696-63-9

Basic information

• Product Name: 4-METHOXYBENZENETHIOL
• Synonyms: 4-METHOXYTHIOPHENOL;4-METHOXYBENZENE-1-THIOL;4-METHOXYBENZENETHIOL;4-MERCAPTOANISOLE;P-METHOXYBENZENETHIOL;Benzenethiol, p-methoxy-;para-Methoxybenzenethiol;p-Methoxy thiophenol
• CAS NO: 696-63-9
• Molecular Formula: C7H8OS
• Molecular Weight: 140.2
• EINECS: 211-799-2
• Product Categories: Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;Miscellaneous;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans
• Mol File: 696-63-9.mol
• Article Data: 53

Chemical Properties

• Melting Point: 291.7-295.8 °C (decomp)
• Boiling Point: 100-103 °C13 mm Hg(lit.)
• Flash Point: 205 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.14 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.133mmHg at 25°C
• Refractive Index: n20/D 1.5831(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Not miscible or difficult to mix.
• PKA: 6.76±0.10(Predicted)
• Sensitive: Stench
• BRN: 1446910
• CAS DataBase Reference: 4-METHOXYBENZENETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYBENZENETHIOL(696-63-9)
• EPA Substance Registry System: 4-METHOXYBENZENETHIOL(696-63-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37-37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: DC1800000
• F: 10-13-23
• HazardClass: IRRITANT, STENCH
• PackingGroup: III
• Hazardous Substances Data: 696-63-9(Hazardous Substances Data)

Usage

Description

4-Methoxybenzenethiol, also known as p-methoxythiophenol, is an organic compound with the chemical formula C7H8OS. It is a colorless to light yellow liquid that is soluble in organic solvents and has a distinctive odor. The presence of the methoxy group (-OCH3) on the benzene ring and the thiol group (-SH) attached to the benzene ring gives 4-methoxybenzenethiol unique chemical properties and reactivity.

Uses

Used in Electronics Industry:
4-Methoxybenzenethiol is used as a precursor in the preparation of self-assembled monolayers (SAMs) for the characterization of SAMs and to study their effect on both nand p-channel organic thin film transistors. The formation of SAMs on various substrates can improve the performance and stability of organic thin film transistors by providing a well-ordered and functional interface.
Used in Chemical Synthesis:
4-Methoxybenzenethiol is used as a reagent in the cesium fluoride-Celite catalyzed preparation of thioethers and thioesters. Thioethers and thioesters are important functional groups in organic chemistry, and their synthesis can lead to the development of new compounds with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2637, 1984 DOI: 10.1021/jo00188a028

InChI:InChI=1/C7H8OS/c1-8-6-2-4-7(9)5-3-6/h2-5,9H,1H3/p-1

Upstream product

• 17333-79-8 p-methoxybenzenediazonium 
• 100-66-3 methoxybenzene 
• 123-75-1 pyrrolidine 
• 99186-33-1 O-ethyl S-(4-methoxyphenyl) dithiocarbonate 
• 110-89-4 piperidine 
• 13511-98-3 S-(4-methoxyphenyl) N,N-dimethylcarbamothioate 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 10387-40-3 potassium thioacetate 
• 3406-77-7 (4-methoxy-phenylsulfanyl)-acetic acid 
• 7647-01-0 hydrogenchloride 
• 75-15-0 carbon disulfide 
• 7664-93-9 sulfuric acid 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 67-56-1 methanol 

Downstream Products

• 132752-95-5 (Z)-1,2-bis(p-methoxyphenylsulfanyl)ethylene 
• 132752-96-6 trans-1,2-bis-(4-methoxy-phenylsulfanyl)-ethene 
• 13739-36-1 β-(4-methoxyphenylmercapto)propionic acid 
• 78597-95-2 1-(butylsulfanyl)-4-methoxybenzene 
• 165735-59-1 2-{2-[(4-methoxyphenyl)thio]ethyl}-1H-isoindole-1,3(2H)-dione 
• 26905-24-8 1-benzylsulfanyl-4-methoxy-benzene 
• 98098-60-3 S-(4-methoxyphenyl) 4-methoxybenzothioate 
• 62291-63-8 p-methoxyphenyl propyl sulfide 
• 109943-26-2 1-(4-methanesulfonyl-phenylsulfanyl)-4-methoxy-benzene 
• 714-32-9 (Z)-3-(4-methoxyphenylthio)acrylic acid 
• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 
• 91906-21-7 4-methoxythiophenoxylacetaldehyde dimethyl acetal 
• 52872-94-3 4-(4-methoxy-phenylsulfanyl)-butyric acid 
• 39248-86-7 4-Methoxyphenylthiolchloroformat 

Relevant articles and documents

Spontaneous substitution of azulene-derived benzylic alcohols by thiols and its application to labeling/protection of biothiols

By mixing guaiazulene-3-methanol derivatives and thiols at room temperature, benzylic substitution of the alcohol proceeded to yield the corresponding sulfide. Because of the blue color of the guaiazulene derivative, this spontaneous reaction was used for labeling of paper-immobilized biothiols. By treatment with tris(2-carboxyethyl)phosphine hydrochloride, the guaiazulene-3-ylmethyl part of the sulfide could be removed and the original thiol recovered. Based on these findings, a guaiazulene-3-methanol derivative was used as a protective group for the synthesis of cysteine derivatives.

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.

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.