2388-68-3

Basic information

• Product Name: 1,2-BENZENEDIMETHANETHIOL
• Synonyms: 1,2-BENZENEDIMETHANETHIOL;1,2-Benzenebis(methanethiol);1,2-Phenylenebis(methanethiol);Benzene-1,2-bis(methanethiol);Benzene-1,2-bismethanethiol;o-Phenylenebis(methanethiol);1,2-bis(methylsulfanyl)benzene;1,2-bis(methylthio)benzene
• CAS NO: 2388-68-3
• Molecular Formula: C₈H₁₀S₂
• Molecular Weight: 170.29
• Product Categories: Sulfur;Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans
• Mol File: 2388-68-3.mol

Chemical Properties

• Melting Point: 43-45 °C(lit.)
• Boiling Point: 160 °C20 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.1604 (rough estimate)
• Vapor Pressure: 0.00514mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• CAS DataBase Reference: 1,2-BENZENEDIMETHANETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BENZENEDIMETHANETHIOL(2388-68-3)
• EPA Substance Registry System: 1,2-BENZENEDIMETHANETHIOL(2388-68-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 2388-68-3(Hazardous Substances Data)

Usage

Uses

Used in Nanotechnology:
1,2-Benzenedimethanethiol is used as a stabilizing agent for lead sulfide (PbS) quantum dots. It plays a crucial role in the synthesis process, helping to control the size, shape, and optical properties of the quantum dots. The use of 1,2-benzenedithiol in this application allows for the creation of highly stable and uniform quantum dots with improved performance in various electronic and optoelectronic devices.
Used in Organic Synthesis:
1,2-Benzenedimethanethiol is used as a key intermediate in the synthesis of various organic compounds, including 1,3-dihydrobenzo[c]thiophene. This heterocyclic compound is an important building block in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. The presence of the thiol groups in 1,2-benzenedithiol allows for versatile synthetic routes and the formation of a wide range of target molecules through various chemical reactions, such as condensation, substitution, and cyclization.

InChI:InChI=1/C8H10S2/c9-5-7-3-1-2-4-8(7)6-10/h1-4,9-10H,5-6H2

Upstream product

• 624-92-0 Dimethyldisulphide 
• 367-11-3 ortho-difluorobenzene 
• 124-38-9 carbon dioxide 
• 17534-15-5 Benzene-1,2-dithiol 
• 2987-53-3 2-(Methylthio)aniline 
• 108-98-5 thiophenol 
• 6461-76-3 1,2-benzenedisulfonyl dichloride 
• 5188-07-8 sodium thiomethoxide 
• 74-88-4 methyl iodide 
• 71-43-2 benzene 
• 87-61-6 1,2,3-trichlorobenzene 
• 917-64-6 methyl magnesium iodide 
• 92-85-3 Thianthrene 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 85609-04-7 1,2-bis(ethylthio)benzene 
• 36198-83-1 2-({2-[(2-hydroxy-2-oxoethyl)thio]phenyl}thio)acetic acid 
• 87453-67-6 1,2-bis(propylthio)benzene 
• 29906-21-6 2-phenyl-1,3-dithia-5,6-benzcycloheptene 
• 138709-30-5 1-bromo-3,4-bis(methylthio)benzene 
• 132719-61-0 1,2-Bis(trichloromethylthio)benzene 
• 934-36-1 2-thioxo-1,3-benzodithiole 
• 132180-52-0 1,2-bis-(2,4-dinitro-phenylsulfanyl)-benzene 
• 60036-44-4 1,2-bis(methanesulfonyl)benzene 

Relevant articles and documents

Enantioselective Oxidation of Thioethers: an Easy Route to Enantiopure C2 Symmetrical bis-Methylsulfinylbenzenes

The direct oxidation of bis-methylthioethers 1 by t-butyl hydroperoxide, titanium tetra-isopropylate and (+)-diethyl tartrate, affords the almost enantiomerically pure dl bis-methylsulfinylbenzenes 2 (e.e. >/= 99percent) in a process which is also charact

Synthesis and properties of novel medium-sized heterocyclic compounds containing two sulfur atoms in the ring and synthetic approaches to conjugated cyclic disulfonium ylides

Tribenzo[bf,h][1,4]dithiecin (8) was prepared by coupling 2,2'- bis(bromomethyl)biphenyl (10) with 1,2-benzenedithiol (11) in the presence of Nail in acetonitrile. Another novel dithiecin derivative, 1,8-dihydro-2,7benzodithiecin (9) was synthesized by coupling of 1,4-dimercapto-2,3-Oisopropylidene-Lg-threitol (13a) with α,α'-dibromo-o-xylene (12), followed by hydrolysis and subsequent dehydration via the mesylate derivative (16). The benzodithiecin (9) was also prepared by treatment of dithiol (18) with butadiyne along with α,α'-bis(1-buten-3-ynylthio)-o-xylene (19) as a byproduct. Compound (19) was subjected to an intramolecular coupling reaction using CuCl-pyridine-O2 in benzene to yield the 12-membered ring compound (23). We also describe our effort to prepare the corresponding cyclic diylide compounds from the above new dithiecins (8) and (9), and known dithiecin (7).

ALTERNATIVE SYNTHESES OF DIBENZOTETRASELENAFULVALENE, OF SOME OF ITS PRECURSORS AND OF TETRASELENOALKENES ANALOGS

We report alternative syntheses of dibenzotetraselenafulvalene, of a key precursor and of tetramethylselenoethylene.

t-BuOK-promoted methylthiolation of aryl fluorides with dimethyldisulfide under transition-metal-free and mild conditions

In the presence of potassium tert-butoxide (t-BuOK), the cross-coupling reaction between aryl fluorides and dimethyldisulfide was developed. A series of aryl methyl sulfides were obtained in moderate to good yields under transition-metal-free and mild conditions.

Meta -Non-flat substituents: A novel molecular design to improve aqueous solubility in small molecule drug discovery

Aqueous solubility is a key requirement for small-molecule drug candidates. Here, we investigated the regioisomer-physicochemical property relationships of disubstituted benzenes. We found that meta-isomers bearing non-flat substituents tend to possess the lowest melting point and the highest thermodynamic aqueous solubility among the regioisomers. The examination of pharmaceutical compounds containing a disubstituted benzene moiety supported the idea that the introduction of a non-flat substituent at the meta position of a benzene substructure would be a promising approach for medicinal chemists aiming to improve the thermodynamic aqueous solubility of drug candidates, even though it might not be universally effective. This journal is

Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides

We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.

Metal-free radical thiolations mediated by very weak bases

Aromatic thioethers and analogous heavier chalcogenides were prepared by reaction of arene-diazonium salts with disulfides in the presence of the cheap and weak base NaOAc. The mild and practical reaction conditions (equimolar reagents, DMSO, r.t., 8 h) tolerate various functional groups (e.g. Br, Cl, NO2, CO2R, OH, SCF3, furans). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals.

Oximesulfonic acid esters and the use thereof as latent sulfonic acids

The invention relates to the use of oximesulfonic acid esters of formula I wherein m is 0 or 1 and x is 1 or 2; R1 is, for example, substituted phenyl, R2 has, for example, one of the meanings of R1 or is unsubstituted phe

Alkyl- and Arylthiodediazoniations of Dry Arenediazonium o-Benzenedisulfonimides. Efficient and Safe Modifications of the Stadler and Ziegler Reactions to Prepare Alkyl Aryl and Diaryl Sulfides

The reaction between dry arenediazonium o-benzenedisulfonimides 1 and sodium thiolates in anhydrous methanol represents an efficient and safe procedure, of general validity, for the preparation of unfunctionalized or variously functionalized alkyl aryl and diaryl sulfides. As a rule, the reaction temperature was maintained at 0-5°C for the alkylthiodediazoniations and at room temperature (20-25°C) for the arylthiodediazoniations. The sulfide yields are generally high; of the 63 considered examples, 43 gave yields greater than 80% and 13 were between 70% and 80%. Lower yields were obtained only when sterically hindered diazonium salts or thiols were used. A good amount of the o-benzenedisulfonimide (8) was always recovered from the reactions and could be reused to prepare salts 1. The copious experimental data collected in homogeneous conditions have offered several starting points for the study of the mechanism of these reactions.

ORGANOMETALLOIDAL COMPOUNDS WITH o-PHENYLENESUBSTITUENTS, PART XXVII. SYNTHESIS, CHARACTERIZATION AND STRUCTURE DETERMINATION OF 2,3,7,8-TETRAKIS(METHYLTHIO)- AND 2,3;7,8-BIS(ETHYLENEDITHIO)THIANTHRENE

A generally applicable synthesis synthesis via the sequence thiophenol (3), 1,2-bis(alkylthio)benzene (6), 1-bromo-3,4-bis(alkylthio)benzene (7), bissulfide (8), bissulfide (9), 2,3,7,8-tetrakis(