39511-08-5

Basic information

• Product Name: 3-(2-FURYL)ACROLEIN
• Synonyms: B-(2-FURFURYLIDENE)ACETALDEHYDE;B-(2-FURYL)ACROLEIN;AKOS BBS-00003241;2-FURYL ACROLEIN;3-(2-FURYL)ACROLEIN;3-(2-FUROYL)ACROLEIN;3-(2-FURYL)PROPENAL;(E)-3-(furan-2-yl)acrylaldehyde
• CAS NO: 39511-08-5
• Molecular Formula: C₇H₆O₂
• Molecular Weight: 122.12
• EINECS: 210-785-3
• Product Categories: Aldehydes;Building Blocks;C4 to C7;C7;Carbonyl Compounds;Chemical Synthesis;Furans;Heterocyclic Building Blocks;Organic Building Blocks
• Mol File: 39511-08-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 49-55 °C(lit.)
• Boiling Point: 143 °C37 mm Hg(lit.)
• Flash Point: 211 °F
• Appearance: /
• Density: 1.1483 (rough estimate)
• Vapor Pressure: 0.0351mmHg at 25°C
• Refractive Index: 1.5286 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: 3-(2-FURYL)ACROLEIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-FURYL)ACROLEIN(39511-08-5)
• EPA Substance Registry System: 3-(2-FURYL)ACROLEIN(39511-08-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• RTECS: LT8528500
• Hazardous Substances Data: 39511-08-5(Hazardous Substances Data)

Usage

Description

3-(2-FURYL)ACROLEIN, also known as (E)-3-(Furan-2-yl)acrylaldehyde, is an organic compound that serves as a valuable reagent in the chemical synthesis process. It is characterized by its unique structure, which includes a furan ring and an acrolein group, making it a versatile building block for creating complex organic molecules.

Uses

Used in Pharmaceutical Industry:
3-(2-FURYL)ACROLEIN is used as a synthesis intermediate for the production of highly substituted tetrahydrofurans and tetrahydropyrans. These complex organic molecules are essential components in the development of various pharmaceutical compounds, including those with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-(2-FURYL)ACROLEIN is used as a key reagent in the double Michael addition strategy. This approach allows for the efficient construction of complex molecular structures, which are often required in the development of new materials, pharmaceuticals, and other specialty chemicals.
Overall, 3-(2-FURYL)ACROLEIN plays a crucial role in the synthesis of various complex organic molecules, particularly in the pharmaceutical and chemical industries. Its unique structure and reactivity make it a valuable building block for the development of new compounds with potential applications in medicine and other fields.

InChI:InChI=1/C7H6O2/c8-5-1-3-7-4-2-6-9-7/h1-6H/b3-1+

Upstream product

• 98-01-1 furfural 
• 119619-38-4 1-(furan-2-yl)-2-propen-1-ol 
• 1562381-54-7 N-((3E,5E)-6-(furan-2-yl)hexa-3,5-dien-1-ynyl)-N,4-dimethylbenzenesulfonamide 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 63583-34-6 4-(3t-[2]furyl-allylidene)-2-phenyl-4H-oxazol-5-one 
• 37530-63-5 5-(3t-[2]furyl-allylidene)-2-thioxo-thiazolidin-4-one 
• 100728-22-1 isonicotinic acid-(3t-[2]furyl-allylidenehydrazide) 
• 99974-02-4 5-(3-furan-2-yl-allylidene)-2-thioxodihydropyrimidine-4,6-dione 
• 93323-69-4 4-(3t-[2]furyl-allylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 20164-02-7 2-(4t-nitro-buta-1,3-dien-t-yl)-furan 
• 25671-98-1 2,6-bis-((Ξ)-3t-[2]furyl-allylidene)-cyclohexanone 
• 100914-84-9 5t-[2]furyl-2-phenyl-penta-2ξ,4-dienal 
• 87025-13-6 N-(3t-[2]furyl-allylidene)-p-toluidine 
• 90361-56-1 N-(4-Methoxyphenyl)-3-(2-furyl)propenaldimine 
• 5466-26-2 3t-[2]furyl-acrylaldehyde thiosemicarbazone 
• 6052-18-2 α-furylacrolein-N-phenylimine 
• 4280-88-0 (2E,4E)-5-(furan-2-yl)-1-phenylpenta-2,4-dien-1-one 
• 39583-37-4 5t-[2]furyl-1-p-tolyl-penta-2t,4-dien-1-one 

Relevant articles and documents

Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols

We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5?mol?%) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents as well as a range of functional groups.

A catalytic asymmetric bioorganic route to enantioenriched tetrahydro- and dihydropyranones

A conceptually novel approach to hetero Diels-Alder adducts of carbonyl compounds is described using as the key steps an antibody-mediated kinetic resolution of hydroxyenones followed by a ring-closure process. Various β-hydroxyenones proved to be very good substrates for antibodies 84G3- and 93F3-catalyzed retro-aldol reactions, allowing the preparation of highly enantiomerically enriched (up to 99% ee) precursors of pyranones. An attractive feature of this methodology is the possibility to convert these acyclicenantioenriched β-hydroxyenones into tetrahydropyranones by a conventional Michael-type addition procedure or into the corresponding dihydropyranones using an alternative palladium-catalyzed oxidative ring closure. For the palladium-mediated cyclization, a biphasic system has been implemented that allows the direct preparation of enantiopure dihydropyranones from the corresponding racemic aldol precursors using a sequential antibody-resolution/palladium-cyclization strategy, without isolation of the intermediate enantioenriched hydroxyenones. This bioorganic route is best applied to the preparation of hetero Diels-Alder adducts otherwise derived from less nucleophilic dienes and unactivated dienophiles.