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CAS No.: | 624-48-6 |
---|---|
Name: | Dimethyl maleate |
Article Data: | 150 |
Molecular Structure: | |
Formula: | C6H8O4 |
Molecular Weight: | 144.127 |
Synonyms: | 2-Butenedioicacid (2Z)-, dimethyl ester (9CI);2-Butenedioic acid (Z)-, dimethyl ester;Maleic acid, dimethyl ester (6CI,8CI);(2Z)-2-Butenedioic acid dimethyl ester;(Z)-Dimethyl 2-butenedioate;Dimethyl (Z)-butenedioate;Dimethylcis-butenedioate;Dimethyl cis-ethenedicarboxylate;Dimethylcis-ethylenedicarboxylate;Methyl maleate;Sipomer DMM; |
EINECS: | 210-848-5 |
Density: | 1.124 g/cm3 |
Melting Point: | -19 °C |
Boiling Point: | 193 °C at 760 mmHg |
Flash Point: | 91.1 °C |
Solubility: | Miscible with water. |
Appearance: | colourless liquid |
Hazard Symbols: | Xn |
Risk Codes: | 21/22-36/37/38-43 |
Safety: | 26-36/37-23 |
Transport Information: | UN 2810 6.1/PG 3 |
PSA: | 52.60000 |
LogP: | -0.11140 |
Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
With sulfuric acid at 75℃; for 16h; | 97% |
With sulfuric acid at 75℃; for 16h; Reflux; | 97% |
Conditions | Yield |
---|---|
With hydrogen; montmorillonit-bipyridinpalladium(II)-acetate In tetrahydrofuran Ambient temperature; | 98% |
With isocyanate de chlorosulfonyle; hydrogen; palladium diacetate; borohydride exchange resin In ethanol for 2h; | 98% |
With borohydride exchange resin; hydrogen; nickel diacetate In methanol at -15℃; under 760 Torr; for 2h; | 96% |
Conditions | Yield |
---|---|
With sulfuric acid at 10 - 20℃; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate at 120℃; for 1h; Catalytic behavior; Reagent/catalyst; Microwave irradiation; | 94.59% |
With acetyl chloride unter Lichtausschluss; |
A
dimethyl cis-but-2-ene-1,4-dioate
B
N-p-tolylsulfonylphosphine imide
C
dimethylfumarate
Conditions | Yield |
---|---|
In toluene for 14h; Heating; | A n/a B 93% C n/a |
methanol
carbon monoxide
acetylene
A
cis,cis-dimethyl muconate
B
dimethyl cis-but-2-ene-1,4-dioate
C
dimethylfumarate
Conditions | Yield |
---|---|
PdI2-KI at 60℃; under 19000 Torr; for 15h; | A 7% B 89% C 3% |
dimethyl cis-but-2-ene-1,4-dioate
Conditions | Yield |
---|---|
With magnesium iodide In acetonitrile for 0.5h; Ambient temperature; | 88% |
methanol
carbon monoxide
acetylene
A
dimethyl cis-but-2-ene-1,4-dioate
B
dimethylfumarate
Conditions | Yield |
---|---|
With hydrogenchloride; oxygen; copper dichloride; palladium dichloride under 1 Torr; for 2h; | A 86% B 14% |
methyl diazoacetate
3-morpholino-but-2-enoic acid methyl ester
A
dimethyl cis-but-2-ene-1,4-dioate
B
dimethylfumarate
Conditions | Yield |
---|---|
copper acetylacetonate In ethyl acetate Heating; | A n/a B n/a C 86% |
dimethyl acetylenedicarboxylate
A
dimethyl cis-but-2-ene-1,4-dioate
B
Dimethyl succinate
Conditions | Yield |
---|---|
palladium anchored polystyrene In diethyl ether at 25℃; under 1551.4 Torr; for 18h; | A 84% B 4% |
With hydrogen; ethylenediamine; Pd on pumice In tetrahydrofuran for 0.5h; | A 94 % Chromat. B 6 % Chromat. |
With [Pd(p-benzoquinone)(1,3-dimesitylimidazol-2-ylidene)]2; hydrogen In tetrahydrofuran at 20℃; under 750.06 Torr; |
Molecular Structure:
Molecular Formula: C6H8O4
Molecular Weight: 144.1253
IUPAC Name: Dimethyl (Z)-but-2-enedioate
Synonyms of Dimethyl maleate (CAS NO.624-48-6): 2-Butenedioic acid, dimethyl ester, (Z)- ; 4-02-00-02204 (Beilstein Handbook Reference) ; AI3-07869 ; BRN 0471705 ; Dimethyl cis-butenedioate ; Dimethyl cis-ethylenedicarboxylate ; Dimethylester kyseliny maleinove ; Dimethylester kyseliny maleinove [Czech] ; EINECS 210-848-5 ; Maleic acid, dimethyl ester ; Methyl maleate ; NSC 5161 ; Sipomer DMM ; 2-Butenedioic acid (2Z)-, 1,4-dimethyl ester ; 2-Butenedioic acid (2Z)-, dimethyl ester ; 2-Butenedioic acid (Z)-, dimethyl ester ; Maleic acid, dimethyl ester (8CI)
CAS NO: 624-48-6
Classification Code: Skin / Eye Irritant
Melting point: -19°C
Index of Refraction: 1.435
Molar Refractivity: 33.45 cm3
Molar Volume: 128.1 cm3
Surface Tension: 33.1 dyne/cm
Density: 1.124 g/cm3
Flash Point: 91.1 °C
Enthalpy of Vaporization: 42.92 kJ/mol
Boiling Point: 193 °C at 760 mmHg
Vapour Pressure: 0.475 mmHg at 25°C
Dimethyl maleate (CAS NO.624-48-6) is used in many organic syntheses as a dienophile for diene synthesis. It is used as an additive and intermediate for plastics, pigments, pharmaceuticals, and agricultural products. It is also an intermediate for the production of paints, adhesives, and copolymers. It has also found use in applications where improvements in the hardness and toughness of polymer films are desired. This includes, in particular, the improvement of anti-blocking properties of copolymers of vinyl acetate with DMM. It is also used as an internal modifier to increase the glass transition temperature of styrene or vinyl chloride polymers.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC | inhalation | > 1500mg/m3/10 (1500mg/m3) | National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. Aug, 1942. | |
rabbit | LD50 | skin | 530uL/kg (0.53mL/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. | |
rat | LD50 | oral | 1410mg/kg (1410mg/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion and skin contact. An eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO2, dry chemical. Safety Information of Dimethyl maleate (CAS NO.624-48-6):
Hazard Codes : Xn
Xn : Harmful
Risk Statements :21/22-36/37/38-43 ( Harmful in contact with skin and if swallowed ; Irritating to eyes, respiratory system and skin ;May cause sensitization by skin contact )
Safety Statements: 26-36/37-23 ( In case of contact with eyes, rinse immediately with plenty of water and seek medical advice ; Wear suitable protective clothing and gloves ;Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) )
RIDADR UN 2810 6.1/PG 3
WGK Germany 1
RTECS EM6300000
HazardClass 6.1(b)
PackingGroup III
HS Code 29171990