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Cas Database

624-49-7

624-49-7

Identification

  • Product Name:Dimethyl fumarate

  • CAS Number: 624-49-7

  • EINECS:210-849-0

  • Molecular Weight:144.127

  • Molecular Formula: C6H8O4

  • HS Code:29171990

  • Mol File:624-49-7.mol

Synonyms:2-Butenedioic acid (E)-, dimethyl ester;Fumaric acid, dimethyl ester (6CI,8CI);(2E)-2-Butenedioic acid dimethyl ester;(E)-But-2-enedioic acid dimethyl ester;AZL-O 211089;Dimethyl (E)-2-butenedioate;Dimethyl(E)-butenedioate;2-Butenedioic acid(2E)-, 1,4-dimethyl ester;Dimethyl trans-ethylenedicarboxylate;NSC 167432;trans-1,2-Ethylenedicarboxylic aciddimethyl ester;trans-Butenedioic acid dimethyl ester;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes: Xn:Harmful;

  • Signal Word:Warning

  • Hazard Statement:H312 Harmful in contact with skin

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Seek medical attention if you feel unwell. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention if skin irritation occurs. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

  • Fire-fighting measures: Suitable extinguishing media 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. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. If appropriate, moisten first to prevent dusting. Sweep spilled substance into sealable containers. Then store and dispose of according to local regulations. Wash away remainder with plenty of water. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. If appropriate, moisten first to prevent dusting. Sweep spilled substance into sealable containers. Then store and dispose of according to local regulations. Wash away remainder with plenty of water.

  • 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. Keep in a well-ventilated room. Well closed. Keep in the dark. Separated from strong oxidants.Store at 15°C to 30°C (59 to 86 deg F). Protect the capsules from light. Store in original container.

  • 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

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:Dimethyl Fumarate
  • Packaging:50mg
  • Price:$ 312
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl Fumarate >98.0%(GC)
  • Packaging:500g
  • Price:$ 160
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl Fumarate >98.0%(GC)
  • Packaging:25g
  • Price:$ 31
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dimethyl fumarate 97%
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  • Price:$ 28.7
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dimethyl fumarate for synthesis. CAS 624-49-7, chemical formula CH OOCCH=CHCOOCH ., for synthesis
  • Packaging:8205830100
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dimethyl fumarate 97%
  • Packaging:100g
  • Price:$ 58.5
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dimethyl fumarate certified reference material, TraceCERT
  • Packaging:100mg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dimethyl fumarate for synthesis. CAS 624-49-7, chemical formula CH OOCCH=CHCOOCH ., for synthesis
  • Packaging:8205830250
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Dimethyl fumarate
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Dimethyl fumarate
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Relevant articles and documentsAll total 145 Articles be found

Dimethyl fumarate is an allosteric covalent inhibitor of the p90 ribosomal S6 kinases

Andersen, Jacob Lauwring,Nielsen, Christine Juul F?lled,Gotfred-Rasmussen, Helle,Nissen, Poul,Gesser, Borbala,Rasmussen, Mads Kirchheiner,Iversen, Lars,Funder, Erik Daa,Gothelf, Kurt Vesterager,Toth, Rachel,Arthur, J. Simon C.

, (2018)

Dimethyl fumarate (DMF)?has been applied for decades in the treatment of psoriasis and now also multiple sclerosis. However, the mechanism of action has remained obscure and involves high dose over long time of this small, reactive compound implicating many potential targets. Based on a 1.9 ? resolution crystal structure of the C-terminal kinase domain of the mouse p90 Ribosomal S6 Kinase 2 (RSK2) inhibited by DMF?we describe a central binding site in RSKs and the closely related Mitogen and Stress-activated Kinases (MSKs). DMF reacts covalently as a Michael acceptor to a conserved cysteine residue in the αF-helix of RSK/MSKs. Binding of DMF prevents the activation loop of the kinase from engaging substrate, and stabilizes an auto-inhibitory αL-helix, thus pointing to an effective, allosteric mechanism of kinase inhibition. The biochemical and cell biological characteristics of DMF inhibition of RSK/MSKs are consistent with the clinical protocols of DMF treatment.

REACTIONS OF BENZYLCHLOROBIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) WITH DIMETHYL ACETYLENEDICARBOXYLATE

Hiraki, Katsuma,Itoh, Toshihiro,Eguchi, Katsuya,Onishi, Masayoshi

, p. C16 - C20 (1983)

Benzylchlorobis(triphenylphosphine)palladium(II) reacted with dimethyl acetylenedicarboxylate to give Cl(PPh3)>2> (II) and PdCl(PPh3)> (III).Complexes II and III reacted with Tl(acac) to afford

Protic, imidazolium ionic liquids as media for (Z)- to (E)-alkene isomerization

Janus, Ewa,Lozynski, Marek,Pernak, Juliusz

, p. 210 - 211 (2006)

The quantitative isomerization of (Z)- to (E-alkene in protic, imidazolium ionic liquids is demonstrated. The isomerization parameters were determined. The mechanism on the addition of the protic imidazolium species to carbon-carbon double bond is presented. Copyright

Aminal-catalyzed isomerization of and addition to dimethyl maleate

Cook,Voges, Andrea B,Kammrath, Aster E

, p. 7349 - 7352 (2001)

The amine moiety of aminals adds to dimethyl maleate via azomethine ylid intermediates. The products of this reaction, in turn, cause dimethyl maleate to isomerize to dimethyl fumarate.

Unusual formation of tetrahydropyridazine-3,4,5,6-tetracarboxylic and pyrroletetracarboxylic esters upon decomposition of methyl diazoacetate in the presence of pyridine

Tomilov,Platonov,Averkiev,Shulishov,Nefedov

, p. 187 - 191 (2003)

Thermal, photolytic, and thermocatalytic decomposition of methyl diazoacetate (MDA) in the presence of Rh2(OAc)4 or Cu(acac)2 in refluxing pyridine afforded isomeric trans, cis- and cis, trans-3,4,5,6-tetra(methoxycarbonyl)-1,4,5,6-tetrahydropyridazines (~1 : 1) in a total yield of 30-70%. Decomposition of MDA in refluxing o-xylene in the presence of Rh2(OAc)4 and pyridine (20 mol.%) gave rise to 2,3,4,5-tetra(methoxycarbonyl)pyrrole in a yield of up to 40%. In these transformations of MDA, neither dimethyl fumarate (or dimethyl maleate) nor the corresponding 2-pyrazolines were generated as intermediates.

Generation and cycloaddition of polymer-supported azomethine ylide via a 1,2-silatropic shift of α-silylimines: Traceless synthesis of pyrrolidine derivatives

Komatsu, Mitsuo,Okada, Hirofumi,Akaki, Tatsuo,Oderaotoshi, Yoji,Minakata, Satoshi

, p. 3505 - 3508 (2002)

(matrix presented) The 1,3-bipolar cycloaddition of polymer-supported azomethine ylides to dipolarophiles gave pyrrolidine derivatives in good yields. The azomethine ylides were generated from resin-bound α-silylimines via a 1,2-silatropic shift. The features of this method are not only a traceless synthesis but also a uniaue solid-phase route to pyrrolidines with extensive diversity.

Zwitterion-Catalyzed Isomerization of Maleic to Fumaric Acid Diesters

Lam, Ying-Pong,Lam, Zachary,Yeung, Ying-Yeung

, p. 1183 - 1190 (2021/01/09)

Fumaric acid diesters are important building blocks for organic synthesis. A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair were found to be effective in catalyzing the isomerization of maleic acid diesters to give fumaric acid diesters. Comparison of the performance of different zwitterionic organocatalysts toward the reaction revealed that nonclassical hydrogen bonding was involved in the stabilization of the Michael adduct intermediate.

Small-Molecule Investigation of Diels-Alder Complexes for Thermoreversible Crosslinking in Polymeric Applications

Rowlett, Jarrett R.,Deglmann, Peter,Sprafke, Johannes,Roy, Nabarun,Mülhaupt, Rolf,Bruchmann, Bernd

, p. 8933 - 8944 (2021/07/20)

Combinations of dienes and dienophiles were examined in order to elicit possible combinations for thermoreversible crosslinking units. Comparison of experimental results and quantum calculations indicated that reaction kinetics and activation energy were much better prediction factors than change in enthalpy for the prediction of successful cycloaddition. Further testing on diene-dienophile pairs that underwent successful cycloaddition determined the feasibility of thermoreversibility/retro-reaction of each of the Diels-Alder compounds. Heating and testing of the compounds in the presence of a trapping agent allowed for experimental determination of reverse kinetics and activation energy for the retro-reaction. The experimental values were in good agreement with quantum calculations. The combination of chemical calculations with experimental results provided a strong insight into the structure-property relationships and how quantum calculations can be used to examine the feasibility of the thermoreversibility of new Diels-Alder complexes in potential polymer systems or to fine-tune thermoreversible Diels-Alder systems already in use.

A donor-acceptor complex enables the synthesis of: E -olefins from alcohols, amines and carboxylic acids

Chen, Kun-Quan,Shen, Jie,Wang, Zhi-Xiang,Chen, Xiang-Yu

, p. 6684 - 6690 (2021/05/31)

Olefins are prevalent substrates and functionalities. The synthesis of olefins from readily available starting materials such as alcohols, amines and carboxylic acids is of great significance to address the sustainability concerns in organic synthesis. Metallaphotoredox-catalyzed defunctionalizations were reported to achieve such transformations under mild conditions. However, all these valuable strategies require a transition metal catalyst, a ligand or an expensive photocatalyst, with the challenges of controlling the region- and stereoselectivities remaining. Herein, we present a fundamentally distinct strategy enabled by electron donor-acceptor (EDA) complexes, for the selective synthesis of olefins from these simple and easily available starting materials. The conversions took place via photoactivation of the EDA complexes of the activated substrates with alkali salts, followed by hydrogen atom elimination from in situ generated alkyl radicals. This method is operationally simple and straightforward and free of photocatalysts and transition-metals, and shows high regio- and stereoselectivities.

Dimethyl Fumarate: Heterogeneous Catalysis for the Development of an Innovative Flow Synthesis

Dedè, Fabiana,Piccolo, Oreste,Vigo, Daniele

, p. 292 - 299 (2021/02/20)

The present work describes the development of an improved synthesis of the active pharmaceutical ingredient (API) dimethyl fumarate. The use of continuous flow technology and the newly developed methylation conditions solve some of the issues of previous commercial production strategies, e.g., reaching complete conversion and avoiding the formation of toxic impurities. The optimization was carried out using the design of experiment approach and afforded a very efficient, sustainable process, suitable for the industrial application.

Continuous-flow synthesis of dimethyl fumarate: A powerful small molecule for the treatment of psoriasis and multiple sclerosis

Lima, Marcelo T.,Finelli, Fernanda G.,De Oliveira, Alline V. B.,Kartnaller, Vinicius,Cajaiba, Joa? F.,Lea?, Raquel A. C.,De Souza, Rodrigo O. M. A.

, p. 2490 - 2494 (2020/02/03)

Dimethyl fumarate (DMF) is a methyl ester of fumaric acid and has recently gained attention due to its use as a pro-drug in different pharmaceutical preparations, besides the low price of the final molecule and no active patents being available for the synthesis of DMF, the prices of multiple sclerosis treatment are still high. In our continuous effort for the development of process intensification strategies towards the synthesis of active pharmaceutical ingredients, here we present our work on a cascade methodology for dimethyl fumarate synthesis in short reaction times and quantitative yields.

Process route upstream and downstream products

Process route

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;
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.
(+/-)-3<i>c</i>,6<i>c</i>-diphenyl-cyclohex-4-ene-1<i>r</i>,2<i>t</i>-dicarboxylic acid dimethyl ester
74725-37-4

(+/-)-3c,6c-diphenyl-cyclohex-4-ene-1r,2t-dicarboxylic acid dimethyl ester

trans,trans-1,4-Diphenyl-1,3-butadiene
886-65-7,538-81-8

trans,trans-1,4-Diphenyl-1,3-butadiene

dimethylfumarate
624-49-7

dimethylfumarate

Conditions
Conditions Yield
In diethyl ether; ethanol; methylbutane; at -190.15 ℃; Title compound not separated from byproducts; UV-irradiation;
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;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

methyl diazoacetate
6832-16-2

methyl diazoacetate

methyl ethyl maleic acid ester
19896-44-7

methyl ethyl maleic acid ester

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

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

dimethylfumarate
624-49-7

dimethylfumarate

diethyl Fumarate
623-91-6

diethyl Fumarate

methyl ethyl fumaric acid ester
4749-70-6

methyl ethyl fumaric acid ester

Diethyl maleate
141-05-9

Diethyl maleate

Conditions
Conditions Yield
With nickel; at 99.9 ℃; Product distribution;
dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

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
With formic acid; dihydridotetrakis(triphenylphosphine)ruthenium; In N,N-dimethyl-formamide; at 20 ℃; for 48h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
23%
68%
With 1-n-butyronitrile-2,3-dimethylimidazolium bis(trifluoromethanesulfonimide); nickel; hydrogen; In cyclohexane; at 30 ℃; for 6h; under 3000.3 Torr; Autoclave; Glovebox;
26%
palladium; at 100 ℃; for 160h; Yield given. Yields of byproduct given;
With TPPMS (meta-monosulfonated triphenylphosphane, Na salt); water; for 0.0833333h;
With trichlorosilane; silica gel; acetic acid; tetrakis(triphenylphosphine) palladium(0); In dichloromethane; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
With TPPMS (meta-monosulfonated triphenylphosphane, Na salt); water; for 1h;
With diiron nonacarbonyl; tributylphosphine; Triethoxysilane; In tetrahydrofuran; at 60 ℃; for 48h; optical yield given as %de; chemoselective reaction; Inert atmosphere;
With carbon monoxide; C56H52Fe2OP4S2; In tetrahydrofuran; under 310.297 Torr; Inert atmosphere;
With hydrogen; In tetrahydrofuran; under 3800.26 Torr;
8 %Spectr.
6 %Spectr.
With hydrogen; In tetrahydrofuran; under 3800.26 Torr;
8 %Spectr.
9 %Spectr.
methanol
67-56-1

methanol

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

5-hydroxymethyl-2-furfuraldehyde

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

dimethylfumarate
624-49-7

dimethylfumarate

Dimethyl succinate
106-65-0

Dimethyl succinate

Conditions
Conditions Yield
With oxygen; at 130 ℃; for 2h; under 7500.75 Torr; Autoclave;
ethanol
64-17-5

ethanol

2-methyl-5-hydroxymethylfurfural

2-methyl-5-hydroxymethylfurfural

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

dimethylfumarate
624-49-7

dimethylfumarate

Dimethyl succinate
106-65-0

Dimethyl succinate

Conditions
Conditions Yield
With 3H(1+)*Mo10O40PV2(5-)*Cu(2+)*C8H14N2O3S; oxygen; at 130 ℃; for 3h; under 7500.75 Torr; Autoclave;
(E)-3-morpholin-4-yl-1,3-diphenylpropenone
70008-81-0

(E)-3-morpholin-4-yl-1,3-diphenylpropenone

methyl diazoacetate
6832-16-2

methyl diazoacetate

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

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

methyl α,β-dibenzoyl-propionate
90904-37-3

methyl α,β-dibenzoyl-propionate

dimethylfumarate
624-49-7

dimethylfumarate

Conditions
Conditions Yield
copper(I) triflate; In dichloromethane; at 20 ℃;
70%

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