Diethyl(2-chloroethyl)propanedioate

Base Information

• Chemical Name: Diethyl(2-chloroethyl)propanedioate
• CAS No.: 18719-42-1
• Molecular Formula: C9H15ClO4
• Molecular Weight: 222.669
• NSC Number: 107980
• DSSTox Substance ID: DTXSID20296145
• Wikidata: Q82036551
• Mol file: 18719-42-1.mol

Synonyms:18719-42-1;diethyl(2-chloroethyl)propanedioate;diethyl 2-(2-chloroethyl)propanedioate;NSC107980;Propanedioic acid, chloroethyl-, diethyl ester;SCHEMBL9065703;DTXSID20296145;Diethyl 2-(2-chloroethyl)malonate;NSC-107980;CS-0166328;diethyl 2-(2-chloroethyl)malonate? (Cabozantinib Impurity

Chemical Property of Diethyl(2-chloroethyl)propanedioate

Chemical Property:

• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.444
• Boiling Point: 263.9°Cat760mmHg
• Flash Point: 98.7°C
• Density: 1.137g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 222.0658866
• Heavy Atom Count: 14
• Complexity: 175

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCCl)C(=O)OCC

Technology Process of Diethyl(2-chloroethyl)propanedioate

There total 6 articles about Diethyl(2-chloroethyl)propanedioate 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:

diethyl cyclopropane-1,1-dicarboxylate (1559-02-0) → diethyl 2-chloroethylmalonate (18719-42-1)

Guidance literature:

With ethylaluminum dichloride; In hexane; 1,2-dichloro-ethane; for 74h; Yield given; Ambient temperature;

DOI:10.1021/jo00373a010

Reference yield:

5-(2-chloroacetyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (505048-19-1) → diethyl 2-chloroethylmalonate (18719-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 56.1 percent / NaBH₄ / acetic acid / 1 h / 20 °C

2: aq. HCl / Heating

With hydrogenchloride; sodium tetrahydroborate; In acetic acid;

DOI:10.1081/SCC-120014984

Reference yield:

diethyl 2-(2-bromoethyl)-malonate (18721-64-7) → diethyl 2-chloroethylmalonate (18719-42-1)

Guidance literature:

With lithium chloride; In water; acetone; Heating;

DOI:10.1039/j29680000067

upstream raw materials:

1-carbethoxy-1-cyanocyclopropane

diethyl 2-(2-bromoethyl)-malonate

diethyl cyclopropane-1,1-dicarboxylate

hydrogenchloride

Downstream raw materials:

di-tert-butyl cyclopropane-1,1-dicarboxylate

diethyl cyclopropane-1,1-dicarboxylate

(2S,3S)-diethyl 2-phenyl-3-((S)-1-phenylethylcarbamoyl)cyclopentane-1,1-dicarboxylate

(2S,3S)-diethyl 3-(hydroxymethyl)-2-phenylcyclopentane-1,1-dicarboxylate

Refernces

• 1、 Beal, Richard B.,Dombroski, Mark A.,Snider, Barry B.. "EtAlCl2-Catalyzed Reactions of Alkenes with Electrophillic Cyclopropanes. A New Cyclopentane Annelation Reaction". . p. 4391 - 4399. Retrieved 2007/10/02.