19133-70-1

Basic information

• Product Name: 8-hydroxy-5-methyl-3,4-dihydronaphthalen-1(2H)-one
• CAS NO: 19133-70-1
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.2118
• Mol File: 19133-70-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 356.1°C at 760 mmHg
• Flash Point: 151.8°C
• Density: 1.194g/cm³
• Vapor Pressure: 1.46E-05mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 8-hydroxy-5-methyl-3,4-dihydronaphthalen-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-hydroxy-5-methyl-3,4-dihydronaphthalen-1(2H)-one(19133-70-1)
• EPA Substance Registry System: 8-hydroxy-5-methyl-3,4-dihydronaphthalen-1(2H)-one(19133-70-1)

Safety Data

• Hazardous Substances Data: 19133-70-1(Hazardous Substances Data)

Upstream product

• 20007-99-2 Wieland-Miescher ketone 
• 1130-66-1 3,5,6,7-Tetrahydro-8-hydroxy-4-methyl-1(2H)-naphthalinon 

Relevant articles and documents

Synthesis of a 4-Acylcyclohexa-2,5-dienone: 3,4-Dihydro-3,3,8a-trimethylnaphtalene-1,6(2H,8aH)-dione

The synthesis is reported of 3,4-dihydro-3,3,8a-trimethylnaphtalene-1,6-(2H,8aH)-dione (11; R = Me).This is the first isolated 4-acylcyclohexa-2,5-dienone, a class of compounds postulated particularly as intermediates in the Fries and photo-Fries rearrangements.The dienone undergoes very easy acyl cleavage in the presence of bases or dilute acids, to form a phenolic acid (18).Similar cleavage, or a retro-Fries migration of the acyl group from the 4-position to the dienone ring oxygen, has prevented isolation of 4-acetyl-4-methylcyclohexa-2,5-dienone.Concentrated aqueous sulphuric acid causes rearrangement of the dienone to 3,4-dihydro-8-hydroxy-3,3,5-trimethylnaphtalen-1(2H)-one (13; R = Me), via recyclisation of 18.In trifluoroacetic acid solutions the same product (13, R = Me) is formed from the dienone by direct, formal dienone-phenol rearrangement.