Diethyl chloromalonate

Base Information

• Chemical Name: Diethyl chloromalonate
• CAS No.: 14064-10-9
• Deprecated CAS: 1448892-10-1
• Molecular Formula: C7H11ClO4
• Molecular Weight: 194.615
• Hs Code.: 2917.39 DERIVATION
• European Community (EC) Number: 237-913-0
• NSC Number: 227952
• UNII: 8Y5J45M964
• DSSTox Substance ID: DTXSID2022258
• Nikkaji Number: J267D
• Wikidata: Q27271193
• Mol file: 14064-10-9.mol

Synonyms:Diethyl chloromalonate;14064-10-9;Diethyl 2-chloromalonate;Ethyl chloromalonate;diethyl 2-chloropropanedioate;Ethylmonochloromalonate;Propanedioic acid, chloro-, diethyl ester;diethyl chloropropanedioate;Chloromalonic acid, diethyl ester;Malonic acid, chloro-, diethyl ester;1,3-diethyl 2-chloropropanedioate;Propanedioic acid, 2-chloro-, 1,3-diethyl ester;EINECS 237-913-0;NSC 227952;2-Chloromalonic acid diethyl;chloromalonic acid diethyl ester;UNII-8Y5J45M964;MFCD00009140;8Y5J45M964;NSC-227952;EC 237-913-0;diethylchloromalonate;Bosentan impurity 16;ClCH(COOC2H5)2;Diethyl 2-chloromalonate #;Diethyl chloromalonate, 95%;SCHEMBL1444159;DIETHYL MONOCHLOROMALONATE;DTXSID2022258;WLWCQKMQYZFTDR-UHFFFAOYSA-;2-chloro-malonic acid diethyl ester;BBL103910;NSC227952;STL557720;.ALPHA.-CHLORODIETHYL MALONATE;AKOS015843271;CS-W010637;2-Chloro-malonic acid 1,3-diethyl ester;AS-40995;CHLOROPROPANEDIOIC ACID ETHYL ESTER;LS-184961;FT-0637003;EN300-91664;Q-200972;Q27271193;F8889-0706

Chemical Property of Diethyl chloromalonate

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 0.104mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 222 °C at 760 mmHg
• PKA: 9.07±0.46(Predicted)
• Flash Point: 103.3 °C
• PSA: 52.60000
• Density: 1.195 g/cm³
• LogP: 0.72000
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 194.0345865
• Heavy Atom Count: 12
• Complexity: 151

Purity/Quality:

99% ^*data from raw suppliers

Diethyl chloromalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(C(=O)OCC)Cl
• General Description: Diethyl chloromalonate (also known as diethyl 2-chloromalonate) is a reactive ester used as a key reagent in organic synthesis, particularly in multicomponent reactions to form heterocyclic compounds. In the described study, it serves as an electrophilic component, reacting with an intermediate derived from carbon disulfide and primary amines to efficiently produce functionalized thiazolane derivatives. Its role underscores its utility in facilitating straightforward, high-yielding transformations under mild conditions, making it valuable for applications in pharmaceutical and agrochemical synthesis.

Technology Process of Diethyl chloromalonate

There total 17 articles about Diethyl chloromalonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.4%

Diethyl 2-bromomalonate (685-87-0) → diethyl 2-chloromalonate (14064-10-9)

Guidance literature:

With N-chloro-succinimide; In dimethyl sulfoxide; at 20 ℃; for 24h;

DOI:10.1039/c7ra09727a

Reference yield: 90.0%

diethyl malonate (105-53-3) → diethyl 2-chloromalonate (14064-10-9)

Guidance literature:

With sodium hydride; copper dichloride; In dimethyl sulfoxide; 1.) 20 deg C, 2 h, 2.) 40 deg C, 16 h;

DOI:10.1021/jo00069a020

Reference yield: 85.0%

trifluoromethane sulfonyl chloride (421-83-0) + diethyl malonate (105-53-3) → diethyl 2-chloromalonate (14064-10-9) + trifluoromethanesulfinic acid (34642-42-7)

Guidance literature:

diethyl malonate; With magnesium ethylate;

trifluoromethane sulfonyl chloride; In tetrahydrofuran;

DOI:10.1134/S1070428009090176

upstream raw materials:

ethyl hypochlorite

sodium diethylmalonate

diethyl malonate

diethyl dichloromalonate

Downstream raw materials:

tetraethyl ethane-1,1,2,2-tetracarboxylate

diethyl 2-phenoxymalonate

1,1,2,2-tetracarboethoxy-ethylene

m-tolyloxy-malonic acid diethyl ester

Refernces

Efficient synthesis of ethyl 3-alkyl-4-oxo-2-thioxo-1,3-thiazolane-5- carboxylates from the reaction of carbon disulfide and primary amines in the presence of diethyl 2-chloromalonate

10.1007/s00706-008-0900-x

The study presents an efficient method for synthesizing ethyl 3-alkyl-4-oxo-2-thioxo-1,3-thiazolane-5-carboxylates, which are compounds with potential applications in various fields such as agrochemicals, pharmaceuticals, and material chemistry. The synthesis involves a three-component reaction using carbon disulfide (CS2), primary amines (alkylamines), and diethyl 2-chloromalonate. These chemicals serve as reactants in the synthesis process, with CS2 and primary amines reacting to form an intermediate adduct, which then reacts with diethyl 2-chloromalonate to produce the final product. The study highlights the advantages of this procedure, including its simplicity, as it is performed under neutral conditions by simply mixing the starting materials, and its efficiency, yielding the desired products in good yields.