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Cas Database

624-48-6

624-48-6

Identification

  • Product Name:Dimethyl maleate

  • CAS Number: 624-48-6

  • EINECS:210-848-5

  • Molecular Weight:144.127

  • Molecular Formula: C6H8O4

  • HS Code:2917.19

  • Mol File:624-48-6.mol

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;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn,C

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH317 May cause an allergic skin reaction H319 Causes serious eye irritation H335 May cause respiratory irritation H373 May cause damage to organs through prolonged or repeated exposure

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Dimethyl maleate
  • Packaging:10g
  • Price:$ 150
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl Maleate >97.0%(GC)
  • Packaging:500mL
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl Maleate >97.0%(GC)
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  • Product Description:Dimethyl maleate 96%
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  • Product Description:Dimethyl maleate 96%
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  • Product Description:Dimethyl maleate 96%
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Relevant articles and documentsAll total 113 Articles be found

Hetero-NMR enhancement via parahydrogen labeling

Barkemeyer, Jens,Haake, Mathias,Bargon, Joachim

, p. 2927 - 2928 (1995)

-

Long-lived 1H nuclear spin singlet in dimethyl maleate revealed by addition of thiols

Zhang, Yuning,Soon, Pei Che,Jerschow, Alexej,Canary, James W.

, p. 3396 - 3399 (2014)

Nuclear magnetic resonance (NMR) spectroscopy and magnetic resonance imaging (MRI) have become important techniques in many research areas. One major limitation is the relatively low sensitivity of these methods, which recently has been addressed by hyperpolarization. However, once hyperpolarization is imparted on a molecule, the magnetization typically decays within relatively short times. Singlet states are well isolated from the environment, such that they acquire long lifetimes. We describe herein a model reaction for read-out of a hyperpolarized long-lived state in dimethyl maleate using thiol conjugate addition. This type of reaction could lend itself to monitoring oxidative stress or hypoxia by sensitive detection of thiols. Similar reactions could be used in biosensors or assays that exploit molecular switching. Singlet lifetimes of about 4.7 min for 1H spins in [D4]MeOH are seen in this system. Hyperpolarized singlet states are well isolated from the environment, such that they acquire long lifetimes. Here, we used the thiol conjugate addition to unveil the hyperpolarized long-lived singlet state in deuterated dimethyl maleate (see picture). Singlet lifetimes of 4.7 min for 1H spins in [D4]MeOH are seen in this system.

Cu(OAc)2-2,4-lutidine-ZnCl2 as an effective catalyst of functionalization of isobutylene oligomers and 1,2-polybutadiene with methyl diazoacetate

Gareev,Yangirov,Volodina,Sultanova,Biglova,Dokichev

, p. 1305 - 1309 (2009)

The possibility of [1+2]-cycloaddition of methoxycarbonylcarbene generated by catalytic decomposition of methyl diazoacetate in the presence of the Cu(OAc)2-2,4-lutidine-ZnCl2 system to the carbon-carbon double bound in isobutylene o

Limits in Proton Nuclear Singlet-State Lifetimes Measured with para-Hydrogen-Induced Polarization

Zhang, Yuning,Duan, Xueyou,Soon, Pei Che,Canary, James W.,Jerschow, Alexej,Sychrovsky, Vladimír

, p. 2967 - 2971 (2016)

The synthesis of a hyperpolarized molecule was developed, where the polarization and the singlet state were preserved over two controlled chemical steps. Nuclear singlet-state lifetimes close to 6 min for protons are reported in dimethyl fumarate. Owing to the high symmetry (AA′X3X3′ and A2 systems), the singlet-state readout requires either a chemical desymmetrization or a long and repeated spin lock. Using DFT calculations and relaxation models, we further determine nuclear spin singlet lifetime limiting factors, which include the intramolecular dipolar coupling mechanism (proton–proton and proton–deuterium), the chemical shift anisotropy mechanism (symmetric and antisymmetric), and the intermolecular dipolar coupling mechanism (to oxygen and deuterium). If the limit of paramagnetic relaxation caused by residual oxygen could be lifted, the intramolecular dipolar coupling to deuterium would become the limiting relaxation mechanism and proton lifetimes upwards of 26 min could become available in the molecules considered here (dimethyl maleate and dimethyl fumarate).

Self-Assembled Open Porous Nanoparticle Superstructures

Liu, Rongjuan,Wei, Jingjing,Wei, Yanze,Yang, Zhijie,Zhang, Fenghua

supporting information, (2021/08/20)

Imparting porosity to inorganic nanoparticle assemblies to build up self-assembled open porous nanoparticle superstructures represents one of the most challenging issues and will reshape the property and application scope of traditional inorganic nanoparticle solids. Herein, we discovered how to engineer open pores into diverse ordered nanoparticle superstructures via their inclusion-induced assembly within 1D nanotubes, akin to the molecular host-guest complexation. The open porous structure of self-assembled composites is generated from nonclose-packing of nanoparticles in 1D confined space. Tuning the size ratios of the tube-to-nanoparticle enables the structural modulation of these porous nanoparticle superstructures, with symmetries such as C1, zigzag, C2, C4, and C5. Moreover, when the internal surface of the nanotubes is blocked by molecular additives, the nanoparticles would switch their assembly pathway and self-assemble on the external surface of the nanotubes without the formation of porous nanoparticle assemblies. We also show that the open porous nanoparticle superstructures can be ideal candidate for catalysis with accelerated reaction rates.

A Br?nsted acidic, ionic liquid containing, heteropolyacid functionalized polysiloxane network as a highly selective catalyst for the esterification of dicarboxylic acids

Rajabi, Fatemeh,Wilhelm, Christian,Thiel, Werner R.

supporting information, p. 4438 - 4444 (2020/08/10)

A Br?nsted acidic, ionic liquid containing, heteropolyanion functionalized polysiloxane network was formed by self-condensation of dodecatungstophosphoric acid and a zwitterionic organosilane precursor containing both imidazolinium and sulfonate groups. The resulting hybrid material POS-HPA-IL was investigated as a catalyst for the selective esterification of dicarboxylic acids.

Process route upstream and downstream products

Process route

dimethyl 2-bromosuccinate
760-90-7

dimethyl 2-bromosuccinate

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

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

dimethyl cis-but-2-ene-1,4-dioate

Conditions
Conditions Yield
bei der Destillation unter gewoehnlichem Druck;
4-(pyrrolidin-1-yl)pent-3-en-2-one
23652-59-7

4-(pyrrolidin-1-yl)pent-3-en-2-one

methyl diazoacetate
6832-16-2

methyl diazoacetate

methyl 2-acetyl-4-oxovalerate
85392-47-8

methyl 2-acetyl-4-oxovalerate

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

dimethyl cis-but-2-ene-1,4-dioate

dimethylfumarate
624-49-7

dimethylfumarate

Conditions
Conditions Yield
copper(I) triflate; In dichloromethane; at 20 ℃; for 24h;
84%
4-(pyrrolidin-1-yl)pent-3-en-2-one
23652-59-7

4-(pyrrolidin-1-yl)pent-3-en-2-one

methyl diazoacetate
6832-16-2

methyl diazoacetate

methyl 2-acetyl-4-oxovalerate
85392-47-8

methyl 2-acetyl-4-oxovalerate

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

dimethyl cis-but-2-ene-1,4-dioate

dimethylfumarate
624-49-7

dimethylfumarate

4-Oxo-2-[1-pyrrolidin-1-yl-eth-(E)-ylidene]-pentanoic acid methyl ester

4-Oxo-2-[1-pyrrolidin-1-yl-eth-(E)-ylidene]-pentanoic acid methyl ester

Conditions
Conditions Yield
copper(I) triflate; In dichloromethane; at 20 ℃; for 24h; Product distribution; Mechanism; var. of catalyst, solvent, temp., ratio;
styrenesulfide
1498-99-3

styrenesulfide

methyl (triphenylphosphoranylidene)acetate
21204-67-1,2605-67-6

methyl (triphenylphosphoranylidene)acetate

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

dimethyl cis-but-2-ene-1,4-dioate

Conditions
Conditions Yield
In toluene; for 48h; Heating;
42 % Spectr.
77 % Spectr.
2-phenyl-1,3-dioxolane
936-51-6

2-phenyl-1,3-dioxolane

methyl diazoacetate
6832-16-2

methyl diazoacetate

C<sub>12</sub>H<sub>14</sub>O<sub>4</sub>

C12H14O4

benzaldehyde
100-52-7

benzaldehyde

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

dimethyl cis-but-2-ene-1,4-dioate

dimethylfumarate
624-49-7

dimethylfumarate

methyl 3-phenyl-1,4-dioxane-2-carboxylate

methyl 3-phenyl-1,4-dioxane-2-carboxylate

Conditions
Conditions Yield
With copper(II) bis(trifluoromethanesulfonate); 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; In dichloromethane; at 40 ℃; for 24h; optical yield given as %de;
10 %Spectr.
With copper(II) bis(trifluoromethanesulfonate); 1-butyl-3-methylimidazolium Tetrafluoroborate; In dichloromethane; at 75 ℃; for 24h; optical yield given as %de;
42 %Spectr.
methanol
67-56-1

methanol

4-chloro-phenol
106-48-9,82344-39-6

4-chloro-phenol

Dimethyl oxalate
553-90-2

Dimethyl oxalate

(R)-dimethyl malate
70681-41-3

(R)-dimethyl malate

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

dimethyl cis-but-2-ene-1,4-dioate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
4-chloro-phenol; In water; at 20 ℃; Darkness;
With dihydrogen peroxide; In water; Irradiation;
methanol; With sulfuric acid; Reflux;
ClCH<sub>2</sub>Co(COOCH<sub>3</sub>)(CO)3<sup>(1-)</sup>
106865-88-7

ClCH2Co(COOCH3)(CO)3(1-)

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

dimethyl cis-but-2-ene-1,4-dioate

methyl chloroacetate
96-34-4

methyl chloroacetate

1,2-dichloro-ethane
107-06-2,52399-93-6

1,2-dichloro-ethane

1,3-Dichloroacetone
534-07-6

1,3-Dichloroacetone

Dimethyl succinate
106-65-0

Dimethyl succinate

Conditions
Conditions Yield
In tetrahydrofuran; byproducts: Co(CO)4(1-); soln. of the Co-complex was gradually warmed from -40°C to room temp. in 2 h under Ar atmosphere; reaction mixt. was analyzed by IR spectroscopy and gas chromy.; GC yield of dimethyl malonate 9.5% (from the two stages);
0%
0%
0%
0%
With ClCH2Cl; In tetrahydrofuran; byproducts: Co(CO)4(1-); ClCH2Cl was added to the soln. of the Co-complex at -40°C, soln. was gradually warmed to room temp. in 2 h under Ar atmosphere; reaction mixt. was analyzed by IR spectroscopy and gas chromy.; GC yield of dimethyl malonate 24.4% (from the two stages);
0%
0%
0%
0%
With ClCH2Cl; In methanol; byproducts: Co(CO)4(1-); ClCH2Cl was added to the soln. of the Co-complex at -40°C, soln. was gradually warmed to room temp. in 2 h under Ar atmosphere; reaction mixt. was analyzed by IR spectroscopy and gas chromy.; GC yield of dimethyl malonate 56.9% (from the two stages);
0%
0%
0%
0%
In methanol; byproducts: Co(CO)4(1-); soln. of the Co-complex was gradually warmed from -40°C to room temp. in 2 h under Ar atmosphere; reaction mixt. was analyzed by IR spectroscopy and gas chromy.; GC yield of dimethyl malonate 25% (from the two stages);
0%
0%
0%
0%
Na<sup>(1+)</sup>*ClCH<sub>2</sub>Co(COOCH<sub>3</sub>)(CO)3<sup>(1-)</sup>=Na(ClCH<sub>2</sub>Co(COOCH<sub>3</sub>)(CO)3)
106865-88-7

Na(1+)*ClCH2Co(COOCH3)(CO)3(1-)=Na(ClCH2Co(COOCH3)(CO)3)

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

dimethyl cis-but-2-ene-1,4-dioate

methyl chloroacetate
96-34-4

methyl chloroacetate

1,2-dichloro-ethane
107-06-2,52399-93-6

1,2-dichloro-ethane

1,3-Dichloroacetone
534-07-6

1,3-Dichloroacetone

Dimethyl succinate
106-65-0

Dimethyl succinate

Conditions
Conditions Yield
With ClCH2Cl; In tetrahydrofuran; byproducts: NaCo(CO)4; ClCH2Cl was added to the soln. of the Co-complex at -40°C, soln. was gradually warmed to room temp. in 2 h under Ar atmosphere; reaction mixt. was analyzed by IR spectroscopy and gas chromy.; GC yield of dimethyl malonate 24.4% (from the two stages);
0%
0%
0%
0%
With ClCH2Cl; In methanol; byproducts: NaCo(CO)4; ClCH2Cl was added to the soln. of the Co-complex at -40°C, soln. was gradually warmed to room temp. in 2 h under Ar atmosphere; reaction mixt. was analyzed by IR spectroscopy and gas chromy.; GC yield of dimethyl malonate 56.9% (from the two stages);
0%
0%
0%
0%
In tetrahydrofuran; byproducts: NaCo(CO)4; soln. of the Co-complex was gradually warmed from -40°C to room temp. in 2 h under Ar atmosphere; reaction mixt. was analyzed by IR spectroscopy and gas chromy.; GC yield of dimethyl malonate 9.5% (from the two stages);
0%
0%
0%
0%
In methanol; byproducts: NaCo(CO)4; soln. of the Co-complex was gradually warmed from -40°C to room temp. in 2 h under Ar atmosphere; reaction mixt. was analyzed by IR spectroscopy and gas chromy.; GC yield of dimethyl malonate 25% (from the two stages);
0%
0%
0%
0%
methanol
67-56-1

methanol

C<sub>10</sub>H<sub>19</sub>O<sub>8</sub>P
74783-15-6

C10H19O8P

trimethyl phosphite
512-56-1

trimethyl phosphite

methyl (2E)-3-methoxy-2-propenoate
5788-17-0

methyl (2E)-3-methoxy-2-propenoate

dimethyl 2-methoxybutanedioate
4148-97-4

dimethyl 2-methoxybutanedioate

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

dimethyl cis-but-2-ene-1,4-dioate

Conditions
Conditions Yield
for 40h; Further byproducts given; Heating;
methanol
67-56-1

methanol

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

maleic anhydride
108-31-6

maleic anhydride

Dimethyl oxalate
553-90-2

Dimethyl oxalate

2,5-diformylfurane
823-82-5,163857-09-8

2,5-diformylfurane

glycolic acid methyl ester
96-35-5

glycolic acid methyl ester

levulinic acid methyl ester
624-45-3

levulinic acid methyl ester

monomethyl maleate
3052-50-4

monomethyl maleate

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

dimethyl cis-but-2-ene-1,4-dioate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethylfumarate
624-49-7

dimethylfumarate

Dimethyl succinate
106-65-0

Dimethyl succinate

Conditions
Conditions Yield
5-hydroxymethyl-2-furfuraldehyde; With vanadium(IV) oxide sulfate hydrate; oxygen; under 7500.75 Torr;
methanol; With boron trifluoride diethyl etherate;

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