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105-76-0

Basic Information
CAS No.: 105-76-0
Name: Dibutyl maleate
Molecular Structure:
Molecular Structure of 105-76-0 (Dibutyl maleate)
Formula: C12H20O4
Molecular Weight: 228.29
Synonyms: Dibutyl maleate;DBM
EINECS: 203-328-4
Density: 1.004 g/cm3
Melting Point: -85 °C
Boiling Point: 280 °C at 760 mmHg
Flash Point: 136.4 °C
Solubility: Insoluble in water
Appearance: clear colourless to slightly yellowish liquid
Hazard Symbols: IrritantXi,DangerousN
Risk Codes: 36/37/38-51/53-43
Safety: 26-36-61-37-29-24
Transport Information:
PSA: 52.60000
LogP: 2.22920
Synthetic route
108-31-6

maleic anhydride

71-36-3

butan-1-ol

105-76-0

Dibutyl maleate

Conditions
ConditionsYield
With diacidic ionic liquid supported on magnetic-silica nanoparticles In neat (no solvent) at 118℃; for 3h; Dean-Stark;100%
With 3,3′-(2,2-bis(hydroxymethyl)propane-1,3-diyl)bis(1-methyl-1H-imidazol-3-ium) hydrogen sulfate for 4h; Dean-Stark; Reflux;98%
With N-(4-sulphonic acid)butylpyridinium hydrogen sulphate at 120℃; for 1h; Catalytic behavior; Reagent/catalyst; Microwave irradiation;84.38%
592-84-7

n-butyl formate

110-16-7

maleic acid

A

105-76-0

Dibutyl maleate

B

925-21-3

mon-n-butyl maleate

Conditions
ConditionsYield
With Dowex 50Wx2 In octane at 100℃; for 1.66667h; Esterification;A 6%
B 89%
108-31-6

maleic anhydride

71-41-0

pentan-1-ol

71-36-3

butan-1-ol

105-76-0

Dibutyl maleate

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 124.85℃; for 2h;80%
147-73-9

meso-tartaric acid

71-36-3

butan-1-ol

105-76-0

Dibutyl maleate

Conditions
ConditionsYield
With per-rhenic acid In water at 170℃; for 3h; Inert atmosphere;75%
24761-88-4

1-butyl diazoacetate

A

105-76-0

Dibutyl maleate

B

105-75-9

dibutyl 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 74%
B n/a
110-16-7

maleic acid

71-36-3

butan-1-ol

105-76-0

Dibutyl maleate

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 16h;60%
With sulfuric acid; benzene beim Entfernen des gebildeten Wassers;
With sulfuric acid; toluene beim Entfernen des gebildeten Wassers;
With dodecatungstosilic acid at 95℃; for 5h; Reagent/catalyst; Flow reactor;
With Amberlyst-15 at 80℃; for 4h; Kinetics; Reagent/catalyst; Temperature; Molecular sieve;
75-15-0

carbon disulfide

105-76-0

Dibutyl maleate

111-42-2

2,2'-iminobis[ethanol]

C17H31NO6S2

Conditions
ConditionsYield
at 80℃; for 6.25h;96.5%
105-76-0

Dibutyl maleate

67-63-0

isopropyl alcohol

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

Conditions
ConditionsYield
With Benzoylformic acid for 72h; Irradiation; Green chemistry;96%
75-15-0

carbon disulfide

105-76-0

Dibutyl maleate

110-73-6

2-(Ethylamino)ethanol

885700-65-2

C17H31NO5S2

Conditions
ConditionsYield
at 70℃; for 6.66667h;94%
105-76-0

Dibutyl maleate

141-03-7

dibutyl succinate

Conditions
ConditionsYield
With water; 5-methoxy-1,3,4-triphenyl-4,5-dihydro-1H-1,2-4-triazoline In 1,2-dimethoxyethane at 150℃; for 2h; Inert atmosphere; Microwave irradiation;94%
105-76-0

Dibutyl maleate

5144-51-4

di-n-butyl 2-sulfosuccinate sodium salt

Conditions
ConditionsYield
With sodium hydrogensulfite In ethanol at 119.85℃;90.4%
With sodium hydrogensulfite In water at 99.85℃; sulfonation;
With sodium hydrogensulfite In ethanol Heating;
With sodium hydrogensulfite In water at 99.84℃;
105-76-0

Dibutyl maleate

301677-76-9

3,4-Dibromo-2,5-dimethylthiophene S-monoxide

1252031-08-5

dibutyl 2,3-dibromo-1,4-dimethyl-7-thiabicyclo[2.2.1]hept-2-ene-5,6-dicarboxylate 7-oxide

Conditions
ConditionsYield
In chloroform for 24h; Reflux;89%
105-76-0

Dibutyl maleate

6637-53-2, 144252-21-1, 144252-22-2

3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one

dibutyl 3′-oxo-2,3-dihydrospiro[indene-1,1′-isoindoline]-2,3-dicarboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid In 1,2-dichloro-ethane at 120℃; for 20h; Sealed tube;86%
105-76-0

Dibutyl maleate

C15H10BrNO

dibutyl 2-(1-benzoyl-6-bromo-1H-indol-2-yl)succinate

Conditions
ConditionsYield
With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate; acetic acid In dichloromethane at 120℃; for 24h; Inert atmosphere; regioselective reaction;81%
105-76-0

Dibutyl maleate

22841-92-5

(3-chloro-2-pyridyl)hydrazine

71-36-3

butan-1-ol

n-butyl 2-(3-chloropyridin-2-yl)-5-oxo-pyrazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: butan-1-ol With sodium at 80℃;
Stage #2: (3-chloro-2-pyridyl)hydrazine With iodotris(triphenylphosphine)silver(I) In butan-1-ol at 30℃;
Stage #3: Dibutyl maleate In butan-1-ol at 28 - 32℃; Reagent/catalyst;
80%
105-76-0

Dibutyl maleate

1436417-01-4

methyl 1-benzoyl-1H-indole-5-carboxylate

dibutyl 2-(1-benzoyl-5-(methoxycarbonyl)-1H-indol-2-yl)succinate

Conditions
ConditionsYield
With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate; acetic acid In dichloromethane at 120℃; for 24h; Inert atmosphere; regioselective reaction;78%
105-76-0

Dibutyl maleate

1436590-99-6

N-benzoyl-6-chloroindole

dibutyl 2-(1-benzoyl-6-chloro-1H-indol-2-yl)succinate

Conditions
ConditionsYield
With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate; acetic acid In dichloromethane at 120℃; for 24h; Inert atmosphere; regioselective reaction;77%
14729-20-5

tetracarbonyl(1,10-phenanthroline)tungsten(0)

105-76-0

Dibutyl maleate

225373-58-0, 396727-60-9, 396718-44-8

W(CO)2(C12H8N2)(C12H20O4)2

Conditions
ConditionsYield
In toluene (N2(; reflux (19 h); concn., layering with light petroleum (7-10 d), filtration, washing, drying (vac.); elem. anal.;75%
105-76-0

Dibutyl maleate

1127562-54-2

(5-bromoindol-1-yl)phenylmethanone

dibutyl 2-(1-benzoyl-5-bromo-1H-indol-2-yl)succinate

Conditions
ConditionsYield
With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate; acetic acid In dichloromethane at 120℃; for 24h; Inert atmosphere; regioselective reaction;75%
75-15-0

carbon disulfide

105-76-0

Dibutyl maleate

107-11-9

1-amino-2-propene

butyl [4-oxo-3-(prop-2-en-1-yl)-2-sulfanylidene-1,3-thiazolidin-5-yl]acetate

Conditions
ConditionsYield
Heating;75%
15740-78-0

(1,10-phenanthroline)molybdenum tetracarbonyl

105-76-0

Dibutyl maleate

60342-24-7, 60384-25-0

Mo(CO)2(C12H8N2)(C12H20O4)2

Conditions
ConditionsYield
In toluene (N2(; reflux (17 h); concn., layering with light petroleum (7-10 d), filtration, washing, drying (vac.); elem. anal.;72%
105-76-0

Dibutyl maleate

135822-90-1

o-chloro-N-tosylbenzaldimine

dibutyl rac-(1S,2R,3S)-4-chloro-3-((4-methylphenyl)sulfonamido)-2,3-dihydro-1H-indene-1,2-dicarboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; lithium acetate In 1,2-dichloro-ethane at 80℃; for 16h; Sealed tube; diastereoselective reaction;72%
105-76-0

Dibutyl maleate

135822-90-1

o-chloro-N-tosylbenzaldimine

dibutyl (1S,2R,3S)-4-chloro-3-((4-methylphenyl)sulfonamido)-2,3-dihydro-1H-indene-1,2-dicarboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; lithium acetate In 1,2-dichloro-ethane at 80℃; for 16h;72%
105-76-0

Dibutyl maleate

98217-62-0

(E)-1,2-bis(4-(trifluoromethyl)phenyl)diazene

dibutyl 5-(trifluoromethyl)-1H-indole-2,3-dicarboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1,2-dichloro-ethane at 130℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Sealed tube; chemoselective reaction;71%
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1,2-dichloro-ethane at 130℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;71%

4,4′-bis(trifluoromethoxy)azobenzene

105-76-0

Dibutyl maleate

dibutyl 5-(trifluoromethoxy)-1H-indole-2,3-dicarboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1,2-dichloro-ethane at 130℃; for 12h; Sealed tube; chemoselective reaction;70%
1496-76-0

N-benzoylindole

105-76-0

Dibutyl maleate

dibutyl 2-(1-benzoyl-1H-indol-2-yl)succinate

Conditions
ConditionsYield
With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate; acetic acid In dichloromethane at 120℃; for 24h; Inert atmosphere; regioselective reaction;68%
105-76-0

Dibutyl maleate

7250-68-2

4,4'-bis(ethoxycarbonyl)azobenzene

2,3-dibutyl 5-ethyl 1H-indole-2,3,5-tricarboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1,2-dichloro-ethane at 130℃; for 12h; Sealed tube; chemoselective reaction;67%
105-76-0

Dibutyl maleate

100-52-7

benzaldehyde

77425-65-1, 77480-79-6, 91278-68-1

3,6-diphenyltetrahydrofuro[3,4-c]furan-1,4-dione

Conditions
ConditionsYield
With samarium; copper(l) iodide; toluene-4-sulfonic acid; potassium iodide In tetrahydrofuran at 20℃; Molecular sieve; Inert atmosphere; diastereoselective reaction;65%
105-76-0

Dibutyl maleate

588-00-1

1,2-bis((3-trifluoromethyl)phenyl)diazene

dibutyl 6-(trifluoromethyl)-1H-indole-2,3-dicarboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1,2-dichloro-ethane at 130℃; for 12h; Sealed tube; chemoselective reaction;65%
105-76-0

Dibutyl maleate

dibutyl 6-chloro-1H-indole-2,3-dicarboxylate

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1,2-dichloro-ethane at 130℃; for 12h; Sealed tube; chemoselective reaction;64%
16632-93-2

tetracarbonyl(4,7-diphenyl-1,10-phenanthroline-N,N')molybdenum(0)

105-76-0

Dibutyl maleate

390387-45-8

[molybdenum(CO)2(4,7-diphenyl-1,10-phenanthroline)(dibutylfumarate)2]

Conditions
ConditionsYield
In toluene all manipulations under N2 atm.; org. compd. added to soln. of complex, refluxed for 21 h; concd., chromy., solvent removed, dried in vac., elem. anal.;63%
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    Dibutyl Maleate (DBM)CAS NO.: 105-76-0

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The CAS registry number of Dibutyl maleate is 105-76-0. Its EINECS registry number is 203-328-4. The systematic name is dibutyl but-2-enedioate. In addition, the molecular formula is C12H20O4 and the molecular weight is 228.28. What's more, it is a kind of clear colourless to slightly yellowish liquid and belongs to the classes of Plasticizer; Carbonyl Compounds; Esters. It can be used as raw material for synthetic resin, and used as organic synthesis intermediates.

Physical properties about this chemical are: (1)ACD/LogP: 3.81; (2)ACD/LogD (pH 5.5): 3.81; (3)ACD/LogD (pH 7.4): 3.81; (4)ACD/BCF (pH 5.5): 461.68; (5)ACD/BCF (pH 7.4): 461.68; (6)ACD/KOC (pH 5.5): 2810.22; (7)ACD/KOC (pH 7.4): 2810.22; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 10; (10)Polar Surface Area: 52.6 Å2; (11)Index of Refraction: 1.451; (12)Molar Refractivity: 61.25 cm3; (13)Molar Volume: 227.1 cm3; (14)Polarizability: 24.28 ×10-24cm3; (15)Surface Tension: 33.4 dyne/cm; (16)Density: 1.004 g/cm3; (17)Flash Point: 136.4 °C; (18)Enthalpy of Vaporization: 51.87 kJ/mol; (19)Boiling Point: 280 °C at 760 mmHg; (20)Vapour Pressure: 0.00388 mmHg at 25°C.

Preparation of Dibutyl maleate: it can be prepared by cisbutenedioic anhydride and butanol in the presence of sulfuric acid through esterification reaction. After a series of neutralization, washing, dehydroxylation, distillation and filtration you can get the desired product from the reaction product.

Uses of Dibutyl maleate: it is used as impregnants, dispersants, lubricants and plasticizers. And it can react with 1H-imidazole to get 2-imidazol-1-yl-succinic acid dibutyl ester. The reaction time is 7 hours at reaction temperature of 100 °C. The yield is about 50%.

Dibutyl maleate can react with 1H-imidazole to get 2-imidazol-1-yl-succinic acid dibutyl ester

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. It may cause sensitization by skin contact. In addition, it is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing and gloves and avoid contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Moreover, you should avoid release to the environment and you can refer to special instructions safety data sheet. You can not empty it into drains.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCCCC)C=CC(=O)OCCCC
(2)InChI: InChI=1/C12H20O4/c1-3-5-9-15-11(13)7-8-12(14)16-10-6-4-2/h7-8H,3-6,9-10H2,1-2H3
(3)InChIKey: JBSLOWBPDRZSMB-UHFFFAOYAY

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,
rabbit LD50 skin 10gm/kg (10000mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 2, Pg. 19, 1975.
rat LD50 oral 3700mg/kg (3700mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 2, Pg. 19, 1975.