5903-23-1

Basic information

• Product Name: 1-(Methoxymethyl)-naphthalene
• Synonyms: 1-(Methoxymethyl)-naphthalene;METHYL1-NAPHTHYLMETHYLETHER
• CAS NO: 5903-23-1
• Molecular Formula: C₁₂H₁₂O
• Molecular Weight: 172.22308
• Mol File: 5903-23-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 270.5°Cat760mmHg
• Flash Point: 122.5°C
• Appearance: /
• Density: 1.058g/cm³
• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: 1-(Methoxymethyl)-naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Methoxymethyl)-naphthalene(5903-23-1)
• EPA Substance Registry System: 1-(Methoxymethyl)-naphthalene(5903-23-1)

Safety Data

• Hazardous Substances Data: 5903-23-1(Hazardous Substances Data)

Usage

General Description

1-(Methoxymethyl)-naphthalene is a chemical compound with the molecular formula C12H12O which consists of a naphthalene ring with a methoxymethyl group attached at the first position. It is commonly used as a flavoring agent and fragrance compound in the production of perfumes, soaps, and other personal care products. It has a sweet, floral odor and is considered safe for use in these applications. Additionally, it has been studied for its potential as an antimicrobial agent and is being investigated for its application in medical and pharmaceutical formulations. This chemical is soluble in organic solvents and has a low volatility, making it suitable for a variety of industrial and consumer uses.

InChI:InChI=1/C12H12O/c1-13-9-11-7-4-6-10-5-2-3-8-12(10)11/h2-8H,9H2,1H3

Upstream product

• 67-56-1 methanol 
• 1930-16-1 N,N,N-trimethyl-1-(naphthalene-1-yl)methanaminium chloride 
• 856199-35-4 1-naphthylmethyl N-phenyl carbamate 
• 13098-90-3 1-naphthylmethyl propanoate 
• 5925-59-7 methyl (1-naphthyl)methyl sulfone 
• 36707-29-6 1-naphthylmethyl phenylacetate 
• 13098-88-9 naphthalen-1-ylmethyl acetate 
• 83469-36-7 4-methoxy-1-<(methoxytrimethylsilyl)methyl>naphthalene 
• 83469-34-5 1-<(methoxytrimethylsilyl)methyl>naphthalene 
• 158833-25-1 naphthalen-1-ylmethyl phenyl carbonate 
• 3163-27-7 2-(bromomethyl)naphthalene 
• 86-52-2 1-Chloromethylnaphthalene 
• 24471-54-3 (naphtalen-1-yl)methyl iodide 
• 145224-15-3 naphthalen-1-ylmethyl 4-methoxybenzoate 

Downstream Products

• 56048-50-1 2-(1-naphthyl)benzothiazole 
• 475250-57-8 4,4,5,5-tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane 
• 42758-54-3 4-nitro-1-naphthaldehyde 
• 1975-43-5 4-nitro-1-naphthoic acid 
• 1706-15-6 α-methyl-1-naphthalenometanol 
• 66-77-3 1-naphthaldehyde 
• 57605-95-5 1-(1-naphthyl)ethanol 

Relevant articles and documents

Synthesis of peri-cyclobutarenes by thermolysis of [methoxy(trimethylsilyl)methyl]arenes

[Methoxy(trimethylsilyl)methyl]arenes are readily prepared by reactions of chlorotrimethylsilane with (α-methoxy)arenylmethyllithium reagents as obtained from (methoxymethyl)arenes and t-BuLi. The [methoxy(trimethylsilyl)methyl]arenes eliminate methoxytrimethylsilane at 525-675 °C/0.05-0.10 mm to yield peri-cyclobutarenes as derived from arenylcarbenes. Of importance is the fact that the initial arenylcarbenes generated insert into adjacent peri C-H bonds and/or isomerize to other arenylcarbenes that insert into their peri C-H bonds to give peri- cyclobutarenes. Thus, flash-vacuum pyrolysis of 1- [methoxy(trimethylsilyl)methyl]naphthalene (13) at 575-675 °C/0.05-0.10 mm yields 1H-cyclobuta[de]naphthalene (6, up to 39%) in practical quantities. 2- [Methoxy(trimethylsilyl)methyl]naphthalene (23) also affords 6 as a major thermolysis product. At 510 °C/0.05-0.10 mm 4-methoxy-1- [methoxy(trimethylsilyl)methyl]naphthalene (29) decomposes to 4-methoxy-1H- cyclobuta[de]naphthalene (31, 46%). Under similar conditions, 2-methoxy-1- [methoxy(trimethylsilyl)methyl]naphthalene (33) converts to 1,2- dihydronaphtho[2,1-b]furan (35, 64%) and naphtho[2,1-b]furan (36, 31%), presumably by insertion of 2-methoxy-1-naphthylcarbene (34) into a C-H bond of its o-methoxy group and then dehydrogenation of the resultant dihydrofuran. Further, 1-[methoxy(trimethylsilyl)methyl]-6-methylnaphthalene (39) pyrolyzes (510 °C/0.10-0.20 mm) to 6-methyl-1-naphthylcarbene (40), which isomerizes in part to 7-methyl-1-naphthylcarbene (49); carbenes 40 and 49 then undergo peri C-H insertion to give 3-methyl-1H- cyclobuta[de]naphthalene (41) and 2-methyl-1H-cyclobuta[de]naphthalene (42) in an 8:1 ratio and a combined yield of 44%. The pyrolytic method is particularly valuable for preparing higher peri single carbon atom bridged arenes such as 4H-cyclobuta[jk]phenanthrene (53, 65%) and 3H- cyclobuta[cd]pyrene (59, 86%).

Photolysis of the 1-naphthylmethyl ester of substituted phenylacetic acids: intramolecular charge transfer and rates of decarboxylation of arylacyl radicals

The photolysis of esters 6 and 8 in methanol leads to products resulting from both naphthylmethyl cations and radicals.The product distribution is nearly independent of X for the esters 6 except when X equals methoxy.A mechanism involving initial homolytic cleavage of the carbon-oxygen bond in the excited singlet state of the ester is proposed.Competition between electron transfer in the radical pair to form the ion pair and decarboxylation of the arylacyloxy radical allows calculations of the rates of this decarboxylation process.The ρ values versus ? is close to zero.When X equals methoxy, intramolecular electron transfer occurs with the naphthalene ring serving as the acceptor and the methoxyaromatic as the donor.This exciplex fragments to carbon dioxide and 1-(1-naphthyl)-2-arylethane. Key words: acyloxy radical, decarboxylation, photolysis of benzylic esters.

Rates of decarboxylation of acyloxy radicals formed in the photocleavage of substituted 1-naphthylmethyl alkanoates

Rates of decarboxylation (kCO2R) have been estimated for the acyloxy racicals 7a-f formed in the photolysis of substituted 1-naphthylmethyl 6a-f. These rates are on a mechanism involving initial carbon-oxygen homolytic bond cleavage from the excited singlet state. The products are formed by two competing pathways: electron transfer in the radical pair to give an ion pair and decarboxylation. Measured product yields along with an of the electron-transfer rate (kET) allow calculation of kCO2R as a function of R. The values obtained are the following (R, k (109 s-1)): CH3, 3CH2, 2.0; (CH3)2CH, 6.5; (CH3)3C, 11; PhCH2, 5.0; PhCH2CH2, 2.3.