60023-09-8

Basic information

• Product Name: Naphthalene, 1-methoxy-8-methyl- (6CI,7CI,9CI)
• Synonyms: Naphthalene, 1-methoxy-8-methyl- (6CI,7CI,9CI);1-Methoxy-8-methylnaphthalene
• CAS NO: 60023-09-8
• Molecular Formula: C12H12O
• Molecular Weight: 172.22308
• Product Categories: NAPHTALENE
• Mol File: 60023-09-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Naphthalene, 1-methoxy-8-methyl- (6CI,7CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 1-methoxy-8-methyl- (6CI,7CI,9CI)(60023-09-8)
• EPA Substance Registry System: Naphthalene, 1-methoxy-8-methyl- (6CI,7CI,9CI)(60023-09-8)

Safety Data

• Hazardous Substances Data: 60023-09-8(Hazardous Substances Data)

Upstream product

• 2216-69-5 1-Methoxynaphthalene 
• 74-88-4 methyl iodide 
• 100370-18-1 γ--valeramid 
• 15148-43-3 4-(2-methoxyphenyl)pentanoic acid 
• 105908-97-2 3-(2-methoxy-phenyl)-butyryl chloride 
• 104216-85-5 3-(2-methoxy-phenyl)-butyric acid 
• 15149-88-9 5-methoxy-4-methyl-3,4-dihydronaphthalen-1(2H)-one 
• 66004-25-9 methyl-(8-methyl-5,6,7,8-tetrahydro-[1]naphthyl)-ether 

Relevant articles and documents

NMR and calculational studies on the regioselective lithiation of 1-methoxynaphthalene

1-Methoxynaphthalene (1) undergoes regioselective lithiation in position 2 (n-BuLi/TMEDA) or in position 8 (t-BuLi), respectively. The detected formation of a n-BuLi/1 complex (1:1 n-BuLi/1 mixture) appears to have only minor influence on the regioselectivity (both products are obtained). The exchange of hydrogen atom H2 by deuterium results in a remarkably reduced reaction rate for the lithiation with n-BuLi in THF-d8. This isotope effect and the formation of the thermodynamically less favorable 2-lithio compound suggest a kinetically controlled mechanism. The lack of an isotope effect for the reaction of 8-deuterio-1-methoxynaphthalene with t-BuLi and the formation of the thermodynamically preferred 8-lithiated product indicate a thermodynamically controlled mechanism. Slow conversion of the 2- into the 8-lithiated species (at higher temperatures) gives further evidence that n-BuLi and t-BuLi afford the kinetically and thermodynamically preferred products, respectively.