19353-89-0

Basic information

• Product Name: Naphthalene, 1,2,3,4-tetrahydro-1-(4-methoxyphenyl)-
• CAS NO: 19353-89-0
• Molecular Formula: C17H18O
• Molecular Weight: 238.329
• Mol File: 19353-89-0.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: Naphthalene, 1,2,3,4-tetrahydro-1-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 1,2,3,4-tetrahydro-1-(4-methoxyphenyl)-(19353-89-0)
• EPA Substance Registry System: Naphthalene, 1,2,3,4-tetrahydro-1-(4-methoxyphenyl)-(19353-89-0)

Safety Data

• Hazardous Substances Data: 19353-89-0(Hazardous Substances Data)

Upstream product

• 100-66-3 methoxybenzene 
• 447-53-0 1,2-Dihydronaphthalene 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 25108-63-8 1-methylene-1,2,3,4-tetrahydronaphthalene 
• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 1333226-30-4 C₂₄H₂₅NO₄S₂ 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 93407-33-1 4-methyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)benzenesulfonamide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 612-17-9 1,4-dihydronaphthalene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 17336-59-3 1-tetralone tosylhydrazone 
• 696-62-8 para-iodoanisole 

Downstream Products

• 3771-17-3 4-(1,2,3,4-tetrahydro-1-naphthyl)-phenol 
• 79560-28-4 4-hydroxy-4-(4-methoxyphenyl)-1-tetralone 
• 79560-29-5 N-methyl-4-hydroxy-4-(4-methoxyphenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 79560-31-9 N-methyl-4-(4-methoxyphenyl)-1,2-dihydro-1-naphthalenamine hydrochloride 
• 79560-05-7 cis-N-methyl-4-(methoxyphenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride 
• 79836-63-8 trans-N-methyl-4-(methoxyphenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride 

Relevant articles and documents

Ligand-Enabled Nickel-Catalyzed Redox-Relay Migratory Hydroarylation of Alkenes with Arylborons

A redox-relay migratory hydroarylation of isomeric mixtures of olefins with arylboronic acids catalyzed by nickel complexes bearing diamine ligands is described. A range of structurally diverse 1,1-diarylalkanes, including those containing a 1,1-diarylated quaternary carbon, were obtained in excellent yields and with high regioselectivity. Preliminary experimental evidence supports the proposed non-dissociated chainwalking of aryl-nickel(II)-hydride species along the alkyl chain of alkenes before selective reductive elimination at a benzylic position. A catalyst loading as low as 0.5 mol % proved to be sufficient in large-scale synthesis while retaining high reactivity, highlighting the practical value of this transformation.

Effect of methoxyl groups on the NMR spectra: configuration and conformation of natural and synthetic indanic and tetralinic structures

Here, we studied the influence of the methoxyl groups attached at C-7 and C-2′ of natural and synthetic 1-arylindanes on the chemical shift of the signal of bibenzylic hydrogen and carbon atoms and J1,2 coupling constants. This influence was also analysed in natural 1-aryltetralins and related compounds that possess methoxyl and/or hydroxyl groups bound at C-8 and C-2′. The methoxyl groups attached at C-7 in indanes or at C-8 in tetralins produce a deshielding signal at H-1 and shield at C-1 and a strong decrease in the value of J1,2 due to the pseudoequatorial location adopted by the aryl group bound at C-1, avoiding an ‘A1,3 strain’. Furthermore, compounds with hydroxyl or methoxyl groups in C-2′, in the absence of substituents of C-7 or C-8, present a strong deshielding signal at H-1, strong shield of the C-1 signal and a decrease in the value of J1,2. This is attributed to the stereoelectronic effects of the methoxyl or hydroxyl groups, which we have called ‘Asarone effect’. NOESY experiments were conducted to confirm the configuration and conformation of some of the compounds included in this work. This study shows that both effects, A1,3 strain and Asarone effect, must be taken into account when the structure of natural indanes and tetralins is analysed by using 1H-NMR and 13C-NMR spectra. Copyright

Mild and regioselective benzylic C-H functionalization: Ni-catalyzed reductive arylation of remote and proximal olefins

The synergistic combination of NiH-catalyzed alkene isomerization with nickel-catalyzed cross-coupling has yielded a general protocol for the synthesis of a wide range of structurally diverse 1,1-diarylalkanes in excellent yields and high regioselectivities from readily accessible olefin starting materials. Furthermore, the practicality and synthetic flexibility of this approach is highlighted by the successful employment of isomeric mixtures of olefins for regioconvergent arylation.