84716-82-5

Basic information

• Product Name: 4-METHOXY-1,2-DIHYDRO-NAPHTHALENE
• Synonyms: 4-METHOXY-1,2-DIHYDRO-NAPHTHALENE
• CAS NO: 84716-82-5
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21238
• Mol File: 84716-82-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 272.7°C at 760 mmHg
• Flash Point: 113.1°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 0.00999mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: 4-METHOXY-1,2-DIHYDRO-NAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-1,2-DIHYDRO-NAPHTHALENE(84716-82-5)
• EPA Substance Registry System: 4-METHOXY-1,2-DIHYDRO-NAPHTHALENE(84716-82-5)

Safety Data

• Hazardous Substances Data: 84716-82-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12O/c1-12-11-8-4-6-9-5-2-3-7-10(9)11/h2-3,5,7-8H,4,6H2,1H3

Upstream product

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 77-76-9 2,2-dimethoxy-propane 
• 512-56-1 trimethyl phosphite 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 71019-06-2 2-fluoro-1-tetralone 
• 2216-69-5 1-Methoxynaphthalene 
• 64559-97-3 2-hydroxy-1-tetralone 
• 1056246-70-8 2-bromo-1-tetralone 

Relevant articles and documents

Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates

Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).

Studies of the condensation of sulfones with ketones and aldehydes

The condensation of ketones or aldehydes with sulfunes was shown to give a variety of products. Condensation of 2-methylcyclohexanone with dimethyl sulfone using potassium t-butoxide as base gave useful yields of 1,2- dimethylenecyclohexane. Under the same conditions, cycloheptanone, 3-methyl-2-butanone, and 2-bulanone were converted to dienes. Remarkably, these reaction conditions converted acetophenone into p-terphenyl (10%) and (E)-1,4-diphenyl-3-penten-1-one (44%). Propiophenone was converted to 2′-methyl-p-terphenyl (61%). Using α-tetralone produced 1-methynaphthalene and naphthalene. No reaction took place with β-tetralone. Using diethyl sulfone with α-tetralone lead to pure naphthalene. Condensation of isobutyraldehyde and dimethyl sulfone using potassium t-butoxide gave isoprene in low yield. Using benzaldehyde and benzyl phenyl sulfone in N,N-dimethylcinnamide gave 1,2-diphenyl-1- phenylsulfonylethylene, N,N-dimethylcinnamide, and a complex condensation product. Only 1,2-diphenyl-1-phenylsulfonylethylene was obtained when the solvent was THF.

A novel electrophilic methoxylation (with a little help from F2)

Methyl hypofluorite, MeOF, easily made from MeOH and F2, proved to be an excellent source for the novel electrophilic methoxylium ion "MeO+". MeOF was reacted with the enol forms of carbonyls, producing in good to excellent yields the corresponding α-methoxy carbonyl derivatives. It was found that the methoxylation is best carried out on methyl enol ethers. Silyl enol ethers and enol acetates were also tested but with limited success. The reaction proceeds through an addition elimination mechanism.