17448-96-3

Basic information

• Product Name: DIETHYL FURFURYLIDENE MALONATE
• Synonyms: [(2-Furyl)methylene]malonic acid diethyl ester;2-(2-Furanylmethylene)malonic acid diethyl ester;2-[(2-Furyl)methylene]malonic acid diethyl ester;2-Furfurylidenemalonic acid diethyl ester;(2-furanylmethylene)-propanedioicacidiethylester;Diethyl 2-furfurylidenemalonate;diethyl2-furfurylidenemalonate;furfurylidene-malonicacidiethylester
• CAS NO: 17448-96-3
• Molecular Formula: C₁₂H₁₄O₅
• Molecular Weight: 238.24
• EINECS: 241-463-0
• Mol File: 17448-96-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 140-141 °C(Solv: chloroform (67-66-3))
• Boiling Point: 286.4°Cat760mmHg
• Flash Point: 127°C
• Appearance: /
• Density: 1.176g/cm³
• Vapor Pressure: 0.00265mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: DIETHYL FURFURYLIDENE MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL FURFURYLIDENE MALONATE(17448-96-3)
• EPA Substance Registry System: DIETHYL FURFURYLIDENE MALONATE(17448-96-3)

Safety Data

• Hazardous Substances Data: 17448-96-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 5460, 1988 DOI: 10.1021/jo00258a012

InChI:InChI=1/C12H14O5/c1-3-15-11(13)10(12(14)16-4-2)8-9-6-5-7-17-9/h5-8H,3-4H2,1-2H3

Upstream product

• 617-89-0 furan-2-ylmethanamine 
• 105-53-3 diethyl malonate 
• 156462-95-2 2-(2-furyl)naphtho<1,8-de>-1,3-dithiin 
• 98-01-1 furfural 
• 181023-32-5 9-Furan-2-yl-7,10-dithia-cyclohepta[de]naphthalene-8,8-dicarboxylic acid diethyl ester 
• 110-00-9 furan 
• 95306-66-4 diethyl (acetoxymethylene)malonate 
• 108-24-7 acetic anhydride 
• 110-89-4 piperidine 
• 2460-44-8 β-D-xylopyranoside 
• 685-87-0 Diethyl 2-bromomalonate 

Downstream Products

• 4440-16-8 2-(2-furanylmethylene)-propanedioic acid 
• 37136-39-3 diethyl 2-((tetrahydrofuran-2-yl)methyl)malonate 
• 1368855-73-5 C₂₄H₂₅O₅P 
• 1312929-67-1 (2S,3S)-1,1-diethyl 3-methyl 3-(diphenylmethyleneamino)-2-(furan-2-yl)propane-1,1,3-tricarboxylate 
• 1310582-90-1 bis[(S)-4-phenylthiazoline-2-yl]-2-furylethene 
• 1310582-89-8 bis[(S)-4-benzylthiazoline-2-yl]-2-furylethene 
• 1310582-84-3 C₃₆H₅₂N₂O₃S₂Si₂ 

Relevant articles and documents

High Pressure Mediated Diels-Alder Reaction of Furan with Dialkyl (Acetoxymethylene)malonate

The Diels-Alder reaction of furan with dialkyl (acetoxymethylene)malonates 1 did not proceed even in the presence of Lewis acid catalysts under conventional conditions.However, the reaction under high pressure (1.1 GPa) gave the expected cycloadducts, dialkyl 3-acetoxy-7-oxabicyclohept-5-ene-2,2-dicarboxylates 2.The bis-, tris-, and tetrakisadducts 3-6 were also produced in some amounts.Similar high-pressure reactions in the presence of zinc iodide as a catalyst yielded dialkyl 2-furfurylidenemalonate 8, and none of the adducts were obtained.

α,β-Unsaturated esters from the tri-n-butylarsine-promoted reaction of bromomalonic esters with aldehydes

A convenient synthesis of α,β-unsaturated esters (in 68-96percent yields) from the reaction of a bromomalonic ester with aldehydes promoted by tri-n-butylarsine is descriebed.A mechanism involving halophilic attack of tri-n-butylarsine leading to the formation of a salt followed by reaction with carbonyl compounds is proposed.This methodology provides a convenient route to α,β-unsaturated esters and represents an alternative to the Knoevenagel reaction.

Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope, and Limitations

Vinylcyclopropanes are versatile intermediates in organic synthesis which undergo various rearrangements. We report a new rearrangement of vinylcyclopropane into skipped diene. A detailed mechanistic study revealed that this transformation involves regioselective ring-opening of the cyclopropane ring followed by 1,2-migration of one of the cyclopropane substituents. Interestingly, our investigations showed that skipped diene is the kinetic product of the process but formation of a more stable cyclopentene is also accessible. The fundamental understanding of the processes involved enabled the development of divergent methodologies allowing to obtain cyclopentene or skipped diene from vinylcyclopropane in a selective and controlled manner.

Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds

An unprecedented direct C-C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol-1 for the conversion of a key intermediate of the reaction.