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
• Uses: Diethyl chloromalonate is a compound used in the models of aquatic toxicity developed A compound used in the models of aquatic toxicity developed (QSAR). Combinatorial QSAR modeling of chemical toxicants tested against Tetrahymena pyriformis.

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:

2-benzyl-2-chloromalonic acid diethyl ester

3-methyl-4-oxo-2-thioxo-thiazolidine-5-carboxylic acid ethyl ester

ethyl 2-(ethoxycarbonyl)-4-(p-methoxyphenyl)butanoate

diethyl <2-(p-methylphenyl)ethyl>malonate

Refernces

• 1、 Winter,Gard. "The addition of SF5Br to acrylic esters: Pathways to γ-SF5-propane derivatives". . p. 79 - 87. Retrieved 2000.
• 2、 Shainyan,Danilevich, Yu. S.. "Reaction of trifluoromethanesulfonyl chloride with CH acids". . p. 1412 - 1413. Retrieved 2009.
• 3、 Mazenauer, Manuel R.,Manov, Stole,Galati, Vanessa M.,Kappeler, Philipp,Stohner, Jürgen. "Synthetic routes for a variety of halogenated (chiral) acetic acids from diethyl malonate". . p. 55434 - 55440. Retrieved 2017.
• 4、 -. "Synthesis method of 4,5,6-trichloropyrimidine". Paragraph 0027-0028. . Retrieved 2020/08/02.
• 5、 Silva, Saúl,Maycock, Christopher D.. "Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate". supporting information. p. 1233 - 1238. Retrieved 2018/02/27.