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Cas Database

108-59-8

108-59-8

Identification

  • Product Name:Propanedioicacid, 1,3-dimethyl ester

  • CAS Number: 108-59-8

  • EINECS:203-597-8

  • Molecular Weight:132.116

  • Molecular Formula: C5H8O4

  • HS Code:29171910

  • Mol File:108-59-8.mol

Synonyms:Malonicacid, dimethyl ester (6CI,8CI);Propanedioic acid, dimethyl ester (9CI);Dimethyl 1,3-propanedioate;Dimethyl propanedioate;Methylmalonate;NSC 620046;Dimethyl Malonate (DMM);Dimethyl malonate;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:No signal word.

  • Hazard Statement:none

  • 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:Usbiological
  • Product Description:Methylmalonate
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  • Product Description:Methylmalonate ≥98%
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  • Product Description:Dimethyl Malonate >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl Malonate >98.0%(GC)
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  • Product Description:Dimethyl malonate for synthesis. CAS 108-59-8, chemical formula CH (COOCH ) ., for synthesis
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Relevant articles and documentsAll total 78 Articles be found

Catalytic oxidative decarboxylation of malic acid into dimethyl malonate in methanol with dioxygen

Liu, Junxia,Du, Zhongtian,Yang, Yanliang,Lu, Tianliang,Lu, Fang,Xu, Jie

, p. 2151 - 2154 (2012)

If you've got it, use it: Malic acid is converted into dimethyl malonate by a direct, one-pot process. The process is cyanide- and halide-free. Phosphovanadomolybdates serve as bifunctional catalysts, effecting the oxidative decarboxylation and esterification in a consecutive manner. Oxidative C-C bond cleavage first forms hemiacetals. The results serve as example for the production of valuable chemicals by fully utilizing the oxygen atoms and basic structure inherent to biomass products.

A stereospecific transannular Diels-Alder approach to the [6.6.7] tricyclic skeleton related to aphidicolin and scopadulan natural products

Hall,Caille,Drouin,Lamothe,Muller,Deslongchamps

, p. 1081 - 1088 (1995)

Model trans-cis-cis (TCC) macrocyclic triene 7 was synthesized using a convergent approach. Upon heating at 200°C, a 1,5-hydrogen-shift on the diene moiety was found to compete with the transannular Diels-Alder (TADA) reaction, thus leading to a mixture of tricyclic products. However, the diene rearrangement could be avoided by using boron trifluoride-diethyl ether complex as catalyst at reduced temperature (60°C). The exclusive formation of the trans-syn-cis [6.6.7] (TSC) tricyclic product 8 through an endo approach was observed. This result demonstrates the feasibility of a TADA strategy for synthesizing the title compounds and analogs.

Liquid Phase Carbonylation with Solid Catalyst. Carboxy Methylation of Dihalo Methane with Group VIII Metals Supported on Active Carbon

Yagita, Hiroshi,Kuwahara, Hiroyuki,Omata, Kohji,Fujimoto, Kaoru

, p. 335 - 338 (1990)

It was found that cobalt supported on active carbon showed an excellent catalytic activity for the carbonylation of dibromo methane in the liquid phase.For example, when the reaction was conducted under the conditions of 140 deg C, P (CO) = 31 atm, the yields of dimethyl malonate and bromomethyl acetate were 34.4percent and 22.2percent, respectively.Pd and Rh also showed catalytic activities.

STRUCTURE OF MONARDAEIN, A BIS-MALONYLATED ANTHOCYANIN ISOLATED FROM GOLDEN BALM, MONARDA DIDYMA

Kondo, Tadao,Nakane, Yukari,Tamura, Hirotoshi,Goto, Toshio,Eugster, C.H.

, p. 5879 - 5882 (1985)

Structure of monardaein was determined to be 3-O-(6-O-trans-p-coumaryl-β-D-glucopyranosyl)-5-O-(4,6-di-O-malonyl-β-D-glucopyranosyl) pelargonidin (1).

On the most powerful chemical traps for bis(methoxycarbonyl)carbene (=2-methoxy-1-(methoxycarbonyl)-2-oxoethylidene)

Shevchenko, Vladimir V.,Zhegalova, Natalya G.,Borzenko, Andey O.,Nikolaev, Valerij A.

, p. 501 - 509 (2008)

The efficiency and validity of different chemical substrates for trapping bis(methoxycarbonyl)carbene (=2-methoxy-1-(methoxycarbonyl)-2-oxoethylidene; 1) is dependent on the conditions of carbene generation. On conventional photolysis of dimethyldiazomalonate (=2-diazopropanedioic acid dimethyl ester; 2) by long-wave UV light (through a Pyrex filter, λ > 290 nm), the most powerful trap for carbene 1 in the series of substrates Me2S, MeOH, cyclohexane, and pyridine is Me2S (with an efficiency ratio of ca. 6 :4 : 2 : 1, resp.). When short-wave decomposition of diazomalonate 2 is employed (through a quartz filter, λ > 210 nm), more reliable and useful chemical traps for bis(methoxycarbonyl)carbene (1) are pyridine and cyclohexane, whose adducts with 1 are rather stable under short-wave-irradiation conditions. Application of alcohols for the trapping of 1 proves to be preferential when simultaneous monitoring of carbene and oxoketene formation during photolysis is necessary.

Synthesis of Alkyl(alkoxycarbonyl)tetracarbonyliron Complexes : the First Evidence of their Relevance to the Catalytic Cycle in the Carbonylation of Organic Halides induced by Pentacarbonyliron

Laurent, Pascale,Sabo-Etienne, Sylviane,Larsonneur, Anne-Marie,Abbayes, Herve des

, p. 929 - 930 (1988)

Reaction of (1-) (1) (R = Me or But) with BrCH2CO2Me produces stable complexes (3) which thermally decompose to yield Fe(CO)5 and malonic esters under a CO atmosphere; these reactions provide the first demonstration of possible key steps in the catalytic cycle of the carbonylation of reactive halides into esters with Fe(CO)5 and an alkoxide anion.

Esterification by ZrO2 and Mo-ZrO2 eco-friendly solid acid catalysts

Manohar, Basude,Reddy, Vangala R.,Reddy, Benjaram M.

, p. 3183 - 3187 (1998)

Esterification of mono- and dicarboxylic acids catalysed by single (ZrO2) and mixed oxide (Mo-ZrO2) eco-friendly solid acid catalysts is described. The Mo-ZrO2 catalyst exhibits better catalytic performance than ZrO2.

-

Soulen,Paul

, p. 261,263, 268 (1977)

-

6-O-MALONYL-β-METHYL-D-GLUCOPYRANOSIDE FROM ROOTS OF RUMEX OBTUSIFOLIUS

Kasai, Takanori,Okuda, Michiko,Sakamura, Sadao

, p. 1131 - 1132 (1981)

From the methanol-soluble acidic fraction of Rumex obtusifolius 6-O-malonyl-β-methyl-D-glucopyranoside and ascorbalamic acid were isolated and identified.The identity of the former compound was confirmed by synthesis.Key Word Index- Rumex obtusifolius; Polygonaceae; roots; 6-O-malonyl-β-methyl-D-glucopyranoside; organic acids.

VAPOR PHASE CARBONYLATION OF METHYL CHLOROACETATE

Shinoda, Kiyonori,Yasuda, Kensei

, p. 9 - 10 (1985)

The vapor phase carbonylation of methyl chloroacetate (MCA) with rhodium trichloride supported on active carbon was carried out at 200-300 deg C.Dimethyl malonate (DMM) was obtained in good yield without any side reactions.

Palladium phthalocyaninesulfonate functionalized mesoporous polymer: A highly efficient photocatalyst for degradation of 4-chlorophenol under visible light irradiation

Xing, Rong,Wu, Lin,Fei, Zhenghao,Wu, Peng

, p. 15 - 20 (2013)

A novel sulfonated palladium phthalocyanine (PdPcS) modified FDU-15 mesoporous polymer (FDU-PdPcS) has been prepared by rationally chemical modification process. The PdPcS molecules were highly dispersed inside the confined mesopores, and were further stabilized through a π-π interaction with mesopolymer, which may prevent the PdPcS molecules from agglomerating and deactivating in photodegradation reactions. The physicochemical properties of thus prepared FDU-PdPcS material were characterized by XRD, N2 adsorption-desorption, UV-vis and inductively coupled plasma techniques. FDU-PdPcS proved to be highly efficient heterogeneous photocatalyst for the degradation of 4-chlorophenol (4-CP) in the presence of H2O 2 under visible light irradiation. The photodegradation of 4-CP with an initial concentration 0.6 mM was completed within 5 h at pH 11 using a dose of 0.2 g/L of the 0.12 wt% FDU-PdPcS photocatalyst. The photodegradation intermediates were identified by GC-MS. A possible mechanism involved in the photodegradation of 4-CP has also been discussed.

Catalytic hydrophosphorylation of dialkyl 2-allylmalonates

Reznikov,Skvortsov

, p. 1170 - 1176 (2007)

The reaction of dialkyl hydrogen phosphites and diphenylphosphine oxide with dialkyl 2-allylmalonates in the presence of [Pd(Ph3P) 4] is studied. The addition of the hydrophosphoryl compounds to the multiple bond is established to proceed by the Markovnikov rule. The reaction is accompanied by the side process of malonate dealkoxycarbonylation whose contribution to the main process depends on the nature of the reagents.

Insight into the Claisen condensation of methyl acetate and dimethyl carbonate to dimethyl malonate

Zheng, Sainan,Xu, Shiwei,Zhou, Jinghong,Shen, Rongchun,Ji, Yang,Shen, Ming,Li, Wei

, p. 6689 - 6694 (2018)

A mechanistic study on the synthesis of dimethyl malonate (DMM) via condensation of methyl acetate (MA) and dimethyl carbonate (DMC), catalyzed by sodium methoxide, has been conducted using gas chromatography-mass spectrometry, liquid chromatography-electrospray ionization-mass spectrometry, X-ray diffraction, solid-state nuclear magnetic resonance spectroscopy and density functional theory calculations. The results indicated that the Claisen condensation of MA and DMC in the presence of methoxide yielded (CH3OCO)2CHNa (DMNa) instead of DMM since DMM is easily deprotonated by the methoxide catalyst. Further protonation after the condensation by adding a proton-donor reagent is essential to obtain DMM. Based on the experimental results, a detailed reaction mechanism for the condensation of MA and DMC into DMM in the presence of methoxide has been proposed and disclosed by computational calculations. Besides, it has been proven that the base strength of the catalyst has a critical effect on the condensation reaction and the DMM yield.

SYNTHESIS OF ESTERS OF 3-FLUORO-3-NITROACRYLIC ACID

Oreshko, G. V.,Lagodzinskaya, G. V.,Eremenko, L. T.

, p. 635 - 637 (1989)

-

Method for preparing diacid diester compound under catalysis of deep eutectic solvent

-

Paragraph 0035-0038, (2021/05/19)

The invention belongs to the technical field of organic synthesis, and discloses a method for preparing a diacid diester compound through catalysis of a deep eutectic solvent, wherein the deep eutectic solvent takes ammonium salt and ferric salt as hydrogen acceptors, takes p-toluenesulfonic acid as a hydrogen donor, takes diacid or anhydride of the diacid and an alcohol compound as raw materials, and adopts a one-pot method to prepare the diacid diester compound; and under the catalysis of the deep eutectic solvent, the esterification reaction is performed to generate the diester product. The selected deep eutectic solvent has characteristics of environmental protection, easy preparation, cheap components and easy recovery; the preparation method has characteristics of simple operation, simple separation, no water-carrying agent, repeated use of the deep eutectic solvent, and high diester yield.

Modulation of cancer therapy using nano-organometallic compounds: Preparation, spectroscopic characterization and cytotoxic evaluation

El-Tabl, Abdou S.,Wahed, Moshira M. Abd-El,Mohamed, Eman A,Abu-Setta, Mohammed H. H.

, p. 3873 - 3887 (2021/07/17)

New series of Mn(II), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) organometallic complexes with hydroxyl benzylidene malonohydrazide ligand have much potential as therapeutic and diagnostic agents. The ligand allows the thermodynamic and kinetic reactivity of the metal ion to be controlled and also provide a scaffold for functionalization. The establishment of structure activity relationships and elucidation of the specification of complexes under conditions relevant to drug testing and formulation are crucial for the further development of promising medicinal applications of organometallic complexes. Specific examples involving the design of metal complexes as anticancer agents are discussed. These complexes have been synthesized and characterized by (1H-NMR, mass, IR, UV-VIS and ESR) spectroscopy, as well as magnetic moments, conductance, elemental and thermal analyses. Molar conductance in DMF solution indicates that, the complexes are non-electrolytes. The ESR spectra of solid Cu(II) complexes (7) and (8) showed isotropic and anisotropic types indicating an octahedral geometry with covalent bond character. However, Co(II) complexes (3) and (4) showed anisotropic type where, g g >2.0023, indicating compressed tetragonal distortion around Co(II) ion. Cytotoxic evolution of the ligand and its complexes have been carried out. Complexes showed enhanced activity in comparison to the parent ligand or standard drug applied.

FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES

-

Paragraph 0175; 0186-0187, (2021/06/22)

The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

Tailorable carbazolyl cyanobenzene-based photocatalysts for visible light-induced reduction of aryl halides

Ou, Wei,Zou, Ru,Han, Mengting,Yu, Lei,Su, Chenliang

supporting information, p. 1899 - 1902 (2019/12/27)

Herein, a series of carbazolyl cyanobenzene (CCB)-based organic photocatalysts with a broad range of photoredox capabilities were designed and synthesized, allowing precise control of the photocatalytic reactivity for the controllable reduction of aryl halides via a metal-free process. The screened-out CCB (5CzBN), a metal-free, low-cost, scalable and sustainable photocatalyst with both strong oxidative and reductive ability, exhibits superior performance for both dehalogenation and C[sbnd]C bond-forming arylation reactions.

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

cis-(CO)4Fe(COOMe)(CH<sub>2</sub>COOMe)

cis-(CO)4Fe(COOMe)(CH2COOMe)

iron pentacarbonyl
13463-40-6,37220-42-1

iron pentacarbonyl

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
With carbon monoxide; Co atmosphere, 30°C, 3 h;
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;
bromo-(3-oxo-1,3-diphenyl-propyl)-malonic acid dimethyl ester

bromo-(3-oxo-1,3-diphenyl-propyl)-malonic acid dimethyl ester

2,3-dibromo-1,3-diphenylpropane-1-one
611-91-6

2,3-dibromo-1,3-diphenylpropane-1-one

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
at 200 - 225 ℃;
methanol
67-56-1

methanol

dibenzothiophenium bismethoxycarbonylmethylide
34297-79-5

dibenzothiophenium bismethoxycarbonylmethylide

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
In acetonitrile; UV-irradiation;
With benzophenone; Inert atmosphere; UV-irradiation;
9 %Chromat.
57 %Chromat.
methanol
67-56-1

methanol

benzothiophenium bismethoxycarbonylmethylide
72932-82-2

benzothiophenium bismethoxycarbonylmethylide

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
In acetonitrile; UV-irradiation;
methanol
67-56-1

methanol

thiophenium bis(methoxycarbonyl)methylide
63196-84-9

thiophenium bis(methoxycarbonyl)methylide

dimethyl (2-thienyl)propanedioate
66946-94-9

dimethyl (2-thienyl)propanedioate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
In acetonitrile; UV-irradiation;
methanol
67-56-1

methanol

C<sub>9</sub>H<sub>8</sub>Br<sub>2</sub>O<sub>4</sub>S
1107692-57-8

C9H8Br2O4S

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
Inert atmosphere; UV-irradiation;
86.5 %Chromat.
9.4 %Chromat.
methanol
67-56-1

methanol

dimethylmalonate-3,4-dibromothiophene-S,C-ylide
1107692-58-9

dimethylmalonate-3,4-dibromothiophene-S,C-ylide

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
Inert atmosphere; UV-irradiation;
86.2 %Chromat.
12.0 %Chromat.
methanol
67-56-1

methanol

C<sub>9</sub>H<sub>9</sub>IO<sub>4</sub>S
1107692-59-0

C9H9IO4S

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
Inert atmosphere; UV-irradiation;
49.3 %Chromat.
27.6 %Chromat.
methanol
67-56-1

methanol

C<sub>17</sub>H<sub>13</sub>BrO<sub>4</sub>S
1107692-60-3

C17H13BrO4S

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
Inert atmosphere; UV-irradiation;
50.3 %Chromat.
44.6 %Chromat.

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