl ester

Conditions
ConditionsYield
With titanium(IV) iodide In dichloromethane at 20℃; for 8h;34%
diisopropyl maleate
10099-70-4

diisopropyl maleate

3-thia-pentane-1,2,4,5-tetracarboxylic acid tetraisopropyl ester

3-thia-pentane-1,2,4,5-tetracarboxylic acid tetraisopropyl ester

Conditions
ConditionsYield
With hydrogen sulfide; triethylamine
diisopropyl maleate
10099-70-4

diisopropyl maleate

O,O-Diethyl hydrogen phosphorodithioate
298-06-6

O,O-Diethyl hydrogen phosphorodithioate

diethoxythiophosphorylsulfanyl-succinic acid diisopropyl ester

diethoxythiophosphorylsulfanyl-succinic acid diisopropyl ester

Conditions
ConditionsYield
With triethylamine; hydroquinone
With triethylamine; hydroquinone
diisopropyl maleate
10099-70-4

diisopropyl maleate

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

O,O-dimethyl phosphorodithioic acid

dimethoxythiophosphorylsulfanyl-succinic acid diisopropyl ester
3700-90-1

dimethoxythiophosphorylsulfanyl-succinic acid diisopropyl ester

Conditions
ConditionsYield
With triethylamine; hydroquinone
With triethylamine; hydroquinone
diisopropyl maleate
10099-70-4

diisopropyl maleate

O.O-Dipropyl-dithyophosphat
2253-43-2

O.O-Dipropyl-dithyophosphat

dipropoxythiophosphorylsulfanyl-succinic acid diisopropyl ester

dipropoxythiophosphorylsulfanyl-succinic acid diisopropyl ester

diisopropyl maleate
10099-70-4

diisopropyl maleate

hexachlorocyclopentadiene
77-47-4

hexachlorocyclopentadiene

1,4,5,6,7,7-hexachloro-norborn-5-ene-2endo,3endo-dicarboxylic acid diisopropyl ester

1,4,5,6,7,7-hexachloro-norborn-5-ene-2endo,3endo-dicarboxylic acid diisopropyl ester

Conditions
ConditionsYield
With toluene
diisopropyl maleate
10099-70-4

diisopropyl maleate

α,α-di(methoxycarbonyl)-N-methyl nitrone
62619-42-5

α,α-di(methoxycarbonyl)-N-methyl nitrone

2-methyl-isoxazolidine-3,3,4r,5c-tetracarboxylic acid 4,5-diisopropyl ester 3,3-dimethyl ester
71167-59-4

2-methyl-isoxazolidine-3,3,4r,5c-tetracarboxylic acid 4,5-diisopropyl ester 3,3-dimethyl ester

Conditions
ConditionsYield
In benzene
diisopropyl maleate
10099-70-4

diisopropyl maleate

isopropyl alcohol
67-63-0

isopropyl alcohol

A

isopropyl 2,2-dimethyl-5-oxotetrahydrofuran-3-carboxylate
34341-66-7

isopropyl 2,2-dimethyl-5-oxotetrahydrofuran-3-carboxylate

B

diaterebic acid diisopropylester

diaterebic acid diisopropylester

C

2,2-dimethyl-4-(1,2-dicarboxyethyl)-5-oxo-tetrahydrofuran-4-carboxylic acid triisopropyl ester
77666-66-1

2,2-dimethyl-4-(1,2-dicarboxyethyl)-5-oxo-tetrahydrofuran-4-carboxylic acid triisopropyl ester

Conditions
ConditionsYield
In isopropyl alcohol at 25℃; for 100h; Product distribution; Rate constant; Irradiation; products distribution as function of time, lactonization rate;
...Expand
diisopropyl maleate
10099-70-4

diisopropyl maleate

(3S)-3-(triisopropylsilyl)oxy-1-pyrroline N-oxide
227954-56-5

(3S)-3-(triisopropylsilyl)oxy-1-pyrroline N-oxide

A

(2R,3S,3aS,4S)-4-Triisopropylsilanyloxy-hexahydro-pyrrolo[1,2-b]isoxazole-2,3-dicarboxylic acid diisopropyl ester

(2R,3S,3aS,4S)-4-Triisopropylsilanyloxy-hexahydro-pyrrolo[1,2-b]isoxazole-2,3-dicarboxylic acid diisopropyl ester

B

(2R,3S,3aR,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole
227954-57-6

(2R,3S,3aR,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole

C

(2S,3R,3aR,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole

(2S,3R,3aR,4S)-2,3-bis(isopropyloxycarbonyl)-4-[(triisopropyl)silyloxy]hexahydropyrrolo[1,2-b]isoxazole

Conditions
ConditionsYield
In benzene at 20℃; for 120h; Cycloaddition;
...Expand
diisopropyl maleate
10099-70-4

diisopropyl maleate

1-benzyl-4-phenyl-4,5-dihydro-1H-imidazole 3-oxide; hydrochloride

1-benzyl-4-phenyl-4,5-dihydro-1H-imidazole 3-oxide; hydrochloride

(3S,6S,7R,7aS)-1-Benzyl-3-phenyl-hexahydro-imidazo[1,2-b]isoxazole-6,7-dicarboxylic acid diisopropyl ester

(3S,6S,7R,7aS)-1-Benzyl-3-phenyl-hexahydro-imidazo[1,2-b]isoxazole-6,7-dicarboxylic acid diisopropyl ester

Conditions
ConditionsYield
With triethylamine In toluene at 60℃; for 18h; Cycloaddition;
diisopropyl maleate
10099-70-4

diisopropyl maleate

(E)-N-benzylideneglycine methyl ester
66646-88-6, 120238-40-6, 138495-05-3

(E)-N-benzylideneglycine methyl ester

A

(2S,3R,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylic acid-3, 4-isopropyl ester-2-methyl ester

(2S,3R,4S,5R)-5-phenylpyrrolidine-2,3,4-tricarboxylic acid-3, 4-isopropyl ester-2-methyl ester

B

(2R,3S,4R,5S)-5-phenylpyrrolidine-2,3,4-tricarboxylic acid-3, 4-isopropyl ester-2-methyl ester

(2R,3S,4R,5S)-5-phenylpyrrolidine-2,3,4-tricarboxylic acid-3, 4-isopropyl ester-2-methyl ester

Conditions
ConditionsYield
With (S,S,Sp)-xylyl-(bis-ferrocenyl amide phosphine); silver(I) acetate; N-ethyl-N,N-diisopropylamine In toluene Title compound not separated from byproducts.;
...Expand
diisopropyl maleate
10099-70-4

diisopropyl maleate

(1S,2R,7S,7aR)-2-hydroxy-1-isopropyloxycarbonyl-7-[(triisopropyl)silyloxy]hexahydropyrrolizin-3-one

(1S,2R,7S,7aR)-2-hydroxy-1-isopropyloxycarbonyl-7-[(triisopropyl)silyloxy]hexahydropyrrolizin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 67 percent / benzene / 120 h / 20 °C
2: 85 percent / Mo(CO)6 / acetonitrile; H2O / 18 h / Heating
View Scheme

2-Butenedioic acid, bis(1-methylethyl) ester Chemical Properties

Empirical Formula: C10H16O4
Molecular Weight: 200.2316 g/mol
EINECS: 233-242-2 
Index of Refraction: 1.445
Density: 1.027 g/cm3
Flash Point: 112.3 °C
Enthalpy of Vaporization: 46.2 kJ/mol
Boiling Point: 225.5 °C at 760 mmHg
Vapour Pressure: 0.0861 mmHg at 25 °C
Structure of 2-Butenedioic acid, bis(1-methylethyl) ester (CAS NO.10099-70-4):
                  
IUPAC Name of 2-Butenedioic acid, bis(1-methylethyl) ester (CAS NO.10099-70-4): Dipropan-2-yl (Z)-but-2-enedioate

2-Butenedioic acid, bis(1-methylethyl) ester Toxicity Data With Reference

1.    

skn-rbt 10 mg/24H open MLD

     AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.
2.    

eye-rbt 500 mg open

     AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.
3.    

orl-rat LD50:2140 mg/kg

     AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 10 (1954),61.

2-Butenedioic acid, bis(1-methylethyl) ester Consensus Reports

 2-Butenedioic acid, bis(1-methylethyl) ester (CAS NO.10099-70-4) has been reported in EPA TSCA Inventory.

2-Butenedioic acid, bis(1-methylethyl) ester Safety Profile

Moderately toxic by ingestion. A skin and eye irritant. See also ESTERS. When heated to decomposition it emits acrid smoke and irritating fumes.

2-Butenedioic acid, bis(1-methylethyl) ester Specification

 2-Butenedioic acid, bis(1-methylethyl) ester ,its cas register number is 10099-70-4. It also can be called Diisopropylester kyseliny fumarove ; 2-Butenedioic acid (E)-, bis(1-methylethyl) ester ; and Diisopropyl fumarate .

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