56679-88-0

Usage

Uses

Used in Perfumery Industry:
3-Methoxy-2-naphthaldehyde is used as a fragrance ingredient for its unique scent, contributing to the creation of perfumes and air fresheners.
Used in Air Freshener Production:
3-Methoxy-2-naphthaldehyde is used as an aromatic compound in air fresheners to provide a pleasant smell and improve indoor air quality.
It is important to handle 3-Methoxy-2-naphthaldehyde with care, following the guidelines provided in Safety Data Sheets to minimize potential risks and exposure during its production and use.

Upstream product

• 102174-69-6 N-(3-methoxy-[2]naphthoyl)-N'-(toluene-4-sulfonyl)-hydrazine 
• 93-04-9 2-Methoxynaphthalene 
• 93-61-8 N-methyl-N-phenylformamide 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 13041-60-6 methyl 3-methoxy-2-naphthoate 
• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 39110-92-4 (3-methoxy-naphthalen-2-yl)-methanol 
• 408528-30-3 N-benzenesulfonyl-N'-(3-methoxy-[2]naphthoyl)-hydrazine 

Downstream Products

• 281198-50-3 (+)-(R)-2-phenyl-2-(1-(3-methoxynaphthyl)methyleneamino)ethanol 
• 123239-66-7 (3-methoxynaphthalen-2-yl)phenylmethanol 
• 1274918-34-1 2-(4-chlorobenzyl)-3-methoxynaphthalene 
• 17324-04-8 3-methyl-naphthalen-2-ol 
• 123239-68-9 3-benzyl-2-methoxynaphthalene 
• 123239-70-3 2-benzyloxy-3-hydroxynaphthalene 
• 443911-29-3 (3-aminooxalyl-1-cyclohexylmethyl-2-methyl-1H-benzo[g]indol-4-yloxy)-acetic acid methyl ester 

Relevant academic research and scientific papers

Design and synthesis of intramolecular hydrogen bonding systems. Their application in metal cation sensing based on excited-state proton transfer reaction

We reported the design and synthesis of a new type of metal-cation probes, 3-hydroxy-4-(1,4,7,10-tetraoxa-13-azacyclopentadec-13-ylmethyl) naphthalene-2-carbaldehyde (1a) and its single hydrogen-bond analogue 1-(1,4,7,10-tetraoxa-13-azacylopentadec-13-ylmethyl)-2-naphthol (2a), in which 1-aza-15-crown-5 ether in combination with the naphthol oxygen acts as a receptor, while the mechanism of excited-state intramolecular proton transfer (ESIPT) is exploited as a signal transducer. The association constant of (2.5±0.5)×104, (3.8±0.4)×104, (5.5±0.5)×103 and (1.2±0.3)×104 M-1 for the formation of 1a/Na+, 1a/Ca2+, 2a/Na+ and 2a/Ca2+ complexes, respectively, in CH 3CN plus drastic fluorescence changes due to the fine-tuning of ESIPT reaction upon complexation, lead 1a and 2a to be highly sensitive fluorescent sensors. The results add a new class into the category of metal-cation probes, with the perspective of designing ESIPT systems capable of sensing bio-analytes. Graphical Abstract

Design, synthesis and biological evaluation of novel triaryldimethylaminobutan-2-ol derivatives against Mycobacterium tuberculosis

Bedaquiline (TMC207), a typical diarylquinoline anti-tuberculosis drug, has been approved by FDA to specifically treat MDR-TB. Herein we describe design, synthesis, and in vitro biological evaluation against Mycobacterium tuberculosis of a series of triaryldimethylaminobutan-2-ol derivatives obtaining from the structural modification of TMC207. Compounds 23, 25, 28, 32, 39 and 43 provided superior anti-mycobacterial activity than positive control PC01 which shows the same configuration and contains TMC207. Compounds 16, 20, 29, 34, 37, 45 and 47 exhibited the similar activity to positive control PC01. Most importantly, the series of compounds showed excellent activity against XDR-Mtb. The result of acute toxicity suggested that this class of triaryldimethylaminobutan-2-ol derivatives should be graded as low. Further SAR analysis indicates that a large steric bulk of triaryl and 7-Br, 3-OCH3 on 1-naphthyl are critical.

Solid state multicolor emission in substitutional solid solutions of metal-organic frameworks

Preparing crystalline materials that produce tunable organic-based multicolor emission is a challenge due to the inherent inability to control the packing of organic molecules in the solid state. Utilizing multivariate, high-symmetry metal-organic frameworks, MOFs, as matrices for organic-based substitutional solid solutions allows for the incorporation of multiple fluorophores with different emission profiles into a single material. By combining nonfluorescent links with dilute mixtures of red, green, and blue fluorescent links, we prepared zirconia-Type MOFs and found that the bulk materials exhibit features of solution-like fluorescence. Our study found that MOFs with a fluorophore link concentration of around 1 mol % exhibit fluorescence with decreased inner filtering, demonstrated by changes in spectral profiles, increased quantum yields, and lifetime dynamics expected for excited-state proton-Transfer emitters. Our findings enabled us to prepare organic-based substitutional solid solutions with tunable chromaticity regulated only by the initial amounts of fluorophores. These materials emit multicolor and white light with high quantum yields (-2-14%), high color-rendering indices (>93), long shelf life, and superb hydrolytic stability at ambient conditions.

MULTIVARIATE METAL-ORGANIC FRAMEWORKS FOR FINE-TUNING LIGHT EMISSION

Multivariate metal-organic framework compositions and methods of producing multivariate metal-organic frameworks. The metal-organic framework including at least one light-emitting linker in an amount sufficient for the composition to produce broadband emission spectra in high efficiencies.

Coumarin derivative, and preparation method and use thereof

The invention relates to a coumarin derivative and a use thereof. The coumarin derivative is a compound represented by formula I. The compound represented by formula I can be applied as an organic pigment. The application field of the coumarin derivative with a large pi conjugated system is developed, and foundation is laid for commercial preparation of like coumarin derivatives. In the formula I, R1-R7 are respectively independently selected from hydrogen, halogens, C1-C4 linear or branched alkyl groups, fluorine-containing C1-C4 linear or branched alkyl groups, hydroxyl groups, C1-C3 linear or branched alkyloxy groups, trifluoromethylsulfo groups or C6-C10 aryl groups; or R1, R4, R5, R6 and R7 are respectively independently selected from one of H and C1-C3 linear or branched alkyl groups, and a combination of R2 and R3 is a bivalent phenyl group.

Molecular tweezers: Synthesis and formation of host-guest complexes

A chiral molecular tweezer obtained from (+)-usnic acid placed in solution in the presence of various aromatic compounds afforded complexes with low association constants. Thus, the X-ray structure of assembly 31 is presented, where the guest is sandwiched between the two pincers of the tweezer. The association constants for various guests were determined through different methods. Finally, other tweezers with electron-rich aromatic aldehydes and ketones were prepared from (1R,2R)-1,2-diaminocyclohexane. The most interesting complexes were also confirmed through structural analysis, and the best results were obtained with 10-hydroxyphenanthrene-9-carbaldehyde (51) as the aromatic moiety.

New efficient route to fused aryltetrahydroindolizinones via N-Acyliminium intermediates

Straightforward routes to fused tetrahydroindolizinones by two routes A and B, starting either from. 2-formylbenzoic acid and esters or from, β-hydroxy lactones via acyl iminium ions, are described. A plausible mechanism and limitations are given. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

Highly specific and broadly potent inhibitors of mammalian secreted phospholipases A2

We report a series of inhibitors of secreted phospholipases A2 (sPLA2s) based on substituted indoles, 6,7-benzoindoles, and indolizines derived from LY315920, a well-known indole-based sPLA2 inhibitor. Using the human group X sPLA2 crystal structure, we prepared a highly potent and selective indole-based inhibitor of this enzyme. Also, we report human and mouse group IIA and IIE specific inhibitors and a substituted 6,7-benzoindole that inhibits nearly all human and mouse sPLA 2s in the low nanomolar range.

Novel aldosterone synthase inhibitors with extended carbocyclic skeleton by a combined ligand-based and structure-based drug design approach

Pharmacophore modeling of a series of aldosterone synthase (CYP11B2) inhibitors triggered the design of compounds 11 and 12 by extending a previously established naphthalene molecular scaffold (e.g., present in molecules 1 and 2) via introduction of a phenyl or benzyl residue in 3-position. These additional aromatic moieties have been hypothesized to fit into the newly identified hydrophobic pharmacophore feature HY3. Subsequent docking studies in our refined CYP11B2 protein model have been performed prior to synthesis to estimate the inhibitory properties of the proposed molecules. While phenyl-substituted compound 11 (IC50 > 500 nM) did not dock under the given pharmacophore constraint (i.e., the Fe(heme)-N(ligand) interaction), benzyl-substituted compound 12 (IC50 = 154 nM) was found to exploit a previously unexplored subpocket of the inhibitor binding site. By structural optimization based on the pharmacophore hypothesis, 25 novel compounds were synthesized, among them highly potent CYP11B2 inhibitors (e.g., 17, IC 50 = 2.7 nM) with pronounced selectivity toward the most important steroidogenic and hepatic CYP enzymes.

Carbocyclic[g]indole inhibitors of human nonpancreatic s-PLA2

A vinyl azide cyclization method was used to synthesize three different carbocyclic[g]indole scaffolds as inhibitors of human nonpancreatic secretory phospholipase A2. Each scaffold demonstrated potent enzyme activity in a chromogenic assay sys