Ethyl hydrogen malonate

Base Information

• Chemical Name: Ethyl hydrogen malonate
• CAS No.: 1071-46-1
• Molecular Formula: C5H8O4
• Molecular Weight: 132.116
• Hs Code.: 29171900
• European Community (EC) Number: 213-992-7
• DSSTox Substance ID: DTXSID10147915
• Nikkaji Number: J21.761A
• Wikidata: Q72475137
• Metabolomics Workbench ID: 37318
• Mol file: 1071-46-1.mol

Synonyms:monoethyl malonate

Chemical Property of Ethyl hydrogen malonate

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 0.0155mmHg at 25°C
• Melting Point: -13°C(lit.)
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 237.2 °C at 760 mmHg
• PKA: pK1:3.55 (25°C)
• Flash Point: 100.8 °C
• PSA: 63.60000
• Density: 1.21 g/cm³
• LogP: 0.02420
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly)
• Water Solubility.: Miscible with water, chloroform and other solvents.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 132.04225873
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

Ethyl hydrogen malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)O
• Uses: Ethyl Hydrogen Malonate has been shown to impair brain mitochondrial succinate and malate transport. It is also found in the extract of Hericum erinaceus mushroom which shows antitumor effects in tumo r-bearing mice. Ethyl hydrogen malonate is used as a reactant for the preparation of tetramic acids through Dieckmann ring closure and organocatalytic decarboxylative Doebner-Knoevenagel reactions. It is involved in the acylation reactions and Knoevenagel condensation with aldehydes. It is also used in the preparation of gamma-lactones from olefins by intermolecular carbolactonization in presence of Mn(III) acetate as a catalyst.

Technology Process of Ethyl hydrogen malonate

There total 31 articles about Ethyl hydrogen malonate 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: 100.0%

ethyl potassium malonate (6148-64-7) → hydrogen ethyl malonate (1071-46-1)

Guidance literature:

With hydrogenchloride; In water; at 5 ℃; for 1h;

DOI:10.1016/j.bmc.2004.06.037

Reference yield: 94.0%

diethyl malonate (105-53-3) → hydrogen ethyl malonate (1071-46-1)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 25 ℃; for 1h;

DOI:10.1016/j.tet.2018.07.017

Reference yield: 94.0%

ethyl 2-cyanoacetate (105-56-6) → hydrogen ethyl malonate (1071-46-1)

Guidance literature:

With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC₈₇₅₀; at 30 ℃; for 7h; pH=7.3;

DOI:10.1021/jf048827q

upstream raw materials:

ethanol

malonic acid

ethyl acetate

diethyl malonate

Downstream raw materials:

3-hydroxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamic acid ethyl ester

(E)-3-thiophen-3-yl-acrylic acid ethyl ester

12-fluoro-3-oxo-dodecanoic acid ethyl ester

malonic acid monomenthyl ester

Refernces

• 1、 Toshima, Minoru,Watanabe, Shoji,Uchiyama, Katsuya,Takasaki, Tsuyoshi,Bhogle, Nandkumar N.,Zhao, Hang,Filios, Mike,Takahashi, Kazuhiko,Snoonian, John R.,Saranteas, Kostas. "First Kilogram-Scale Application of the Lanthanum Catalyzed Asymmetric Amination to Synthesis of the Chiral Succinimide Derivative, A Key Intermediate for the Preparation of AS-3201". . p. 1239 - 1245. Retrieved 2016.
• 2、 Bixa, Thobela,Hunter, Roger,Andrijevic, Ana,Petersen, Wade,Su, Hong,Dhoro, Francis. "Stereoselective formation of quaternary stereogenic centers via alkylation of α-substituted malonate-imidazolidinones". . p. 762 - 769. Retrieved 2015.
• 3、 Krapcho,A.P. et al.. "-". . p. 2721 - 2723. Retrieved 1974.
• 4、 Niwayama, Satomi,Cho, Hanjoung. "Practical large scale synthesis of half-esters of malonic acid". . p. 508 - 510. Retrieved 2009.
• 5、 Perrin, Charles L.,Flach, Agnes,Manalo, Marlon N.. "Decomposition of malonic anhydrides". . p. 9698 - 9707. Retrieved 2012.
• 6、 Porey, Arka,Mondal, Bhaskar Deb,Guin, Joyram. "Hydrogen-Bonding Assisted Catalytic Kinetic Resolution of Acyclic β-Hydroxy Amides". supporting information. p. 8786 - 8791. Retrieved 2021/03/17.
• 7、 -. "NOVEL COMPOUNDS AS ANTI-MYCOBACTERIALS". Page/Page column 120. . Retrieved 2018/07/05.