3709-18-0

Basic information

• Product Name: 2,2,5-Trimethyl-1,3-dioxane-4,6-dione
• Synonyms: CHEMPACIFIC 41980;CYCL-ISOPROPYLIDENE METHYLMALONATE;METHYLMALONIC ACID CYCLIC ISOPROPYLIDENE ESTER;METHYL MELDRUM'S ACID;2,2,5-TRIMETHYL-1,3-DIOXANE-4,6-DIONE;1,3-DIOXANE-4,6-DIONE, 2,2,5-TRIMETHYL;2-METHYLCYCLOPROPANECARBOXYLIC ACID, 98% , MIXTURE OF CIS AND TRANS;2,2,5-Trimethyl-1,3-Dioxane-4,6-Dione 98%
• CAS NO: 3709-18-0
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• EINECS: 223-050-7
• Mol File: 3709-18-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 111-114 °C(lit.)
• Boiling Point: 203.22°C (rough estimate)
• Flash Point: 183.4 °C
• Appearance: White to slightly pink crystalline powder
• Density: 1.1229 (rough estimate)
• Vapor Pressure: 6.96E-05mmHg at 25°C
• Refractive Index: 1.4610 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• PKA: 13.14±0.40(Predicted)
• BRN: 124044
• CAS DataBase Reference: 2,2,5-Trimethyl-1,3-dioxane-4,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,5-Trimethyl-1,3-dioxane-4,6-dione(3709-18-0)
• EPA Substance Registry System: 2,2,5-Trimethyl-1,3-dioxane-4,6-dione(3709-18-0)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 3709-18-0(Hazardous Substances Data)

Usage

Description

2,2,5-Trimethyl-1,3-dioxane-4,6-dione is an organic compound known for its unique chemical structure and properties. It is characterized by its dioxane ring with three methyl groups and two酮 (keto) groups at the 4 and 6 positions. 2,2,5-Trimethyl-1,3-dioxane-4,6-dione has been investigated for its potential applications in various fields due to its reactivity and structural features.

Uses

Used in Pharmaceutical Synthesis:
2,2,5-Trimethyl-1,3-dioxane-4,6-dione is used as a reagent in the synthesis of 3'',4''-bis-difluoromethoxycinnamoylanthranilate (FT061), which is an orally-active antifibrotic agent. This agent is particularly effective in reducing albuminuria in rat models of progressive diabetic nephropathy, making it a valuable compound in the development of treatments for kidney diseases.
Used in Chemical Trapping:
2,2,5-Trimethyl-1,3-dioxane-4,6-dione has also been utilized for trapping the adduct formed during the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates. This application highlights its role in understanding and controlling chemical reactions, which can be crucial in the development of new materials and compounds.
Used in X-ray Crystallography:
2,2,5-Trimethyl-1,3-dioxane-4,6-dione has been investigated in the context of X-ray irradiated single crystals. Through techniques such as electron spin resonance (ESR), electron nuclear double resonance (ENDOR), and electron-electron double resonance (ELDOR) spectra, researchers have gained insights into the compound's behavior under various conditions. This information can be valuable for furthering our understanding of its properties and potential applications in different industries.

InChI:InChI=1/C7H10O4/c1-4-5(8)10-7(2,3)11-6(4)9/h4H,1-3H3

Upstream product

• 516-05-2 methyl-propanedioic acid 
• 67-64-1 acetone 
• 152125-90-1 1-<(6-hydroxy-2,2-dimethyl-4-oxo-4H-1,3-dioxin-5-yl)methyl>pyridinium hydroxide 
• 5362-80-1 5-dimethylsulfonio-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide 
• 67-56-1 methanol 
• 7270-63-5 5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion 
• 2033-24-1 cycl-isopropylidene malonate 
• 66145-20-8 5-bromo-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 50-00-0 formaldehyd 
• 1190929-77-1 2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)butan-2-yl)-1,3-dioxane-4,6-dione 
• 1190929-78-2 2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)hexan-2-yl)-1,3-dioxane-4,6-dione 
• 1190929-76-0 2,2-dimethyl-5(1-(4-(octyloxy)phenyl)cyclohexyl)-1,3-dioxane-4,6-dione 
• 1190929-79-3 2,2-dimethyl-5-(3-methyl-2-(4-(octyloxy)phenyl)butan-2-yl)-1,3-dioxane-4,6-dione 
• 81710-07-8 2,2-dimethyl-5-(1-methyl-1-phenylethyl)-1,3-dioxane-4,6-dione 

Downstream Products

• 74610-75-6 5-(4-methoxyphenyl)-2,2,5-trimethyl-1,3-dioxane-4,6-dione 
• 92978-26-2 5-(4-isobutylphenyl)-2,2,5-trimethyl-1,3-dioxane-4,6-dione 
• 121721-29-7 2,2,5-trimethyl-5-(phenylethynyl)-1,3-dioxane-4,6-dione 
• 60179-41-1 Methylmalonsaeuremono-(4-chlorphenylester) 
• 60179-38-6 2-methyl-malonic acid monophenyl ester 
• 197520-97-1 6-(tert-Butyl-diphenyl-silanyloxy)-2,2,5-trimethyl-[1,3]dioxin-4-one 
• 24131-01-9 2,2,5-trimethyl-5-phenyl-1,3-dioxane-4,6-dione 
• 83540-59-4 5-Methyl-5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxane 
• 821794-54-1 methylmalonylcarnitine hydrochloride 
• 30409-97-3 rac-2-methyl-3-oxo-3-(phenylthio)propanoic acid 
• 140184-28-7 5-cinnamyl-2,2,5-trimethyl-1,3-dioxane-4,6-dione 

Relevant articles and documents

New convenient method of isopropylidene methylmalonate synthesis [1]

-

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.

Quaternary β2,2-Amino Acids: Catalytic Asymmetric Synthesis and Incorporation into Peptides by Fmoc-Based Solid-Phase Peptide Synthesis

β-Amino acid incorporation has emerged as a promising approach to enhance the stability of parent peptides and to improve their biological activity. Owing to the lack of reliable access to β2,2-amino acids in a setting suitable for peptide synthesis, most contemporary research efforts focus on the use of β3- and certain β2,3-amino acids. Herein, we report the catalytic asymmetric synthesis of β2,2-amino acids and their incorporation into peptides by Fmoc-based solid-phase peptide synthesis (Fmoc-SPPS). A quaternary carbon center was constructed by the palladium-catalyzed decarboxylative allylation of 4-substituted isoxazolidin-5-ones. The N?O bond in the products not only acts as a traceless protecting group for β-amino acids but also undergoes amide formation with α-ketoacids derived from Fmoc-protected α-amino acids, thus providing expeditious access to α-β2,2-dipeptides ready for Fmoc-SPPS.