17920-23-9

Basic information

• Product Name: 2-Propynylmalonic acid diethyl ester
• Synonyms: 2-Propynylmalonic acid diethyl ester;Malonic acid, (2-propynyl)-, diethyl ester;Malonic acid, 2-(2-propynyl)-, diethyl ester;Nsc28575;Propanedioic acid,2-propynyl-, diethyl ester;Diethyl propargylMalonate;2-(Propargyl)malonic acid diethyl ester;Diethyl (prop-2-ynyl)malonate
• CAS NO: 17920-23-9
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.2158
• Mol File: 17920-23-9.mol

Chemical Properties

• Melting Point: 178℃
• Boiling Point: 129℃ (22 Torr)
• Flash Point: 121.3°C
• Appearance: /
• Density: 1.073g/cm³
• Vapor Pressure: 0.0128mmHg at 25°C
• Refractive Index: 1.4405 (20℃)
• PKA: 11.79±0.59(Predicted)
• CAS DataBase Reference: 2-Propynylmalonic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propynylmalonic acid diethyl ester(17920-23-9)
• EPA Substance Registry System: 2-Propynylmalonic acid diethyl ester(17920-23-9)

Safety Data

• RTECS: OO1630000
• Hazardous Substances Data: 17920-23-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Propynylmalonic acid diethyl ester is used as a key intermediate for the synthesis of pharmaceuticals, given its reactivity and capacity to form a variety of biologically active compounds. Its role in drug development is significant, as it contributes to the creation of new medications and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Propynylmalonic acid diethyl ester is employed as a building block, facilitating the construction of complex organic molecules. Its ability to undergo multiple chemical reactions makes it an indispensable reagent for the preparation of a wide array of chemical products.
Used in Fine Chemicals Industry:
2-Propynylmalonic acid diethyl ester is also utilized in the production of fine chemicals, where its unique properties and reactivity are harnessed to create specialty chemicals used in various applications, including but not limited to fragrances, dyes, and other high-value chemical products.
Safety Note:
Given its potential hazards if not handled and stored properly, 2-Propynylmalonic acid diethyl ester requires careful management to ensure safety in laboratory and industrial settings. Proper safety protocols and equipment should be employed when working with this compound to minimize risks.

InChI:InChI=1/C10H14O4/c1-4-7-8(9(11)13-5-2)10(12)14-6-3/h1,8H,5-7H2,2-3H3

Upstream product

• 6165-76-0 propargyl p-toluenesulfonate 
• 105-53-3 diethyl malonate 
• 6279-86-3 methanetricarboxylic acid triethyl ester 
• 68922-87-2 sodium 1,3-diethoxy-2-(ethoxycarbonyl)-1,3-dioxopropan-2-ide 
• 106-96-7 propargyl bromide 
• 64-17-5 ethanol 
• 996-82-7 sodium diethylmalonate 
• 491862-29-4 2-ethoxycarbonyl-2-(2-propynyl)malonic acid diethyl ester 
• 624-65-7 2-propynyl chloride 
• 996-82-7 sodium diethylmalonate 

Downstream Products

• 2689-88-5 diethyl 2,2-di(prop-2-yn-1-yl)malonate 
• 17889-82-6 Propin-⁽²⁾-yl-malonsaeure-di-(o-anisidid) 
• 2583-25-7 allylmalonic acid 
• 288632-91-7 (2-propynyl)-[(2-trimethylsilylphenyl)methyl]propanedioic acid diethyl ester 
• 454243-47-1 diethyl 2-(2-propynyl)-2-(2-cyclohexyl)propane-1,3-dioate 
• 917989-40-3 2-{2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-allyl}-2-prop-2-ynyl-malonic acid diethyl ester 
• 1334548-29-6 diethyl 2-(3-(4-methoxyphenyl)prop-2-yn-1-yl)malonate 
• 1204408-17-2 2-methyl-6-hydroxy-5-prop-2-yn-1-ylpyrimidin-4(3H)-one 
• 25716-58-9 4-chloro-2,6-dimethylfuro[2,3-d]pyrimidine 
• 1614235-04-9 N-(3-ethynylphenyl)-2,6-dimethylfuro[2,3-d]pyrimidin-4-amine 
• 1614235-14-1 N-(4-methoxyphenyl)-N,2,6-trimethylfuro[2,3-d]pyrimidin-4-amine hydrochloride 
• 1614235-13-0 N-(4-methoxyphenyl)-2,6-dimethyl-N-(propan-2-yl)furo[2,3-d]pyrimidin-4-amine 
• 1614235-12-9 N-butyl-N-(4-methoxyphenyl)-2,6-dimethylfuro[2,3-d]pyrimidin-4-amine 
• 1614235-11-8 N-(4-methoxyphenyl)-2,6-dimethyl-N-propylfuro[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

Synthesis of oligoenes that contain up to 15 double bonds from 1,6-heptadiynes

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Silver-Catalyzed Cascade 1,6-Addition/Cyclization of para-Quinone Methides with Propargyl Malonates: An Approach to Spiro[4.5]deca-6,9-dien-8-ones

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When cobalt-mediated [2 + 2 + 2] cycloaddition reaction dares go astray: Synthesis of unprecedented cobalt(III)-complexes

In sharp contrast with the standard [2 + 2 + 2] cycloaddition reaction of diyne/ene, cobalt-mediated cycloadditions with γ-alkylidenebutenolide led to unprecedented cobalt(iii) polycyclic complexes. A plausible mechanism supported by a computational study based on an unusual fragmentation of the butenolide moiety was postulated to account for this original reaction.

Periodically clickable polyesters: Study of intrachain self-segregation induced folding, crystallization, and mesophase formation

A series of polyesters based on 2-propargyl-1,3-propanediol or 2,2-dipropargyl-1,3-propanediol or 2-allyl-2-propargyl-1,3-propanediol and 1,20-eicosanedioic acid were prepared by solution polycondensation using the corresponding diacid chloride; these polyesters were quantitatively "clicked" with a fluoroalkyl azide, namely CF3(CF 2)7CH2CH2N3, to yield polyesters carrying long-chain alkylene segments in the backbone and either one or two perfluoroalkyl segments located at periodic intervals along the polymer chain. The immiscibility of the alkylene and fluoroalkyl segments causes the polymer chains to fold in a zigzag fashion to facilitate the segregation of these segments; the folded chains further organize in the solid state to form a lamellar structure with alternating domains of alkyl (HC) and fluoroalkyl (FC) segments. Evidence for the self-segregation is provided by DSC, SAXS, WAXS, and TEM studies; in two of the samples, the DSC thermograms showed two distinct endotherms associated with the melting of the individual domains, while the WAXS patterns confirm the existence of two separate peaks corresponding to the interchain distances within the crystalline lattices of the HC and FC domains. SAXS data, on the other hand, reveal the formation of an extended lamellar morphology with an interlamellar spacing that matches reasonably well with those estimated from TEM studies. Interestingly, a smectic-type liquid crystalline phase is observed at temperatures between the two melting transitions. These systems present a unique opportunity to develop interesting nanostructured polymeric materials with precise control over both the domain size and morphology; importantly, the domain sizes are far smaller than those typically observed in traditional block copolymers.

Practical Synthesis of Phosphinic Dipeptides by Tandem Esterification of Aminophosphinic and Acrylic Acids under Silylating Conditions

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Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

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