3900-49-0

Basic information

• Product Name: 2,5-Dimethoxynaphthalene
• Synonyms: 1,6-DIMETHOXYNAPHTHALENE;2,5-DIMETHOXY NAPHTHALENE;2,5(1,6)-Dimethoxy Naphthalene;1,6-DimethoxylNaphthalene;1,6-DIMETHOXYNAPHTHALENE, 98+%;3,8-DiMethoxynaphthalene;NSC 167477;Naphthalene, 1,6-diMethoxy-
• CAS NO: 3900-49-0
• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.22
• Product Categories: Intermediates of Dyes and Pigments;FINE Chemical & INTERMEDIATES;Naphthalene derivatives;Ethers;Organic Building Blocks;Oxygen Compounds;Aromatics;Intermediates
• Mol File: 3900-49-0.mol

Chemical Properties

• Melting Point: 56-60 °C(lit.)
• Boiling Point: 123°C 0,8mm
• Flash Point: 123°C/0.8mm
• Appearance: /
• Density: 1.097 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane
• BRN: 1945987
• CAS DataBase Reference: 2,5-Dimethoxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethoxynaphthalene(3900-49-0)
• EPA Substance Registry System: 2,5-Dimethoxynaphthalene(3900-49-0)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-36/39
• WGK Germany: 3
• Hazardous Substances Data: 3900-49-0(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Intermediate in the production of tetralin derivatives

InChI:InChI=1S/C12H12O2/c1-13-10-6-7-11-9(8-10)4-3-5-12(11)14-2/h3-8H,1-2H3

Upstream product

• 575-44-0 1,6-dihydroxynaphthalene 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 32940-13-9 1,4-dihydro-2,5-dimethoxynaphthalene 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 90381-44-5 4,7-dimethoxy-1-naphthaldehyde 
• 32940-15-1 5-methoxy-2-tetralone 
• 177594-47-7 C₂₃H₁₄O₃ 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 288389-24-2 2-aminomethyl-3-(3,8-dimethoxynaphthalene-2-yl)propionic acid 

Relevant articles and documents

A simple and efficient process for the preparation of 1,6- dimethoxynaphthalene

1,6-Dimethoxynaphthalene (1,6-DMN) was prepared by the O-dimethylation of 1,6-dihydroxynaphthalene (1,6-DHN) with dimethyl sulfate (DMS) in the presence of sodium hydroxide and additives in different solvents. The main reaction determining factors were divided into three categories with respect to yield and purity of 1,6-DMN: (1) Type of solvents and adding methods of NaOH had the highest effect on the results. (2) Amount of DMS and concentration of NaOH were less important. (3) Reaction time and temperature were the least important factors. The best reductant was Na2S2O4, and it was only under N2 atmosphere that yield and purity were also good. The improved process provides more than 99% yield, which considerably reduces the cost of 1,6-DMN, and more than 98% purity eliminates the purification process in the follow-up industrial production.

Optical Control of Dopamine Receptors Using a Photoswitchable Tethered Inverse Agonist

Family A G protein-coupled receptors (GPCRs) control diverse biological processes and are of great clinical relevance. Their archetype rhodopsin becomes naturally light sensitive by binding covalently to the photoswitchable tethered ligand (PTL) retinal. Other GPCRs, however, neither bind covalently to ligands nor are light sensitive. We sought to impart the logic of rhodopsin to light-insensitive Family A GPCRs in order to enable their remote control in a receptor-specific, cell-type-specific, and spatiotemporally precise manner. Dopamine receptors (DARs) are of particular interest for their roles in motor coordination, appetitive, and aversive behavior, as well as neuropsychiatric disorders such as Parkinson's disease, schizophrenia, mood disorders, and addiction. Using an azobenzene derivative of the well-known DAR ligand 2-(N-phenethyl-N-propyl)amino-5-hydroxytetralin (PPHT), we were able to rapidly, reversibly, and selectively block dopamine D1 and D2 receptors (D1R and D2R) when the PTL was conjugated to an engineered cysteine near the dopamine binding site. Depending on the site of tethering, the ligand behaved as either a photoswitchable tethered neutral antagonist or inverse agonist. Our results indicate that DARs can be chemically engineered for selective remote control by light and provide a template for precision control of Family A GPCRs.

Au(i)-catalyzed triple bond alkoxylation/dienolether aromaticity-driven cascade cyclization to naphthalenes

A novel strategy for the synthesis of multisubstituted naphthalenes was developed via a Au(i)-catalyzed alkyne alkoxylation/dienolether aromaticity-driven cascade cyclization using 1,5-enyne substrates. The functional group toleration was examined by synthesizing a series of substrates and the mechanism was also studied based on intermediates isolated through deuterium labeling experiments. This journal is the Partner Organisations 2014.

Synthesis and biological evaluation of 1-benzylidene-3,4-dihydronaphthalen- 2-one as a new class of microtubule-targeting agents

A series of 1-benzylidene-3,4-dihydronaphthalen-2-one derivatives were designed and synthesized, and their biological activities in vitro and in vivo were evaluated. The results showed a number of the title compounds exhibiting potent nanomolar activity in several human cancer cell lines. Of these, compound 22b showed the strongest inhibitory activity against human CEM, MDA-MBA-435, and K562 cells (IC50 = 1 nM), displayed in vitro inhibition of tubulin polymerization (IC50 = 3.93 μM), and significantly induced cell cycle arrest in G2/M phase. In addition, compound 22b could inhibit the tumor growth in colon nude mouse xenograft tumor model significantly and seemed safer than CA-4 when achieving a similar tumor suppression. This study provided a new molecular scaffold for the further development of antitumor agents that target tubulin.

Adenosine A2A receptor-antagonist/dopamine D2 receptor-agonist bivalent ligands as pharmacological tools to detect A 2A-D2 receptor heteromers

Adenosine A2A (A2AR) and dopamine D2 (D2R) receptors mediate the antagonism between adenosinergic and dopaminergic transmission in striatopallidal GABAergic neurons and are pharmacological targets for the treatment of Parkinson's disease.Here, a family of heterobivalent ligands containing a D2R agonist and an A 2AR antagonist linked through a spacer of variable size was designed and synthesized to study A2AR-D2R heteromers. Bivalent ligands with shorter linkers bound to D2R or A2AR with higher affinity than the corresponding monovalent controls in membranes from brain striatum and from cells coexpressing both receptors. In contrast, no differences in affinity of bivalent versus monovalent ligands were detected in experiments using membranes from cells expressing only one receptor. These findings indicate the existence of A2AR-D2R heteromers and of a simultaneous interaction of heterobivalent ligands with both receptors. The cooperative effect derived from the simultaneous interaction suggests the occurrence of A2AR-D2R heteromers in cotransfected cells and in brain striatum. The dopamine/adenosine bivalent action could constitute a novel concept in Parkinson's disease pharmacotherapy.

Synthesis and antifungal activities of novel 2-aminotetralin derivatives

Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoline ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14α-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

An unexpected double-bond isomerization catalyzed by Crabtree's iridium(I) catalyst

The first iridium-catalyzed isomerization of an exocyclic into an endocyclic double bond is described. A mechanism is proposed for this reaction. Crabtree's catalyst thus allows the migration of a double bond that does not occur under classical conditions. Georg Thieme Verlag Stuttgart.

Bicyclic aromatic compounds as therapeutic agents

Compounds of formula I STR1 and pharmaceutically acceptable salts thereof in which A is methylene or --O--; B is methylene or --O--; and g is 0, 1, 2, 3 or 4; R1, R2, R3, R4, U, Q and T are defined in claim 1. The compounds have utility in the treatment of central nervous system disorders, for example depression, anxiety, psychoses (for example schizophrenia), tardive dyskinesia, Parkinson's disease, obesity, hypertension, Tourette's syndrome, sexual dysfunction, drug addiction, drug abuse, cognitive disorders, Alzheimer's disease, senile dementia, obsessive-compulsive behaviour, panic attacks, eating disorders and anorexia, cardiovascular and cerebrovascular disorders, non-insulin dependent diabetes mellitus, hyperglycaemia, constipation, arrhythmia, disorders of the neuroendocrine system, stress, prostatic hypertrophy, and spasticity.

The preparation and biological activity of lactam-based, non-steroidal, inhibitors of human type-1 steroid 5α-reductase

A Beckmann rearrangement of cis- and trans-fused 3,4,4a,9,10,10a-hexahydrophenanthren-1(2H)-one oximes has yielded three azepines. An in vitro assay of the azepines and (3aSR,9bSR)-6-methoxy-3-methyl-1,3,3a,4,5,9b-hexahydro-2H-benz[e]indol-2-one, prepared in four steps from naphthalene-1,6-diol, against human type-1 steroid 5α-reductase, revealed the tricyclic five-membered lactam to be a potent inhibitor (IC50 733 nM).