5254-86-4

Usage

Uses

Used in Fragrance Industry:
1-(Mercaptomethyl)naphthalene is used as a fragrance ingredient for its ability to add a sweet, floral note to various scents. It is incorporated into a wide range of products such as perfumes, soaps, and household cleaners, enhancing their olfactory appeal with its distinctive aroma.
Used in Chemical Synthesis:
As an intermediate in the synthesis of other organic compounds, 1-(Mercaptomethyl)naphthalene plays a crucial role in the production of various chemical products. Its reactivity allows it to participate in multiple chemical reactions, contributing to the creation of a diverse array of organic molecules.
Used in Dye Production:
1-(Mercaptomethyl)naphthalene is also utilized in the dye industry, where its aromatic properties are harnessed to produce dyes with specific color characteristics. Its involvement in dye production processes highlights its versatility in the realm of chemical applications.
Used in Industrial Chemical Reactions:
Beyond its applications in fragrances and dyes, 1-(Mercaptomethyl)naphthalene is employed in various industrial chemical reactions. Its participation in these processes underscores its importance in the broader chemical industry, where it contributes to the synthesis of a multitude of products.

Upstream product

• 17356-08-0 thiourea 
• 86-52-2 1-Chloromethylnaphthalene 
• 46396-26-3 naphthalen-1-ylmethyl carbamimidothioate 
• 233266-70-1 N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(1-naphthylmethylthio)methyl-carbamic acid allyl ester 
• 4780-79-4 1-naphthalene methanol 
• 88766-11-4 1-naphthylmethylisothiouronium chloride 

Downstream Products

• 90-12-0 1-Methylnaphthalene 
• 233266-66-5 N-pentafluorophenyl-N-(1-naphthylmethylthio)methyl-carbamic acid allyl ester 
• 233266-70-1 N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(1-naphthylmethylthio)methyl-carbamic acid allyl ester 
• 66-77-3 1-naphthaldehyde 
• 100728-67-4 2-Amino-5-napthyl-⁽¹⁾-methylmercapto-1.3.4-thiadiazol 
• 5261-46-1 2-[1]naphthylmethylsulfanyl-propionic acid 
• 5254-92-2 α-Naphthylmethylenthioessigsaeure 
• 1127-76-0 1-ethylnapthelene 
• 88430-88-0 (+/-)-1-naphthylmethyl 1-phenylethyl sulfone 
• 114073-54-0 1-(1-naphthyl)-2-phenylpropane 
• 109996-25-0 [(S)-1-((S)-1-{(S)-1-[(R)-1-Hydroxy-2-(naphthalen-1-ylmethylsulfanyl)-ethyl]-3-methyl-butylcarbamoyl}-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 98977-90-3 (E)-3-phenyl-2-propenyl 1-naphthylmethyl sulfone 
• 98977-89-0 (E)-3-phenyl-2-propenyl 1-naphthylmethyl sulfoxide 
• 125698-13-7 N-<2-<(1-naphthalenylmethyl)thio>ethyl>benzeneethanamine 

Relevant academic research and scientific papers

Method for preparing sulfhydryl compounds by hydroxyl substitution and sulfhydryl compounds

The invention provides a method for preparing sulfhydryl compounds by hydroxyl substitution and the sulfhydryl compounds. According to the method, low-cost and easily-obtained benzene or fused ring compounds with phenolic hydroxyl groups or benzyl hydroxyl substituents serving as raw materials to react with the raw materials such as inorganic sulfide under the catalysis conditions to prepare the corresponding sulfhydryl compounds. The method has the advantages that the preparation method is simple, convenient and rapid, low in cost, mild in reaction condition, high in reaction site selectivity and high in yield, a post-processing process is simple, and no pollution is caused.

Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus

The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.

Allylic protection of thiols and cysteine: II: The N-[2,3,5,6- tetrafluoro-4-(N'-piperidino)-phenyl], N-allyloxycarbonylaminomethyl (Fnam) group

S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)-phenyl], N- allyloxycarbonyl]-aminomethyl (Fnam) derivatives of thiols in general and cysteine in particular are readily deprotected by palladium catalysed allylic cleavage in the presence of various nucleophilic species. They are perfectly stable in both the basic conditions (piperidine/DMF) of Fmoc group removal and the acidic conditions (TFA/CH2Cl2) of t-Bu and Boc group removal.

Study of Reactions Leading to Sulfine Formation. 3. Competition of Reaction Pathways in the Reaction of Methoxide Ion with Methyl 1-Naphthylmethanesulfinates

In CD3O1-/CD3OD methyl 1-naphthylmethanesulfinates, NpCH2S(O)OCH3 (2), undergo both exchange of CH3O by CD3O by substitution at the sulfinyl group and elimination to form the sulfine, NpCH=S=O.With use of methyl (2-methoxy-1-naphthyl)methanesulfinate (2a) it has been shown that formation of the sulfine takes place by an (E1cB)irrev mechanism.The rates of substitution (ks) and elimination (ke) of a series of 2 have been determined in CD3O1-/CD3OD by 1H NMR spectroscopy, and the effect of several reaction variables on the competition between substitution and elimination has been examined.Salient results are as follows: (1) the rate of elimination is markedly increased by the presence of electron-withdrawing substituents on the aromatic ring, but the rate of substitution is increased only modestly by the same substituents; (2) substituents at the 2-position of the naphthyl group cause a large decrease in ks (steric hindrance to substitution at S=O) but have little effect on ke (elimination rate not sensitive to steric requirements of ortho substituents); (3) the activation energy for elimination is almost 9 kcal/mol greater than the activation energy for substitution.This large difference in activation energy contrasts with the 1-2 kcal/mol difference for elimination vs substitution found14 with alkyl halides.

Photoextrusion of SO2 from Arylmethyl Sulfones: Exploration of the Mechanism by Chemical Trapping, Chiral, and CIDNP Probes

The photochemistry of eight benzylic sulfones, all of which efficiently extrude sulfur dioxide, was studied by a variety of methods.Optically active sulfones (S)-(-)-8, (S)-(-)-11, (S)-(-)-12, (S)-(+)-13, and (R)-(+)-14 were employed to measure the extent of the "hidden" return of the initial photogenerated intermediates by the stereoequilibration of the chiral center.By comparison of the regioisomeric methyl sulfones 11 vs. 13 and 12 vs. 14, preferential C-S bond fragmentation on the naphthyl side was established for the singlet excited sulfones.Added nucleophilic and proton trapping agents had no effect on the course of the reaction, ruling out ionic intermediates.The three hydrocarbon products of photodesulfonation from the unsymmetrical sulfones 8-14 provided a measure of the cage effects, which were highly structure and multiplicity dependent.Rate constants for reaction, and fluorescence, as well as the energy transfer rates from benzophenone were determined.The reaction rate constant for singlet reactivity from the 1-naphthyl sulfones was about three times greater than that for the 2-naphthyl derivatives.CIDNP studies showed a strong product signal for the 1-naphthyl sulfones from desulfonation of a triplet caged radical pair.Naphthaldehyde formation, a very minor, triplet process, was also detected by the CIDNP study of sulfones 9-12.