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

A series of new monodentate phosphite ligands based on carboranes have been synthesized and used for asymmetric Rh-catalyzed hydrogenation of prochiral olefins in CH2Cl2 with the result of up to 99.5% ee. High reactivities (100% conv

Chiral carborane-derived thiophosphites: A new generation of ligands for Rh-catalyzed asymmetric hydrogenation

A new class of chiral monodentate ligands - carborane-containing thiophosphites have been synthesized and tested in the Rh-catalyzed asymmetric hydrogenation of prochiral olefins with the result of up to 99% ee. The dependence of the enantioselectivity on

Phosphorodiamidite derivatives of 1,1'-bi-2-naphthol containing stereogenic phosphorus atoms as ligands in enantioselective catalysis

P*-Mono- and P*,P*-bidentate phosphorodiamidites containing the (Sa)-1,1'-binaphthyl core and 1,3,2-diazaphospholidine rings were synthesized. The use of these compounds in the rhodium-catalyzed asymmetric hydrogenation, as well as in the palla

Chiral supported ionic liquid phase (CSILP) catalysts for greener asymmetric hydrogenation processes

Chiral supported ionic liquid phase (CSILP) catalysts were prepared by physical adsorption (within highly porous carbons or mesoporous silica) of Ir, Ru and Rh complexes as IrCl(COD)-(S,S)-BDPP, [IrCl-(S)-BINAP]2, RuCl(p-cymene)[(S,S)-Ts-DPEN],

Chiral phosphine-phosphoramidite ester ligand as well as preparation method and application thereof

The invention provides a method for preparing a phosphine-phosphoramidite ester ligand from a chiral beta-aminophosphine intermediate and an application of the phosphine-phosphoramidite ester ligand in an asymmetric reaction. Chiral N-(2-(phosphoryl)-1-phenethyl) amide is prepared from the chiral beta-aminophosphine intermediate through an asymmetric hydrogenation reaction of (Z)-(alpha-aryl-beta-phosphoryl) alkenyl amide, and then hydrolysis reduction. The preparation method comprises the following steps: dissolving newly-prepared chlorinated phosphite in toluene, adding a solution formed by dissolving the chiral phosphine-amine compound and triethylamine in toluene into an ice-water bath according to a molar ratio of the chiral phosphine-amine compound to the chlorinated phosphite to the triethylamine of 1: (1-2): (3-5), heating the reaction solution to 18-25 DEG C, stirring and reacting for 10-30 hours, filtering, and carrying out column chromatography to remove the solvent, and recrystallizing to obtain the required phosphine-phosphoramidite ligand. According to the present invention, the asymmetric hydrogenation reaction of the catalyst formed by the ligand and the metal precursor on the double bonds such as C = C, C = N, C = O and the like can achieve the enantioselectivity of 99%; the catalyst is high in activity, and TON reaches up to 10000.

Chiral ferrocene phosphine-indole aminophosphine ligand as well as preparation method and application thereof

The invention discloses a chiral ferrocene phosphine-indole aminophosphine ligand as well as a preparation method and application thereof. The preparation method comprises the following steps: dissolving a chiral ferrocene phosphine-indole intermediate in