18457-04-0

Basic information

• Product Name: BIS(TRIMETHYLSILYL) MALONATE
• Synonyms: Malonic acid (tms);Malonic acid, bis-TMS;Malonic acid, di(trimethylsilyl) ester;Propanedioic acid, bis(trimethylsilyl) ester;MALONIC ACID BIS(TRIMETHYLSILYL) ESTER;BIS(TRIMETHYLSILYL) MALONATE;MALONIC ACID BIS(TRIMETHYLSILYL) ESTER 95+%;Bis(trimethylsilyl) malonate,98%
• CAS NO: 18457-04-0
• Molecular Formula: C₉H₂₀O₄Si₂
• Molecular Weight: 248.42
• EINECS: 242-342-5
• Product Categories: Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Silyl Esters;Si-O Compounds;Synthetic Organic Chemistry
• Mol File: 18457-04-0.mol

Chemical Properties

• Melting Point: 56 °C
• Boiling Point: 63-66 °C1 mm Hg(lit.)
• Flash Point: 75 °F
• Appearance: Clear colorless to straw/Liquid
• Density: 0.974 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000118mmHg at 25°C
• Refractive Index: n20/D 1.416(lit.)
• Storage Temp.: 2-8°C
• PKA: 12.18±0.46(Predicted)
• BRN: 2212115
• CAS DataBase Reference: BIS(TRIMETHYLSILYL) MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(TRIMETHYLSILYL) MALONATE(18457-04-0)
• EPA Substance Registry System: BIS(TRIMETHYLSILYL) MALONATE(18457-04-0)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16
• RIDADR: UN 3272 3/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 18457-04-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Bis(trimethylsilyl) malonate is used as a cyclocondensation agent in cyclocondensation reactions, which are crucial for the synthesis of various organic compounds.
Used in Thin Film Deposition:
In the semiconductor industry, Bis(trimethylsilyl) malonate is used as a precursor for the MOCVD of HfO2 and ZrO2 thin films, which are essential for the fabrication of advanced electronic devices and components.
Used in Organic Chemistry:
Bis(trimethylsilyl) malonate is used as a reagent in the preparation of β-keto acids and methyl ketones, which are important intermediates in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C18H40Si/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h2-18H2,1,19H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 141-82-2 malonic acid 
• 1066-40-6 Trimethylsilanol 
• 504-64-3 carbon suboxide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 2033-24-1 cycl-isopropylidene malonate 
• 107-46-0 Hexamethyldisiloxane 
• 43112-38-5 3-(trimethylsilyl)-2-oxazolidinone 
• 57421-56-4 disilver(I) malonate 
• 25561-30-2 N,O-bis(trimethylsilyl)trifluoroacetamide 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 1663-67-8 malonoyl dichloride 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 

Downstream Products

• 72531-42-1 3-Oxo-hexanedioic acid 6-benzyl ester 
• 67354-42-1 2-Benzyloxycarbonyl-4-oxo-2-(2,2,2-trichloro-ethoxycarbonylamino)-hexanedioic acid 1-benzyl ester 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 13283-91-5 3-oxooctanoic acid 
• 25832-09-1 3-oxo-4-phenyl-butyric acid 
• 60890-29-1 (3,4-dimethoxybenzoyl)acetic acid 
• 110144-24-6 Methyl 2-acetylpyridine-6-carboxlyate 
• 94111-68-9 methyl 2-(carboxyacetyl)pyridine-6-carboxylate 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 127356-40-5 5-acetyl-2-chloro-3-nitropyridine 
• 98-86-2 acetophenone 
• 563-80-4 3-methyl-butan-2-one 
• 6342-63-8 1-(2-bromo-5-methoxyphenyl)ethanone 
• 143418-80-8 3-Benzyloxy-4,5-dimethoxyacetophenone 

Relevant articles and documents

Chloride-free method to synthesise new ionic liquids with mixed borate anions

A new chloride-free method to synthesize ionic liquids (ILs) with mixed borate anions was demonstrated. The anions used for the study were derived from [BF4]- by replacement of F- by mono- or bidentate ligands. The proposed method was depended on the type of ligand, while moisture exclusion and dried starting materials and solvent were used to minimize water content. The starting materials were heated to reflux in acetonitrile (MeCN) as solvent for monodentate ligands. The [BF 4]- compounds were diluted in MeCN to prevent the formation of bridged anions and the trime-thylsilyl compounds were added at a temperature of 45 °C. The proposed method opened new opportunities for preparing new ILs for different applications including their use as electrolytes in electrochemical double layer capacitors and lithium ion batteries.

Preparation method of silicon-based ester compound, silicon-based ester compound, electrolyte containing silicon-based ester compound and secondary battery

The invention relates to a preparation method of a silicon-based ester compound, the silicon-based ester compound, an electrolyte containing the silicon-based ester compound and a secondary battery. The preparation method of the silicon-based ester compound comprises the following steps: adding organic alkali and organic acid into a solvent and carrying out reacting to obtain an intermediate, andthen, adding halogenated silane to react with the intermediate to obtain the silicon-based ester compound, wherein the intermediate is ionic liquid. The preparation method provided by the invention can relieve the problems of long reaction time, difficult treatment of byproducts, complex operation caused by step-by-step reaction, high cost, difficult industrial scale-up production and the like inthe existing synthesis method.

Synthesis of trimethylsilyl carboxylates by HMDS under solvent-free conditions

A broad set of structurally different carboxylic acids were transformed into their trimethylsilyl esters with HMDS in a practically completely solvent-free process, while a catalytic amount of iodine was required in some cases. The process has several advantages over the known methods: untreated reactants, air atmosphere, mild and neutral conditions, no evolution of hydrogen halide, no need of an additional base, low amount of waste, completely without chromatography, low consumption of energy, and operational simplicity.

Partition coefficients of ketones, phenols, aliphatic and aromatic acids, and esters in n-hexane/nitromethane

Liquid-liquid partition is used in sample preparation and in countercurrent and liquid-liquid chromatographic separations. Partition coefficients are widely used in toxicology, environmental, and analytical chemistry. The K hn determination procedure for the n-hexane/ nitromethane system was optimized and partition coefficients for 99 ketones, esters and trimethylsilyl derivatives of phenols, aliphatic and aromatic acids were determined. For 130 compounds, Khn values were predicted using mathematical relationships between Khn and other physicochemical and structural parameters. Versita Sp. z o.o.

Electrolytic salts for lithium batteries

Orthoborate salts suitable for use as electrolytes in lithium batteries and methods for making the electrolyte salts are provided. The electrolytic salts have one of the formulae (I). In this formula anionic orthoborate groups are capped with two bidentate chelating groups, Y1 and Y2. Certain preferred chelating groups are dibasic acid residues, most preferably oxalyl, malonyl and succinyl, disulfonic acid residues, sulfoacetic acid residues and halo-substituted alkylenes. The salts are soluble in non-aqueous solvents and polymeric gels and are useful components of lithium batteries in electrochemical devices.

Malonates in cyclocondensation reactions

The use of malonates such as diethyl malonates 9, (chlorocarbonyl)ketenes 15 and bis(2,4,6-trichlorophenyl) malonates 18 as reagents for cyclocondensation with 1,3-dinucleophiles to give six-membered heterocycles is described. Further attempts to use malonates such as bis(trimethylsilyl) malonates 19 and bis(carbamimidoyl) malonates 29 as new cyclocondensation agents are described.

Identification of products containing -COOH, -OH, and -C=O in atmospheric oxidation of hydrocarbons

Atmospheric oxidation of hydrocarbons by hydroxyl radicals and ozone leads to products containing -COOH, -OH, and -C=O functional groups. The high polarity of such compounds precludes direct GC-MS analysis. In addition, many such compounds often exist in a single sample at trace levels. An analytical method has been developed to identify compounds containing one or more functional groups of carbonyl, carboxy, and hydroxy in atmospheric samples. In the method, -C=O groups are derivatized using O-(2,3,4,5,6- pentafluorobenzyl) hydroxy amine (PFBHA), and -COOH and -OH groups are derivatized using a silylation reagent N,O-bis(trimethylsilyl)- trifluoroacetamide (BSTFA). The derivatives are easily resolved by a GC column. The chemical ionization mass spectra of these derivatives exhibit several pseudomolecular ions, allowing unambiguous determination of molecular weights. Functional group identification is accomplished by monitoring the ions in the electron ionization mass spectra that are characteristic of each functional group derivative: m/z 181 for carbonyl and m/z 73 and 75 for carboxyl and hydroxy groups. The method is used to identify products in laboratory studies of ozone oxidation of α-pinene and Δ3-carene. Among products from ozone oxidation of α-pinene, we have detected pinonaldehyde, norpinonaldehyde, pinonic acid, norpinonic acid, C10 hydroxy dicarbonyls, pinic acid, 2,2-dimethyl-3-(formylmethyl)-cyclobutane-formic acid, and a product that has a molecular weight of 156 and contains a C=O and a COOH/OH group. The latter two products have not been reported previously. Δ3- Carene is structurally analogous to α-pinene in that both have an internal unsaturated bond where ozone oxidation takes place. We have also identified the corresponding analogous products, of which all but caronaldehyde are reported for the first time. An analytical method was developed to identify compounds containing one or more functional groups of carbonyl, carboxyl and hydroxyl in atmospheric samples. -C-to-O double bond groups are derivatized using 0-(2,3,4,5,6-pentafluorobenzyl)hydroxyl amine, and -COOH and -OH groups are derivatized using a silylation reagent N,O-bis(trimethylsilyl)-trifluoroacetamide. The derivatives are resolved using a gas chromatography column coupled with mass spectrometry. The method identified products in laboratory studies of ozone oxidation of α-pinene and Δ3-carene.

Investigations on the Acid-Strength of Alkanepolysulfonic Acids

The acid strength of alkanepolysulfonic acids was measured using the correlation between the 29Si NMR shift of the corresponding trimethylsilylester of an acid and the pKS1-value of the acid. Alkanepolysulfonic trimethylsilylesters XHC(SO3-SiMe3)2, X2C(SO3-SiMe3)2, XC(SO3-SiMe3)3 and Me3Si-O3S-(CR2)n-SO 3-SiMe3 with X = H, F, Cl, Br, I and R = H, F and n = 1 - 5 were investigated.

1-[2-(4-Hydroxybenzoyl)ethanoyl]-2-piperidone and a process for production as well as alcohol fermentation promoter containing the same as effective ingredient

The present invention relates to 1-[2-(4-hydroxybenzoyl)ethanoyl]-2-piperidone which is a novel compound of N-acyl lactam compounds and exhibit excellent effects in promoting fermentation in alcohol fermentation. This novel compound can be prepared by converting 2-(4-benzyloxybenzoyl)acetic acid into the acid chloride, then coupling the acid chloride with 2-piperidone or an alkylate of 2-piperidone and then subjecting to debenzylation.

REACTION OF TRIMETHYLSILYL DERIVATIVES WITH MELDRUM'S ACID : A NEW AND EASY MONOFUNCTIONALIZATION OF MALONIC ACID

Treament of Meldrum's acid with silylated derivatives (amines, lactams or alcohols) yields very easily monofunctionalized malonic silyl esters.Hydrolysis of these silyl esters leads to the corresponding monoacids with a very good yield.