39520-22-4

Basic information

• Product Name: Dimethyl butylmalonate
• Synonyms: DIMETHYL BUTYLMALONATE;Propanedioic acid,2-butyl-,1,3-dimethyl ester;Butylmalonic acid dimethyl ester;Pentane-1,1-dicarboxylic acid dimethyl ester;Butyl Methyl Malonate;Dimethyl 2-butylmalonate;Dimethyl butylmalote
• CAS NO: 39520-22-4
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.22
• EINECS: 254-489-2
• Mol File: 39520-22-4.mol

Chemical Properties

• Boiling Point: 219.6 °C at 760 mmHg
• Flash Point: 97.3 °C
• Appearance: /
• Density: 1.02 g/cm³
• Vapor Pressure: 0.118mmHg at 25°C
• Refractive Index: 1.425
• PKA: 13.43±0.46(Predicted)
• CAS DataBase Reference: Dimethyl butylmalonate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl butylmalonate(39520-22-4)
• EPA Substance Registry System: Dimethyl butylmalonate(39520-22-4)

Safety Data

• Hazardous Substances Data: 39520-22-4(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
Dimethyl butylmalonate is used as a fragrance ingredient for its pleasant scent, commonly included in perfumes, colognes, and other scented consumer products.
Used in Cosmetic and Personal Care Products:
In the cosmetic and personal care industry, dimethyl butylmalonate is used as a fragrance ingredient to impart a fruity and floral aroma to products, enhancing their sensory appeal.
Used in Food and Beverage Industry:
Dimethyl butylmalonate is used as a flavoring agent in food and beverages, adding a unique taste and aroma to various products.
Overall, dimethyl butylmalonate is a versatile compound with a wide range of applications in the fragrance and flavor industry, contributing to the sensory experience of various consumer products.

InChI:InChI=1/C9H16O4/c1-4-5-6-7(8(10)12-2)9(11)13-3/h7H,4-6H2,1-3H3

Upstream product

• 18795-83-0 dimethyl 2-butylidenemalonate 
• 542-69-8 1-iodo-butane 
• 108-59-8 malonic acid dimethyl ester 
• 67-56-1 methanol 
• 131190-04-0 α-diazo methyl 3-oxoheptanoate 
• 133-08-4 diethyl butylmalonate 
• 109-65-9 1-bromo-butane 

Downstream Products

• 2210-63-1 mofebutazone 
• 20487-91-6 butyl-malonic acid bis-benzylamide 
• 110375-62-7 4-butyl-3,5-dioxo-2-phenyl-pyrazolidine-1-carboxylic acid anilide 
• 4536-23-6 2-methylhexanoic acid 
• 2612-26-2 2-butylpropane-1,3-diol 
• 534-59-8 n-butylmalonic acid 
• 106-70-7 methyl hexanoate 
• 6967-70-0 3-n-Butyl-2,4-dihydroxy-6-methyl-pyridin 
• 122459-74-9 (3S,5S)-3-Butyl-5-[4-(5-octyloxy-pyrimidin-2-yl)-phenoxymethyl]-dihydro-furan-2-one 
• 122459-75-0 (3R,5S)-3-Butyl-5-[4-(5-octyloxy-pyrimidin-2-yl)-phenoxymethyl]-dihydro-furan-2-one 
• 134766-08-8 (3S,5S)-5-(4-Benzyloxy-phenoxymethyl)-3-butyl-dihydro-furan-2-one 
• 134766-09-9 (3R,5S)-5-(4-Benzyloxy-phenoxymethyl)-3-butyl-dihydro-furan-2-one 

Relevant articles and documents

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

Exploiting the Continuous in situ Generation of Mesyl Azide for Use in a Telescoped Process

The hazardous diazo transfer reagent mesyl azide has been safely generated and used in situ for continuous diazo transfer as part of an integrated synthetic process with an embedded safety quench. Diazo transfer to β-keto esters and a β-ketosulfone was successful. In-line phase separation, by means of a continuous liquid–liquid separator, enabled direct telescoping with a thermal Wolff rearrangement.

Synthesis of Enantiomerically Enriched 2-Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3-Diols Mediated by Acetobacter aceti

The stereoselective desymmetrisation of achiral 2-alkyl-1,3-diols is performed by oxidation of one of the two enantiotopic primary alcohol moieties by means of Acetobacter aceti MIM 2000/28 to afford the corresponding chiral 2-hydroxymethyl alkanoic acids (up to 94 % ee). The procedure, carried out in aqueous medium under mild conditions of pH, temperature and pressure, contributes to enlarge the portfolio of enzymatic oxidations available to organic chemists for the development of sustainable manufacturing processes.

Stereoselective synthesis of polyhydroxyl surfactants. Stereochemical influence on Langmuir monolayers

Herein is described the synthesis of surfactants featuring polyhydroxylated head groups. Three head groups were prepared via consecutive stereoselective dihydroxylations of a diene. By coupling of these with lipophilic tail groups six novel surfactants have been prepared. The monolayers prepared from four of these have been investigated at the air-water interface. Significant differences were observed between monolayers consisting of enantiomerically pure surfactants contra racemates as well as between diastereomers.

Preparation of phosphinodipeptide analogs as building blocks for pseudopeptides synthesis

A simple and effective preparation of phosphinodipeptides, in good overall yields, has been developed. This one pot procedure, allowing the variation of the substituents in α and/or β position to the phosphorus atom and also in α position to the nitrogen atom, consists in the addition of alkyl hypophosphites to imines, followed by Michael-addition on acrylates. To show the value of phosphinodipeptides analogs 1 as synthetic intermediates, selective deprotections of the three functional groups are described.

Electrooxidation of malonate and acetylacetate derivatives in the presence of halide ions

β-Dicarbonyl compounds, such as dimethyl malonate derivatives and methyl acetoacetate derivatives, were electrooxidized in methanol in the presence of halogen ions to afford the corresponding dimethyl α-halomalonates and methyl α-halocarboxylates. Electrooxidation of bis(β-dimethoxycarbonyl) derivatives similarly afforded cyclic compounds and dihalides.

Electrochemically induced oxidative rearrangement of alkylidenemalonates

Alkylidenemalonates capable of double bond migration being electrolyzed in methanol or ethanol in the presence of alkali metal halides in an undivided cell equipped with Fe cathode are transformed into 2-alkyl-3,3- dimethoxyalkane-1,2-dicarboxylates in 70-90% yield via electrochemically induced oxidative rearrangement. Acidification of the reaction mixture after the electrolysis leads to the formation of 2-alkyl-3-oxoalkane-1,1- dicarboxylates. In the case of isobutylidenemalonate, the electrolysis intermediate dimethyl 3,3-dimethyl-2-methoxy-cyclopropane-1,1-dicarboxylate was isolated in 70% yield.

Electrochemical Cyclodimerization of Alkylidenemalonates

Electrolysis of dimethyl alkylidenemalonates RCH=C(COOMe)2 (R=n-Alk, Ph) in an undivided cell in MeOH in the presence of alkali metal halide as mediator, leads to the formation of cyclic dimers, i.e., 3,4-disubstituted 1,1,2,2-cyclobutanetetracarboxylates.The reaction proceeds via the reductive coupling of two substrate molecules at cathode and the cyclization of a hydrodimer dianion by its interaction with an active form of a mediator, an anode-generated halogen.

Electrochemical cyclodimerization of alkylidenemalonates into 3,4-disubstituted cyclobutane-1,1,2,2-tetracarboxylates

Alkylidenemalonates being electrolyzed in methanol in undivided cell with glassy carbon, carbon or lead cathode in the presence of sodium iodide or sodium bromide are transformed into 3,4-disubstituted cyclobutane-1,1,2,2-tetracarboxylates.