109-80-8

Usage

Uses

1. Used in Chemical Synthesis:
1,3-Dimercaptopropane is used as a reagent in the preparation of thioketals and thioacetals, which are important intermediates in organic chemistry. It is also used as a precursor in the synthesis of cyclic dithioacetal (1,3-dithiane) derivatives of carbonyl compounds, contributing to the development of various organic compounds.
2. Used in Flavor Industry:
1,3-Dimercaptopropane acts as a flavoring agent, providing a sulfur, meaty odor to the products. It is used as a usual flavor in the flavor industry, enhancing the taste and aroma of various food products.
3. Used in Metal Chelation:
1,3-Dimercaptopropane reacts with metal ions to form chelate rings, which can be useful in various chemical processes and applications.
4. Used in Pharmaceutical Industry:
1,3-Dimercaptopropane is involved in the preparation of diiron propanedithiolate hexacarbonyl by reacting with triiron dodecacarbonyl. 1,3-Dimercaptopropane has potential applications in the pharmaceutical industry, particularly in the development of new drugs and therapies.
5. Used in Food Industry:
Although 1,3-Dimercaptopropane has a disagreeable odor, it is reported to be found in cooked or boiled beef, indicating its natural occurrence in the food industry. The FEMA (Flavor and Extract Manufacturers Association) indicates that the total dithiol added to any food should not exceed 1.0 ppm, ensuring the safe use of 1,3-Dimercaptopropane in the food industry.

Toxicity

GRAS(FEMA)

Usage restriction

FEMA：baked goods, meat product, soups, snack foods, sauces, candy and sugar cream: 0.2mg/kg.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Organosulfides, such as 1,3-Dimercaptopropane, are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. 1,3-Dimercaptopropane may react with oxidizers, bases, reducing agents and alkali metals.

Fire Hazard

1,3-Dimercaptopropane is combustible.

InChI:InChI=1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2

Upstream product

• 7314-74-1 1,3-bis(thiocyanato)propane 
• 36648-08-5 1,3-propyl dithioacetate 
• 2986-36-9 VUF 8333 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 109-64-8 1,3-dibromo-propane 
• 1748-15-8 1,3-dithiane-2-thione 
• 557-22-2 1,2-dithiolane 
• 1191-08-8 1,4-Butanedithiol 
• 108-31-6 maleic anhydride 
• 98449-75-3 (6-(1,3)-dithian-2-yl-benzo[d][1,3]dioxol-5-yl)(benzo[d][1,3]dioxol-5-yl)methanol 
• 98449-74-2 α-3,4-dimethoxyphenyl-6-(1,3-dithian-2-yl)-1,3-benzodioxole-5-methanol 
• 98449-73-1 (6-(1,3)-dithian-2-yl-benzo[d][1,3]dioxol-5-yl)(3,4,5-trimethoxyphenyl)methanol 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 6331-22-2 2-methyl-2-phenyl-[1,3]dithiane 

Downstream Products

• 180-96-1 1,5-dithiaspiro[5.5]undecane 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 7424-45-5 1,7-diphenyl-2,6-dithiaheptane 
• 51021-89-7 1,3-di(benzoylthio)propane 
• 121935-23-7 1,3-bis(o-nitrophenyldithio)propane 
• 6007-26-7 2-methyl-1,3-dithian 
• 6008-55-5 1,4-dithiacycloheptane 
• 6572-95-8 1,5-dithiocane 
• 295-91-0 1,5,9,13-tetrathiacyclohexadecane 
• 6007-22-3 2,2-dimethyl-1,3-dithiane 
• 115412-67-4 (3-(cyclohexylthio)propylthio)cyclohexane 
• 1884-19-1 1,3-bis-phenylmethanesulfonyl-propane 
• 62496-80-4 7,9,11-triphenyl-1,5-dithia-6λ⁵-phospha-spiro[5.5]undeca-6,8,10-triene 
• 39938-36-8 1,3-Propylenbis(Phenyldisulfid) 

Relevant academic research and scientific papers

Photosensitized cleavage of the dithio protecting group by visible light

Dithio derivatives of aldehydes and ketones have been deprotected under neutral conditions using visible light provided by a 120 Watt spotlight and methylene green as a sensitizer. The key step in the deprotection is apparently an electron transfer from the dithio derivative to the electronically excited visible dye. The resulting dithio radical cation undergoes fragmentation, and the corresponding aldehydes and ketones are isolated in excellent yields.

3-(2-aminophenyl)-4-methyl-1,3-thiazole-2(3H)-thione as an ecofriendly sulphur transfer agent to prepare alkanethiols in high yield and high purity

A new process is described for preparing very pure linear alkanethiols and linear α,ω-alkanedithiols using a sequential alkylation of the title compound, followed by a ring closure to quantitatively give the corresponding 3-methyl[1,3]thiazolo[3,2-a]-[3,1

Reduction of thiokols in the system hydrazine hydrate-base as a new route to alkanedithiols

A new procedure for preparative synthesis of alkanedithiols from simple commercially available products is based on reduction of the S-S bond in appropriate polyalkylene disulfides (thiokols) in the system hydrazine hydrate-base. Thiokols were prepared by reaction of dihaloalkanes with Na2S2 or K2S2 generated from elemental sulfur and alkali in aqueous hydrazine hydrate. Reaction of 1,2-dibromocyclohexane with sodium or potassium disulfide yields bis(2-bromocyclohexyl) sulfide as the only product.

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.

Synthesis of thiols via palladium catalyzed methanolysis of thioacetates with borohydride exchange resin

Various thiols are prepared quantitatively from the corresponding thioacetates via Pd catalyzed methanolysis with borohydride exchange resin under a mild and neutral conditions. One-pot synthesis of thiols from alkyl halides through the formation of alkyl thioacetates using thioacetate exchange resin followed by methanolysis is also described.

Kinetics of Hydrolysis of 2-Aryl-2-phenyl-1,3-dithianes in 10percent (v/v) Dioxane-Water, Containing Perchloric Acid. Acidity Functions in this Solvent and the Reactivity of α-Thio Carbocations

The acid-catalysed hydrolysis of 2-aryl-2-phenyl-1,3-dithianes in 10percent (v/v) dioxane-water occurs at a convenient rate at 25 deg C in the presence of 5-8 mol dm-3 perchloric acid.The effect on the rate of changes in substituents, acidity and temperature, and of the use of a deuteriated solvent are described.Measurements of the H0 and X acidity functions for the solvent are reported; their values are very similar to those found for pure water over most of the acidity range.The mechanism of hydrolysis is believed to change from an ASE2 scheme for the most reactive dithianes to an A2-like scheme for the least reactive.In very concentrated acid solutions the dithianes (and other suitable S,S-acetals) lead to stoichiometric amounts of the α-thio carbocations often postulated as low-concentration intermediates in S,S-acetal hydrolysis.The kinetics of the reaction of these ions with water to give the benzenophenone (or corresponding carbonyl compound) are described, and compared with findings for similar α-oxo carbocations.Previous views on the mechansim of this reaction are criticised.

Identification of an ASE2 Mechanism in the Hydrolysis of Cyclic Thioacetals

2-Phenyl-2-methyl-1,3-dithiane and its p-methoxy derivative undergo hydrolysis in concentrated aqueous perchloric acid via the ASE2 mechanism rather than via the A1 mechanism.

Degenerate intermolecular thiolate-disulfide interchange involving cyclic five-membered disulfides is faster by ～103 than that involving six- or seven-membered disulfides

The rate constants for degenerate intermolecular thiolate-disulfide interchange involving 1,2-dithiolane (S(CH2)3S) are higher than those involving 1,2-dithiane (S(CH2)4S) by a factor of ～650 in mixtures of DMSO-d6 and D2O. The extrapolated rate constant for 1,2-dithiolane in DMSO-d6 is fast (k ～ 108 M-1 s-1). The rate constants for cyclic six- and seven-membered disulfides are similar to those for acyclic disulfides. Rate constants for self-exchange were measured by dynamic 1H NMR line-shape analysis. The evolutionary selection of lipoamide as the cofactor in 2-oxo acid dehydrogenases may reflect the fast rate of ring opening of the dithiolane ring by nucleophiles.

Kinetics and Mechanism of the Metal Ion-promoted Hydrolysis of 2-Phenyl-1,3-dithiane in Aqueous Dioxane Solution

In 1percent (v/v) aqueous dioxane the hydrolysis of 2-phenyl-1,3-dithiane (1) is promoted by thallium (III), mercury(II), mercury(I), and silver(I) ions; the qualitative sequence of their efficiencies is Tl3+>/=Hg2+>Hg22+>Ag+.Kinetic studies suggest the reaction mechanism with the thallium and mercury ions involves the rapid formation of a 1:1-adduct between the metal ion and the dithiane (formation constant, K 54.5, 3.0E4,and 630 dm3 mol-1 for Tl3+, Hg2+, and Hg22+, respectively at 25 deg C) followed by a slow ring-opening step (k2 77, 0.20 and 0.07 s-1, respectively) which may not involve water.Added chloride ions inhibit the mercury(II) ion promotion: HgCl+ and HgCl2 have, respectively, ca. 90percent and ca. 14percent of the reactivity of Hg2+.An increase in the dioxane content of the solvent to 20percent (v/v) has relatively little effect on the reaction.The general kinetic pattern, and level of reactivity, is similar to that observed previously for the Tl3+- and Hg2+-promoted hydrolysis of 2-phenyl-1,3-dithiolane (4).Both (1) and (4) are less basic towards Tl3+ than towards Hg2+, and the thallium adducts of (1) and (4) both react more rapidly than the corresponding Hg2+ adducts.However, (1) is less basic than (4) towards Tl3+, whereas the reverse is true for Hg2+, and the Tl3+ adduct of (1) is more reactive than that of (4), whereas the reverse is true of the reactivities of the corresponding Hg2+ adducts.These differences of detail suggest that the (unknown) conformations of the adducts control to some extent the values of K and k2.