37136-39-3

Basic information

• Product Name: diethyl tetrahydrofurfurylmalonate
• Synonyms: diethyl tetrahydrofurfurylmalonate;DIETHYL TETRAHYDROFUFURYLMALONATE;[[(Tetrahydrofuran)-2-yl]methyl]propanedioic acid diethyl ester
• CAS NO: 37136-39-3
• Molecular Formula: C₁₂H₂₀O₅
• Molecular Weight: 244.2842
• EINECS: 253-357-1
• Mol File: 37136-39-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 304.6 °C at 760 mmHg
• Flash Point: 129.4 °C
• Appearance: /
• Density: 1.091 g/cm³
• Vapor Pressure: 0.000867mmHg at 25°C
• Refractive Index: 1.454
• Solubility: DCM, Ethyl Acetate, Methanol
• CAS DataBase Reference: diethyl tetrahydrofurfurylmalonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl tetrahydrofurfurylmalonate(37136-39-3)
• EPA Substance Registry System: diethyl tetrahydrofurfurylmalonate(37136-39-3)

Safety Data

• Hazardous Substances Data: 37136-39-3(Hazardous Substances Data)

Usage

Uses

Diethyl Tetrahydrofurfurylmalonate is an intermediate in synthesizing Nafronyl (N215000), which is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication.

InChI:InChI=1/C12H20O5/c1-3-15-11(13)10(12(14)16-4-2)8-9-6-5-7-17-9/h9-10H,3-8H2,1-2H3

Upstream product

• 1192-30-9 tetrahydrofurfuryl bromide 
• 105-53-3 diethyl malonate 
• 821-09-0 n-Pent-4-enyl alcohol 
• 685-87-0 Diethyl 2-bromomalonate 
• 34583-63-6 rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate 
• 64-17-5 ethanol 
• 17448-96-3 ethyl 2-carbethoxy-3-(2-furanyl)propenoate 
• 98-01-1 furfural 
• 97-99-4 Tetrahydrofurfuryl alcohol 
• 996-82-7 sodium diethylmalonate 

Downstream Products

• 1403649-85-3 C₃₁H₃₈Br₂NO₅⁽¹⁺⁾*I^(1-) 
• 85068-37-7 diethyl 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylate 
• 77713-52-1 bis(2-diethylaminoethyl) 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylate 
• 113527-39-2 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid 
• 31329-57-4 nafronyl 
• 25379-26-4 acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 

Relevant articles and documents

Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical

Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.

Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3)?H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates

A novel mild, visible-light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5-HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo- and heterocyclic structures.

Intermolecular atom transfer radical addition to olefins mediated by oxidative quenching of photoredox catalysts

Atom transfer radical addition of haloalkanes and α-halocarbonyls to olefins is efficiently performed with the photocatalyst Ir[(dF(CF 3)ppy)2(dtbbpy)]PF6. This protocol is characterized by excellent yields, mild conditions, low catalyst loading, and broad scope. In addition, the atom transfer protocol can be used to quickly and efficiently introduce vinyl trifluoromethyl groups to olefins and access 1,1-cyclopropane diesters.