19813-90-2

Basic information

• Product Name: 4-Phenylbenzenethiol
• Synonyms: 1,1′-Biphenyl-4-thiol;4-Biphenylylthiol;4-Mercaptobiphenyl;4-Phenylbenzenethiol;Biphenyl-4-thiol;Biphenyl-4-thiol 97%
• CAS NO: 19813-90-2
• Molecular Formula: C₁₂H₁₀S
• Molecular Weight: 186.2728
• Mol File: 19813-90-2.mol
• Article Data: 24

Chemical Properties

• Melting Point: 108-112°C
• Boiling Point: 314.1°C at 760 mmHg
• Flash Point: 145.3°C
• Appearance: /
• Density: 1.113g/cm³
• Vapor Pressure: 0.000876mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: 2-8°C
• PKA: 6.51±0.10(Predicted)
• CAS DataBase Reference: 4-Phenylbenzenethiol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylbenzenethiol(19813-90-2)
• EPA Substance Registry System: 4-Phenylbenzenethiol(19813-90-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 19813-90-2(Hazardous Substances Data)

Usage

Description

4-Phenylbenzenethiol, also known as Biphenyl-4-thiol (BPT), is an alkylthiol that forms a self-assembled monolayer (SAM). It is a compound derived from the chemical process of monolayers and multilayers of conjugated thiols, α,ω-dithiols, and thioacetyl-containing adsorbates being self-assembled. This organic compound possesses unique properties that make it suitable for various applications, particularly in the field of material science and electronics.

Uses

Used in Electronics Industry:
4-Phenylbenzenethiol is used as an engineered material for electron transport through thin organic films in metal-insulator-metal junctions. Its ability to facilitate electron transport makes it a valuable component in the development of advanced electronic devices and systems.
Used in Material Science:
As a component of self-assembled monolayers (SAMs), 4-Phenylbenzenethiol serves as a spacer chain that enhances the adhesion and frictional forces on a variety of surfaces. This property makes it useful in the development of materials with improved surface properties, such as increased durability, reduced friction, and enhanced adhesion.

InChI:InChI=1/C12H10S/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13H

Upstream product

• 19262-78-3 biphenyldiazonium 
• 140-89-6 potassium ethyl xanthogenate 
• 19813-79-7 biphenyl-4-yl-(2,4-dinitro-phenyl)-sulfide 
• 92-67-1 4-phenylalanine 
• 143-66-8 sodium tetraphenyl borate 
• 106-53-6 para-bromobenzenethiol 
• 98-80-6 phenylboronic acid 
• 1591-31-7 4-iodo-biphenyl 
• 92-69-3 4-Phenylphenol 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 62237-50-7 2-(4-pyridinyl)ethyl-4'-bromophenyl sulfide 
• 881664-08-0 3-(4-bromophenylsulfanyl)propionic acid 2-ethylhexyl ester 

Downstream Products

• 19813-92-4 1,2-di([1,1'-biphenyl]-4-yl)disulfane 
• 109880-93-5 2-(biphenyl-4-ylthio)benzophenone 
• 109880-97-9 2,9,9-triphenylthioxanthene 
• 109880-95-7 o-(biphenyl-4-ylthio)phenyl(diphenyl)methanol 
• 59039-58-6 O-ethyl O-(4-phenylthiophenyl) S-n-propyl phosphorothiolate 
• 1345020-97-4 6-aminosulfonyl-3-(4-biphenyl)-1,3,2-benzodithiazolium ylide 1,1-dioxide 
• 144432-80-4 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Characterization of the conductivity of organic thiols by field emission microscopy and field emission spectroscopy

The conducting properties of two organic thiols (5-mercapto-2,2′-bithiophene and 4-mercaptobiphenyl) deposited by the self-assembly method on Pt tips have been characterized in ultrahigh vacuum by field emission microscopy and spectroscopy. It was shown that these two molecular species can be successfully adsorbed from solution on the Pt tip. The presence of the molecules causes a large decrease in the required field emission voltages by a factor of ～3-5. Measurement of the total energy distributions of the emitted electrons showed that the electrons are emitted from a narrow band which is not pinned at the Fermi level but which shifts to lower energy with increased applied field. The molecules thus appear more like an insulator than a conductor. Significant current-induced heating of the molecules was found: for example, ΔT ≈ 80 K for 0.3 nA. Taken together these properties pose problems for the use of these and similar one-dimensional molecules as current-carrying connections in proposed nanoscale electronic applications. However, when used in the subpicoampere range, the current through the wire may be sustainable and dissipation small. In general, these experiments open a door to exploring other molecules.

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Discovery of 3,5-Dimethyl-4-Sulfonyl-1 H-Pyrrole-Based Myeloid Cell Leukemia 1 Inhibitors with High Affinity, Selectivity, and Oral Bioavailability

Myeloid cell leukemia 1 (Mcl-1) protein is a key negative regulator of apoptosis, and developing Mcl-1 inhibitors has been an attractive strategy for cancer therapy. Herein, we describe the rational design, synthesis, and structure-activity relationship study of 3,5-dimethyl-4-sulfonyl-1H-pyrrole-based compounds as Mcl-1 inhibitors. Stepwise optimizations of hit compound 11 with primary Mcl-1 inhibition (52%@30 μM) led to the discovery of the most potent compound 40 with high affinity (Kd = 0.23 nM) and superior selectivity over other Bcl-2 family proteins (>40,000 folds). Mechanistic studies revealed that 40 could activate the apoptosis signal pathway in an Mcl-1-dependent manner. 40 exhibited favorable physicochemical properties and pharmacokinetic profiles (F% = 41.3%). Furthermore, oral administration of 40 was well tolerated to effectively inhibit tumor growth (T/C = 37.3%) in MV4-11 xenograft models. Collectively, these findings implicate that compound 40 is a promising antitumor agent that deserves further preclinical evaluations.

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-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.