35304-86-0

Basic information

• Product Name: (Z)-5-benzylidenefuran-2(5H)-one
• Synonyms: (Z)-5-benzylidenefuran-2(5H)-one;(5Z)-5-Benzylidene-2(5H)-furanone;(5Z)-5-Benzylidene-2,5-dihydrofuran-2-one;(5Z)-5-Benzylidenefuran-2(5H)-one;5-[(Z)-Benzylidene]-2,5-dihydrofuran-2-one;5-[(Z)-Phenylmethylene]-2(5H)-furanone;Einecs 252-502-6
• CAS NO: 35304-86-0
• Molecular Formula: C₁₁H₈O₂
• Molecular Weight: 172.18002
• EINECS: 252-502-6
• Mol File: 35304-86-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 349.9°Cat760mmHg
• Flash Point: 145.8°C
• Appearance: /
• Density: 1.253g/cm³
• Vapor Pressure: 4.56E-05mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: (Z)-5-benzylidenefuran-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-5-benzylidenefuran-2(5H)-one(35304-86-0)
• EPA Substance Registry System: (Z)-5-benzylidenefuran-2(5H)-one(35304-86-0)

Safety Data

• Hazardous Substances Data: 35304-86-0(Hazardous Substances Data)

Usage

Description

(Z)-5-Benzylidenefuran-2(5H)-one, a furan derivative with the molecular formula C14H10O2, is a yellow solid at room temperature. It is widely utilized in organic and medicinal chemistry as a starting material for the synthesis of various pharmaceuticals and bioactive molecules. The unique structure of (Z)-5-benzylidenefuran-2(5H)-one, featuring a furan ring with a benzylidene substituent at the 5-position, endows it with distinctive reactivity and properties. Research has indicated that this compound holds potential anti-inflammatory and antioxidant properties, making it a promising candidate for drug development and research.

Uses

Used in Pharmaceutical Industry:
(Z)-5-Benzylidenefuran-2(5H)-one is used as a starting material for the synthesis of various pharmaceuticals and bioactive molecules due to its unique reactivity and properties. Its structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Drug Development and Research:
(Z)-5-Benzylidenefuran-2(5H)-one is used as a subject of interest in drug development and research because of its potential anti-inflammatory and antioxidant properties. These characteristics make it a valuable compound for exploring new treatments and therapies for various diseases and conditions.
Used in Organic Chemistry:
(Z)-5-Benzylidenefuran-2(5H)-one is used as a key intermediate in organic chemistry for the synthesis of complex molecules and compounds. Its unique structure and reactivity make it a versatile building block for creating a diverse array of chemical products.

InChI:InChI=1/C11H8O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-8H/b10-8+

Upstream product

• 3112-88-7 Benzyl phenyl sulfone 
• 6214-35-3 (Z)-3-iodoprop-2-enoic acid 
• 536-74-3 phenylacetylene 
• 16900-64-4 4-phenylbut-1-en-3-yne-1,1-dicarboxylic acid 
• 960-16-7 tributylphenylstannane 
• 1775-46-8 3,5-dibromolevulinic acid 
• 32323-44-7 5-(dibromomethylene)-2(5H)-furanone 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 
• 676556-29-9 (Z)-4-bromo-5-(phenylmethylene)furan-2-(5H)-one 
• 676556-25-5 (Z)-5-(1-bromo-1-phenylmethylene)-2(5H)-furanone 
• 3757-88-8 tributylstannylethynylbenzene 
• 1609-92-3 (Z)-3-bromoacrylic acid 
• 27948-29-4 (Z)-5-phenyl-2-penten-4-ynoic acid 

Relevant articles and documents

A convenient synthesis of γ-(Z)-alkylidene butenolides

A convenient synthesis of γ-(Z)-alkylidene butenolides starting from (Z)-3-bromopropenoic acid was described.

Ring-Closing Metathesis Reactions of Acyloxysulfones: Synthesis of γ-Alkylidene Butenolides

An acyloxysulfone ring-closing metathesis/sulfone elimination sequence has been developed for the preparation of various γ-alkylidene butenolides. The elimination is proposed to proceed via an E1cb mechanism leading to (Z)-γ-alkylidene butenolides as the major products.

Copper-catalyzed preparation of γ-alkylidenebutenolides and isocoumarins under mild palladium-free conditions

A general and efficient copper(I)-catalyzed cross-coupling and heterocyclization reaction of terminal alkynes and β-iodo-α,β- unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5-ylidenebutenolides and 3-substituted isocoumarins with excellent regio- and stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium-free.

Regioselective synthesis of (E)-5-(tributylstannylmethylidene)-5H-furan-2- ones and (E)-3-(tributylstannylmethylidene)-3H-isobenzofuran-1-ones: Easy access to γ-alkylidenebutenolide and phthalide skeletons

Regio- and stereoselective synthesis of γ-alkylidene-butenolides and γ-alkylidenephthalides has been achieved through the palladium-catalysed tandem cross-coupling/cyclisation reactions of tributylstannyl-3-iodopropenoate or the 2-iodo benzoate derivatives with tributyltinacetylene. Iododestannylation occurred with inversion of the configuration of the exocyclic double bond in the case of butenolides, but with retention of configuration for the phthalide. The selectivity observed in the Stille reaction was found to be dependent on the nature of the vinyl or the aryl halide. Georg Thieme Verlag Stuttgart.