4756-13-2

Basic information

• Product Name: propane-1,2,3-trithiol
• Synonyms: propane-1,2,3-trithiol;1,2,3-TRIMERCAPTOPROPANE;TRIMERCAPTOPROPANE;1,2,3-Propanetristhiol
• CAS NO: 4756-13-2
• Molecular Formula: C₃H₈S₃
• Molecular Weight: 140.29062
• EINECS: 225-288-7
• Mol File: 4756-13-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 250°Cat760mmHg
• Flash Point: 111.7°C
• Appearance: /
• Density: 1.163g/cm³
• Vapor Pressure: 0.0352mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: propane-1,2,3-trithiol(CAS DataBase Reference)
• NIST Chemistry Reference: propane-1,2,3-trithiol(4756-13-2)
• EPA Substance Registry System: propane-1,2,3-trithiol(4756-13-2)

Safety Data

• Hazardous Substances Data: 4756-13-2(Hazardous Substances Data)

Usage

General Description

Propane-1,2,3-trithiol, also known as trithiolane, is a chemical compound with the formula C3H6S3. It is a colorless liquid with a strong and unpleasant odor, similar to that of garlic or rotten eggs. Trithiolane is commonly used in the rubber industry as a vulcanizing agent, helping to improve the elasticity, durability, and strength of rubber products. It is also used as a cross-linking agent in polymers and as an intermediate in organic synthesis. Additionally, trithiolane is used as a chemical intermediate in the production of pharmaceuticals and agrochemicals. Due to its strong odor and potential health hazards, trithiolane should be handled and stored with care.

InChI:InChI=1/C3H8S3/c4-1-3(6)2-5/h3-6H,1-2H2

Synthetic route

Benzeneselenol (645-96-5) + Polymer; Monomer(s): 1,2,3-trichloropropane; sodium disulfide → 1,2,3-propanetrithiol (4756-13-2) + diphenyl diselenide (1666-13-3)

Conditions	Yield
at 60 - 70℃; for 0.5h; Reduction; oxidation;	A 5.4% B 98.6%
at 100 - 120℃; for 5h; Reduction; oxidation;	A 92.5% B 95.6%

polymer; monomer(s): 1,2,3-trichloropropane → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate at 80 - 90℃; for 1h;	59%

polymer, product of thiylation with 0.19 g/mol of sulfur, where content of sulfur moieties 6.0 in repeating units; monomer(s): 1,2,3-trichloropropane, charged content 0.06 g/mol → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate at 80 - 85℃; for 2h;	30%

polymer, product of thiylation by thiylation with 0.19 g/mol of sulfur; monomer(s): 1,2,3-trichloropropane, charged content 0.063 g/mol → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate at 80 - 85℃;	26%

1,2,3-trichloropropane (96-18-4) → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield
With ethanol; potassium hydrosulfide
With sodium hydrogensulfide; tetrabutyl-ammonium chloride at 90℃; for 4h; Temperature; Reagent/catalyst;	137.2 g

1,2,3-tribromopropane (96-11-7) → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield
With ammonium sulfide; ethanol at 60℃;
With sodium tetrasulfide; ethanol Behandeln des Reaktionsprodukts mit Natrium und fluessigem Ammoniak;
With sodium hydrogensulfide; ethanol at 60 - 90℃;

1,2,3-tris-acetylsulfanyl-propane (108518-72-5) → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield
With sodium hydroxide
With sodium hydroxide In methanol

2,3-dibromo-propylamine; hydrochloride → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield
With hydrogen sulfide; ammonia In methanol at 90℃; for 16h;

3-chloro-propylene sulfide → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield
With ethanol; potassium hydrosulfide

1,2,3-trichloropropane (96-18-4) + alcoholic KHS → 1,2,3-propanetrithiol (4756-13-2)

Conditions	Yield

methanol (67-56-1) + 2,3-dichloro-1-propyl benzoate (856816-70-1) + sodium hydrogensulfide → 1,2,3-propanetrithiol (4756-13-2) + 1.2-dimercapto-propanol-(3)

Conditions	Yield
at 70 - 80℃;

phosgene (75-44-5) + 1,2,3-propanetrithiol (4756-13-2) → 4-mercaptomethyl-1,3-dithiolane-2-one (96864-47-0)

Conditions	Yield
With triethylamine In dichloromethane; toluene 1.) -20 - -30 deg C, 1 h, 2.) -20 - -30 deg C to room temperature, 1 h, 3.) room temperature, 30 min;	66%

1,2,3-propanetrithiol (4756-13-2) → 2,4-bis(mercaptomethyl)-1,3-dithiolane (153729-29-4)

Conditions	Yield
With sodium hydroxide; trifluoroborane diethyl ether In methanol; dichloromethane	65%

tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate (53317-87-6) + 1,2,3-propanetrithiol (4756-13-2) → (propane-1,2,3-trithiolato)tetrakis[(triphenylphosphine)gold(I)] tetrafluoroborate (177281-80-0)

Conditions	Yield
In dichloromethane byproducts: water; N2-atmosphere; stirring at room temp. for 1 h; layering with Et2O (pptn. and oil formation during 12 h), decantation; elem. anal.;	65%

1,2,3-propanetrithiol (4756-13-2) + dimethyl sulfate (77-78-1) → 1,2,3-tris-methylsulfanyl-propane (69631-98-7) + 3-Methylsulfanyl-propane-1,2-dithiol (85365-95-3) + 2-methylthio-1,3-propanedithiol (85365-94-2) + 2,3-Bis-methylsulfanyl-propane-1-thiol (85365-96-4)

Conditions	Yield
With potassium carbonate In various solvent(s) for 2h; Yield given. Further byproducts given;	A n/a B 12% C 40% D n/a

1,2,3-propanetrithiol (4756-13-2) + dimethyl sulfate (77-78-1) → 3-Methylsulfanyl-propane-1,2-dithiol (85365-95-3) + 2-methylthio-1,3-propanedithiol (85365-94-2) + 2,3-Bis-methylsulfanyl-propane-1-thiol (85365-96-4) + 1,3-bismethylthio-2-propanethiol (85365-97-5)

Conditions	Yield
With potassium carbonate In various solvent(s) for 2h; Further byproducts given;	A 12% B 40% C n/a D n/a
With potassium carbonate In various solvent(s) for 2h; Further byproducts given. Title compound not separated from byproducts;	A 12% B 40% C n/a D n/a
With potassium carbonate In various solvent(s) for 2h; Yield given. Further byproducts given;	A 12% B 40% C n/a D n/a

1,2,3-propanetrithiol (4756-13-2) + benzyltriethylammonium bromide (5197-95-5) + manganese(ll) chloride → 2N(C2H5)3CH2C6H5(1+)*Mn2(S2CHCH2CH2SSCH2CH2CHS2)2(2-)=[N(C2H5)3CH2C6H5]2[Mn2(S2CHCH2CH2SSCH2CH2CHS2)2]

Conditions	Yield
With Na; EtOH; air In ethanol addn. of trithiol to soln. of Na in EtOH (under N2), addn. of Et3NCH2PhBr and MnCl2, stirring and controlled exposing to air (dissoln., then pptn.); N2-atmosphere; collection (filtration), washing (EtOH), drying (vac.), dissoln. in MeCN, filtration, Et2O addn., crystn. (-20°C, overnight), collection (filtration), washing (Et2O), drying (vac.); elem. anal.;	35%

9-fluorenone (486-25-9) + 1,2,3-propanetrithiol (4756-13-2) + 2-chloropropionyl chloride (625-36-5) → C19H16OS3

Conditions	Yield
Stage #1: 9-fluorenone; 1,2,3-propanetrithiol With iodine In chloroform at 20℃; for 18h; Stage #2: 2-chloropropionyl chloride In toluene at 20 - 50℃; for 30.5h; Inert atmosphere; Stage #3: With sodium hydrogencarbonate In water for 0.5h;	34%

1,2,3-propanetrithiol (4756-13-2) → 3-mercapto-1,2-propylenesulfide (4755-98-0)

Conditions	Yield
at 140℃;

1,2,3-propanetrithiol (4756-13-2) + cyclohexane-1,2-epoxide (286-20-4) → optically inactive trans-1-acetoxy-2-(2,3-bis-acetylsulfanyl-propylsulfanyl)-cyclohexane

Conditions	Yield
With ethanol; sodium ethanolate anschliessendes Behandeln mit Acetanhydrid in Pyridin;

1,2,3-propanetrithiol (4756-13-2) + orthoformic acid triethyl ester (122-51-0) → 2,6,7-trithia-norbornane (279-60-7)

Conditions	Yield
Erhitzen des Reaktionsgemisches unter vermindertem Druck;

1,2,3-propanetrithiol (4756-13-2) + 1-chloro-2,4-dinitro-benzene (97-00-7) → 1,2,3-tris-(2,4-dinitro-phenylsulfanyl)-propane

Conditions	Yield
With potassium hydroxide

1,2,3-propanetrithiol (4756-13-2) + dimethyl sulfate (77-78-1) → 1,2,3-tris-methylsulfanyl-propane (69631-98-7)

Conditions	Yield
With sodium hydroxide

1,2,3-propanetrithiol (4756-13-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → ((Ξ)-2,3-bis-acetylmercapto-propyl)-(tetra-O-acetyl-1-thio-β-D-glucopyranoside) + 2-acetylmercapto-1,3-bis-(tetra-O-acetyl-β-D-glucopyranosylmercapto)-propane

Conditions	Yield
With methanol; sodium methylate Erwaermen des Reaktionsprodukts mit Acetanhydrid und Natriumacetat;

1,2,3-propanetrithiol (4756-13-2) + methyl iodide (74-88-4) → 1,2,3-tris-methylsulfanyl-propane (69631-98-7)

Conditions	Yield
With sodium hydroxide

1,2,3-propanetrithiol (4756-13-2) + n-hexadecanoyl chloride (112-67-4) → 1,2,3-tris-palmitoylmercapto-propane (113021-38-8)

Conditions	Yield
With pyridine; chloroform

1,2,3-propanetrithiol (4756-13-2) + propylene sulphide (1072-43-1) → 3-[(2-sulfanylpropyl)sulfanyl]propane-1,2-dithiol (100450-24-6)

Conditions	Yield
With sodium ethanolate In ethanol

1,2,3-propanetrithiol (4756-13-2) + propylene sulphide (1072-43-1) → 1,3-bis-(2-mercapto-propylsulfanyl)-propane-2-thiol (115307-64-7)

Conditions	Yield
With sodium ethanolate In ethanol

1,2,3-propanetrithiol (4756-13-2) + acetic anhydride (108-24-7) + methyloxirane (75-56-9, 16033-71-9) → 2-Acetoxypropyl-2,3-diacetylthiopropyl-sulfid (108955-91-5)

Conditions	Yield
(i) Na, EtOH, (ii) /BRN= 385737/, NaOAc; Multistep reaction;

1,2,3-propanetrithiol (4756-13-2) + methyl iodide (74-88-4) → 1,2,3-tris-methylsulfanyl-propane (69631-98-7) + 3-Methylsulfanyl-propane-1,2-dithiol (85365-95-3) + 2,3-Bis-methylsulfanyl-propane-1-thiol (85365-96-4) + 1,3-bismethylthio-2-propanethiol (85365-97-5)

Conditions	Yield
With n-butyllithium 1.) hexane/tetrahydrofuran, -78 deg C, 2.) THF, 0 deg C, then room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

Upstream product

• 96-18-4 1,2,3-trichloropropane 
• 108518-72-5 1,2,3-tris-acetylsulfanyl-propane 
• 67-56-1 methanol 
• 856816-70-1 2,3-dichloro-1-propyl benzoate 
• 645-96-5 Benzeneselenol 
• 96-11-7 1,2,3-tribromopropane 

Downstream Products

• 4755-98-0 thiiranemethanethiol 
• 7783-06-4 hydrogen sulfide 
• 177281-80-0 (propane-1,2,3-trithiolato)tetrakis[(triphenylphosphine)gold(I)] tetrafluoroborate 

Relevant articles and documents

Thiylation of polyelectrophiles with sulfur in hydrazine hydrate-amine systems

Thiylation of polyhaloalkanes and Paraform with elemental sulfur activated in hydrazine hydrate-organic amine systems is performed. Monoethanolamine, triethanolamine, and triethylamine were used as amines. The reactions gave thiocols of various structures. The products were characterized by elemental analysis and IR spectroscopy. Reductive cleavage of the synthesized thiocols was performed to obtain di- and polythiols. 2005 Pleiades Publishing, Inc.

A New Route to 1,2,3-Propanetrithiol

A new procedure was developed for preparing 1,2,3-propanetrithiol from available initial com-pounds. 1,2,3-Trichloroethane reacts with sodium disulfide prepared by dissolving sulfur in the system NaOH-N2H4 * H2O-H2O to give a disulfide dendrimeric polymer, thiokol, in almost quantitative yield. This polymer is subjected to reductive cleavage with an alkaline solution of hydrazine hydrate, which is followed by acidification with HCl. The yield of 1,2,3-propanetrithiol exceeds 60 percent. The synthesis can be performed as a one-pot procedure.

Reduction of thiocols to alkanepolythiols with benzeneselenol

Heating of benzeneselenol with polymethylene disulfides to 40-120°C results in formation of the corresponding alkanedithiols or alkanetrithiols and diphenyl diselenide. Poly(tetramethylene disulfide) reacts with benzeneselenol to give 1,2-dithiane and diphenyl diselenide. A radical mechanism of this reaction is discussed.