1008-19-1

Basic information

• Product Name: 1-Methoxy-5,6,7,8-tetrahydronaphthalene
• Synonyms: 1,2,3,4-Tetrahydro-5-methoxynaphthalene;1-Methoxy-5,6,7,8-tetrahydronaphthalene;5-Methoxytetralin;5-METHOXY-1,2,3,4-TETRAHYDRO-NAPHTHALEN;NSC 5242;5,6,7,8-Tetrahydro-1-methoxynaphthalene
• CAS NO: 1008-19-1
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.2283
• Mol File: 1008-19-1.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 271.7°Cat760mmHg
• Flash Point: 111.8°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: 1-Methoxy-5,6,7,8-tetrahydronaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methoxy-5,6,7,8-tetrahydronaphthalene(1008-19-1)
• EPA Substance Registry System: 1-Methoxy-5,6,7,8-tetrahydronaphthalene(1008-19-1)

Safety Data

• Hazardous Substances Data: 1008-19-1(Hazardous Substances Data)

Usage

General Description

1-Methoxy-5,6,7,8-tetrahydronaphthalene, also known as Ethanone, 1-(1,2,3,4-tetrahydronaphthalen-1-yl)-, is a light yellow coloured organic chemical compound. Having a molecular formula of C12H14O, this chemical is often used in perfumery for its floral-like scent that is similar to that of naturally occurring substances such as linalool. It is produced by Robinson annulation, where a 6-membered cyclic ketone (like Cyclohexanone) reacts with a three-carbon unit (like Methyl vinyl ketone). As an alkene, it has a potential to undergo reactions characteristic of this group of compounds, including various addition and polymerization reactions. It may also be unsafe for the environment if not disposed properly.

InChI:InChI=1/C11H14O/c1-12-11-8-4-6-9-5-2-3-7-10(9)11/h4,6,8H,2-3,5,7H2,1H3

Upstream product

• 529-35-1 5,6,7,8-Tetrahydronaphthalen-1-ol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 2216-69-5 1-Methoxynaphthalene 
• 529-28-2 4-iodoanisol 
• 32940-15-1 5-methoxy-2-tetralone 
• 143325-89-7 1,2,3,4-tetrahydro-5-methoxynaphthalen-2-ol 
• 199285-65-9 spiro<2,5-dithiacyclopentane-1,1'-(5'-methoxy-1',2',3',4'-tetrahydronaphthalene)> 
• 61982-91-0 1,2,3,4-tetrahydro-5-methoxynaphthalen-1-ol 
• 33892-75-0 5-Methoxy-1-tetralone 
• 7772-99-8 stannous chloride 
• 27673-48-9 5,8-dihydro-1-naphthol 
• 36230-47-4 1,4-dihydro-5-methoxynaphthalene 
• 3019-88-3 sodium naphtholate 

Downstream Products

• 37418-88-5 3-hydroxyphthalic anhydride 
• 601-97-8 3-hydroxyphthalic acid 
• 883531-98-4 4-methoxy-5,6,7,8-tetrahydronaphthalene-1-carbaldehyde 
• 1613708-30-7 C₃₉H₅₅ClN₁₀O₄ 
• 1613708-29-4 C₃₃H₅₀N₄O₃*C₂H₄O₂ 
• 1613708-27-2 C₄₁H₅₂N₄O₅ 

Relevant articles and documents

A sliding cyclohexane rearrangement mediated by zirconium tetrachloride

6-Methoxytetralins may be smoothly transformed into 5-methoxytetralins through the action of zirconium tetrachloride. The rearrangement occurs at ambient temperature in chloroform and proceeds via fragmentation of the carbon-carbon bond para to the methoxy substituent followed by an intramolecular Friedel-Crafts alkylation.

Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer

The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.

Alkyl Carbagermatrane Enabled Synthesis of Seven-Membered Carbocycle-Fused Aromatics through Catellani Strategy

Synthesis of seven-membered carbocycle-fused aromatics was realized by Catellani reaction using terminally brominated alkyl carbagermatranes through intermolecular cyclization manner. Various functional groups were well tolerated, and this transformation was also expanded to the synthesis of carbocycles of other size. The utility of this method was demonstrated by modification of natural product derivatives and synthesis of bioactive molecules.

Site-Selective Alkoxylation of Benzylic C?H Bonds by Photoredox Catalysis

Methods that enable the direct C?H alkoxylation of complex organic molecules are significantly underdeveloped, particularly in comparison to analogous strategies for C?N and C?C bond formation. In particular, almost all methods for the incorporation of alcohols by C?H oxidation require the use of the alcohol component as a solvent or co-solvent. This condition limits the practical scope of these reactions to simple, inexpensive alcohols. Reported here is a photocatalytic protocol for the functionalization of benzylic C?H bonds with a wide range of oxygen nucleophiles. This strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C?O bonds with high site selectivity, chemoselectivity, and functional-group tolerance using only two equivalents of the alcohol coupling partner. This method enables the late-stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential applications in synthesis and medicinal chemistry.