1,3-Propanedithiol

Base Information

• Chemical Name: 1,3-Propanedithiol
• CAS No.: 109-80-8
• Molecular Formula: C3H8S2
• Molecular Weight: 108.229
• Hs Code.: 29309070
• European Community (EC) Number: 203-706-9
• UN Number: 3336
• UNII: R4LUJ82U52
• DSSTox Substance ID: DTXSID0059376
• Nikkaji Number: J4.503I
• Wikipedia: Propane-1,3-dithiol
• Wikidata: Q4545685
• Metabolomics Workbench ID: 45003
• Mol file: 109-80-8.mol

Synonyms:1,3-propanedithiol

Chemical Property of 1,3-Propanedithiol

Chemical Property:

• Appearance/Colour: Colourless to slightly yellow liquid
• Vapor Pressure: 5 mm Hg ( 37.7 °C)
• Melting Point: -79 °C
• Refractive Index: n20/D 1.539(lit.)
• Boiling Point: 170.4 °C at 760 mmHg
• PKA: 9.86±0.10(Predicted)
• Flash Point: 58.9 °C
• PSA: 77.60000
• Density: 1.019 g/cm³
• LogP: 1.23610
• Storage Temp.: 2-8°C
• Water Solubility.: <0.1 g/100 mL at 21℃
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 108.00674260
• Heavy Atom Count: 5
• Complexity: 12.4
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

1,3-Propanedithiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Thiols
• Canonical SMILES: C(CS)CS
• Uses: 1,3-Propanedithiol is used as a reagent in the preparation of thioketals and thioacetals. It acts as a flavoring agent. It is used as a precursor in the synthesis of cyclic dithioacetal (1,3-dithiane) derivatives of carbonyl compounds. It is involved in the preparation of diiron propanedithiolate hexacarbonyl by reacting reaction with triiron dodecacarbonyl. Further, it is used for the protection of aldehydes and ketones through their reversible formation of dithianes. In addition to this, it reacts with metal ions to form chelate rings.

Technology Process of 1,3-Propanedithiol

There total 47 articles about 1,3-Propanedithiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2-styryl-1,3-dithiane (69178-10-5) → 1.3-propanedithiol (109-80-8) + (E)-3-phenylpropenal (14371-10-9)

Guidance literature:

With magnesium(II) perchlorate; water; methylene green; In acetonitrile; Irradiation;

DOI:10.1016/S0040-4039(00)61086-9

Reference yield: 94.0%

2-methyl-2-trans-β-styryl-1,3-dithiane (72047-50-8) → 1.3-propanedithiol (109-80-8) + (E)-benzalacetone (1896-62-4)

Guidance literature:

With magnesium(II) perchlorate; water; methylene green; In acetonitrile; Irradiation;

DOI:10.1016/S0040-4039(00)61086-9

Reference yield: 91.0%

2-(3,4-methylenedioxyphenyl)-1,3-dithiane (56579-86-3) → 1.3-propanedithiol (109-80-8) + piperonal (120-57-0,30024-74-9)

Guidance literature:

With magnesium(II) perchlorate; water; methylene green; In acetonitrile; Irradiation;

DOI:10.1016/S0040-4039(00)61086-9

upstream raw materials:

1,3-bis(thiocyanato)propane

1,3-propyl dithioacetate

VUF 8333

1-methyl-4-nitrosobenzene

Downstream raw materials:

1,5-Dithiacyclononane

1,5,10,14-tetrathia-cyclooctadecane

1,3-dithiane 1,1,3,3-tetraoxide

1,5,12,16-tetrathia-cyclodocosane

Refernces

Enantiospecific synthesis of functionalized polyols from tartaric acid using Ley's dithiaketalization: Application to the total synthesis of achaetolide

10.1016/j.tet.2016.11.035

The research focuses on the enantiospecific synthesis of functionalized polyols derived from tartaric acid, utilizing Ley's dithiaketalization method. The study demonstrates the application of this strategy in the total synthesis of achaetolide, a decanolactone natural product. The experiments involved the synthesis of chiral tetrols and 1,2,4-triols with varied substitutions, with a key reaction being the Ley’s dithianylation of an alkynyl ketone derived from tartaric acid. The synthesis strategy was executed in several steps, starting from the addition of alkynyl Grignard reagents to tartaric acid amides, followed by stereoselective reduction, and elaboration to polyol systems. The research employed various reactants, including tartaric acid, alkynyl Grignard reagents, 1,3-propanedithiol, and NaBH4, among others. Analytical techniques used throughout the experiments included column chromatography, TLC, NMR spectroscopy, and HRMS for compound characterization and yield determination. The study resulted in the total synthesis of achaetolide in 14 steps from the bis-Weinreb amide of tartaric acid, with an overall yield of 9.5%.

Synthesis of acylsilanes via oxidative hydrolysis of 2-silyl-1,3-dithianes mediated by N-bromosuccinimide

10.1016/S0022-328X(00)00181-9

This study focused on the synthesis of acylsilanes, a class of compounds with unique chemical properties that are widely used in various synthetic methods. The researchers used an oxidative hydrolysis method to generate acylsilanes in high yields in a short reaction time using N-bromosuccinimide (NBS) as a medium for the hydrolysis of 2-silyl-1,3-dithianes. This study aimed to find an alternative to the traditional mercuric chloride hydrolysis method, which is time-consuming and toxic. The chemicals used in the study included aldehydes, 1,3-propanedithiol, BF3·OEt2, n-BuLi, trimethylsilyl chloride, and various bases such as Et3N, Ba(OH)2, and imidazole. These chemicals were used to convert aldehydes into 1,3-dithianes, which were then converted into 2-silyl-1,3-dithianes, and finally hydrolyzed to generate acylsilanes. The use of NBS was intended to improve the efficiency and safety of the hydrolysis process and avoid the formation of undesirable byproducts such as carboxylic acids due to the oxidation of aromatic acylsilanes.