626-04-0

Basic information

• Product Name: 1,3-BENZENEDITHIOL
• Synonyms: 1,3-DIMERCAPTOBENZENE;1,3-BENZENEDITHIOL;1,3-BENZENEDITHIOLE;BENZENE-1,3-DITHIOL;M-BDT;1,3-Benzedithiol;1,3-Dimercaptobenzene~Dithioresorcinol;Dithioresorcinol
• CAS NO: 626-04-0
• Molecular Formula: C₆H₆S₂
• Molecular Weight: 142.24
• EINECS: 210-925-3
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans
• Mol File: 626-04-0.mol

Chemical Properties

• Melting Point: 24-25 °C(lit.)
• Boiling Point: 128-129 °C16 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /solid
• Density: 1.24
• Vapor Pressure: 0.0477mmHg at 25°C
• Refractive Index: 1.6625
• Solubility: Miscible with acetonitrile.
• PKA: 5.84±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 1634412
• CAS DataBase Reference: 1,3-BENZENEDITHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BENZENEDITHIOL(626-04-0)
• EPA Substance Registry System: 1,3-BENZENEDITHIOL(626-04-0)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• RIDADR: UN 3335
• WGK Germany: 3
• F: 9-13
• PackingGroup: III
• Hazardous Substances Data: 626-04-0(Hazardous Substances Data)

Usage

Uses

Used in Solar Cell Industry:
1,3-Benzenedithiol is used as an intermediate in the preparation of 1,3-bis(-styrylthio)-benzol, which is a key component in the fabrication of hybrid solar cells. It helps to improve the power conversion efficiency of cadmium selenide nanorods/poly(3-hexylthiophene) hybrid solar cells by enhancing the charge transport and separation properties of the active layer.
Used in Organic Synthesis:
1,3-Benzenedithiol is used as a building block in the synthesis of various organic compounds, including dyes, pharmaceuticals, and polymers. Its unique chemical structure allows for the formation of stable thioether linkages, which can be used to create a wide range of functional materials with diverse properties.
Used in Analytical Chemistry:
1,3-Benzenedithiol can be used as a reagent in analytical chemistry for the detection and quantification of metal ions, such as copper, silver, and mercury. It forms stable complexes with these metal ions, which can be analyzed using various spectroscopic techniques, such as UV-Vis and fluorescence spectroscopy.

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

Synthetic route

1,3-Bis-(dimethylcarbamoylthio)-benzol (50667-85-1) → 3-mercaptothiophenol (626-04-0)

Conditions	Yield
With potassium hydroxide In ethylene glycol for 1h; Heating;	98.5%
With potassium hydroxide In methanol Heating;

3-aminobenzenesulfonic acid (121-47-1) → 3-mercaptothiophenol (626-04-0)

Conditions	Yield
Reaktion ueber mehrere Stufen;

1,3-bis-trichloromethylsulfanyl-benzene (861601-41-4) + aniline (62-53-3) → 3-mercaptothiophenol (626-04-0) + N,N',N''-triphenylguanidine (101-01-9)

1,3-Dichlorobenzene (541-73-1) → 3-mercaptothiophenol (626-04-0)

Conditions	Yield
With sodium isopropanethiolate; sodium 1.) HMPA, 2.) 100 deg C; Yield given. Multistep reaction;

benzene-1,3-disulfonyl chloride (585-47-7) + tin + hydrochloric acid → 3-mercaptothiophenol (626-04-0)

hydrogenchloride (7647-01-0) + benzene-1,3-disulfonyl chloride (585-47-7) + zinc → 3-mercaptothiophenol (626-04-0)

3-mercaptothiophenol (626-04-0) + 1,10-dibromodecane (4101-68-2) → 2,4-Benzo-1,5-dithiacyclopentadec-2-ene (75703-91-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 45 - 50℃;	95%
With caesium carbonate In N,N-dimethyl-formamide at 50℃;	95%

3-mercaptothiophenol (626-04-0) + η6-m-chlorotoluene-η5-cyclopentadienyliron hexafluorophosphate → (η6-phenylene-1,3-dithiobis(3-methylbenzene))bis(η5-cyclopentadienyliron) hexafluorophosphate

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide stirring under N2 atmosphere for 16 h at room temperature; filtn. through a sintered glass crucible into a HCl soln., evapn. (reduced pressure), addn. of aq. NH4PF6, filtn., drying (vac.), washing (ether), drying;	95%

3-mercaptothiophenol (626-04-0) + chloro-diphenylphosphine (1079-66-9) → C30H24P2S2

Conditions	Yield
Stage #1: 3-mercaptothiophenol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: chloro-diphenylphosphine In tetrahydrofuran Reflux; Inert atmosphere; Schlenk technique; Glovebox;	95%

3-mercaptothiophenol (626-04-0) + diphenyllead(IV) diacetate → {(C6H5)2Pb(C6H4S2)}2 (95151-76-1)

Conditions	Yield
In methanol exclusion of light; addn. of soln. of dithiol in abs. methanol to a suspension of Pb compd. in abs. methanol (preparing suspension with ice cooling); sepn. of a yellow compd.;; filtration of ppt. after 1h; washing with methanol or acetone; drying in vac.; elem. anal.;;	93%
In acetone exclusion of light; addn. of soln. of dithiol in acetone to a suspension of Pb compd. in acetone (preparing suspension with ice cooling); sepn. of a yellow compd.;; filtration of ppt. after 1h; washing with methanol or acetone; drying in vac.; elem. anal.;;	93%

3-mercaptothiophenol (626-04-0) + Chlorodiisopropylphosphane (40244-90-4) → C18H32P2S2

Conditions	Yield
Stage #1: 3-mercaptothiophenol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: Chlorodiisopropylphosphane In tetrahydrofuran at 20℃; for 1h; Glovebox; Schlenk technique; Inert atmosphere;	93%

3-mercaptothiophenol (626-04-0) + methyl iodide (74-88-4) → 1,3-bis(methylthio)benzene (2388-69-4)

Conditions	Yield
With sodium hydroxide In methanol for 3h; Heating;	92%
With potassium carbonate In acetone at 50℃;	88%

sodium tetrafluoroborate (13755-29-8) + 3-mercaptothiophenol (626-04-0) + tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate (53317-87-6) → phenylene-1-bis[(triphenylphosphine)gold(I)]sulfonio-3-[(triphenylphosphine)gold(I)]thiolate tetrafluoroborate (448280-28-2)

Conditions	Yield
In dichloromethane byproducts: H2O; a soln. of complex in CH2Cl2 was treated with a soln. of dithiol in CH2Cl2 and a small quantity of NaBF4 at 20°C for 1 h (N2); ppt. was filtered off, crystd. upon addn. of pentane and cooling to -20°C, crystals were dried in vac.; elem. anal.;	92%

3-mercaptothiophenol (626-04-0) + acrylonitrile (107-13-1) → 3,3'-(m-phenylenedithio)dipropionitrile (16079-08-6)

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran; methanol at -78 - 20℃; Inert atmosphere;	90%
With trimethylamine

3-mercaptothiophenol (626-04-0) + [5-(4-tert-Butyl-benzoyl)-2,4-dichloro-phenyl]-(4-tert-butyl-phenyl)-methanone → 3,5,17,19-tetra(4'-tert-butylbenzoyl)-1,8,15,22-tetrathia[1.1.1.1]metacyclophane

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 100℃;	90%

3-mercaptothiophenol (626-04-0) + (η6-chlorobenzene)(η5-cyclopentadienyl)iron(II) hexafluorophosphate → (η6-phenylene-1,3-dithiobis(benzene))bis(η5-cyclopentadienyliron) hexafluorophosphate

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide stirring under N2 atmosphere for 16 h at room temperature; filtn. through a sintered glass crucible into a HCl soln., evapn. (reduced pressure), addn. of aq. NH4PF6, filtn., drying (vac.), washing (ether), drying;	90%

3-mercaptothiophenol (626-04-0) + η6-2,6-dimethylchlorobenzene-η5-cyclopentadienyliron hexafluorophosphate → (η6-phenylene-1,3-dithiobis(2,6-dimethylbenzene))bis(η5-cyclopentadienyliron) hexafluorophosphate

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide stirring under N2 atmosphere for 16 h at room temperature; filtn. through a sintered glass crucible into a HCl soln., evapn. (reduced pressure), addn. of aq. NH4PF6, filtn., drying (vac.), washing (ether), drying;	90%

Upstream product

• 121-47-1 3-aminobenzenesulfonic acid 
• 50667-85-1 1,3-Bis-(dimethylcarbamoylthio)-benzol 
• 541-73-1 1,3-Dichlorobenzene 
• 585-47-7 benzene-1,3-disulfonyl chloride 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 861601-41-4 1,3-bis-trichloromethylsulfanyl-benzene 
• 62-53-3 aniline 

Downstream Products

• 861601-60-7 1,3-bis-ethylsulfanyl-benzene 
• 855242-32-9 1,3-bis-(2,2-dimethoxy-ethylsulfanyl)-benzene 
• 856811-24-0 3,3'-m-phenylenedimercapto-di-propionic acid 
• 95800-91-2 m-bis(benzylthio)benzene 
• 96847-76-6 1,3-bis-(4-nitro-phenylsulfanyl)-benzene 
• 20084-31-5 m-phenylenedimercaptodi-acetic acid 
• 861377-72-2 1,3-bis-phenacylmercapto-benzene 
• 2388-69-4 1,3-bis(methylthio)benzene 
• 65144-65-2 3-(methylthio)benzenethiol 
• 16079-06-4 1,3-bis-vinylmercapto-benzene 
• 56510-29-3 1,3-bis-ethenesulfonyl-benzene 
• 30818-52-1 4,4'-m-phenylenebissulfanyl-bis-morpholine 
• 41562-20-3 C₁₈H₂₆N₄O₈S₂ 
• 87010-67-1 1,3-bis<2-(1-benzoyl-2-pyrrolidinyl)ethylthio>benzene 

Relevant articles and documents

Organophotoreceptor with a charge transport material having two (9-fluorenylidene) malononitrile groups

The present invention provides an organophotoreceptor comprising an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising:(a) a charge transport material having the formulaX―Z―X'???where X and X' are, each independently, a (9-fluorenylidene)malononitrile group, and Z is a linking group having the formula -(CH2)m-, branched or linear, where m is an integer between 1 and 30, inclusive, and one or more of the methylene groups may be replaced by O, S, C=O, Si=O, S(=O)2, P(=O)2, an aromatic group, a heterocyclic group, an aliphatic cyclic group, a Si(R1)(R2) group, a BR3 group, a NR4 group, a CHR5 group, or a CR6R7 group where R1, R2, R3, R4, R5, R6, and R7 are, each independently, H, halogen, hydroxyl, thiol, an alkoxy group, an alkyl group, an alkenyl group, an aromatic group, a heterocyclic group, or a part of a cyclic ring; and(b) a charge generating compound.Corresponding electrophotographic apparatuses and imaging methods are described.

Syntheses d'analogues soufres d'isocannabinoides et de tetrahydrocannabinols

A systematic synthesis of thio compounds of isocannabinoids and tetrahydrocannabinols is described.The thiophenols were prepared by the Newman-Kwart reaction.The reaction of > has been used for the synthesis of citrylidene thiophenol.The structure of citrylidene monothioolivetol was established by spectroscopic and chemical methods.The synthesis of (-) 1'thio Δ1,6 THC is also described; this compound has potential biologic properties.

Fragmentation of Aryl Alkyl Sulfides. A Simple, One-Pot Synthesis of Polymercaptobenzenes from Polychlorobenzenes

A simple procedure is described which allows one to prepare polymercaptobenzenes starting from chlorobenzenes.The reactions of all the possible chlorobenzenes with Me2CHSNa in HMPA give the corresponding (isopropylthio)benzenes which can be cleaved by adding sodium to the reaction mixtures to give the arenethiolates in good yields.In some cases the polymercaptobenzenes were isolated after treatment with acid; in other cases methyl iodide was added to the reaction mixture and poly(methylthio)benzenes were obtained.It is suggested that the (isopropylthio)benzenes react with sodium to give the corresponding radical anions which fragment at the sulfur-alkyl bond to give the arenethiolates.

Pesticidal compositions containing phosphoric esters and divalent sulphur compounds

Pesticidal composition comprising: a pesticidal, phosphoric ester the molecule of which has at least one alkyl group of 1 to 3 carbon atoms, 0.05 to 10% of an agent stabilizing the said ester against decomposition by protonisation, together with adjuvants characterized in that the stabilizing agent comprises at least one sulphur compound containing per molecule at least one divalent sulphur atom of which one valence is bonded to an atom chosen from sulphur, carbon, nitrogen, hydrogen, and metals capable of giving a salt, the other valence being bonded to an atom chosen from hydrogen, the carbon atom already noted, a second carbon atom, the nitrogen atom already noted, a second nitrogen atom, the metal atom already noted in the case of a metal of valence greater than one, a second atom of metal and oxygen when the first valence is not attached to an atom of hydrogen, the proportion of sulphur calculated with reference to the weight of the sulphur compound being between 5 and 99%. Process for stabilizing a phosphoric ester of which the molecule possesses at least one alkyl group containing 1 to 3 carbon atoms characterized in that there is added to the phosphoric ester or to a mixture which contains it, 0.05 to 10% calculated on the weight of the phosphoric acid ester of an agent capable of stabilizing the said phosphoric ester against protonisation and comprising at least one sulphur compound such as that defined thereupon.