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
• Article Data: 4

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

1,3-Benzenedithiol is used to improve power conversion efficiency in cadmium selenide nanorods/poly(3-hexylthiophene) hybrid solar cells. It acts as an intermediate as well as involved in the preparation of 1,3-bis(-styrylthio)-benzol.

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

Downstream Products

• 856811-24-0 3,3'-m-phenylenedimercapto-di-propionic acid 
• 861601-60-7 1,3-bis-ethylsulfanyl-benzene 
• 855242-32-9 1,3-bis-(2,2-dimethoxy-ethylsulfanyl)-benzene 
• 95800-91-2 m-bis(benzylthio)benzene 
• 20084-31-5 m-phenylenedimercaptodi-acetic acid 
• 16079-04-2 1,3-bis-(2-hydroxy-ethylsulfanyl)-benzene 
• 16079-06-4 1,3-bis-vinylmercapto-benzene 
• 56510-29-3 1,3-bis-ethenesulfonyl-benzene 
• 16132-81-3 m-Phenylen-bis-(δ-hydroxy-butyl)-sulfid 
• 70530-28-8 C₁₆H₃₄B₆N₆S₂ 
• 87010-67-1 1,3-bis<2-(1-benzoyl-2-pyrrolidinyl)ethylthio>benzene 
• 126441-04-1 2,2'-(1,3-Phenylenedithio)bis(1,4-benzoquinone) 
• 24197-91-9 1.3-Bis-(4-chlor-benzoylmercapto)-benzol 
• 24252-94-6 1.3-Bis-(4-nitro-benzoylmercapto)-benzol 

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.

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.