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Name	Dimethyl maleate	EINECS	210-848-5
CAS No.	624-48-6	Density	1.124 g/cm³
PSA	52.60000	LogP	-0.11140
Solubility	Miscible with water.	Melting Point	-19 °C
Formula	C₆H₈O₄	Boiling Point	193 °C at 760 mmHg
Molecular Weight	144.127	Flash Point	91.1 °C
Transport Information	UN 2810 6.1/PG 3	Appearance	colourless liquid
Safety	26-36/37-23	Risk Codes	21/22-36/37/38-43
Molecular Structure		Hazard Symbols	Xn
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;	Article Data	150

Dimethyl maleate Synthetic route

: 67-56-1
methanol

: 110-16-7
maleic acid

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

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%

: 762-42-5
dimethyl acetylenedicarboxylate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

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%

: 108-31-6
maleic anhydride

: 1634-04-4
tert-butyl methyl ether

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With sulfuric acid at 10 - 20℃; regioselective reaction;	95%

: 108-31-6
maleic anhydride

: 67-56-1
methanol

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

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;

: dimethyl 2-(p-toluenesulfonamido)-3-(triphenylphosphoranylidene)butanedioate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 1058-14-6
N-p-tolylsulfonylphosphine imide

C: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
In toluene for 14h; Heating;	A n/a B 93% C n/a

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 74-86-2
acetylene

A: 692-91-1, 692-92-2, 1119-43-3, 1733-37-5
cis,cis-dimethyl muconate

B: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

C: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
PdI2-KI at 60℃; under 19000 Torr; for 15h;	A 7% B 89% C 3%

...Expand

: dimethyl meso-tartrate cyclic sulfate

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

Conditions

Conditions	Yield
With magnesium iodide In acetonitrile for 0.5h; Ambient temperature;	88%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 74-86-2
acetylene

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

Conditions

Conditions	Yield
With hydrogenchloride; oxygen; copper dichloride; palladium dichloride under 1 Torr; for 2h;	A 86% B 14%

: 6832-16-2
methyl diazoacetate

: 55261-56-8
3-morpholino-but-2-enoic acid methyl ester

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 624-49-7
dimethylfumarate

: (1R,2R)-3-Methyl-3-morpholin-4-yl-cyclopropane-1,2-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
copper acetylacetonate In ethyl acetate Heating;	A n/a B n/a C 86%

: 762-42-5
dimethyl acetylenedicarboxylate

A: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

B: 106-65-0
Dimethyl succinate

Conditions

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;

Dimethyl maleate Chemical Properties

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 Uses

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.

Dimethyl maleate Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	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.

Dimethyl maleate Consensus Reports

Reported in EPA TSCA Inventory.

Dimethyl maleate Safety Profile

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

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