539-47-9

Basic information

• Product Name: Furylacrylic acid
• Synonyms: (2E)-3-(2-Furyl)-2-propenoic acid;(2-Furyl)acrylic acid;3-(2-Furanyl)-2-propenoic acid;3-(2-furanyl)-2-propenoicaci;3-(2-Furanyl)-2-propenoicacid;3-(2-furyl)propenoicacid;Acrylic acid, beta-2-furyl-;a-Furylacrylicacid
• CAS NO: 539-47-9
• Molecular Formula: C₇H₆O₃
• Molecular Weight: 138.12
• EINECS: 208-718-8
• Product Categories: Pharmaceutical Intermediates;Aromatic Cinnamic Acids, Esters and Derivatives;Furan&Benzofuran;Organic acids;Heterocyclic Compounds;Furans;Heterocycles;Building Blocks;C4 to C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 539-47-9.mol
• Article Data: 81

Chemical Properties

• Melting Point: 139-141 °C(lit.)
• Boiling Point: 286 °C(lit.)
• Flash Point: 286°C
• Appearance: white to light yellow crystal powder
• Density: 1.2667 (rough estimate)
• Vapor Pressure: 0.00127mmHg at 25°C
• Refractive Index: 1.4600 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in dichloromethane and diethyl ether.
• PKA: 4.39±0.10(Predicted)
• Water Solubility: 2g/L(20 oC)
• Stability: Light Sensitive
• Merck: 14,4297
• BRN: 81046
• CAS DataBase Reference: Furylacrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Furylacrylic acid(539-47-9)
• EPA Substance Registry System: Furylacrylic acid(539-47-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: LT8560000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 539-47-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 539-47-9 differently. You can refer to the following data:
1. 3-(2-Furyl)acrylic acid is derivatives used in perfumes.
2. 3-(2-Furyl)acrylic acid is a reactant used in the preparation of heteroaryl-substituted bis-trifluoromethyl carbinols and trifluoroacetophenone derivatives malonyl-CoA decarboxylase (MCD) inhibitors.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 3425, 1956 DOI: 10.1021/ja01595a044Organic Syntheses, Coll. Vol. 3, p. 426, 1955

Purification Methods

Crystallise the cis-isomer from *C6H6 and the trans-isomer from H2O, *C6H6 or pet ether (b 80-100o)(charcoal). [Beilstein 18 H 301, 18 III/IV 4143, 18/6 V 306.]

InChI:InChI=1/C7H6O3/c8-7(9)4-3-6-2-1-5-10-6/h1-5H,(H,8,9)/p-1

Upstream product

• 98-01-1 furfural 
• 463-51-4 Ketene 
• 19264-34-7 N-acetylpropionamide 
• 127-09-3 sodium acetate 
• 141-82-2 malonic acid 
• 127-08-2 potassium acetate 
• 108-24-7 acetic anhydride 
• 539-66-2 sodium isovalerate 
• 56-40-6 glycine 
• 302-72-7 rac-Ala-OH 
• 623-15-4 4-(furan-2-yl)but-3-en-2-one 
• 4440-16-8 2-(2-furanylmethylene)-propanedioic acid 
• 39511-08-5 (E)-3-(2-furanyl)-2-propenal 
• 53282-12-5 ethyl (E)-3-(2-furyl)prop-2-enoate 

Downstream Products

• 1487-18-9 (furan-2-yl)ethylene 
• 104431-32-5 2-(4-Nitrophenyl)-1-(5-(4-nitrophenyl)-2-furyl)ethylene 
• 129626-56-8 2-(4-chloro-phenyl)-5-(4-chloro-styryl)-furan 
• 58110-36-4 3-<5-(2-Nitrophenyl)-2-furyl>propenoic acid 
• 20689-54-7 3-furanylacryloyl chloride 
• 935-13-7 3-(2-furyl)propanoic acid 
• 58293-85-9 methyl 3-(2-furyl)acrylate 
• 100725-90-4 N-benzoyl-O-(3t-[2]furyl-acryloyl)-hydroxylamine 
• 6317-49-3 4-oxopimelate 
• 18649-64-4 2-ethynylfuran 
• 26956-43-4 5H-furo[3,2-c]pyridin-4-one 
• 35666-22-9 (E)-3-Furan-2-yl-acrylic acid 4-nitro-phenyl ester 
• 77800-46-5 3t-[2]furyl-acrylic acid p-tolyl ester 
• 129632-19-5 (E)-3-Furan-2-yl-acrylic acid 2-acetyl-4-methyl-phenyl ester 

Relevant articles and documents

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

Biomass-derived rctt-3,4-di-2-furanyl-1,2-cyclobutanedicarboxylic acid: a polytopic ligand for synthesizing green metal-organic materials

Biomass is an abundant and environmentally friendly source for materials that can be used in a multitude of applications in the effort to replace petrochemicals. Furfural and malonic acid are biomass-sourced platforms that can be utilized in the synthesis of biobased compounds; rctt-3,4-di-2-furanyl-1,2-cyclobutanedicarboxylic acid (CBDA-2) is one such compound. In this study, CBDA-2 has been introduced into metal-organic materials chemistry as a semi-rigid polytopic ligand. This compound has been utilized as a polytopic ligand in the formation of two different 2D coordination polymers with Cu2+ and Co2+ as the metal centers via a conventional solution method. Both complexes have been characterized by X-ray crystal structure determination and showed visual thermochromic behaviors. This study demonstrates that CBDA-2 is a promising green building block in coordination chemistry.

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.