2,2'-Thiodiethanethiol supplier

Name
Bis(2-mercaptoethyl) sulfide
EINECS 222-671-0
CAS No. 3570-55-6
Article Data19
CAS DataBase
Density 1.129 g/cm³
Solubility 620mg/L at 20℃
Melting Point -11°C
Formula C₄H₁₀S₃
Boiling Point 275.983 °C at 760 mmHg
Molecular Weight 154.321
Flash Point 90.556 °C
Transport Information UN 2810 6.1/PG 3
Appearance Liquid with a stench.
Safety 23-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Ethanethiol,2,2'-thiodi- (6CI,7CI,8CI);1,4,7-Trithiaheptane;1,5-Dimercapto-3-thiapentane;1-Mercapto-2-(mercaptoethylthio)ethane;2-Mercaptoethyl sulfide;2-Mercaptoethyl thioether;2-[(2-Mercaptoethyl)thio]ethanethiol;3-Thia-1,5-pentanedithiol;Bis(2-mercaptoethyl) sulfide;Bis(2-sulfanylethyl) sulfide;
PSA 102.90000
LogP 1.57920

Synthetic route

: 111-48-8
2,2'-thiobis-ethanol

A: 3570-55-6
3-thiapentan-1,5-dithiol

B: bis-mercaptodiethylsulphide

Conditions

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: polymer: monomers(s): 1,2-dichloroethane; sulfur

A: 3570-55-6
3-thiapentan-1,5-dithiol

B: 540-63-6
ethane-1,2-dithiol

Conditions

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

polymer: monomers(s): bis(β-chloroethyl) sulfide; sulfur: polymer: monomers(s): bis(β-chloroethyl) sulfide; sulfur

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

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

: 540-63-6
ethane-1,2-dithiol

A: 3570-55-6
3-thiapentan-1,5-dithiol

B: 25423-55-6
3,6-dithiaoctan-1,8-dithiol

C: 60147-09-3
2,2’-[thiobis(2,1-ethanediylthio)]bis(ethanethiol)

Conditions

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

...Expand

: 420-12-2
thirane

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

Conditions	Yield
With methanol; hydrogen sulfide at 60℃;

: 540-63-6
ethane-1,2-dithiol

: 107-06-2
1,2-dichloro-ethane

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

Conditions	Yield
With ethanol; potassium hydrosulfide

: 106-93-4
ethylene dibromide

: 17356-08-0
thiourea

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

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

: 505-60-2
bis (2-chloroethyl) sulphide

: 17356-08-0
thiourea

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

Conditions	Yield
Behandeln des Reaktionsprodukts mit wss.Natronlauge;

: 7617-64-3
bis(2-bromoethyl)sulfide

: 17356-08-0
thiourea

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

Conditions	Yield
Behandeln des Reaktionsprodukts mit wss.Natronlauge;

: 60177-05-1
bis-(2-acetylsulfanyl-ethyl)-sulfane

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

Conditions	Yield
With hydrogenchloride; methanol

: 6576-93-8
1,2,5-trithiacycloheptane

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

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

: 505-60-2
bis (2-chloroethyl) sulphide

: 3570-55-6
3-thiapentan-1,5-dithiol

Conditions

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;

: 107-06-2
1,2-dichloro-ethane

aqueous NaHS: aqueous NaHS

A: 505-29-3
1,4-Dithiane

B: 3570-55-6
3-thiapentan-1,5-dithiol

C: 25423-55-6
3,6-dithiaoctan-1,8-dithiol

D: 540-63-6
ethane-1,2-dithiol

Conditions

Conditions	Yield
at 100℃; unter Druck;

...Expand

: 6943-65-3
ethylenebisisothiuronium dihydrobromide

KOH: KOH

A: 3570-55-6
3-thiapentan-1,5-dithiol

B: 540-63-6
ethane-1,2-dithiol

...Expand

: 420-12-2
thirane

: 7783-06-4
hydrogen sulfide

A: 3570-55-6
3-thiapentan-1,5-dithiol

B: 540-63-6
ethane-1,2-dithiol

Conditions

Conditions	Yield
In methanol at 60°C;

...Expand

: 540-63-6
ethane-1,2-dithiol

A: 3570-55-6
3-thiapentan-1,5-dithiol

B: 25423-55-6
3,6-dithiaoctan-1,8-dithiol

C: 60147-09-3
2,2’-[thiobis(2,1-ethanediylthio)]bis(ethanethiol)

D: 124491-07-2
3,6,9,12-tetrathiatetradecane-1,14-dithiol

Conditions

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

...Expand

: 3570-55-6
3-thiapentan-1,5-dithiol

: 111080-49-0
o-(ethoxycarbonylmethoxy)benzyl chloride

: 506444-33-3
(2-{2-[2-(2-ethoxycarbonylmethoxy-benzylsulfanyl)-ethylsulfanyl]-ethylsulfanylmethyl}-phenoxy)-acetic acid ethyl ester

Conditions

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

: 188829-97-2
bis(β-epithiopropyl)sulfide

: 3570-55-6
3-thiapentan-1,5-dithiol

: 1-[2-(2-mercaptoethylthio)ethylthio]-3-{2-mercapto-3-[2-(2-mercaptoethylthio)ethylthio]propylthio}propane-2-thiol

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 98485-71-3
bis(β-epithiopropyl)disulfide

: 1-[2-(2-mercaptoethylthio)ethylthio]-3-{2-mercapto-3-[2-(2-mercaptoethylthio)ethylthio]propyldithio}propane-2-thiol

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 821-10-3
1,4-Dichloro-2-butyne

: 158548-70-0
1,4,7-trithiacycloundec-9-yne

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 6959-47-3
2-chloromethylpyridine hydrochloride

: 124284-36-2
bis(2-pyridylmethyl)-2,2’-thiodiethanethiol

Conditions

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;

: 3570-55-6
3-thiapentan-1,5-dithiol

: 14165-55-0
tetraethoxygermanium

: C8H18GeO2S3

Conditions

Conditions	Yield
In benzene Reflux;	99%

: 3570-55-6
3-thiapentan-1,5-dithiol

: 1134503-88-0
germanium tetra-isopropoxide

: C10H22GeO2S3

Conditions

Conditions	Yield
In benzene Reflux;	98%

: 3570-55-6
3-thiapentan-1,5-dithiol

: 14165-55-0
tetraethoxygermanium

: 150082-03-4
bis(2,2'-thiodiethanethiolato-S,S'')germanium(IV)

Conditions

Conditions	Yield
In benzene Reflux;	98%

: 3570-55-6
3-thiapentan-1,5-dithiol

: 513-88-2
1,1-Dichloroacetone

: PTE dithiol 1

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 60633-78-5
2-(2-bromoethoxy)benzaldehyde

: 887502-63-8
1,17-diformyl-1,2;16,17-dibenzo-3,15-dioxa-6,9,12-trithiaheptadeca-1,16-diene

Conditions

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

: 75-21-8
oxirane

: 3570-55-6
3-thiapentan-1,5-dithiol

: 14440-77-8
3,6,9-trithia-1,11-undecanediol

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 204324-97-0, 53061-41-9
2-chloro-1,3,6-trithia-2-bismocane

: 175880-71-4
bis(((1,3,6-trithia-2-bismocan-2-yl)thio)ethyl)sulfide

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 920-46-7
Methacryloyl chloride

: bis-[(2-methacryloylthio)ethyl]sulfide

Conditions

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%

: 3570-55-6
3-thiapentan-1,5-dithiol

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: 486448-64-0
[(η6-1,4-MeC6H4CHMe2)Ru(eta.3-C4H8S3)]

Conditions

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%

: 4377-41-7
2-Chloromethylquinoline

: 3570-55-6
3-thiapentan-1,5-dithiol

: S,S''-bis(2-quinolylmethyl)-3-thia-1,5-pentanedithiol

Conditions

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

: 50-00-0
formaldehyd

: 3570-55-6
3-thiapentan-1,5-dithiol

: 1-oxa-3,6,9-trithiacyclodecane

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 107-07-3
2-chloro-ethanol

: 14440-77-8
3,6,9-trithia-1,11-undecanediol

Conditions

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;

: 3570-55-6
3-thiapentan-1,5-dithiol

: 555-16-8
4-nitrobenzaldehdye

A: 2-(4-nitrophenyl)-1,3,6-trithiacyclooctane

B: 2,10-bis(4-nitrophehyl)-1,3,6,9,11,14-hexathiacyclohexadecane

Conditions

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%

...Expand

: 3570-55-6
3-thiapentan-1,5-dithiol

: 1118-46-3
Trichlorbutylstannan

: 2-chloro-2-n-butyl-1,3,6-trithia-2-stannocane

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: [(PhS)2ReO(μ-SPh)]2

: 108-88-3
toluene

: [PhSReO(2-mercaptoethyl sulfide(-2H))] * n(toluene)

Conditions

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%

...Expand

: 104-53-0
3-phenyl-propionaldehyde

: 3570-55-6
3-thiapentan-1,5-dithiol

A: 2-(2-phenylethyl)-1,3,6-trithiacyclooctane

B: 2,10-bis-(2-phenylethyl)-1,3,6,9,11,14-hexathiacyclohexadecane

Conditions

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%

...Expand

: 3570-55-6
3-thiapentan-1,5-dithiol

: 158263-03-7
1,2,4,5-tetra(bromomethyl)-3,6-bis(ethoxy)benzene

: 2,5,8,17,20,23-hexathia<9>(1,3)<9>(4,6)-2,5-bis(ethoxy)cyclophane

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 15442-91-8
1,2,4,5-tetrabromomethylbenzene

: 2,5,8,17,20,23-hexathia<9>(1,3)<9>(4,6)cyclophane

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 513-88-2
1,1-Dichloroacetone

: PTE dithiol 2

Conditions

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%

: 3570-55-6
3-thiapentan-1,5-dithiol

: 119461-40-4
S-(+)-2-methyl-N-p-tosylaziridine

: 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

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%

: 3570-55-6
3-thiapentan-1,5-dithiol

: 14647-23-5
1,2-bis(diphenylphosphino)ethane nickel(II) chloride

: 86991-88-0
[(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6

: 2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi

: C40H47FeNiP2S3(1+)*F6P(1-)

Conditions

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%

...Expand

: 3570-55-6
3-thiapentan-1,5-dithiol

: 51472-73-2
1,1'-[thiobis(ethylene)dithio]-bis(2-chloroethane)

: 296-41-3
1,4,7,10,13,16-hexathiacyclooctadecan

Conditions

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

: 3570-55-6
3-thiapentan-1,5-dithiol

: 2043-61-0
cyclohexanecarbaldehyde

A: 2-cyclohexyl-1,3,6-trithiacycloheptane

B: 2,10-dicyclohexyl-1,3,6,9,11,14-hexathiacyclohexadecane

Conditions

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%

...Expand

: 3570-55-6
3-thiapentan-1,5-dithiol

: O-(N,N-diethylacetamidooxy)benzyl chloride

: 1403755-66-7
1,5-bis[2-(N,N-diethylacetamidooxy)thiabenzyl]-3-thiapentane

Conditions

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

2,2'-Thiodiethanethiol Specification

The Ethanethiol,2,2'-thiobis-, with CAS registry number 3570-55-6, has the systematic name of 2,2'-sulfanediyldiethanethiol. And its IUPAC name is 2-(2-sulfanylethylsulfanyl)ethanethiol. And this chemical should be stored in cool, dry place in tightly closed containers. What's more, its EINECS is 222-671-0.

Physical properties of Ethanethiol,2,2'-thiobis-: (1)ACD/LogP: 2.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.07; (4)ACD/LogD (pH 7.4): 2.07; (5)ACD/BCF (pH 5.5): 22.16; (6)ACD/BCF (pH 7.4): 21.98; (7)ACD/KOC (pH 5.5): 319.69; (8)ACD/KOC (pH 7.4): 317.07; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 75.9 Å²; (13)Index of Refraction: 1.562; (14)Molar Refractivity: 44.37 cm³; (15)Molar Volume: 136.6 cm³; (16)Polarizability: 17.58×10^-24cm³; (17)Surface Tension: 40.9 dyne/cm; (18)Enthalpy of Vaporization: 49.38 kJ/mol; (19)Vapour Pressure: 0.00829 mmHg at 25°C.

Uses of p-Chloropropiophenone: it can be used to produce [1,2,5]trithiepane. This reaction will need reagents iron (III)-chloride-hexahydrate, acetic acid and diethyl ether.

When you are using this chemical, please be cautious about it as the following:
The Ethanethiol,2,2'-thiobis- irritates to eyes, respiratory system and skin. When use this chemical, do not breathe vapour and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: SCCSCCS
(2)InChI: InChI=1/C4H10S3/c5-1-3-7-4-2-6/h5-6H,1-4H2
(3)InChIKey: KSJBMDCFYZKAFH-UHFFFAOYAM
(4)Std. InChI: InChI=1S/C4H10S3/c5-1-3-7-4-2-6/h5-6H,1-4H2
(5)Std. InChIKey: KSJBMDCFYZKAFH-UHFFFAOYSA-N

Product Name

Bis(2-mercaptoethyl) sulfide

Synthetic route

2,2'-Thiodiethanethiol Specification

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