529-36-2

Basic information

• Product Name: 1-NAPHTHALENETHIOL
• Synonyms: 1-THIONAPHTHOL;1-THIONAPHTOL;1-NAPHTHALENETHIOL;naphthalene-1-thiol;1-Thionaphthol,99%;1-mercaptonaphthalene;Naphthalin-1-thiol;1-Naphthalenethiol,99%
• CAS NO: 529-36-2
• Molecular Formula: C₁₀H₈S
• Molecular Weight: 160.24
• EINECS: 208-462-7
• Product Categories: Building Blocks;Chemical Synthesis;Contact Printing;Materials Science;Micro/NanoElectronics;Organic Building Blocks;Ring Thiols;Self Assembly &Self-Assembly Materials;Sulfur Compounds;Thiols;Thiols/Mercaptans
• Mol File: 529-36-2.mol

Chemical Properties

• Melting Point: 15 °C
• Boiling Point: 131 °C (5 mmHg)
• Flash Point: >110°C
• Appearance: Clear light yellow to yellow/Liquid
• Density: 1.15
• Vapor Pressure: 0.00495mmHg at 25°C
• Refractive Index: 1.679-1.681
• PKA: 6?+-.0.30(Predicted)
• Water Solubility: Soluble in diethyl ether and ethanol. Slightly soluble in water and dilute alkalis.
• CAS DataBase Reference: 1-NAPHTHALENETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NAPHTHALENETHIOL(529-36-2)
• EPA Substance Registry System: 1-NAPHTHALENETHIOL(529-36-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20/21/22-36/37/38-51-22
• Safety Statements: 24/25-61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 529-36-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Naphthalenethiol is used as a key component in the production of di-[1]naphthyl disulfide, which is an important intermediate in the synthesis of various organic compounds.
Used in Organic Synthesis:
1-Naphthalenethiol serves as a valuable building block in the creation of complex organic molecules, contributing to the development of new pharmaceuticals, agrochemicals, and dyes.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 1-Naphthalenethiol is utilized as a starting material for the synthesis of various drugs, thanks to its unique chemical properties.
Used in Agrochemicals:
1-Naphthalenethiol is employed in the development of agrochemicals, such as pesticides and herbicides, due to its ability to form stable and effective compounds.
Used in Dye Industry:
1-Naphthalenethiol is also used in the dye industry to produce a range of colors for various applications, including textiles and plastics.
Used in Surface Enhanced Raman Scattering (SERS):
1-Naphthalenethiol can be used as a model analyte to characterize the performance of SERS, a powerful analytical technique that enhances the Raman scattering signal of molecules adsorbed on certain surfaces.
Used in Polymeric Network for Optical Property Detection:
1-Naphthalenethiol is a standard analyte that can be diffused in the polymeric network for the detection of optical properties, making it a valuable tool in the study and development of advanced materials.

Purification Methods

It is steam volatile and is purified by distillation in the absence of O2, as it oxidises to the disulfide. It is soluble in Et2O and EtOH but very slightly soluble in H2O and dilute alkalis. The S-ethyl derivative, [17539-31-0] M 188.2, has b 175-176o/25mm, and do 1.120. [Beilstein 6 III 2943, 6 IV 4241.]

InChI:InChI=1/C10H8S/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H/p-1

Upstream product

• 1950-75-0 naphthalene-1-sulfonyl bromide 
• 140-89-6 potassium ethyl xanthogenate 
• 3177-49-9 1-naphthyldiazonium chloride 
• 703-55-9 1-naphthylmagnesiumbromide 
• 90-11-9 1-Bromonaphthalene 
• 39178-11-5 1,2-di(naphthalen-1-yl)disulfane 
• 75-08-1 ethanethiol 
• 90-13-1 1-Chloronaphthalene 
• 7664-93-9 sulfuric acid 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 7732-18-5 water 
• 85-47-2 1-naphthalenesulfonic acid 
• 7783-06-4 hydrogen sulfide 
• 90-14-2 1-Iodonaphthalene 

Downstream Products

• 61623-80-1 [1]naphthyl-trityl sulfide 
• 92795-29-4 [1]naphthyl-(2-nitro-phenyl)-sulfide 
• 16928-76-0 Benzhydryl-2-naphthyl-sulfid 
• 108897-63-8 2-[1]naphthylsulfanyl-5-nitro-benzaldehyde 
• 5335-81-9 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(naphthalen-1-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 19343-29-4 1-Isopropylamino-3--propanol-(2) 
• 77900-98-2 6-(Naphthalen-1-ylsulfanyl)-pteridine-2,4-diamine 
• 5398-91-4 (naphthalen-1-ylsulfanyl)-acetonitrile 
• 234-41-3 naphtho[1,2-b]thiophene 
• 203-93-0 naphtho<1,8-b,c>thiopyran 
• 91-20-3 naphthalene 
• 85-01-8 phenanthrene 
• 123231-71-0 2-(1-naphthylthio)cyclohexanone 
• 94573-70-3 3-Methyl-2-nitrophenyl-naphth-1-yl-sulfid 

Relevant articles and documents

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.

Copper-Catalyzed Direct Synthesis of Aryl Thiols from Aryl Iodides Using Sodium Sulfide Aided by Catalytic 1,2-Ethanedithiol

A copper-catalyzed direct and effective synthesis of aryl thiols from aryl iodides using readily available Na 2 S·9H 2 O and 1,2-ethanedithiol was described. A variety of aryl thiols were readily obtained in yields of 76-99%. In this protocol, Na 2 S·9H 2 O was used as ultimate sulfur source, and 1,2-ethanedithiol functioned as an indispensable catalytic reagent.

SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF

The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017

Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol

A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.

Vinyl sulfone-based peptidomimetics as anti-trypanosomal agents: Design, synthesis, biological and computational evaluation

A series of vinyl sulfone-containing peptidomimetics were rationally designed, synthesized, and evaluated against Trypanosoma brucei brucei. These electrophilic compounds are likely to exert their antitrypanosomal activity via inhibition of trypanosomal cysteine proteases, TbCatB and rhodesain, through alkylation of a key cysteine residue within the protease active site. The series was designed to present complementary groups to naturally recognized peptide substrates while probing tolerance to a range of substitutions at the P1, P1′, and P2 positions. The most potent compound, 29 (EC50 = 70 nM, T. b. brucei whole cell assay), displayed minimal toxicity (>785 times selectivity) when assayed for cytotoxicity against the human promyelocytic leukemia (HL-60) cell line. Cells treated with compound 29, as with K777 (2), exhibited an increase in both the number of multinucleated cells and cells with swollen flagellar pockets. Computational analysis revealed a strong correlation between the hypothetical binding mode in TbCatB/rhodesain and trypanocidal activity in vitro.

Palladium catalyzed synthesis of aryl thiols: Sodium thiosulfate as a cheap and nontoxic mercapto surrogate

A Pd-catalyzed coupling reaction of ArBr/ArCl/ArOTf with sodium thiosulfate takes place in presence of Cs2CO3 at 80 °C. The reaction mixture is directly treated with Zn/HCl to afford aryl thiols in good to excellent yields.

One-pot synthesis of unsymmetrical diaryl thioethers by palladium-catalyzed coupling of two aryl bromides and a thiol surrogate

Extraordinarily simple, convenient, and efficient: A general and operationally simple one-pot synthesis of unsymmetrical diaryl sulfides by coupling two different bromoarenes and triisopropylsilanethiol (TIPS-SH) is reported. This protocol overcomes the narrow availability of arene thiols and their instability to oxidation. These reactions catalyzed by palladium complexes generated from the alkylbisphosphine CyPF-tBu occur in good to excellent yields with wide scope and high tolerance of functional groups.

Copper-catalyzed coupling of thiourea with aryl iodides: The direct synthesis of aryl thiols

A general, economical and efficient protocol for the direct copper-catalyzed coupling of thiourea with aryl iodides is developed and it will be potentially applied in large-scale industry as a preferred process.

Interaction of naphthyl heterocycles with DNA: Effects of thiono and thio groups

The intercalation and photocleavage of DNA by N-[β-(N′,N′-dimethylamino)ethyl]dithiono-1,8-naphthalimide (2) were extremely effective compared to the use of the oxygen-containing counterpart (1). Their photocleavage action under 366 nm UV light is proposed to proceed by electron transfer from bases to the triplet state of the naphthalimides. The enhancement of the intercalation of DNA and the photocleavage of DNA were also observed for other compounds possessing a thiono or thio group compared with their oxygen-containing counterparts.

A novel, practical and highly chemoselective methodology for reduction of disulphides to thiols

A novel, simple and efficient method for the reduction of disulfides to thiols using In/NH4Cl is described.