1604-11-1

Basic information

• Product Name: DIMETHYL METHYLSUCCINATE
• Synonyms: DIMETHYL METHYLSUCCINATE;Dimethyl 2-methylsuccinate;Ethyl methyl ester of butanedioic acid;methyl-butanedioicacidimethylester;Methylsuccinic acid dimethyl ester;Succinic acid, methyl-, dimethyl ester;2-Methylsuccinic acid dimethyl;2-Methylsuccinic acid dimethyl ester
• CAS NO: 1604-11-1
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• EINECS: 216-506-1
• Product Categories: C6 to C7;Carbonyl Compounds;Esters
• Mol File: 1604-11-1.mol

Chemical Properties

• Boiling Point: 196 °C(lit.)
• Flash Point: 182 °F
• Appearance: /
• Density: 1.076 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.408mmHg at 25°C
• Refractive Index: n20/D 1.42(lit.)
• CAS DataBase Reference: DIMETHYL METHYLSUCCINATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL METHYLSUCCINATE(1604-11-1)
• EPA Substance Registry System: DIMETHYL METHYLSUCCINATE(1604-11-1)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 1604-11-1(Hazardous Substances Data)

Usage

Uses

Dimethyl methylsuccinate was used in the synthesis of β-half esters.

InChI:InChI=1/C7H12O4/c1-5(7(9)11-3)4-6(8)10-2/h5H,4H2,1-3H3/t5-/m0/s1

Upstream product

• 67-56-1 methanol 
• 498-21-5 2-methylbutanedioic acid 
• 186581-53-3 diazomethane 
• 187737-37-7 propene 
• 144-62-7 oxalic acid 
• 75-36-5 acetyl chloride 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 3674-77-9 2-methyl-2-phenyl-1,3-dioxolane 
• 712-74-3 1,2,4,5-tetracyanobenzene 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 155800-02-5 S-ethyl O-methyl 2-(bromomethyl)-2-methylmonothiomalonate 
• 557-93-7 2-bromoprop-1-ene 
• 201230-82-2 carbon monoxide 
• 80-62-6 methacrylic acid methyl ester 

Downstream Products

• 83509-04-0 (R)-2-methylsuccinate-1-monomethyl ester 
• 111266-16-1 L-malic acid methyl ester 
• 23268-03-3 3-methoxycarbonyl-2-R-methylpropionic acid 
• 56108-32-8 methyl-succinic acid dipropyl ester 
• 111195-88-1 (R)-2-Methyl-succinic acid 4-methyl ester 1-propyl ester 
• 111195-87-0 (R)-2-Methyl-succinic acid 1-methyl ester 4-propyl ester 
• 111195-87-0 (S)-2-Methyl-succinic acid 1-methyl ester 4-propyl ester 
• 111195-87-0 2-Methyl-succinic acid 1-methyl ester 4-propyl ester 
• 22644-27-5 (R)-methylsuccinic acid dimethyl ester 
• 23268-03-3 (R)-2-methyl-succinic acid 4-methyl ester 
• 1604-11-1 (S)-dimethyl 2-methylsuccinate 
• 498-21-5 2-methylbutanedioic acid 
• 1227258-94-7 2-(4-fluoro-benzylidene)-3-methyl-succinic acid 1-methyl ester 
• 111266-27-4 (2S)-4-methoxy-2-methyl-4-oxobutanoic acid 

Relevant articles and documents

BINOL derived monodentate acylphosphite ligands for homogeneously catalyzed enantioselective hydrogenation

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Chiral monophosphites and monophosphonites derived from BINOL are more effective ligands in enantioselective rhodium-catalyzed hydrogenation of olefins, as compared to bidentate bis-phosphites. An appreciable increase in enantioselectivity is attained with the use of mixtures of two different monodentate phosphites and phosphonites in rhodium-catalyzed hydrogentation.

Selective flux of organic liquids and solids using nanoporous membranes of polydicyclopentadiene

Membranes were fabricated from the ring opening metathesis polymerization of dicyclopentadiene with the Grubbs first generation catalyst, and the permeability of twenty-one molecules through them was studied. Both polar and apolar molecules with molecular weights from 101 to 583 g mol-1 permeated these membranes with values for flux of 10-5 to 10 -6 mol cm-2 h-1 but selected molecules did not permeate them and had flux 104 to 105 times slower. The difference in flux was large between molecules that permeated and those that did not permeate, but no trend was observed that correlated flux with molecular weight or hydrophobicity. Rather, molecules that did not permeate the membranes had large cross-sectional areas that led to low rates of diffusion within the highly cross-linked polydicyclopentadiene membranes. The degree of cross-linking within the polydicyclopentadiene membranes was measured using infrared spectroscopy and approximately 84% of the dicyclopentadiene monomer had reacted to form cross-links. These are the first organic solvent nanofiltration membranes that separate molecules with molecular weights from 100 to 600 g mol-1 based on cross-sectional areas.

On the economic application of DuPHOS rhodium(I) catalysts: A comparison of COD versus NBD precatalysts

The effectiveness of cyclooctadiene and norbornadiene precatalysts of the type [Rh(DuPHOS)(diolefin)]BF4 in catalytic asymmetric hydrogenation of various prochiral olefins has been examined. In some of the systems studied, the NBD complex gave

Asymmetric activation of conformationally flexible monodentate phosphites for enantioselective hydrogenation

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Fluorinated alcohols as solvents for enantioselective hydrognation with chiral self-assembling rhodium catalysts

We herein describe the beneficial effect of fluorinated alcohols on asymmetric hydrogenation using chiral self-assembling rhodium complexes. Previously, the application of these catalysts has been hampered by low reaction rates in non-polar solvents, which are essential for establishing the self-assembling architecture via hydrogen bonding. Excellent reaction rates are usually observed in alcohols as solvents, but the characteristic hydrogen bonds are cleaved in those media, resulting in poor ee values. We now show for the first time that the disadvantageous properties of both solvent classes on the catalytic reaction can be overcome by using fluorinated alcohols. Due to this key finding, homogeneous catalysis with self-assembling catalysts is much closer to practical application.

Rh(I) coordination chemistry of hexacationic Dendriphos ligands and their application in hydroformylation catalysis

The coordination chemistry of hexacationic Dendriphos ligands L* with respect to Rh(I), as well as their application in Rh-catalyzed hydroformylation reactions, is described. Complexes of the type RhCl(CO)(L*)2 were synthesized and characterized. The results show that Dendriphos ligands are weaker σ-donors and/or stronger π-acceptors compared to PPh 3. The reaction of L* with [Rh(cod)2]BF4 in MeCN afforded monophosphine-Rh(I) complexes of the type Rh(cod)(MeCN) (L*), which points to the tendency of these ligands to form coordinatively unsaturated metal complexes. The catalytic performance of Dendriphos ligands in the Rh-catalyzed hydroformylation appeared to be dominated by steric effects arising from the large dendritic shells of these ligands. Furthermore, the possibility of tuning the catalytic activity and selectivity of the catalytic species, by changing the six counteranions of the hexacationic Dendriphos ligand, has been investigated. Changing the anions from BF4- to the chiral anions camphorsulphonate or Δ-Trisphat did not render the hydroformylation reaction of styrene enantioselective, albeit small changes in its regioselectivity were observed.

Mixtures of configurationally stable and fluxional atropisomeric monodentate P ligands in asymmetric Rh-catalyzed olefin hydrogenation

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