575-41-7

Usage

Uses

Used in Chemical Industry:
1,3-Dimethylnaphthalene is used as a solvent for its ability to dissolve a wide range of substances, facilitating various chemical processes and reactions.
Used in Dye and Pigment Production:
1,3-Dimethylnaphthalene is utilized as an intermediate in the production of dyes and pigments, contributing to the coloration and stability of these products.
Used in Perfumes and Cosmetics:
1,3-Dimethylnaphthalene is employed as a flavor and fragrance ingredient, enhancing the sensory characteristics of perfumes and cosmetics, while also providing a pleasant and lasting scent.
Environmental Considerations:
Due to its persistence and potential for bioaccumulation, 1,3-Dimethylnaphthalene is considered a potential environmental hazard. It is crucial to handle and dispose of 1,3-Dimethylnaphthalene properly to prevent environmental contamination and protect human health. This includes taking measures to minimize skin and eye irritation, which can occur upon prolonged exposure.

InChI:InChI=1/C12H12/c1-9-7-10(2)12-6-4-3-5-11(12)8-9/h3-8H,1-2H3

Upstream product

• 16020-37-4 1,1,3-trimethyl-1,2-dihydro-naphthalene 
• 34599-66-1 1-hydroxy-1,3-dimethyl-1,2,3,4-tetrahydronaphthalene 
• 854817-88-2 2,4,4-trimethyl-1,4,4a,7-tetrahydro-naphthalene 
• 132277-09-9 1-chloro-3-methylnaphthalene 
• 77-78-1 dimethyl sulfate 
• 39172-86-6 trans-1,3-dimethyl-1,2,3,4-tetrahydronaphthalene 
• 39172-85-5 cis-1,3-dimethyl-1,2,3,4-tetrahydronaphthalene 
• 5195-37-9 1,3-dimethyl-1,2,3,4-tetrahydro-naphthalene 
• 21693-54-9 5,7-dimethyltetralin 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 765-43-5 Cyclopropyl methyl ketone 
• 872-75-3 1-(2,2-dimethyl-cyclopropyl)-ethanone 
• 14114-01-3 cyclobutyl cyclopropyl ketone 

Downstream Products

• 23802-75-7 trans-1,3-Bis-(3,4-dimethoxy-styryl)-naphthalin 
• 64977-45-3 3-Fluor-5-methylchrysen 
• 121373-46-4 (E,E)-1,3-Bis(2-phenylethenyl)naphthalin 
• 64977-44-2 1-Fluor-5-methylchrysen 
• 87-87-6 2,3,5,6-tetrachlorobenzene-1,4-diol 
• 112740-51-9 2,3,5,6-Tetrachloro-4-(3-methyl-naphthalen-1-ylmethoxy)-phenol 
• 63409-02-9 3-methylnaphthalene-1-carbaldehyde 
• 102606-07-5 4-methyl-naphthalene-2-carbaldehyde 
• 102606-08-6 Acetic acid 3-methyl-naphthalen-1-ylmethyl ester 
• 33828-52-3 C₂₆H₂₂ 
• 33828-53-4 C₂₆H₂₂ 
• 857596-44-2 2-(2,4-dimethyl-[1]naphthyl)-aniline 
• 858458-21-6 2,4-dimethyl-1-(2-nitro-phenyl)-naphthalene 
• 2089-93-2 1,3-naphthalenedicarboxylic acid 

Relevant academic research and scientific papers

Type 1 ring-opening reactions of cyclopropanated 7-oxabenzonorbornadienes with organocuprates

For the first time, nucleophilic ring-openings of cyclopropanated 7-oxabenzonorbornadiene were investigated, providing a novel approach to the preparation of 2-methyl-1,2-dihydronaphthalen-1-ols. Satisfactory yields (up to 95%) were achieved using n-Bu2CuCNLi2 as the nucleophile and Et2O as the solvent. The reaction demonstrated successful incorporation of primary, secondary, tertiary and aromatic nucleophiles, as well as ring-openings of substrates bearing arene substituents and C1-bridgehead substituents. A generalized mechanism for these transformations is also proposed.

Gold(I)-Catalyzed Cycloisomerization-Dimerization Cascade of Benzene-Tethered 1,6-Enynes

An unprecedented stereoselective domino reaction of 1,6-enynes with an aryl ring at C3-C4 in the presence of gold(I) catalysts at low temperature is described. This process involves a novel 5-exo-dig cycloisomerization-dimerization sequence to afford formal Diels-Alder adducts that undergo a smooth gold-catalyzed double bond migration at room temperature. In addition, the first examples of the gold mesoionic carbene mediated [2+2+2] cycloaddition of these enynes with benzaldehyde are reported.

Experiment and Theory of Bimetallic Pd-Catalyzed α-Arylation and Annulation for Naphthalene Synthesis

We report the synthesis of bimetallic Pd(I) and Pd(II) complexes with bidentate 2-phosphinoimidazole ligands and their catalytic activity to generate substituted naphthalenes. This process involves the coupling of an aryl iodide and 2 equiv of a ketone via sequential ketone α-arylation and then annulation to generate disubstituted and tetrasubstituted naphthalenes in a regioselective manner. Excellent substrate scope for both aryl iodide and ketone partners is demonstrated, including that for heteroaryl iodides. Bimetallic Pd complexes are much more reactive than monometallic Pd catalysts in this transformation. Density functional theory calculations, isotope effect experiments, and substrate competition experiments were used to examine bimetallic mechanisms, reactivity, and selectivity.

Methylation of 2-methylnaphthalene over metal-impregnated mesoporous MCM-41 for the synthesis of 2,6-triad dimethylnaphthalene isomers

2,6-Dimethylnaphthalene (2,6-DMN) is one of the key intermediates for the production of polyethylene naphthalate (PEN), which demonstrates superior properties compared with the polyethylene terephthalate. However, the complex synthesis procedure of 2,6-DMN increases the production cost and decreases the commercialisation of PEN. In this study, selective synthesis of 2,6-triad DMN isomers (1,5-DMN, 1,6-DMN and 2,6-DMN) has been investigated by the methylation of 2-methylnaphthalene (2-MN) over mesoporous Cu/MCM-41 and Zr/MCM-41 zeolite catalysts. On the contrary of other DMN isomers, 2.6-triad isomers can effectively be converted to be profitable 2,6-DMN with an additional isomerisation reaction, which is a new approach to reach higher 2,6-DMN yield. The methylation reactions of 2-MN were investigated in a fixed-bed reactor at 400?°C and weight hourly space velocity of 1–3?h?1. The results showed that the activity of MCM-41 on the methylation of 2-MN has been enhanced with the impregnation of Cu. The conversion increased from about 17% to 35 wt% with the impregnation of Cu. Similarly, the 2,6-triad DMN selectivity and 2,6-/2,7-DMN ratio reached the maximum level (48 wt% and 1.95, respectively) over Cu-impregnated MCM-41 zeolite catalyst.

Selective synthesis of 2,6-triad dimethylnaphthalene isomers by disproportionation of 2-methylnaphthalene over mesoporous MCM-41

2,6-Dimethylnaphthalene (2,6-DMN) is one of the crucial intermediates for the synthesis of polybutylenenaphthalate and polyethylene naphthalate (PEN). The complex synthesis procedure and the high cost of 2,6-DMN production significantly reduce the commercialisation of PEN even though PEN demonstrates superior properties compared with polyethylene terephthalate. 2,6-DMN can be produced by methylation of 2-methylnaphthalene (2-MN) and/or naphthalene, disproportionation of 2-MN, and/or isomerisation of dimethylnaphthalenes (DMNs). In this study, synthesis of 2,6-triad DMN isomers consisting of 2,6-DMN, 1,6-DMN, and 1,5-DMN have been investigated with the disproportionation of 2-MN over unmodified and Zr-modified mesoporous MCM-41 zeolite catalysts. In contrast to other DMN isomers, both 1,5-DMN and 1,6-DMN can be effectively isomerised to be profitable 2,6-DMN. The disproportionation of 2-MN experiments were carried out in a catalytic fixed-bed reactor in the presence of 1?g of catalyst at a temperature range of 350–500?°C and weight hourly space velocity between 1 to 3?h?1. The results demonstrated that mesoporous MCM-41 zeolite catalyst has a selective pore shape for 2,6-triad DMN isomers, which may allow a decrease in the production cost of 2,6-DMN. Additionally, 2,6-DMN was successfully synthesised by the disproportionation of 2-MN over MCM-41 zeolite catalyst. Furthermore, both the conversion of 2-MN and the selectivity of 2,6-DMN were considerably enhanced by the Zr impregnation on MCM-41.

Intermediacy of Ni-Ni Species in sp2 C-O Bond Cleavage of Aryl Esters: Relevance in Catalytic C-Si Bond Formation

Monodentate phosphine ligands are frequently employed in the Ni-catalyzed C-O functionalization of aryl esters. However, the extensive body of preparative work on such reactions contrasts with the lack of information concerning the structure and reactivity of the relevant nickel intermediates. In fact, experimental evidence for a seemingly trivial oxidative addition into the C-O bond of aryl esters with monodentate phosphines and low-valent nickel complexes still remains elusive. Herein, we report a combined experimental and theoretical study on the Ni(0)/PCy3-catalyzed silylation of aryl pivalates with CuF2/CsF additives that reveals the involvement of unorthodox dinickel oxidative addition complexes in C-O bond cleavage and their relevance in C-Si bond formation. We have obtained a mechanistic picture that clarifies the role of the additives and demonstrates that dinickel complexes act as reservoirs of the propagating monomeric nickel complexes by disproportionation. We believe this study will serve as a useful entry point to unravelling the mechanistic underpinnings of other related Ni-catalyzed C-O functionalization reactions employing monodentate phosphines.

Cyclization of (2-alkenylphenyl)carbonyl compounds to polycyclic arenes catalyzed by copper(II) trifluoromethanesulfonate or trifluoromethanesulfuric acid

Various polycyclic arenes, such as naphthalenes, tetrahydroantharacenes, tetrahydrotetracenes, dihydropentacenes, and dihydropentaphenes are prepared from 2-alkenylphenyl ketones and aldehydes by the catalytic use of copper(II) trifluoromethanesulfonate (Cu(OTf)2) or trifluoromethanesulfuric acid (TfOH). Copyright

Cyclization of (2-alkenylphenyl)carbonyl compounds to polycyclic arenes catalyzed by copper(II) trifluoromethanesulfonate or trifluoromethanesulfuric acid

Various polycyclic arenes, such as naphthalenes, tetrahydroantharacenes, tetrahydrotetracenes, dihydropentacenes, and dihydropentaphenes are prepared from 2-alkenylphenyl ketones and aldehydes by the catalytic use of copper(II) trifluoromethanesulfonate (Cu(OTf)2) or trifluoromethanesulfuric acid (TfOH). Copyright

Cyclization reaction for the synthesis of polysubstituted naphthalenes in the presence of Au(I) precatalysts

Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the π-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.

Chelate-assisted oxidative coupling reaction of arylamides and unactivated alkenes: Mechanistic evidence for vinyl C-H bond activation promoted by an electrophilic ruthenium hydride catalyst

The cationic ruthenium hydride complex [(η6-C 6H6)(PCy3)(CO)RuH]+BF 4- was found to be a highly regioselective catalyst for the oxidative C-H coupling reaction of aryl-substituted amides and unactivated alkenes to give o-alkenylamide products. The kinetic and spectroscopic analyses support a mechanism involving a rapid vinyl C-H activation followed by a rate-limiting C-C bond formation step.