3570-55-6

Basic information

• Product Name: Bis(2-mercaptoethyl) sulfide
• Synonyms: 1-Mercapto-2-(Mercaptoethylthio)ethane;2,2’-Thiobis[ethanethiol];2,2’-thiobis-ethanethio;2,2'-Dimercaptodiethyl sulfide;2-[(2-Sulfanylethyl)sulfanyl]ethyl hydrosulfide;3-Thia-1,5-pentanedithiol;Bis(beta-mercaptoethyl) sulfide;Bis(mercaptoethyl) sulfide
• CAS NO: 3570-55-6
• Molecular Formula: C₄H₁₀S₃
• Molecular Weight: 154.32
• EINECS: 222-671-0
• Mol File: 3570-55-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: -11°C
• Boiling Point: 135-136 °C10 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: Clear colorless/Liquid
• Density: 1.183 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.61Pa at 20℃
• Refractive Index: n20/D 1.5961(lit.)
• Solubility: Difficult to mix.
• PKA: 9.47±0.10(Predicted)
• Water Solubility: 620mg/L at 20℃
• BRN: 1445994
• CAS DataBase Reference: Bis(2-mercaptoethyl) sulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(2-mercaptoethyl) sulfide(3570-55-6)
• EPA Substance Registry System: Bis(2-mercaptoethyl) sulfide(3570-55-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 23-24/25
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 10-13-23
• TSCA: Yes
• Hazardous Substances Data: 3570-55-6(Hazardous Substances Data)

Usage

Uses

2,2?-Thiodiethanol is used in the synthesis of novel luminescent polynuclear gold(I) phosphine complexes 2,2'-Thiodiethanethiol is used for extraction photometric determination of Ni, gives color reaction with metals.

Synthetic route

2,2'-thiobis-ethanol (111-48-8) → 3-thiapentan-1,5-dithiol (3570-55-6) + bis-mercaptodiethylsulphide

Conditions	Yield
With hydrogenchloride; hydrazine hydrate; thiourea In 5,5-dimethyl-1,3-cyclohexadiene; water	A n/a B 93%

polymer: monomers(s): 1,2-dichloroethane; sulfur → 3-thiapentan-1,5-dithiol (3570-55-6) + ethane-1,2-dithiol (540-63-6)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate Heating;	A 37% B 37%

polymer: monomers(s): bis(β-chloroethyl) sulfide; sulfur → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate at 80 - 90℃; for 3h;	34%

ethane-1,2-dithiol (540-63-6) → 3-thiapentan-1,5-dithiol (3570-55-6) + 3,6-dithiaoctan-1,8-dithiol (25423-55-6) + 2,2’-[thiobis(2,1-ethanediylthio)]bis(ethanethiol) (60147-09-3)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 4.33h; Inert atmosphere; Reflux;	A 29% B 25% C 15%

thirane (420-12-2) → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
With methanol; hydrogen sulfide at 60℃;

ethane-1,2-dithiol (540-63-6) + 1,2-dichloro-ethane (107-06-2) → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
With ethanol; potassium hydrosulfide

ethylene dibromide (106-93-4) + thiourea (17356-08-0) → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
und Verseifung des entstandenen Isothioharnstoff-Derivats mit Kalilauge;

bis (2-chloroethyl) sulphide (505-60-2) + thiourea (17356-08-0) → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
Behandeln des Reaktionsprodukts mit wss.Natronlauge;

bis(2-bromoethyl)sulfide (7617-64-3) + thiourea (17356-08-0) → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
Behandeln des Reaktionsprodukts mit wss.Natronlauge;

bis-(2-acetylsulfanyl-ethyl)-sulfane (60177-05-1) → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
With hydrogenchloride; methanol

1,2,5-trithiacycloheptane (6576-93-8) → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
With DL-dithiothreitol In d(4)-methanol; water-d2 at 25℃; Equilibrium constant; phosphate buffer(0.5 mM, pH 7.0);

bis (2-chloroethyl) sulphide (505-60-2) → 3-thiapentan-1,5-dithiol (3570-55-6)

Conditions	Yield
With lithium aluminium tetrahydride; Cs(SCOCH2)2 1.) DMF, overnight; 2.) ether; Yield given. Multistep reaction;
With sodium hydrogen sulfide at 140℃; under 22502.3 Torr; for 2h; Temperature; Pressure; Reagent/catalyst;

1,2-dichloro-ethane (107-06-2) + aqueous NaHS → 1,4-Dithiane (505-29-3) + 3-thiapentan-1,5-dithiol (3570-55-6) + 3,6-dithiaoctan-1,8-dithiol (25423-55-6) + ethane-1,2-dithiol (540-63-6)

Conditions	Yield
at 100℃; unter Druck;

ethylenebisisothiuronium dihydrobromide (6943-65-3) + KOH → 3-thiapentan-1,5-dithiol (3570-55-6) + ethane-1,2-dithiol (540-63-6)

thirane (420-12-2) + hydrogen sulfide (7783-06-4) → 3-thiapentan-1,5-dithiol (3570-55-6) + ethane-1,2-dithiol (540-63-6)

Conditions	Yield
In methanol at 60°C;

ethane-1,2-dithiol (540-63-6) → 3-thiapentan-1,5-dithiol (3570-55-6) + 3,6-dithiaoctan-1,8-dithiol (25423-55-6) + 2,2’-[thiobis(2,1-ethanediylthio)]bis(ethanethiol) (60147-09-3) + 3,6,9,12-tetrathiatetradecane-1,14-dithiol (124491-07-2)

Conditions	Yield
With potassium carbonate In water at 20 - 105℃; for 1.08333h; Inert atmosphere; Microwave irradiation;

3-thiapentan-1,5-dithiol (3570-55-6) + o-(ethoxycarbonylmethoxy)benzyl chloride (111080-49-0) → (2-{2-[2-(2-ethoxycarbonylmethoxy-benzylsulfanyl)-ethylsulfanyl]-ethylsulfanylmethyl}-phenoxy)-acetic acid ethyl ester (506444-33-3)

Conditions	Yield
With potassium hydroxide In ethanol; benzene at 20℃; for 1h;	100%

bis(β-epithiopropyl)sulfide (188829-97-2) + 3-thiapentan-1,5-dithiol (3570-55-6) → 1-[2-(2-mercaptoethylthio)ethylthio]-3-{2-mercapto-3-[2-(2-mercaptoethylthio)ethylthio]propylthio}propane-2-thiol

Conditions	Yield
With triphenylphosphine at 20 - 60℃; for 10h; Inert atmosphere;	100%
With sodium ethanolate In methanol at 25℃; for 3.5h;

3-thiapentan-1,5-dithiol (3570-55-6) + bis(β-epithiopropyl)disulfide (98485-71-3) → 1-[2-(2-mercaptoethylthio)ethylthio]-3-{2-mercapto-3-[2-(2-mercaptoethylthio)ethylthio]propyldithio}propane-2-thiol

Conditions	Yield
With triphenylphosphine at 20 - 60℃; for 10h; Inert atmosphere;	100%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,4-Dichloro-2-butyne (821-10-3) → 1,4,7-trithiacycloundec-9-yne (158548-70-0)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 5h;	99.7%

3-thiapentan-1,5-dithiol (3570-55-6) + 2-chloromethylpyridine hydrochloride (6959-47-3) → bis(2-pyridylmethyl)-2,2’-thiodiethanethiol (124284-36-2)

Conditions	Yield
Stage #1: 3-thiapentan-1,5-dithiol With sodium In ethanol at 85℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloromethylpyridine hydrochloride In ethanol at 85℃; for 15h; Inert atmosphere;	99.5%
With sodium 1.) EtOH, 2.) EtOH, reflux, 1 h; Yield given. Multistep reaction;
With sodium ethanolate In ethanol at 0℃; Reflux;

3-thiapentan-1,5-dithiol (3570-55-6) + tetraethoxygermanium (14165-55-0) → C8H18GeO2S3

Conditions	Yield
In benzene Reflux;	99%

3-thiapentan-1,5-dithiol (3570-55-6) + germanium tetra-isopropoxide (1134503-88-0) → C10H22GeO2S3

Conditions	Yield
In benzene Reflux;	98%

3-thiapentan-1,5-dithiol (3570-55-6) + tetraethoxygermanium (14165-55-0) → bis(2,2'-thiodiethanethiolato-S,S'')germanium(IV) (150082-03-4)

Conditions	Yield
In benzene Reflux;	98%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,1-Dichloroacetone (513-88-2) → PTE dithiol 1

Conditions	Yield
With sodium hydroxide In water; toluene at 20 - 40℃; for 20h;	96%

3-thiapentan-1,5-dithiol (3570-55-6) + 2-(2-bromoethoxy)benzaldehyde (60633-78-5) → 1,17-diformyl-1,2;16,17-dibenzo-3,15-dioxa-6,9,12-trithiaheptadeca-1,16-diene (887502-63-8)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Heating;	95%

oxirane (75-21-8) + 3-thiapentan-1,5-dithiol (3570-55-6) → 3,6,9-trithia-1,11-undecanediol (14440-77-8)

Conditions	Yield
With sodium hydrogencarbonate; sodium carbonate In ethanol; water at 60 - 70℃; for 2h; Concentration; Reagent/catalyst; Temperature; Inert atmosphere;	95%

3-thiapentan-1,5-dithiol (3570-55-6) + 2-chloro-1,3,6-trithia-2-bismocane (204324-97-0, 53061-41-9) → bis(((1,3,6-trithia-2-bismocan-2-yl)thio)ethyl)sulfide (175880-71-4)

Conditions	Yield
stirring (aqueous NaNO3, room temp., overnight);	94%

3-thiapentan-1,5-dithiol (3570-55-6) + Methacryloyl chloride (920-46-7) → bis-[(2-methacryloylthio)ethyl]sulfide

Conditions	Yield
With potassium hydroxide; Aliquat 336; 4-methoxy-phenol In chloroform for 0.25h; Acylation;	93.1%
With 4-methoxy-phenol; sodium hydroxide In Isopropyl acetate; water at 5℃; for 5.5h; Large scale;	81%

3-thiapentan-1,5-dithiol (3570-55-6) + [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) → [(η6-1,4-MeC6H4CHMe2)Ru(eta.3-C4H8S3)] (486448-64-0)

Conditions	Yield
With sodium methoxide In tetrahydrofuran to suspn. MeONa in THF 2-mercaptoethyl sulfide was added and stirred for1.5 h, Ru complex was added and stirred for 15 min; react. mixt. was evacuated to dryness, extd. with toluene-MeCN (1:1) andfiltered, hexane was added and cooled at 0°C; elem. anal.;	93%

2-Chloromethylquinoline (4377-41-7) + 3-thiapentan-1,5-dithiol (3570-55-6) → S,S''-bis(2-quinolylmethyl)-3-thia-1,5-pentanedithiol

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 48h; Reflux; Inert atmosphere;	93%

formaldehyd (50-00-0) + 3-thiapentan-1,5-dithiol (3570-55-6) → 1-oxa-3,6,9-trithiacyclodecane

Conditions	Yield
In water at 20℃; for 3h;	92%

3-thiapentan-1,5-dithiol (3570-55-6) + 2-chloro-ethanol (107-07-3) → 3,6,9-trithia-1,11-undecanediol (14440-77-8)

Conditions	Yield
With sodium ethanolate In ethanol Heating;	91%
With sodium In ethanol at 60℃; for 4h;	76%
With alkali
With ethanol; sodium ethanolate
With potassium hydroxide; sodium tetrahydroborate 1.) ethanol, water, 2.) ethanol, water, a.) overnight, b.) reflux, 0.5 h; Multistep reaction;

3-thiapentan-1,5-dithiol (3570-55-6) + 4-nitrobenzaldehdye (555-16-8) → 2-(4-nitrophenyl)-1,3,6-trithiacyclooctane + 2,10-bis(4-nitrophehyl)-1,3,6,9,11,14-hexathiacyclohexadecane

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 70℃;	A 91% B n/a
With toluene-4-sulfonic acid In benzene for 1h; Heating;	A 46% B 17%

3-thiapentan-1,5-dithiol (3570-55-6) + Trichlorbutylstannan (1118-46-3) → 2-chloro-2-n-butyl-1,3,6-trithia-2-stannocane

Conditions	Yield
In benzene equimolar amts., refluxing for 10 h; collection (filtration), recrystn. (CH2Cl2/hexane); elem. anal.;	91%

3-thiapentan-1,5-dithiol (3570-55-6) + [(PhS)2ReO(μ-SPh)]2 + toluene (108-88-3) → [PhSReO(2-mercaptoethyl sulfide(-2H))] * n(toluene)

Conditions	Yield
In toluene ligand added to a suspn. of Re complex, stirred under N2; filtered, concd., pptd. (dry ether), filtered, washed (ether), dried (vac.); elem. anal.;	91%

3-phenyl-propionaldehyde (104-53-0) + 3-thiapentan-1,5-dithiol (3570-55-6) → 2-(2-phenylethyl)-1,3,6-trithiacyclooctane + 2,10-bis-(2-phenylethyl)-1,3,6,9,11,14-hexathiacyclohexadecane

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 50 - 55℃;	A 90% B n/a
With toluene-4-sulfonic acid In benzene for 3h; Heating;	A 55% B 12%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,2,4,5-tetra(bromomethyl)-3,6-bis(ethoxy)benzene (158263-03-7) → 2,5,8,17,20,23-hexathia<9>(1,3)<9>(4,6)-2,5-bis(ethoxy)cyclophane

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide for 72h;	90%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,2,4,5-tetrabromomethylbenzene (15442-91-8) → 2,5,8,17,20,23-hexathia<9>(1,3)<9>(4,6)cyclophane

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 55℃; for 48h;	90%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,1-Dichloroacetone (513-88-2) → PTE dithiol 2

Conditions	Yield
Stage #1: 3-thiapentan-1,5-dithiol; 1,1-Dichloroacetone With sodium hydroxide In water at 20 - 25℃; for 2h; Stage #2: With hydrogenchloride In water pH=9;	90%

3-thiapentan-1,5-dithiol (3570-55-6) + S-(+)-2-methyl-N-p-tosylaziridine (119461-40-4) → N,N'-(2S,2'S)-1,1'-(2,2'-thiobis(ethane-2,1-diyl)bis(sulfanediyl))bis(propane-2,1-diyl)bis(4-methylbenzenesulfonamide)

Conditions	Yield
Stage #1: 3-thiapentan-1,5-dithiol With triethylamine In methanol at 20℃; for 0.166667h; Inert atmosphere; Stage #2: S-(+)-2-methyl-N-p-tosylaziridine In methanol at 20 - 35℃; for 5h; Inert atmosphere; regioselective reaction;	90%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + [(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6 (86991-88-0) + 2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi → C40H47FeNiP2S3(1+)*F6P(1-)

Conditions	Yield
Stage #1: 3-thiapentan-1,5-dithiol; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; 2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: [(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6 In tetrahydrofuran; hexane Inert atmosphere; Schlenk technique;	90%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,1'-[thiobis(ethylene)dithio]-bis(2-chloroethane) (51472-73-2) → 1,4,7,10,13,16-hexathiacyclooctadecan (296-41-3)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 4h;	89%

3-thiapentan-1,5-dithiol (3570-55-6) + cyclohexanecarbaldehyde (2043-61-0) → 2-cyclohexyl-1,3,6-trithiacycloheptane + 2,10-dicyclohexyl-1,3,6,9,11,14-hexathiacyclohexadecane

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 50 - 55℃;	A 89% B n/a
With toluene-4-sulfonic acid In benzene for 10h; Heating;	A n/a B 42%

3-thiapentan-1,5-dithiol (3570-55-6) + O-(N,N-diethylacetamidooxy)benzyl chloride → 1,5-bis[2-(N,N-diethylacetamidooxy)thiabenzyl]-3-thiapentane (1403755-66-7)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	89%

Upstream product

• 420-12-2 thirane 
• 540-63-6 ethane-1,2-dithiol 
• 107-06-2 1,2-dichloro-ethane 
• 106-93-4 ethylene dibromide 
• 17356-08-0 thiourea 
• 60177-05-1 bis-(2-acetylsulfanyl-ethyl)-sulfane 
• 6943-65-3 ethylenebisisothiuronium dihydrobromide 
• 7783-06-4 hydrogen sulfide 
• 111-48-8 2,2'-thiobis-ethanol 
• 505-60-2 bis (2-chloroethyl) sulphide 
• 6576-93-8 1,2,5-trithiacycloheptane 
• 7617-64-3 bis(2-bromoethyl)sulfide 

Downstream Products

• 6576-93-8 1,2,5-trithiacycloheptane 
• 168764-50-9 1,1′-{sulfanediylbis[(ethane-2,1-diyl)sulfanediylmethylene]}dibenzene 
• 296-41-3 1,4,7,10,13,16-hexathiacyclooctadecan 
• 111381-84-1 1,4,7-trithiacyclodecane 
• 183310-21-6 2,5,8-trithia-[9](2,9)-1,10-phenanthrolinophane 
• 221300-01-2 10-phenyl-1,4,7-trithia-10-azacyclododecane 
• 117651-91-9 bis(2-methacryloylthioethyl)sulfide 
• 887502-63-8 1,17-diformyl-1,2;16,17-dibenzo-3,15-dioxa-6,9,12-trithiaheptadeca-1,16-diene 
• 374805-44-4 10-(p-tolylsulfonyl)-1,4,7-trithia-10-azacyclododecane 
• 124088-40-0 (3-thiapentane-1,5-dithiolato)(thiophenolato)oxotechnetium(V) 
• 78888-00-3 2-methyl-2-phenyl-1,3,6-trithia-2-stannocane 
• 126600-71-3 TcO(S(CH₂)2S(CH₂)2S)SC₆H₄Cl 
• 200808-34-0 10-(4-Bromo-phenyl)-1,4,7-trithia-10-aza-cyclododecane 

Relevant articles and documents

Synthesis of the macrocyclic thiocrown ethers 1,4,7,10,13,16,19- heptathiaheneicosane (21-S-7) and 1,4,7,10,13,16,19,22-octathiatetraeicosane (24-S-8)

The synthesis and characterization of the two macrocyclic sulfides, 1,4,10,13,16,19-heptathiaheneicosane (21-S-7) and 1,4,7,10,13,16,19,22- octathiatetraeicosane (24-S-8), are described starting from different combinations of dithiols and dichlorides of differing chain lengths. Cs2CO3 is used for the cyclizations.

Oligomerization of 1,2-ethanedithiol: An expedient approach to oligothiaethylenethioglycols

Reactions of ethylenedithioglycol (ETG) with Na2CO3, K2CO3, and Cs2CO3 provided the oligothiaethylenethioglycols (nETG): di(DETG), tri- (TrETG), tetra- (TETG), and pentathiaethylenethioglycol (PETG), along with higher polymers. The most efficient carbonate was K2CO3 and reactions using DETG and TrETG as starting materials-or their mixtures-were also found to afford similar species. This largely unknown oligomerization process was thoroughly explored and potential pathways were put forward. A convenient conversion of ETG to laboratory quantities of the otherwise scarce and/or expensive DETG, TrETG, TETG, and PETG oligomers, in organic or aqueous media was achieved. Notably, this straightforward reaction takes place without the addition of expensive or toxic metal catalysts and with pure water as the solvent, thereby highlighting its potential as a green chemical reaction. Moreover, the process opens up new approaches to dynamic combinatorial libraries (DCLs) of oligomers and macrocycles with manifolded nETG [(SCH2CH2)nS] bridges.

Reactions of bielectrophiles (ClCH2CH2)2Y with sulfur in basic reducing systems

A simple procedure was developed for preparing bis(β-mercaptoethyl) ether and bis(β-mecraptoethyl) sulfide from commercially available chemicals: elemental sulfur, alkali, and bis(β-chloroethyl) ether or sulfide, based on thiylation with elemental sulfur of these substrates in the aqueous system hydrazine hydrate-alkali, with initial formation of the corresponding polysulfide polymers (thiokols). Their reduction with the system hydrazine hydrate-alkali, followed by acidification of dithiolate anions, yields the corresponding dithiols. Thiokols based on bis(β-chloroethyl) ether are soluble in organic solvents; they were studied by 1H NMR.