83540-97-0

Basic information

• Product Name: DIISOPROPYL (R)-(+)-MALATE
• Synonyms: DIISOPROPYL (R)-(+)-MALATE;(2R)-2-Hydroxybutanedioic acid 1,4-bis(1-methylethyl) ester;Diisopropyl (R)-(+)-2-hydroxysuccinate;Diisopropyl D-malate;(R)-Diisopropyl 2-hydroxysuccinate;Butanedioic acid,2-hydroxy-,1,4-bis(1-methylethyl) ester,(2R)-;-Diisopropyl 2-hydroxysuccinate
• CAS NO: 83540-97-0
• Molecular Formula: C₁₀H₁₈O₅
• Molecular Weight: 218.25
• Mol File: 83540-97-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 237 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.055 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000105mmHg at 25°C
• Refractive Index: n20/D 1.43(lit.)
• Storage Temp.: 2-8°C
• PKA: 12.45±0.20(Predicted)
• CAS DataBase Reference: DIISOPROPYL (R)-(+)-MALATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIISOPROPYL (R)-(+)-MALATE(83540-97-0)
• EPA Substance Registry System: DIISOPROPYL (R)-(+)-MALATE(83540-97-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 83540-97-0(Hazardous Substances Data)

Usage

General Description

Diisopropyl (R)-(+)-Malate is a chemical compound usually used in the field of organic synthesis. This chemical has a broad range of applications in the production of pharmaceuticals, agrochemicals and other synthetic materials. As a chiral reagent, it plays an important role in the creation of enantiomerically pure products. Its stereochemistry gives a unique property of choosing one optical isomer over others in a reaction. Diisopropyl (R)-(+)-Malate is usually a colorless liquid and needs to be handled with care due to its reactivity.

InChI:InChI=1/C10H18O5/c1-6(2)14-9(12)5-8(11)10(13)15-7(3)4/h6-8,11H,5H2,1-4H3/t8-/m0/s1

Upstream product

• 2217-15-4 L-(+)-diisopropyl tartrate 
• 636-61-3 D-Malic acid 
• 67-63-0 isopropyl alcohol 
• 371160-97-3 tert-butyl-[(2R,5S,6S)-5,6-dimethoxy-5,6-dimethyl-3-oxo-[1,4]dioxan-2-yl]-acetate 

Downstream Products

• 130713-47-2 2R-hydroxy-3S-(phenylmethyl)butanedioic acid 
• 355126-87-3 (2S,3R)-2-(4-Benzyloxy-3-methoxy-benzyl)-3-hydroxy-succinic acid diisopropyl ester 
• 117471-08-6 (R)-2-Benzyl-3-hydroxy-succinic acid diisopropyl ester 

Relevant articles and documents

Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives

The preparation of butane-2,3-diacetal protected glycolic acid and related systems is described together with highly selective alkylation reactions of (R,R) and (S,S) butanediacetal protected glycolic acid. These compounds are readily deprotected to give

Synthesis of unnatural (R)-malates from L-tartrates

The cyclic thionocarbonates of L-tartrates were cleanly converted to (R)-malates by treating with magnesium iodide or magnesium and iodine.

Ruthenium-catalyzed production of cyclic sulfates

A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.