95124-23-5

Basic information

• Product Name: Benzenamine, 4-methoxy-N-[(5-methyl-2-furanyl)methylene]-
• CAS NO: 95124-23-5
• Molecular Formula: C13H13NO2
• Molecular Weight: 215.252
• Mol File: 95124-23-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzenamine, 4-methoxy-N-[(5-methyl-2-furanyl)methylene]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-methoxy-N-[(5-methyl-2-furanyl)methylene]-(95124-23-5)
• EPA Substance Registry System: Benzenamine, 4-methoxy-N-[(5-methyl-2-furanyl)methylene]-(95124-23-5)

Safety Data

• Hazardous Substances Data: 95124-23-5(Hazardous Substances Data)

Upstream product

• 620-02-0 5-Methylfurfural 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 95124-42-8 1-(4-Methoxy-phenyl)-1-(5-methyl-furan-2-ylmethyl)-3-phenyl-thiourea 
• 95124-41-7 Picric acid; compound with (4-methoxy-phenyl)-(5-methyl-furan-2-ylmethyl)-amine 
• 1446516-56-8 C₁₅H₁₆N₂O₂ 
• 1446516-44-4 C₂₃H₂₀N₂O₅ 
• 112383-92-3 (3S,4S)-1-(4-Methoxy-phenyl)-4-(5-methyl-furan-2-yl)-3-phenoxy-azetidin-2-one 
• 95124-39-3 4-methoxy-N-((5-methylfuran-2-yl)methyl)aniline 

Relevant articles and documents

Ru-Catalyzed Carbonylative Murai Reaction: Directed C3-Acylation of Biomass-Derived 2-Formyl Heteroaromatics

The Murai reaction is a ruthenium-catalyzed transformation leading to alkylated arenes through the C?C bond formation between an alkene and an arene bearing a directing group. Discovered in the nineties, this useful C?H activation based coupling has been the object of intense study since its discovery. After having studied the Murai reaction on 2-formylfurans of biomass derivation, we describe here the carbonylative version applied to 2-formylfurans, 2-formylpyrrols and 2-formylthiophenes. This acylation reaction takes place regioselectively at C3 position of the heterocyclopentadienes thanks to the installation of removable imine directing groups. The transformation can be achieved by treating the two reaction partners with a catalytic amount of Ru3(CO)12, in toluene at 120–150 °C, after CO bubbling, at atmospheric pressure. DFT computations of the full catalytic cycle help in deciphering the mechanism of this transformation, and to rationalize the different behaviors depending on the nature of imine directing groups. (Figure presented.).

METHODS FOR PREPARING ALKYLFURANS

Provided herein are methods for preparing alkylfurans, such as 2,5-dialkylfurans and 2-alkylfurans. Furfural or 5-alkylfurfural can be reacted with aniline or diaminobenzene, or derivatives thereof, to form the corresponding imine, which can be reduced to form alkylfurans and to regenerate the aniline or diaminobenzene, or derivatives thereof. The alkylfuran may be, for example, 2,5-dimethylfuran or 2-methylfuran.

STUDIES IN THE FURAN SERIES. 22. N-ARYLFURFURYL- AND N-ARYL-5-METHYLFURFURYLAMINES AND THEIR N-ALLYL DERIVATIVES.

The compounds, where aryl is a meta- or para-substituted chlorophenyl, methoxyphenyl, or methylphenyl group, were prepared by reduction of corresponding azomethines. Their allylation with allyl iodide or allyl bromide yielded tertiary N-arylfurfurylamines