Methyl 2,2-dimethyl-3-oxopropanoate

Base Information

• Chemical Name: Methyl 2,2-dimethyl-3-oxopropanoate
• CAS No.: 13865-20-8
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 2918300090
• European Community (EC) Number: 866-608-0
• DSSTox Substance ID: DTXSID10456458
• Nikkaji Number: J1.112.995A
• Wikidata: Q82278954
• Mol file: 13865-20-8.mol

Synonyms:Methyl 2,2-dimethyl-3-oxopropanoate;13865-20-8;Propanoic acid, 2,2-dimethyl-3-oxo-, methyl ester;Methyl 2,2-dimethyl-3-oxopropionate;Methyl 2,2-dimethyl-3-oxo-propanoate;Methyl a-formylisobutyrate;Methyl alpha-formylisobutyrate;methyl-alpha-formylisobutyrate;SCHEMBL213629;DTXSID10456458;XFKYUMYFILZJGG-UHFFFAOYSA-N;methyl 2-formyl-2-methylpropionate;Methyl2,2-dimethyl-3-oxopropanoate;MFCD00082184;AKOS016013904;CS-W006356;DS-5566;2-(Methoxycarbonyl)-2-methylpropionaldehyde;2-Formyl-2-methylpropionic acid methyl ester;2,2-dimethyl-3-oxopropanoic acid methyl ester;C72545;EN300-104734;2,2-dimethyl-3-oxo-propionic acid methyl ester;A886196;A1-00388;F8887-4819

Chemical Property of Methyl 2,2-dimethyl-3-oxopropanoate

Chemical Property:

• Boiling Point: 49-50 °C(Press: 12 Torr)
• PSA: 43.37000
• Density: 1.013±0.06 g/cm3(Predicted)
• LogP: 0.38450
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 126

Purity/Quality:

98%min ^*data from raw suppliers

Methyl2,2-dimethyl-3-oxopropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C=O)C(=O)OC

Technology Process of Methyl 2,2-dimethyl-3-oxopropanoate

There total 24 articles about Methyl 2,2-dimethyl-3-oxopropanoate 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: 99.0%

Methyl 2,2-dimethyl-3-hydroxypropionate (14002-80-3) → methyl 2,2-dimethyl-3-oxopropanoate (13865-20-8)

Guidance literature:

With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 22h;

Reference yield: 97.0%

carbon monoxide (201230-82-2) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) → methyl 2,2-dimethyl-3-oxopropanoate (13865-20-8)

Guidance literature:

With hydrogen; acetylacetonatodicarbonylrhodium(l); 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In toluene; at 50 ℃; for 24h; under 37503 Torr;

DOI:10.1002/chem.200600914

Reference yield: 55.0%

methyl 4-hydroxy-2-methylbutanoate (73372-15-3) → methyl 2,2-dimethyl-3-oxopropanoate (13865-20-8) + methyl 3-formyl-2-methylpropionate (13865-21-9) + 3-methyltetrahydro-2-furanone (1679-47-6)

Guidance literature:

methyl 4-hydroxy-2-methylbutanoate; With sodium hydroxide; at 130 ℃; under 97.5098 Torr;

With hydroxylamine hydrochloride; In water; at 40 - 130 ℃; for 12h; under 9.75098 Torr;

upstream raw materials:

Methyl formate

methyl lithioisobutyrate

carbon monoxide

methacrylic acid methyl ester

Downstream raw materials:

(S)-3-[N-(1'-Allyloxy-3'-phenylprop-2'-yl)imino]-2,2-dimethylpropionsaeure-methylester-N-oxid

Refernces

• 1、 Inamoto, Yoshihiro,Kaga, Yuta,Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio. "Gallium trihalide catalyzed sequential addition of two different carbon nucleophiles to esters by using silyl cyanide and ketene silyl acetals". . p. 11664 - 11668. Retrieved 2014.
• 2、 Prokai-Tatrai, K.,Toeroes, S.,Heil, B.. "Hydroformylation of methyl methacrylate via "in-situ" phosphinerhodium catalysis". . p. 331 - 336. Retrieved 1987.
• 3、 Volkman, Jerome,Nicholas, Kenneth M.. "A synthetic quest for tris(imidazolyl) carboxylates and their metal complexes: Active site models for quercetin 2,3-dioxygenases and other non-heme redox metalloenzymes". . p. 3368 - 3376. Retrieved 2012.
• 4、 Pittman, Charles U.,Honnick, William D.,Yang, Jin Jun. "Hydroformylation of Methyl Methacrylate Catalyzed by Homogeneous and Polymer-Attached Rhodium Complexes". . p. 684 - 689. Retrieved 1980.
• 5、 Cunillera, Anton,De Los Bernardos, Miriam Díaz,Urrutigo?ty, Martine,Claver, Carmen,Ruiz, Aurora,Godard, Cyril. "Efficient synthesis of chiral γ-aminobutyric esters: Via direct rhodium-catalysed enantioselective hydroaminomethylation of acrylates". . p. 630 - 634. Retrieved 2020/02/25.
• 6、 Cunillera, Anton,Ruiz, Aurora,Godard, Cyril. "Synthesis of β2,2-Amino Esters via Rh-Catalysed Regioselective Hydroaminomethylation". supporting information. p. 4201 - 4207. Retrieved 2019/08/01.