624-39-5

Basic information

• Product Name: 1,4-BENZENEDITHIOL
• Synonyms: 1,4-Dimercaptobenzene~Dithiohydroquinone;1,4-Benzenedithiol,95%;1,4-Benzenendithiol;1,4-dimercaptobenzene;p-Benzenedithiol;Benzene-1,4-dithiol;Benzene-1,4-dithiol 99% (GC);P-BDT
• CAS NO: 624-39-5
• Molecular Formula: C₆H₆S₂
• Molecular Weight: 142.24
• EINECS: -0
• Product Categories: Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 624-39-5.mol

Chemical Properties

• Melting Point: 90°C
• Boiling Point: 243.3 °C at 760 mmHg
• Flash Point: 111.8 °C
• Appearance: white to light yellow solid
• Density: 1.240±0.06 g/cm3(Predicted)
• Vapor Pressure: 0.0506mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 5.92±0.10(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Air Sensitive
• BRN: 1680022
• CAS DataBase Reference: 1,4-BENZENEDITHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BENZENEDITHIOL(624-39-5)
• EPA Substance Registry System: 1,4-BENZENEDITHIOL(624-39-5)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 9
• Hazardous Substances Data: 624-39-5(Hazardous Substances Data)

Usage

Uses

Used in Electronic Devices:
1,4-Benzenedithiol is used as a component in single molecule junctions for electronic devices. Its unique electronic properties and ability to form stable junctions make it a promising candidate for use in molecular electronics and nanoscale devices.
Used in Nanomaterial Synthesis:
1,4-Benzenedithiol is used as a reducing agent and stabilizing agent in the synthesis of various nanomaterials, including silver and gold nanoparticles. Its strong reducing properties allow it to reduce metal ions to their respective nanoparticles, while its thiol groups provide a stabilizing effect, preventing aggregation and promoting dispersion of the nanoparticles.
Used in Self-Assembled Monolayers:
1,4-Benzenedithiol is used in the formation of self-assembled monolayers (SAMs) on various surfaces, such as gold and silver. The thiol groups of 1,4-Benzenedithiol can form strong covalent bonds with the metal surfaces, creating a well-ordered and stable monolayer. These SAMs have applications in sensors, surface coatings, and other areas where controlled surface properties are required.
Used in Electrode Preparation:
1,4-Benzenedithiol is used in the preparation of gold electrodes for various applications, such as in electrochemistry and biosensors. The formation of a self-assembled monolayer of 1,4-Benzenedithiol on the gold surface can improve the electrode's performance, stability, and selectivity.

InChI:InChI=1/C6H6S2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H/p-2

Upstream product

• 722-27-0 bis(4-aminophenyl)disulfide 
• 17661-83-5 1,4-Bis(ethylthio)benzene 
• 25733-03-3 1,4-dithiocyanatobenzene 
• 179748-74-4 1,4-bis-trichloromethylsulfanyl-benzene 
• 62-53-3 aniline 
• 106-46-7 para-dichlorobenzene 
• 1122-97-0 4-methylsulfanyl-thiophenol 
• 10387-40-3 potassium thioacetate 
• 589-87-7 1,4-bromoiodobenzene 
• 17356-08-0 thiourea 
• 106-39-8 bromochlorobenzene 
• 7647-01-0 hydrogenchloride 
• 6461-77-4 benzene-1,4-disulfonyl chloride 
• 64-17-5 ethanol 

Downstream Products

• 109845-99-0 1,4-bis-(2,2-dimethoxy-ethylsulfanyl)-benzene 
• 6461-77-4 benzene-1,4-disulfonyl chloride 
• 53518-12-0 benzene-1,4-disulfonyl bromide 
• 10154-61-7 S,S'-1,4-phenylene dithioacetate 
• 54952-19-1 1,4-bis(4-nitrophenylsulfenyl)benzene 
• 109559-56-0 1,4-bis-(2-nitro-phenylsulfanyl)-benzene 
• 134520-27-7 1,4-bis-(3-dimethylamino-propylsulfanyl)-benzene 
• 20084-29-1 1,4-benzenebis(thioacetic acid) 
• 129691-60-7 1,4-bis-phenacylmercapto-benzene 
• 132180-53-1 1,4-bis-(2,4-dinitro-phenylsulfanyl)-benzene 
• 699-20-7 1,4-Bis(methylthio)benzene 
• 24589-07-9 1,4-bis-(2-hydroxy-ethylsulfanyl)-benzene 
• 38300-99-1 1,4-Bis-styrylmercaptobenzol 
• 30818-50-9 benzene-1,4-disulfenyl chloride 

Relevant articles and documents

Redox-Active 1D Coordination Polymers of Iron-Sulfur Clusters

Here we describe the combination of an archetypal redox-active metal sulfide cluster, Fe4S4, with an organic linker, 1,4-benzenedithiolate, to prepare coordination polymers containing infinite chains of Fe4S4 cl

Preparation method of p-dithiophenol

The invention discloses a preparation method of p-dithiophenol, wherein the p-dithiophenol is directly synthesized from p-dichlorobenzene and sodium hydrosulfide under a reaction of a catalyst. The p-dithiophenol obtained by the preparation method disclos

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.

Synthetic method for 1,4-dithioalkyl benzene and halide thereof

The invention relates to a synthetic method for 1,4-dithioalkyl benzene and halide thereof. According to the method, 4-bromothiophenol is used as a raw material and reacts with alkyl bromide to synthesize 4-bromo-1-thioalkyl benzene, and then a reaction is carried out to synthesize 1,4-dithioalkyl benzene; or 4-bromothiophenol successively reacts with n-butyl lithium, sulfur powder and acid to synthesize 1,4-benzenedithiol, and then1,4-benzenedithiol reacts with alkyl bromide to synthesize 1,4-dithioalkyl benzene; and 1,4-dithioalkyl benzene can be further halogenated. The synthetic method provided by the invention does not need flammable and combustible t-butyl lithium, so the synthetic method has better security and controllability, is favorable for large-scale industrial production, reduces production cost and is environment friendly.

MALDI-TOF/TOF CID study of poly(p-phenylene sulfide) fragmentation reactions

A study involving the evaporation-grinding MALDI sample preparation method, MALDITOF/TOF CID, and Py-GC/MS is presented to examine the fragmentation mechanisms of poly(p-phenylene sulfide) (PPS). MALDI-TOF/TOF CID fragmentation studies yielded a wealth of information about the mass, structure (linear or cyclic), end-groups, and backbone modifications of the polymer. Additionally, Py-GC/MS experimental data are presented for comparison of the multimolecular free radical reactions in pyrolysis with the unimolecular fragmentation reactions of MS/MS.1,2 TOF/TOF CID results indicate that linear PPS undergoes random main chain fragmentation along the polymer backbone and preferentially fragments at bonds adjacent to dibenzothiophene and phenyl end-groups. Cyclic species produce fragment ions similar to linear species. However, the MS/MS precursor ions for cyclic PPS are, by far, the most intense peaks, while the precursor ions for linear species show relatively low intensity. CID fragmentation results are supported by Py-GC/MS data and are consistent with the proposed degradation mechanisms.

Process for preparation of aromatic thiols

Disclosed is a process for preparation of an aromatic thiol corresponding to the structure wherein A is a substituted or unsubstituted aromatic radical and n is 1, 2, 3, 4, 5 or 6 comprising contacting at a temperature of at least 80° C. an aromatic halide corresponding to the structure wherein A is the same as above, X is bromine or iodine and n is 1, 2, 3, 4, 5, or 6 with thiourea in the presence of nickel metal.

HIGH-TEMPERATURE ORGANIC SYNTHESIS. XLI. REACTIONS OF AROMATIC HALOGEN COMPOUNDS WITH HYDROGEN SULFIDE IN THE PRESENCE OF SULFUR

The reactions of halogenoarenes containing a sufficiently mobile halogen atom with hydrogen sulfide in the presence of elemental sulfur at 90-230 deg C lead to the corresponding sulfides (with yields of up to 87percent).The disulfides, thiols, and arenes are formed at the same time.In the reactions of bromophenols with hydrogen sulfide in the presence of sulfur migration of the halogen atom is observed, and this leads to the formation of isomeric bis(hydroxyphenyl) sulfides and disulfides and 2,4-dibromophenol.It was established that the yield of the reaction products depends on the time, temperature, halogenophenol-sulfur ratio, and delivery rate of hydrogen sulfide.The radical mechanism of the formation of these substances is discussed.

Spectra, Ionization Constants, and Rates of Oxidation of 1,4-Dimercaptobenzene and Properties of the p-Mercaptophenylthiyl and p-Benzodithiyl Anion Radicals

In basic solution, p-dimercaptobenzene, which is found to have pKa's of 6.0 and 7.7, is rapidly oxidized by azide radical (k = 7.4*109 M-1 s-1) to p-benzodithiyl radical anion, the sulfur analog of p-benzosemiqu

THE REACTION BETWEEN ARENEDIAZONIUM TETRAFLUOROBORATES AND ALKALINE THICARBOXYLATES IN DMSO: A CONVENIENT ACCESS TO ARYL THIOLESTERS AND OTHER AROMATIC SULFUR DERIVATIVES.

The reaction between potassium thioacetate or sodium thiobenzoate and arenediazonium tetrafluoroborates in DMSO leads to the corresponding aryl thiolesters 1 which can either be isolated or further reacted providing a convenient one-pot access to a number of other aromatic sulfur derivatives.

SYNTHESIS OF AROMATIC THIOLS FROM ARYL IODIDES AND THIOUREA BY MEANS OF NICKEL CATALYST

Nickel(0) complex, generated in situ from bis(triethylphosphine)nickel(II) chloride and sodium cyanoborohydride, catalyzed the nucleophilic displacement of aryl iodides with thiourea.S-Aryl-isothiuronium salts or aromatic thiols were obtained in good yields after simple work-up procedures.