95124-07-5

Basic information

• Product Name: DIMETHYL PROPARGYLMALONATE
• Synonyms: DIMETHYL PROPARGYLMALONATE;Dimethyl propargylmalonate >=95.0% (GC);Dimethyl2-(prop-2-yn-1-yl)malonate;Dimethyl proparylmalonate
• CAS NO: 95124-07-5
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 170.16
• Product Categories: C8 to C9;Carbonyl Compounds;Esters
• Mol File: 95124-07-5.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 93-95 °C7 mm Hg(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 1.119 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.103mmHg at 25°C
• Refractive Index: n20/D 1.444
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 3539408
• CAS DataBase Reference: DIMETHYL PROPARGYLMALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL PROPARGYLMALONATE(95124-07-5)
• EPA Substance Registry System: DIMETHYL PROPARGYLMALONATE(95124-07-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 95124-07-5(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C8H10O4/c1-4-5-6(7(9)11-2)8(10)12-3/h1,6H,5H2,2-3H3

Upstream product

• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 108-59-8 malonic acid dimethyl ester 
• 659-86-9 propargyl iodide 
• 1180611-55-5 dimethyl 2-(phenyl(tosylamino)methyl)-2-(prop-2-ynyl)malonate 
• 624-65-7 2-propynyl chloride 
• 106-96-7 propargyl bromide 
• 18424-76-5 dimethyl malonate sodium salt 

Downstream Products

• 497172-43-7 dimethyl 2-(2-phenyl-2-propenyl)-2-(2-propynyl)malonate 
• 745071-83-4 2-phenethyl-2-prop-2-ynylmalonic acid dimethyl ester 
• 1000880-00-1 1,3-dimethyl 2-(3-(4-nitrophenyl)prop-2-yn-1-yl)malonate 
• 868388-66-3 2-(3-oxocyclohexyl)-2-prop-2-ynylmalonic acid dimethyl ester 
• 1045758-82-4 C₂₂H₂₈O₇ 
• 1192068-11-3 C₁₆H₂₀O₄ 
• 1180611-25-9 dimethyl 2-(2-fluorophenyl)-5-methylene-1-tosylpyrrolidine-3,3-dicarboxylate 
• 1180611-49-7 dimethyl 5-methylene-2-(pyridin-3-yl)-1-tosylpyrrolidine-3,3-dicarboxylate 
• 1180611-55-5 dimethyl 2-(phenyl(tosylamino)methyl)-2-(prop-2-ynyl)malonate 
• 1180611-11-3 dimethyl 5-methylene-2-phenyl-1-tosylpyrrolidine-3,3-dicarboxylate 
• 1180611-37-3 dimethyl 5-methylene-2-(4-nitrophenyl)-1-tosylpyrrolidine-3,3-dicarboxylate 
• 1180611-39-5 dimethyl 2-(4-bromophenyl)-5-methylene-1-tosylpyrrolidine-3,3-dicarboxylate 
• 1180611-20-4 dimethyl 2-(4-methoxyphenyl)-5-methylene-1-tosylpyrrolidine-3,3-dicarboxylate 
• 1180611-30-6 dimethyl 2-(4-chlorophenyl)-5-methylene-1-tosylpyrrolidine-3,3-dicarboxylate 

Relevant articles and documents

CARBENE LIGANDS AS ANTHRACYCLINONESYNTHONS-II CHROMIUM MEDIATED CYCLOADDITION OF ALKYNES, CARBENES AND CARBON MONOXIDE: APPLICATION TO RING B SYNTHESIS IN ANTHRACYCLINONES

The cycloaddition of Cr-co-ordinated alkyne, carbene and carbonyl ligands provides a variable route to the anthracyclinone skeleton.The key step of a formal total synthesis of 4-demethoxydaunomycinone (1) is based on the reaction of carbonyl-carbene complex 15 -used as a CD ring synthon- and alkyne 9 leading to the formation of ring B.

Silver oxide(I) promoted Conia-ene/radical cyclization for a straightforward access to furan derivatives

A novel access to fused furan cores using silver oxide(I) has been developed. Mechanistic investigations indicate the involvement of a Conia-ene reaction/radical cyclization for an expedient path to complex furan derivatives. The reaction is broad in scop

Visible-Light Mediated Hydrosilylative and Hydrophosphorylative Cyclizations of Enynes and Dienes

Described herein is a visible-light mediated intermolecular radical cyclization approach to access heterocycles. Heteroatom radicals, such as silicon and phosphorus atom radicals, were generated via direct hydrogen atom abstraction by the photoexcited catalyst species with hydro-silanes and phosphine oxides. The radical addition/cyclization/HAT (hydrogen atom transfer) reaction sequences of 1,6-enynes and 1,6-dienes were highly efficient delivering the desired heterocycles in good yields.

Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene

Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.