131538-00-6

Basic information

• Product Name: 1-Propanethiol,2,3-bis[(2-mercaptoethyl)thio]-
• Synonyms: 4-Mercaptomethyl-3,6-dithia-1,8-octanedithiol;2,3-bis((2-mercaptoethyl)thio)-1-propanethiol;1,2-Bis[(2-mercaptoethyl)thio]-3-mercaptopropane;4-(Mercaptomethyl)-1,8-dimercapto-3,6-dithiaoctane;1-Propanethiol,2,3-bis[(2-Mercaptoethyl)thio]-;2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol;Monomer-PETP;YF-FM PETP
• CAS NO: 131538-00-6
• Molecular Formula: C₇H₁₆S₅
• Molecular Weight: 260.53
• EINECS: 411-290-7
• Mol File: 131538-00-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 395.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.214
• Vapor Pressure: 56.2Pa at 20℃
• Solubility: 13190 in mg/100g standard fat at 20 ℃
• PKA: 9.57±0.10(Predicted)
• Water Solubility: 12mg/L at 20℃
• CAS DataBase Reference: 1-Propanethiol,2,3-bis[(2-mercaptoethyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanethiol,2,3-bis[(2-mercaptoethyl)thio]-(131538-00-6)
• EPA Substance Registry System: 1-Propanethiol,2,3-bis[(2-mercaptoethyl)thio]-(131538-00-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-48/22-50/53
• Safety Statements: 23-24/25-36-60-61
• Hazardous Substances Data: 131538-00-6(Hazardous Substances Data)

Usage

Uses

2,3-bis(2-mercaptoethyl)thio)-1-propanethiol is used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Flammability and Explosibility

Nonflammable

Synthetic route

C7H16O3S2 + thiourea (17356-08-0) → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
Stage #1: C7H16O3S2; thiourea With hydrogenchloride In water at 110℃; for 6h; Stage #2: With ammonium hydroxide In toluene at 75℃; for 1h;	93%
Stage #1: C7H16O3S2; thiourea With hydrogenchloride at 110℃; for 6h; Stage #2: With sodium hydroxide at 30 - 65℃; Time; Inert atmosphere;

C7H13Cl3S2 → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
With hydrogen sulfide; sodium hydrogencarbonate In water at 90℃; pH=8; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;	92.5%

2-hydroxyethanethiol (60-24-2) + epichlorohydrin (106-89-8) → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
Stage #1: 2-hydroxyethanethiol; epichlorohydrin With sodium hydroxide In water at 30℃; for 4.5h; Stage #2: With hydrogenchloride; thiourea In water at 110℃; for 3h; Stage #3: With ammonium hydroxide In toluene at 60℃;	87.7%
Stage #1: 2-hydroxyethanethiol With sodium hydroxide In water at 30℃; for 0.5h; Stage #2: epichlorohydrin In water at 30℃; for 4h; Stage #3: With hydrogenchloride; ammonia; thiourea Product distribution / selectivity; more than 3 stages;
Stage #1: 2-hydroxyethanethiol With sodium hydroxide In water at 30℃; for 0.5h; Stage #2: epichlorohydrin In water at 30℃; for 4h; Stage #3: With hydrogenchloride; sodium hydroxide; thiourea Product distribution / selectivity; more than 3 stages;
Stage #1: 2-hydroxyethanethiol; epichlorohydrin With sodium hydroxide In water at 20 - 30℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride; thiourea In water at 110℃; for 3.5h; Stage #3: With hydrazine hydrate; sodium hydroxide In toluene at 50℃; for 2h;
Stage #1: 2-hydroxyethanethiol With water; sodium hydroxide at 30℃; for 0.5h; Inert atmosphere; Stage #2: epichlorohydrin In water at 30℃; for 4h; Inert atmosphere; Further stages;

1,3-dimethylimidazolidine-2-thione (13461-16-0) + C8H18O3S2 → 1,3-dimethyl-2-imidazolidinone (80-73-9) + 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
Stage #1: 1,3-dimethylimidazolidine-2-thione; C8H18O3S2 With hydrogenchloride In water at 110℃; for 3h; Inert atmosphere; Stage #2: With thiourea hydrochloride; sodium hydroxide In water at 60℃; for 2h;	A 27% B 59%

C8H18O3S2 → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
Stage #1: C8H18O3S2 With hydrogenchloride; thiourea In water at 110℃; for 3h; Inert atmosphere; Stage #2: With thiourea hydrochloride; sodium hydroxide In water at 60℃; for 2h;	39%

C10H22N6S5*3ClH → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
With ammonia In water; toluene at 60℃; Product distribution / selectivity;
Stage #1: C10H22N6S5*3ClH With sodium hydroxide In water; toluene at 60℃; for 4h; Stage #2: With hydrogenchloride In water; toluene	222.4 g

1,3-bis(2-hydroxyethylthio)-2-propanol → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
With lithium aluminium tetrahydride; hydrogen sulfide; sodium hydroxide at 30℃; for 2h; Temperature; Inert atmosphere;
With lithium aluminium tetrahydride; hydrogen sulfide; sodium hydroxide at 30℃; for 2h; Temperature; Inert atmosphere;
Multi-step reaction with 2 steps 1: hydrogenchloride / 2 h / 110 °C 2: sodium hydroxide / water; toluene / 4 h / 60 °C View Scheme

1-(2-hydroxyethylthio)-3-chloro-2-propanol (32014-06-5) → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / 2 h / 40 - 80 °C 2: hydrogenchloride / 2 h / 110 °C 3: sodium hydroxide / water; toluene / 4 h / 60 °C View Scheme

C7H13O9S8(3-) → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
With hydrogenchloride In water at 90℃; Reagent/catalyst;

C13H25N9O3S5 → 1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6)

Conditions	Yield
With ammonium hydroxide In water at 60℃; for 22h;	76.3 %Chromat.

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) + bis(β-epithiopropyl)sulfide (188829-97-2) → 1-[2,3-bis-(2-mercaptoethylthio)propylthio]-3-{3-[2,3-bis-(2-mercaptoethylthio)propylthio]-2-mercaptopropylthio}propane-2-thiol

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

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) + propargyl bromide (106-96-7) → 1,8-bis(propargylthio)-4-(propargylthio)methyl-3,6-dithiaoctane

Conditions	Yield
Stage #1: 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane With sodium hydroxide In methanol at 20℃; for 0.333333h; Stage #2: propargyl bromide In methanol at 0℃; for 2.33333h;	91%

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) → Reaxys ID: 12147398

Conditions	Yield
With dimethylphenylene diisocyanate; dibutyltin dilaurate at 20℃; for 0.583333 - 0.666667h;

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) + tris(4-thiophenyl)phosphine sulphide → Reaxys ID: 12147327

Conditions	Yield
With dimethylphenylene diisocyanate; dibutyltin dilaurate at 20℃; for 0.583333 - 0.666667h;

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) + 2-(2-sulfanylethylthio)-3-[3-sulfanyl-2-(2-sulfanylethylthio)propylthio]propane-1-thiol → Reaxys ID: 12147487

Conditions	Yield
Mo(CO)5diazabicyclo[2.2.2]octane for 0.05h; Reactivity; Irradiation;

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) + bicyclo[2.2.1]heptane-2,5-diisocyanate + bicyclo[2.2.1]heptane-2,6-diisocyanate → poly(bicyclo[2.2.1]heptane-2,5(6)-diisocyanate-co-1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane)

Conditions	Yield
With UV absorbing agent; inner release agent (Zelec UN); dibutyltin chloride at 120 - 130℃; for 28h;

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) + tin(IV) chloride (7646-78-8) → C14H28S10Sn (888034-52-4)

Conditions	Yield
Stage #1: 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane With sodium hydroxide In water at 25℃; for 1h; Stage #2: tin(IV) chloride In water at 40℃; for 8h;

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) → C7H14S5

Conditions	Yield
Stage #1: 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane With iodine; sodium carbonate In ethanol at 10℃; for 0.5h; Inert atmosphere; Stage #2: With potassium hydroxide In methanol; toluene for 1.5h; Reflux;

1,2-bis[(2-mercaptoethyl)thio]-3-mercaptopropane (131538-00-6) + 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) → C10H19N5S5 + C10H19N5S5 + C10H19N5S5

Conditions	Yield
With potassium hydroxide In ethanol; isopropyl alcohol for 24h; Reflux;

Upstream product

• 5324-06-1 1,3-bis(2-hydroxyethylthio)-2-propanol 
• 13461-16-0 1,3-dimethylimidazolidine-2-thione 
• 32014-06-5 1-chloro-3-(2-hydroxyethylthio)-2-propanol 
• 17356-08-0 thiourea 
• 60-24-2 2-hydroxyethanethiol 
• 106-89-8 epichlorohydrin 
• 63905-12-4 C₇H₁₃Cl₃S₂ 

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