Ethyl 2-methylacetoacetate

Base Information

• Chemical Name: Ethyl 2-methylacetoacetate
• CAS No.: 609-14-3
• Deprecated CAS: 64854-05-3
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• Hs Code.: 29182300
• European Community (EC) Number: 210-179-9
• NSC Number: 1102
• UNII: NE9WOZ20JE
• DSSTox Substance ID: DTXSID2033493
• Nikkaji Number: J101.360B
• Wikidata: Q27284827
• ChEMBL ID: CHEMBL31596
• Mol file: 609-14-3.mol

Synonyms:ethyl 2-methyl-3-oxobutanoate

Chemical Property of Ethyl 2-methylacetoacetate

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.686mmHg at 25°C
• Melting Point: -45 °C
• Refractive Index: n20/D 1.418(lit.)
• Boiling Point: 185.756 °C at 760 mmHg
• PKA: 11.98±0.46(Predicted)
• Flash Point: 68.857 °C
• PSA: 43.37000
• Density: 0.994 g/cm³
• LogP: 0.77460
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: IMMISCIBLE
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2-methylacetoacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(C)C(=O)C
• Uses: Ethyl 2-methylacetoacetate is used in Japp-Klingemann reaction to prepare hydrazones from beta-keto acid and aryl diazonium salts. It is used as a precursor involved in the synthesis of ethylpyruvate phenylhydrazone via reaction with benzenediazonium chloride. Ethyl 2-methylacetoacetate is used as a substrate in the rhenium-catalyzed synthesis of multisubstituted aromatic compounds.It can be employed in the synthesis of coumarin derivatives via Pechmann condensation.It undergoes dehydration to yield conjugated alkynyl and allenyl esters.It is also used in the total synthesis of chlorotonil A, yangjinhualine A, (+)- and (?)-saudin.

Technology Process of Ethyl 2-methylacetoacetate

There total 59 articles about Ethyl 2-methylacetoacetate 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%

2-Methyl-2-nitro-3-oxo-butyric acid ethyl ester (97383-81-8) → 2-acetylpropanoic acid ethyl ester (609-14-3)

Guidance literature:

With sodium hydrogen telluride; In ethanol; for 0.25h; Ambient temperature;

DOI:10.1246/bcsj.58.1067

Reference yield: 100.0%

1-(3,5-dimethyl-1H-pyrazol-1-yl)ethanone (10199-63-0) + Ethyl 2-bromopropionate (535-11-5,41978-69-2) → 2-acetylpropanoic acid ethyl ester (609-14-3)

Guidance literature:

With zinc; In tetrahydrofuran; for 1h; Heating;

Reference yield: 95.0%

ethyl acetoacetate (141-97-9) + methyl iodide (74-88-4) → 2-acetylpropanoic acid ethyl ester (609-14-3)

Guidance literature:

ethyl acetoacetate; With potassium carbonate; In acetone; at 20 ℃; for 0.166667h; Inert atmosphere;

methyl iodide; In acetone; for 5h; Reflux; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.05.031

upstream raw materials:

tetrahydrofuran

monoethyl methylmalonate

isopropylmagnesium bromide

acetyl chloride

Downstream raw materials:

3-methyltetrahydro-2-furanone

4,4'-(carbonylbis(azanediyl))dibenzoic acid

ethyl 2-methyl-3-phenylpropionate

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

Refernces

• 1、 Bankowska,Zadrozna. "". . . Retrieved 1969.
• 2、 Santi, Micol,Ould, Darren M. C.,Wenz, Jan,Soltani, Yashar,Melen, Rebecca L.,Wirth, Thomas. "Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones". supporting information. p. 7861 - 7865. Retrieved 2019/04/25.
• 3、 -. "Substituted phenyl pyrazolone derivatives and preparation and application (by machine translation)". Paragraph 0034-0036. . Retrieved 2019/01/08.