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

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

Uses

Used in Agricultural Industry:
Diisopropyl malonate is used as a byproduct in the agricultural industry for its role in the disinfection process of Isoprothiolane, a fungicide that helps control planthoppers and blast disease in rice plants.
Used in Pharmaceutical Industry:
Diisopropyl malonate is used as a synthetic compound in the pharmaceutical industry for the production of various medicinal agents, such as 3-substituted coumarins and 2-carboisopropoxy-3-hydroxyquinoxaline-di-N-oxide, which have potential applications in drug development and treatment of various diseases.
Used in Chemical Synthesis:
Diisopropyl malonate is used as a key intermediate in the synthesis of various organic compounds, including 2-carboisopropoxy-3-hydroxy-6-methoxylquinoxaline-di-N-oxide, which can be utilized in the development of new chemical products and materials.

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

Upstream product

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

Downstream Products

• 116476-54-1 Malonsaeure-bis-(2,5-dichlor-anilid) 
• 923019-99-2 isopropyl N-[4-(dimethylamino)phenyl]malonamate 
• 50685-96-6 N,N-Bis-(p-dimethylaminophenyl)-malonamid 
• 923019-97-0 isopropyl N-(4-nitrophenyl)malonamate 
• 1900-40-9 N,N'-bis(p-nitrophenyl)malonamide 
• 115118-68-8 3,3-dimethoxycyclobutane-1,1-dicarboxylic acid diisopropyl ester 
• 1118786-87-0 6,6-dimethoxy-spiro[3.3]heptane-2,2-dicarboxylic acid diisopropyl ester 
• 1166241-68-4 isopropyl 6-hydroxy-1,3-diphenyl-2,4-dithioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 177722-18-8 (R)-3-[bis(isopropoxycarbonyl)methyl]cyclohexanone 
• 334699-05-7 (S)-3-[bis(isopropoxycarbonyl)methyl]cyclohexanone 
• 1402743-44-5 C₂₁H₃₁NO₆ 
• 1207102-53-1 (R)-2-(tert-butoxycarbonylaminophenylmethyl)malonic acid diisopropyl ester 
• 1237542-07-2 diisopropyl 7-phenyl-6,8-dioxaspiro[3.5]nonane-2,2-dicarboxylate 

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.

Preparation method of malonic ester

The invention provides a preparation method of malonic ester. Malonic ester is obtained by using 70-80 wt% of cyanoacetic acid, hydrogen chloride-alcoholic solution and corresponding alcohol as raw materials, and is subjected to the process of esterification, dealcoholic water, alcoholysis esterification, dealcoholization, neutralization and distillation. The preparation method chooses the cyanoacetic acid of reasonable concentration, reduces the heat-sensitive reaction of distillation dehydration when obtaining high concentration cyanoacetic acid, and reduces the difficulty of dehydration ofthe cyanoacetic acid raw materials; the method is high in operability, reasonable and economy, reduces the discharge of three wastes greatly, and has good social benefit.

1,5-Diketones Synthesis via Three-Component Cascade Reaction

A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.

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.

Catalytic asymmetric conjugate allylation of coumarins

A catalytic asymmetric conjugate allylation was successfully developed to synthesize potential pharmacologically active 4-allyl-2-oxochroman skeletons. A dual activation strategy was employed by using N,N′-dioxide-Yb(OTf) 3 to activate coumarins and using (CuOTf)2?C 7H8 to activate tetraallyltin via transmetalation, respectively. Good yields and enantioselectivities were obtained under mild conditions.

Micelle composition of polymer and passenger drug

Hydrophobic drugs become more practical for treatments by being encapsulated in micelle compositions for increasing solubility. Micelle compositions may include an excipient tocopherol and/or prodrug formulations of the drug. Micelles extend the time period the drug remains in the micelles to improve drug circulation time and thereby drug delivery. Hydrophobic drugs for micelle encapsulation may include rapamycin, geldanamycin, and paclitaxel. Administration of these micelle compositions does not require Cremophor EL or Tween 80, avoiding serious side effects associated with these products which would previously accompany such drug administration.

A facile, catalytic and environmentally benign method for esterification of carboxylic acids and transesterification of carboxylic esters with nearly equimolar amounts of alcohols

A practical and green chemical process for the esterification of carboxylic acids with alcohols and transesterification of carboxylic esters in good to excellent yields by using K5CoW12O14· 3H2O (0.1 mol%) as catalyst is reported. The catalyst exhibited remarkable reusable activity. Georg Thieme Verlag Stuttgart.

Catalytic electronic activation as a tool for the addition of stabilised nucleophiles to allylic alcohols

This paper describes the activation of 2-cyclohexen-1-ol (1) and 2-cyclopenten-1-ol (11) through the use of aluminium-catalysed transfer hydrogenation. The electronically activated substrates are demonstrated to undergo facile conjugate addition and, when the alcohol functional group is subsequently restored in a one-pot procedure, this leads to an indirect addition of nucleophiles to allylic alcohols. This novel methodology has been termed catalytic electronic activation. The aluminium tert-butoxide catalysed conversion of 2-cyclohexen-1-ol (1) into 2-(3-hydroxycyclohexyl)-2- methylmalononitrile (18) and 2-cyclopenten-1-ol (11) into 2-(3- hydroxycyclopentyl)-2-methylmalononitrile (16) in 90 and 60% yield, respectively has been demonstrated through an efficient domino Oppenauer/Michael addition/Meerwein-Ponndorf-Verley process.

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.