13195-64-7

Basic information

• Product Name: Diisopropyl malonate
• Synonyms: Propanedioicacid,bis(1-methylethyl)ester;DIPM;DIISOPROPYL MALONATE;MALONIC ACID DIISOPROPYL ESTER;MALONIC ACID DIISOPROPYL ESTER 99%;DiisopropylMalonateC9H16O4;MOLONICACIDDIISO-PROPYLESTER;Malonic acid diisopropyl
• CAS NO: 13195-64-7
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.22
• EINECS: 236-156-3
• Product Categories: API intermediates;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 13195-64-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: -51°C(lit.)
• Boiling Point: 93-95 °C12 mm Hg(lit.)
• Flash Point: 192 °F
• Appearance: clear liquid
• Density: 0.991 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.231mmHg at 25°C
• Refractive Index: n20/D 1.412(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.79±0.46(Predicted)
• CAS DataBase Reference: Diisopropyl malonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diisopropyl malonate(13195-64-7)
• EPA Substance Registry System: Diisopropyl malonate(13195-64-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 13195-64-7(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Different sources of media describe the Uses of 13195-64-7 differently. You can refer to the following data:
1. Diisopropyl Malonate is a disinfection byproduct of Isoprothiolane (I874300); a dithiolane pesticide commonly used in agriculture as a fungicide to control planthoppers and blast disease in rice plants.
2. Diisopropyl malonates may be used in the synthesis of :3-substituted coumarins2-carboisopropoxy-3-hydroxyquinoxaline-di-N-oxide2-carboisopropoxy-3-hydroxy-6-methoxylquinoxaline-di-N-oxide

InChI:InChI=1/C9H16O4/c1-6(2)12-8(10)5-9(11)13-7(3)4/h6-7H,5H2,1-4H3

Upstream product

• 141-82-2 malonic acid 
• 67-63-0 isopropyl alcohol 
• 555-31-7 aluminum isopropoxide 
• 108-59-8 malonic acid dimethyl ester 
• 105-48-6 isopropyl chloroacetate 
• 64-17-5 ethanol 
• 372-09-8 cyanoacetic acid 
• 108-21-4 Isopropyl acetate 
• 35363-39-4 ethyl isopropyl carbonate 
• 75-26-3 isopropyl bromide 
• 105-53-3 diethyl malonate 
• 107-91-5 cyanoacetic acid amide 
• 1663-67-8 malonoyl dichloride 
• 27579-26-6 3-Isopropyloxy-2,2-dichloro-propionsaeure-isopropylester 

Downstream Products

• 155306-02-8 diisopropyl 2-(phenylmethylidene)malonate 
• 109572-58-9 2-(Benzoyloxy-phenyl-methylene)-malonic acid diisopropyl ester 
• 115118-68-8 3,3-dimethoxycyclobutane-1,1-dicarboxylic acid diisopropyl ester 
• 138478-21-4 N-benzoyl-3,4-diisopropyloxycarbonyl-2-pyrrolidone 
• 139692-26-5 isopropyl 4-(benzoylamino)-2,3-diisopropyloxycarbonylbutanoate 
• 138478-16-7 isopropyl 2-(benzoylamino)-4,4-diisopropyloxycarbonylbutanoate 
• 56766-77-9 i-propyl malonic half ester 
• 95359-81-2 diisopropyl 2-(phenylimino)malonate 
• 219311-20-3 5-(4-phenoxyphenyl)pyrimidine-2,4,6-trione 
• 923019-96-9 isopropyl N-(3-chloro-4-methylphenyl)malonamate 

Relevant articles and documents

Ball-Milling-Enabled Reactivity of Manganese Metal**

Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.

Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols

Since esters are important organic synthesis intermediates, an environmentally friendly oxone catalyzed-esterification of carboxylic acids with alcohols has been developed. A series of carboxylic acid esters are obtained in high yield. This strategy requires mild reaction conditions, providing an attractive alternative for the construction of valuable carbonyl esters. Electron-rich and electron-deficient groups are compatible with the standard conditions and a variety of substrates are demonstrated. Moreover, the reaction could easily be adapted to typical prodrugs, drugs and gram-scale synthesis.

Transformation of amides into esters by the use of chlorotrimethylsilane

A mild transformation of various amides and imides into the corresponding esters and diesters in good yields by using chlorotrimethylsilane and alcohols at rt are described. Either primary, secondary, or tertiary amide or imide can be used in this transformation. Primary and secondary alcohols gave better yields than tertiary alcohols.