Dimethyl dipropargylmalonate

Base Information

• Chemical Name: Dimethyl dipropargylmalonate
• CAS No.: 63104-44-9
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.214
• European Community (EC) Number: 811-058-9
• Nikkaji Number: J932.262K
• Mol file: 63104-44-9.mol

Synonyms:dimethyl dipropargylmalonate;63104-44-9;2,2-di-(prop-2-ynyl)-malonic acid dimethyl ester;dimethyl 2,2-bis(prop-2-ynyl)propanedioate;Dimethyl 2,2-di(prop-2-yn-1-yl)malonate;Dimethyl 2,2-dipropargylmalonate;Dipropargylmalonic Acid Dimethyl Ester;CBMicro_005005;SCHEMBL3974919;SMSF0003275;MFCD00455571;Dimethyl 2,2-di(2-propynyl)malonate;AKOS003604071;CB07010;GS-6309;Dimethyl2,2-di(prop-2-yn-1-yl)malonate;BIM-0004827.P001;CS-0158546;D4963;H10313;A917585;1,3-dimethyl 2,2-bis(prop-2-yn-1-yl)propanedioate

Chemical Property of Dimethyl dipropargylmalonate

Chemical Property:

• Melting Point: 87.0 to 91.0 °C
• Boiling Point: 274.7±40.0 °C(Predicted)
• Density: 1.127±0.06 g/cm3(Predicted)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 313

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl Dipropargylmalonate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC#C)(CC#C)C(=O)OC

Technology Process of Dimethyl dipropargylmalonate

There total 6 articles about Dimethyl dipropargylmalonate 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%

propargyl bromide (106-96-7) + malonic acid dimethyl ester (108-59-8) → dimethyl 2,2-di(prop-2-ynyl)malonate (63104-44-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4020(98)00567-5

Reference yield: 82.0%

1,5-dimethoxypentane-2,4-dione (96740-23-7) + propargyl bromide (106-96-7) → dimethyl 2,2-di(prop-2-ynyl)malonate (63104-44-9)

Guidance literature:

With sodium ethanolate; In ethanol; at 20 ℃; for 12h;

DOI:10.1002/chem.200903027

Reference yield: 81.0%

dimethyl malonate sodium salt (18424-76-5) + propargyl bromide (106-96-7) → dimethyl 2,2-di(prop-2-ynyl)malonate (63104-44-9)

Guidance literature:

With sodium methylate; In methanol;

upstream raw materials:

dimethyl malonate sodium salt

propargyl bromide

malonic acid dimethyl ester

dimethyl (prop-2-yn-1-yl)malonate

Downstream raw materials:

dimethyl 5-(2,2-bis(methoxycarbonyl)pent-4-yn-1-yl)-1,3-dihydro-2H-indene-2,2-dicarboxylate

dimethyl 3-phenyl-2-(phenylsulfonyl)-5,7-dihydro-1H-cyclopenta[c]pyridine-6,6(2H)-dicarboxylate

C₂₅H₂₆O₆

dimethyl 2,2-bis(3-(4-methoxyphenyl)prop-2-yn-1-yl)malonate

Refernces

• 1、 Kezuka, Satoko,Tanaka, Shigeru,Ohe, Toshihito,Nakaya, Yoshihiko,Takeuchi, Ryo. "Iridium complex-catalyzed [2+2+2] cycloaddition of α,ω-diynes with monoynes and monoenes". . p. 543 - 552. Retrieved 2006.
• 2、 Watanabe, Keisuke,Satoh, Yasushi,Kamei, Motofumi,Furukawa, Hirohisa,Fuji, Maito,Obora, Yasushi. "Nbcl5/zN/PCy3-system-catalyzed intramolecular [2 + 2 + 2] cycloadditions of diynes and alkenes to form bicyclic cyclohexadienes". . p. 5398 - 5401. Retrieved 2017.
• 3、 Pack, Ji Won,Hur, Young-Jae,Kim, Hwayong,Lee, Youn-Woo. "Cyclopolymerization of dimethyl dipropargylmalonate in supercritical carbon dioxide to give a highly regular polyene containing predominantly five-membered rings". . p. 5208 - 5210. Retrieved 2005.
• 4、 Yang, Feihu,Zheng, Xiaojie,Lei, Yu,Hu, Qiong,Zhu, Wenjing,Hu, Yimin. "Epoxyanthracene Derivatives and Dicarbonylation on Benzene Ring via Hexadehydro-Diels-Alder (HDDA) Derived Benzynes with Oxazoles". supporting information. p. 1125 - 1133. Retrieved 2021/11/22.
• 5、 Kang, Juyeon,Ham, Seunghwan,Seong, Chaehyeon,Oh, Chang Ho. "Synthesis of [6,6,m]-Tricyclic Compounds via [4+2] Cycloaddition with Au or Cu Catalyst". supporting information. p. 1039 - 1043. Retrieved 2021/05/05.