20165-81-5

Basic information

• Product Name: diethyl dichloromalonate
• Synonyms: diethyl dichloromalonate;2,2-Dichloromalonic acid diethyl ester;Dichloromalonic acid diethyl ester
• CAS NO: 20165-81-5
• Molecular Formula: C₇H₁₀Cl₂O₄
• Molecular Weight: 229.0579
• EINECS: 243-550-9
• Mol File: 20165-81-5.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 230°Cat760mmHg
• Flash Point: 85°C
• Appearance: /
• Density: 1.317g/cm³
• Vapor Pressure: 0.0673mmHg at 25°C
• Refractive Index: 1.46
• CAS DataBase Reference: diethyl dichloromalonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl dichloromalonate(20165-81-5)
• EPA Substance Registry System: diethyl dichloromalonate(20165-81-5)

Safety Data

• Hazardous Substances Data: 20165-81-5(Hazardous Substances Data)

Usage

General Description

Diethyl dichloromalonate is a chemical compound with the molecular formula C7H10Cl2O4. It is a colorless liquid with a fruity odor, and is primarily used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used in organic synthesis to introduce the dichloroacetyl functional group into organic molecules. Diethyl dichloromalonate is a highly reactive compound due to the presence of two electrophilic chlorine atoms, and it should be handled with caution as it can cause irritation to the skin, eyes, and respiratory system. Additionally, it should be stored in a cool, dry place away from sources of ignition and incompatible materials.

InChI:InChI=1/C7H10Cl2O4/c1-3-12-5(10)7(8,9)6(11)13-4-2/h3-4H2,1-2H3

Upstream product

• 515-84-4 Ethyl trichloroacetate 
• 105-53-3 diethyl malonate 
• 7782-50-5 chlorine 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 14064-10-9 diethyl 2-chloromalonate 
• 116-15-4 perfluoropropylene 
• 81289-78-3 diethyl chlorobromomalonate 
• 20165-80-4 Phosphorsaeure-dimethyl-(1.2.2-trichlor-1-ethoxy-2-ethoxycarbonyl-ethyl)-ester 
• 64-17-5 ethanol 
• 56857-23-9 dichloromalonic acid 
• 98880-55-8 O.O-Dimethyl-O-<1-athoxy-2-chlor-2-athoxycarbonyl-vinyl>-phosphat 

Downstream Products

• 42760-94-1 bis-(4-nitro-phenoxy)-malonic acid diethyl ester 
• 683-72-7 dichloroacetamide 
• 30989-14-1 dichloro-malonic acid diamide 
• 14064-10-9 diethyl 2-chloromalonate 
• 29263-83-0 diethyl 2-chloro-2-ethylmalonate 
• 6174-95-4 1,1,2,2-tetracarboethoxy-ethylene 
• 63959-94-4 (2-methoxycarbonyl-2-chloroethyl)chloromalonic ester 
• 75911-83-0 1-ethyl 2-methyl 1-(2-methoxyacetyl)cyclopropane-1,2-dicarboxylate 
• 3092-20-4 diethyl 2-phenylcyclopropane-1,1-dicarboxylate 
• 1087-97-4 diethyl benzoylmalonate 
• 130029-34-4 diethyl 2-benzoyl-2-chloromalonate 

Relevant articles and documents

Trihaloisocyanuric acids as convenient reagents for regioselective halogenation of β-dicarbonyl compounds

The reaction of β-dicarbonyl compounds (β-ketoesters and β-diketones) with 0.34 mol equiv of trichloro- and tribromoisocyanuric acids produced regioselectively the corresponding α-monohalo β-dicarbonyl compound. On the other hand, utilization of 0.68 mol equiv of the trihaloisocyanuric acid produced the α,α-dihalo β-dicarbonyl compound.

Base-mediated reactions of diethyl malonates derivatives with perfluorinated olefins: Novel synthetic routes to multifunctional ionomer precursors

A novel synthetic method for the preparation of per- and polyfluorinated unsaturated 2-substituted malonates is presented involving the deprotonation of the starting diethyl malonate by a strong base, followed by in situ addition of the C-nucleophile to the terminal double bond of the perfluorinated olefin. Subsequent elimination of the corresponding leaving groups and restoring of the double bond leads to the target bifunctional perfluorinated olefins. In the case of unsubstituted diethyl malonate, the elimination is accompanied by a prototropic rearrangement with a double bond migration and the addition of a second equivalent of the C-nucleophile forming the tetrafunctional internal olefins. The reaction conditions, factors affecting the reactivity and regioselectivity of the process, the choice of reagent as well as the course of competitive reactions are also discussed.

PRODUCTION METHOD OF KETOMALONIC ACID COMPOUND

Provided is a method for producing an industrially useful ketomalonic acid compound such as ketomalinic acid diesters, or a hydrate thereof, by a method more favorable from an economic and environmental standpoint and from a safety standpoint. The present invention relates to a method involving reacting a malonic acid compound represented by general formula (1) (in the formula, The each Rs indicate an alkyl group, a cycloalkyl group, etc.) with chlorine dioxide to produce a ketomalonic acid compound represented by the general formula (2) (in the formula, R has the same meaning as above), or a hydrate thereof.