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105-76-0

Basic Information
CAS No.: 105-76-0
Name: Dibutyl maleate
Article Data: 27
Cas Database
Molecular Structure:
Molecular Structure of 105-76-0 (Dibutyl maleate)
Formula: C12H20O4
Molecular Weight: 228.288
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: N/A
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%
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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.