22644-27-5

Basic information

• Product Name: Dimethyl (R)-(+)-methylsuccinate
• Synonyms: DIMETHYL (R)-(+)-METHYLSUCCINATE;DIMETHYL (R)-(+)-PYROTARTRATE;DIMETHYL-(R)-2-METHYLSUCCINATE;(R)-(+)-METHYLSUCCINIC ACID DIMETHYL ESTER;(R)-(+)-DIMETHYL (R)-METHYLSUCCINATE;(R)-(+)-PYROTARTARIC ACID DIMETHYL ESTER;(R)-dimethyl-2-methylsuccinate;dimethyl (r)-(+)-pyrotartarate
• CAS NO: 22644-27-5
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• Product Categories: Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 22644-27-5.mol
• Article Data: 348

Chemical Properties

• Melting Point: 140-145 °C (decomp)
• Boiling Point: 80-81 °C12 mm Hg(lit.)
• Flash Point: 184 °F
• Appearance: /
• Density: 1.076 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.408mmHg at 25°C
• Refractive Index: n20/D 1.419
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1706307
• CAS DataBase Reference: Dimethyl (R)-(+)-methylsuccinate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl (R)-(+)-methylsuccinate(22644-27-5)
• EPA Substance Registry System: Dimethyl (R)-(+)-methylsuccinate(22644-27-5)

Safety Data

• Safety Statements: 23-24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 22644-27-5(Hazardous Substances Data)

Usage

Description

Dimethyl (R)-(+)-methylsuccinate, a colorless liquid, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals and chemicals. Its unique chiral structure allows for the creation of enantiomerically pure compounds, which are essential in the development of drugs with targeted effects and reduced side effects.

Uses

Used in Pharmaceutical Industry:
Dimethyl (R)-(+)-methylsuccinate is used as a key intermediate in the synthesis of FK-506, a potent immunosuppressive macrolide antibiotic. Dimethyl (R)-(+)-methylsuccinate is particularly effective in preventing organ transplant rejection and treating autoimmune diseases due to its ability to inhibit the activation of T cells.
Additionally, its chiral nature makes it a valuable building block for the development of other enantiomerically pure pharmaceuticals, which can have improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Chemical Synthesis:
Dimethyl (R)-(+)-methylsuccinate is also used as a versatile building block in the synthesis of various chiral compounds for different applications in the chemical industry. Its unique structure allows for the creation of a wide range of products, including specialty chemicals, fragrances, and agrochemicals, with potential benefits in terms of selectivity and reduced environmental impact.

InChI:InChI=1/C7H12O4/c1-5(7(9)11-3)4-6(8)10-2/h5H,4H2,1-3H3/t5-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 3641-51-8 2-(R)-methylsuccinic acid 
• 90383-11-2 methyl <1-((E)-styryl)ethyl>acetate 
• 21307-96-0 methyl 2-methylsuccinate 
• 617-52-7 Dimethyl itakonate 
• 67-56-1 methanol 
• 97-65-4 2-methylenesuccinic acid 
• 369365-18-4 dimethyl (2RS,3R)-2-chloro-3-methylsuccinate 
• 369365-15-1 dimethyl (2R,3R)-2-methyl-3-phenylsultanylsuccinate 
• 617-54-9 citraconic acid dimethyl ester 
• 118653-61-5 (E)-ethyl 2-oxo-3-pentenoate 
• 60144-26-5 formaldehyde N,N-tetramethylenehydrazone 
• 84569-14-2 citraconic acid dimethyl ester 
• 617-53-8 mesaconic acid dimethyl ester 

Downstream Products

• 1467-37-4 (+/-)-2-((E)-benzylidene)-3-methyl-succinic acid 
• 2938-98-9 2-methyl-1,4-butandiol 
• 179410-39-0 2-Methyl-bernsteinsaeure-dihydrazid 
• 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 
• 23268-03-3 (R)-2-methyl-succinic acid 4-methyl ester 
• 83084-78-0 (R)-4-(4-Benzyl-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-2-methyl-4-oxo-butyric acid methyl ester 
• 412012-73-8 2-Methyl-4-(3-methoxy-2-benzyloxy-phenyl)-3-methoxycarbonyl-buten-⁽³⁾-saeure-⁽¹⁾ 

Relevant articles and documents

The use of new carboranylphosphite ligands in the asymmetric Rh-catalyzed hydrogenation

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PHANE-TetraPHOS, the First D2 Symmetric Chiral Tetraphosphane. Synthesis, Metal Complexation, and Application in Homogeneous Stereoselective Hydrogenation

PHANE-TetraPHOS, a new D2 symmetric tetraphosphane based on the [2.2]paracyclophane scaffold, has been synthesized and characterized. The peculiarity of this system is the presence of four homotopic diphenylphosphane groups, exchangeable through C2 symmetry operations and consequently indistinguishable. Their spatial arrangement allows the simultaneous complexation of two metal atoms. Enantiomeric purity was attained at tetra-phosphane oxide level by fractional crystallization of the diastereomeric adducts obtained from the racemate with enantiopure dibenzoyltartaric acids. Alkaline treatment of diastereomerically pure adducts followed by exhaustive P?O groups reduction with HSiCl3 gave both PHANE-TetraPHOS antipodes in an enantiopure state. They were tested as rhodium ligands in the homogeneous enantioselective hydrogenation of some benchmark unsaturated compounds. Catalytic activity and enantiodiscrimination ability were found comparable to those exhibited by the complexes of the parent bidentate ligand PHANEPHOS, but only half a mole of precious chiral ligand was employed.