17534-15-5

Basic information

• Product Name: 1,2-BENZENEDITHIOL
• Synonyms: 1,2-BENZENEDITHIOL;1,2-DIMERCAPTOBENZENE;1,2-DIMERCAPTOBENZOL;BENZOL-1,2-DITHIOL;BENZENE-1,2-DITHIOL;DITHIOCATECHOL;1,2-Benzenedithiol(9CI);1,2-Benzenedithiol, GC 96 %
• CAS NO: 17534-15-5
• Molecular Formula: C₆H₆S₂
• Molecular Weight: 142.24
• EINECS: 241-530-4
• Product Categories: THIOL;Charge Transfer Complexes (Synthetic Intermediates);Charge Transfer Complexes for Organic Metals;Functional Materials;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 17534-15-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 22-24 °C(lit.)
• Boiling Point: 119-120 °C17 mm Hg(lit.)
• Flash Point: 219 °F
• Appearance: Clear light yellow/Liquid After Melting
• Density: 1.236 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0624mmHg at 25°C
• Refractive Index: 1.6565-1.6585
• Storage Temp.: 2-8°C
• Solubility: water: slightly soluble
• PKA: 5.90±0.43(Predicted)
• Water Solubility: Soluble in water, benzene, ethanol, diethyl ether, ethyl acetate.
• Sensitive: Air Sensitive
• BRN: 636154
• CAS DataBase Reference: 1,2-BENZENEDITHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BENZENEDITHIOL(17534-15-5)
• EPA Substance Registry System: 1,2-BENZENEDITHIOL(17534-15-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• RIDADR: 2810
• WGK Germany: 3
• F: 10-13-23
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 17534-15-5(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid after melting

Uses

1,2-Benzenedithiol is used in preparation of schiff base, which is employed to make new series of copper(II) and zinc(II) complexes.

Synthesis Reference(s)

Synthesis, p. 471, 1976 DOI: 10.1055/s-1976-24088

General Description

The transition metal complexes with benzene-1,2-dithiol as ligand were studied by UV-vis, resonance Raman (rR) and infrared (IR) spectroscopies.

Purification Methods

Likely impurities are the oxidation products, the disulfides which could be polymeric. Dissolve it in aqueous NaOH until the solution is alkaline. Extract with Et2O and discard the extract. Acidify with cold HCl (diluted 1:1 by volume with H2O) to Congo Red paper under N2 and extract it three times with Et2O. Dry the Et2O with Na2SO4, filter, evaporate and distil the residue under reduced pressure in an atmosphere of N2. The distillate solidifies on cooling. [UV: Dewar et al. J Chem Soc 3076 1958, Grunwald & Berkowitz J Am Chem Soc 81 4939 1951, Ferretti Org Synth Coll Vol V 419 1973, Beilstein 6 IV 5651.]

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

Upstream product

• 85609-04-7 1,2-bis(ethylthio)benzene 
• 55315-56-5 2-(3-methylbutoxy)-1,3-benzodithiole 
• 95-50-1 1,2-dichloro-benzene 
• 934-36-1 2-thioxo-1,3-benzodithiole 
• 62576-04-9 benzo[d]-1,3-dithiolane-2-one 
• 7647-01-0 hydrogenchloride 
• 6461-76-3 1,2-benzenedisulfonyl dichloride 
• 809277-86-9 bromo(dithiocatechol)borane 
• 861304-67-8 5,5'-dibromo-2,2'-disulfanediyl-bis-benzenesulfonyl chloride 
• 60655-82-5 5-chloro-2-(methylthio)benzenesulfonyl chloride 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 137-07-5 2-amino-benzenethiol 
• 273-77-8 benzo[1,2,3]thiadiazole 
• 60655-83-6 4-bromo-1,2-benzenedithiol 

Downstream Products

• 63928-30-3 1,2-bis-acetylsulfanyl-benzene 
• 61666-78-2 2-phenylbenzo--1,3-dithiolane 
• 76381-53-8 4-Benzo[1,3]dithiol-2-yl-phenol 
• 61666-75-9 2-(4-metoxyphenyl)benzo[d][1,3]dithiole 
• 36198-83-1 2-({2-[(2-hydroxy-2-oxoethyl)thio]phenyl}thio)acetic acid 
• 854877-35-3 bis-[2-(2,2-diethoxy-ethylsulfanyl)-phenyl]-disulfide 
• 934-36-1 2-thioxo-1,3-benzodithiole 
• 109502-48-9 4-(trans-2-benzo[1,3]dithiol-2-ylvinyl)-N,N-dimethyl-aniline 
• 20534-18-3 2-phenyl-benzo[1,3,2]oxathiaborole 
• 76381-50-5 2-(2-nitrophenyl)-1,3-benzodithiolane 
• 2388-68-3 o-bis(mercaptomethyl)benzene 
• 54615-64-4 o-methylthiobenzolthiol 
• 84384-24-7 N,N'-Carbonylbis(1,3-benzodithiol-2-imin) 
• 147089-19-8 1-Benzenesulfonyl-3-[2-(4-chloro-phenyl)-benzo[1,3]dithiol-2-yl]-1H-pyrrole 

Relevant articles and documents

Copper(I) and Copper(II) Chelates containing Imidazole and Thioether Groups; Synthesis of the Ligand 1,2-Bis(benzimidazol-2'-ylmethylthio)-benzene (bbtb) and the X-Ray Crystal Structure at -52 deg C of 2*5EtOH

Stable copper(I) and copper(II) complexes of the title ligand (bbtb) have been prepared.The design of the ligand prevents planar four-co-ordination of CuII.The X-ray structure of 2*5EtOH shows that the co-ordination geometry around the metal ion is trigonal bipyramidal.Two benzimidazole nitrogen atoms occupy axial positions, the equatorial positions being occupied by the two thioether sulphur atoms and an oxygen atom of a co-ordinated water molecule.The structure is compared with recently solved structures of closely related imidazole-thioether chelates.The compound crystallizes in the monoclinic space group P21/n with a=18.865(3), b=12.652(2), c=17.902(7) Angstroem, β=101.99(2) deg, and Z=4.The intensities of 5 095 independent reflections were measured on an automatic diffractometer at -52 deg C (to prevent decomposition).The structure was solved by direct methods and refined using full-matrix least-squares techniques to a residual R of 0.069 for 2 869 reflections with l>2δ(l).The e.s.r. spectrum of the solid compound 2*2H2O is 'exchange narrowed' and shows only one signal.The ligand-field spectrum is consistent with a trigonal-bipyramidal geometry.The e.s.r. and ligand-field data indicate a co-ordination geometry in solution which is different from the solid state, and in which the unpaired electron is mainly in a dx2-Y2 orbital.

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An efficient one-pot synthesis of 1,2-benzenedithiol from benzenethiol

1,2-Benzenedithiol (3) can be prepared on a molar scale and isolated in 96% yield by a convenient one-pot procedure starting from benzenethiol. This method utilizes recent discoveries on the formation of dilithium 1,2-benzenedithiolate (2) via directed ortho-lithiation of lithium benzenethiolate.

Photochemical studies on bis-sulfide and -sulfone tethered polyenic derivatives

This study focusses on the [2 + 2]-photocycloaddition of a symmetric polyenic system tethered by an aryl bis-sulfide or sulfone platform. Using direct irradiation or photosensitization, no expected ladderane product was isolated. In most cases, only tricyclic products including a single cyclobutane moiety were formed. Irradiation of bis-acrylic precursors in water with encapsulation by a host (cyclodextrin or cucurbituril) provided a stereoselective access to valuable cyclobutyl adducts.

2-FLUORO-1,3-BENZODITHIOL 1,1,3,3-TETRAOXIDE DERIVATIVE, PRODUCTION METHOD THEREOF, AND PRODUCTION METHOD OF MONOFLUOROMETHYL GROUP-CONTAINING COMPOUND USING THE SAME

A 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative as a monofluoromethyl group introduction agent that is effective as an intermediate in pharmaceutical and agrochemical synthesis, a production method thereof, and a production method of a monofluoromethyl group-containing compound using this 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative are provided. The 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative represented by the following general formula (1) (wherein R1, R2, R3, and R4 each independently represent a hydrogen atom, a straight-chain or branched alkyl group having 1 to 4 carbon atoms, a straight-chain or branched alkyloxy group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group), the production method thereof, and various monofluoromethyl group-containing compounds are manufactured using this 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative as a monofluoromethylating agent.