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

Uses

Different sources of media describe the Uses of 3709-18-0 differently. You can refer to the following data:
1. 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 that reduces albuminuria in rat models of progressive diabetic nephropathy.
2. 2,2,5-Trimethyl-1,3-dioxane-4,6-dione was used for trapping the adduct formed during the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates.

General Description

X-ray irradiated single crystals of 2,2,5-trimethyl-1,3-dioxane-4,6-dione have been investigated by electron spin resonance (ESR), electron nuclear double resonance (ENDOR) and electron-electron double resonance (ELDOR) spectra.

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 
• 67-56-1 methanol 
• 5362-80-1 5-dimethylsulfonio-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide 
• 7270-63-5 5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion 
• 2033-24-1 cycl-isopropylidene malonate 
• 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 
• 1190929-69-1 5-(2-([1,1'-biphenyl]-4-yl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 1190929-65-7 2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)propan-2-yl)-1,3-dioxane-4,6-dione 

Downstream Products

• 60179-41-1 Methylmalonsaeuremono-(4-chlorphenylester) 
• 60179-38-6 2-methyl-malonic acid monophenyl ester 
• 821794-54-1 methylmalonylcarnitine hydrochloride 
• 874484-13-6 (S)-5-(1-benzyloxy-allyl)-2,2,5-trimethyl-[1,3]-dioxa-4,6-dione 
• 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]

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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.

Structural Basis of a Broadly Selective Acyltransferase from the Polyketide Synthase of Splenocin

Polyketides are a large family of pharmaceutically important natural products, and the structural modification of their scaffolds is significant for drug development. Herein, we report high-resolution X-ray crystal structures of the broadly selective acyltransferase (AT) from the splenocin polyketide synthase (SpnD-AT) in the apo form and in complex with benzylmalonyl and pentynylmalonyl extender unit mimics. These structures revealed the molecular basis for the stereoselectivity and substrate specificity of SpnD-AT, and enabled the engineering of the industrially important Ery-AT6 to broaden its substrate scope to include three new types of extender units.