2049-70-9

Basic information

• Product Name: DIETHYL ISOPROPYLMALONATE
• Synonyms: ethyl-methyl-malonicaciddiethylester;2-Ethyl-2-methylmalonic Acid Diethyl Ester;Diethyl 2-Ethyl-2-methylmalonate;2-Ethyl-2-methylpropanedioic acid diethyl ester;2-Methyl-2-ethylmalonic acid diethyl ester;Butane-2,2-dicarboxylic acid diethyl ester;Methylethylmalonic acid diethyl ester;diethyl 2-isopropylmalonate
• CAS NO: 2049-70-9
• Molecular Formula: C₁₀H₁₈O₄
• Molecular Weight: 202.25
• EINECS: 212-068-0
• Mol File: 2049-70-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 62 °C0.35 mm Hg(lit.)
• Flash Point: 198 °F
• Appearance: /
• Density: 0.981 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.151mmHg at 25°C
• Refractive Index: n20/D 1.42(lit.)
• CAS DataBase Reference: DIETHYL ISOPROPYLMALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL ISOPROPYLMALONATE(2049-70-9)
• EPA Substance Registry System: DIETHYL ISOPROPYLMALONATE(2049-70-9)

Safety Data

• Safety Statements: S24/25:
• WGK Germany: 1
• Hazardous Substances Data: 2049-70-9(Hazardous Substances Data)

Usage

General Description

Diethyl isopropylmalonate is a chemical compound with the formula C12H22O4. It is an ester of isopropylmalonic acid and is commonly used as a flavoring agent in the food and beverage industry. It is also used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. Diethyl isopropylmalonate has a fruity odor and is often added to perfumes and cosmetics. It is also used as a solvent in the production of various products. This chemical is considered safe for use in these applications when used in accordance with good manufacturing practices.

InChI:InChI=1/C10H18O4/c1-5-13-9(11)8(7(3)4)10(12)14-6-2/h7-8H,5-6H2,1-4H3

Upstream product

• 60-29-7 diethyl ether 
• 873421-51-3 3-methyl-hexane-2,4,4-tricarboxylic acid triethyl ester 
• 141-52-6 sodium ethanolate 
• 75-03-6 ethyl iodide 
• 609-08-5 Diethyl methylmalonate 
• 74-85-1 ethene 
• 62116-54-5 sodium diethyl methylmalonate 
• 996-82-7 sodium diethylmalonate 
• 74-96-4 ethyl bromide 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 133-13-1 ethyl diethyl malonate 
• 3494-86-8 Ethyl-<2,2-diethoxy-ethyl>-malonsaeure-diethylester 
• 105-53-3 diethyl malonate 
• 442672-21-1 tert-butyl 4-ethoxy-3-(ethoxycarbonyl)-3-methyl-4-oxobutaneperoxoate 

Downstream Products

• 77-84-9 2-ethyl-2-methyl-1,3-propanediol 
• 137-32-6 (+/-)-2-methyl-1-butanol 
• 595-84-6 2-ethyl-2-methylmalonic acid 
• 39122-19-5 ethosuximide 
• 10422-35-2 1-bromo-2-methyl-butane 
• 66016-23-7 3-Methyl-3-ethylcyclobutan-1-carbonsaeure 
• 7452-79-1 ethyl 2-methylbutyrate 
• 27653-63-0 5-ethyl-5-methyl-1H,3H,5H-pyrimidin-2,4,6-trione 

Relevant articles and documents

Synthesis and mass spectra of rearrangement bio-signature metabolites of anaerobic alkane degradation via fumarate addition

Metabolite profiling in anaerobic alkane biodegradation plays an important role in revealing activation mechanisms. Apart from alkylsuccinates, which are considered to be the usual biomarkers via fumarate addition, the downstream metabolites of C-skeleton rearrangement can also be regarded as biomarkers. However, it is difficult to detect intermediate metabolites in both environmental samples and enrichment cultures, resulting in lacking direct evidence to prove the occurrence of fumarate addition pathway. In this work, a synthetic method of rearrangement metabolites was established. Four compounds, namely, propylmalonic acid, 2-(2-methylbutyl)malonic acid, 2-(2-methylpentyl)malonic acid and 2-(2-methyloctyl)malonic acid, were synthesized and determined by four derivatization approaches. Besides, their mass spectra were obtained. Four characteristic ions were observed at m/z 133 + 14n, 160 + 28n, 173 + 28n and [M - (45 + 14n)]+ (n = 0 and 2 for ethyl and n-butyl esters, respectively). For methyl esterification, mass spectral features were m/z 132, 145 and [M - 31]+, while for silylation, fragments were m/z 73, 147, 217, 248, 261 and [M - 15]+. These data provide basis on identification of potential rearrangement metabolites in anaerobic alkane biodegradation via fumarate addition.

A practical chemoenzymatic synthesis of (R)-isovaline based on the asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide

(R)-Isovaline has potential applications in drug development, and therefore the development of an efficient method for the production of (R)-isovaline is desired. Herein we have investigated the asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide into (S)-2-ethyl-2-methyl-malonamic acid, a useful synthetic intermediate in the production of (R)-isovaline, using CsAM, which is a recombinant amidase originally derived from Cupriavidus sp. KNK-J915. The produced (S)-2-ethyl-2-methyl-malonamic acid (98.6% ee) could be easily converted into (R)-isovaline by the Hofmann rearrangement. Starting from diethyl 2-methylmalonate, we obtained (R)-isovaline (99.1% ee) in 58.6% yield over eight steps, including the CsAM-catalyzed asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide.

Effect of supramolecular inclusion on the 1,2-rearrangement of free radicals

The free radicals 3-ethoxy-2-(ethoxycarbonyl)-3-oxopropyl (1′) and 3-ethoxy-2-(ethoxycarbonyl)-2-methyl-3-oxopropyl (2′) were generated by photolysis of perester precursors in i) hexane solution, ii) in the presence of β-cyclodextrin, and iii) in NaY zeolite. While free radicals in solution are reluctant to rearrange, they do so when encapsulated in β-cyclodextrin or NaY zeolite. The coenzyme-B12-dependent enzymic rearrangement of methylmalonyl-CoA to succinyl-CoA could be mimicked by photochemical generation of an analogue of the putative intermediate radical in a molecular container.