Dimethyl propargylmalonate

Base Information

• Chemical Name: Dimethyl propargylmalonate
• CAS No.: 95124-07-5
• Molecular Formula: C8H10 O4
• Molecular Weight: 170.165
• Hs Code.: 2917190090
• European Community (EC) Number: 882-483-5
• DSSTox Substance ID: DTXSID30404971
• Nikkaji Number: J660.587G
• Wikidata: Q82209337
• Mol file: 95124-07-5.mol

Synonyms:Dimethyl propargylmalonate;95124-07-5;Dimethyl 2-prop-2-ynylpropanedioate;Dimethylpropargylmalonate;MFCD00077856;Dimethyl 2-(Prop-2-yn-1-yl)malonate;Dimethyl propargymalonate;SCHEMBL3476921;DTXSID30404971;PWQAXFWWMXTVFT-UHFFFAOYSA-N;VDA12407;AKOS037649422;SB40191;BS-18274;SY122075;CS-0187377;Dimethyl propargylmalonate, >=95.0% (GC);DIMETHYL2-(PROP-2-YN-1-YL)MALONATE;FT-0693240;1,3-dimethyl 2-(prop-2-yn-1-yl)propanedioate;EN300-4290251

Chemical Property of Dimethyl propargylmalonate

Chemical Property:

• Vapor Pressure: 0.103mmHg at 25°C
• Refractive Index: n20/D 1.444
• Boiling Point: 93-95 °C7 mm Hg(lit.)
• Flash Point: 113 °C
• PSA: 52.60000
• Density: 1.119 g/mL at 20 °C(lit.)
• LogP: -0.02810
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 170.05790880
• Heavy Atom Count: 12
• Complexity: 207

Purity/Quality:

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

Dimethyl propargylmalonate ≥95.0% (GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC#C)C(=O)OC
• Uses: Dimethyl propargylmalonate can be used as a reactant to synthesize:Nitro methylenecyclopentanes by [3+2] annulation reaction with various nitroalkenes in the presence of Triton B.Propargylmalonamides intermediates, applicable in the preparation of ″click BOX″ ligands by copper-catalyzed cycloaddition and oxazoline ring formation reaction.Cyclopentene derivatives by reacting with various α, β-unsaturated ketones using a combination of organocatalysts and transition metal catalysts.

Technology Process of Dimethyl propargylmalonate

There total 7 articles about Dimethyl propargylmalonate 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%

propargyl bromide (106-96-7) + malonic acid dimethyl ester (108-59-8) → dimethyl (prop-2-yn-1-yl)malonate (95124-07-5)

Guidance literature:

With potassium carbonate; In acetone; at 23 ℃; for 24h;

DOI:10.1002/anie.201402433

Reference yield: 89.0%

dimethyl 2-(phenyl(tosylamino)methyl)-2-(prop-2-ynyl)malonate (1180611-55-5) → dimethyl (prop-2-yn-1-yl)malonate (95124-07-5)

Guidance literature:

With potassium tert-butylate; In methanol; at 20 ℃; for 1h;

DOI:10.1039/b905629g

Reference yield: 52.0%

3-butyn-1-yl p-toluenesulfonate (23418-85-1) + malonic acid dimethyl ester (108-59-8) → dimethyl (prop-2-yn-1-yl)malonate (95124-07-5)

Guidance literature:

malonic acid dimethyl ester; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 15 ℃; for 0.25h;

3-butyn-1-yl p-toluenesulfonate; In N,N-dimethyl-formamide; mineral oil; at 90 ℃; for 21h;

DOI:10.1021/ol9017694

upstream raw materials:

dimethyl malonate sodium salt

propargyl bromide

malonic acid dimethyl ester

2-propynyl chloride

Downstream raw materials:

dimethyl 2-[(E)-cinnamyl]-2-propargylmalonate

propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester

1,3-dimethyl 2-benzyl-2-(prop-2-yn-1-yl)propanedioate

dimethyl 2-(p-nitrocinnamyl)-2-propargylmalonate

Refernces

• 1、 Bao, Xiucong,Zhao, Qian,Yang, Tangpo,Fung, Yi Man Eva,Li, Xiang David. "A chemical probe for lysine malonylation". . p. 4883 - 4886. Retrieved 2013.
• 2、 Tian, Tian,Wang, Xin,Lv, Leiyang,Li, Zhiping. "Iron-Catalyzed [2+2+2] Annulation of Aliphatic Bridged 1,n-Enynes with Aldehydes for the Synthesis of Fused Pyrans". supporting information. p. 4425 - 4428. Retrieved 2020/06/05.
• 3、 -. "SUBSTITUTED HETEROCYCLES AS c-MYC TARGETING AGENTS". Paragraph 0400; 0403-0404. . Retrieved 2020/12/25.