109-80-8

Basic information

• Product Name: 1,3-Dimercaptopropane
• Synonyms: 1,3-Propanedimercaptan;1,3-propyldimercaptan;NDR-132;FEMA 3588;DITHIOTRIMETHYLENEGLYCOL;1,3-DIMERCAPTOPROPANE;1,3-PROPANEDITHIOL;propane-1,3-dithiol
• CAS NO: 109-80-8
• Molecular Formula: C₃H₈S₂
• Molecular Weight: 108.23
• EINECS: 203-706-9
• Product Categories: thiol Flavor;Building Blocks;Chemical Synthesis;Contact Printing;Dithiols;Materials Science;Micro/NanoElectronics;Organic Building Blocks;Self Assembly &Self-Assembly Materials;Sulfur Compounds;Thiols;Thiols/Mercaptans
• Mol File: 109-80-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: −79 °C(lit.)
• Boiling Point: 169 °C(lit.)
• Flash Point: 138 °F
• Appearance: Clear light yellow/Liquid
• Density: 1.078 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 5 mm Hg ( 37.7 °C)
• Refractive Index: n20/D 1.539(lit.)
• Storage Temp.: 2-8°C
• PKA: 9.86±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 21℃
• Stability: Stable. Incompatible with oxidizing agents, bases, reducing agents, alkali metals. Store cool.
• Merck: 14,7801
• BRN: 1071197
• CAS DataBase Reference: 1,3-Dimercaptopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimercaptopropane(109-80-8)
• EPA Substance Registry System: 1,3-Dimercaptopropane(109-80-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25
• RIDADR: 3336
• WGK Germany: 3
• RTECS: TZ2585500
• F: 13
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 109-80-8(Hazardous Substances Data)

Usage

Description

1,3-Dimercaptopropane, also known as 1,3-Propanedithiol, is a dithiol compound that is propane substituted by thiol groups at positions 1 and 3. It is a clear orange oil with a disagreeable, sulfur, meaty odor. 1,3-Dimercaptopropane has various applications across different industries due to its unique chemical properties.

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 this compound 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

• 2986-36-9 VUF 8333 
• 6331-22-2 2-methyl-2-phenyl-[1,3]dithiane 
• 64-17-5 ethanol 
• 109-64-8 1,3-dibromo-propane 
• 89568-79-6 2-(4-methylphenyl)-2-phenyl-1,3-dithiane 
• 77464-22-3 2-Methyl-2-(4-methoxyphenyl)-1,3-dithiane 
• 73495-64-4 (2R*,3R*)-α-<2-(3,5-dimethoxyphenyl)-m-dithian-2-yl>-3-methyl-1,4-dioxaspiro<4.5>decane-2-methanol 
• 129976-26-7 2-(1-phenylethyl)-1,3-dithiane 
• 10359-08-7 2,2-diphenyl-1,3-dithiane 
• 72047-50-8 2-methyl-2-trans-β-styryl-1,3-dithiane 
• 69178-10-5 2-styryl-1,3-dithiane 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 1748-15-8 1,3-dithiane-2-thione 
• 108-31-6 maleic anhydride 

Downstream Products

• 121935-23-7 1,3-bis(o-nitrophenyldithio)propane 
• 74552-14-0 (S)-4-[(1R,3S)-3-(Tetrahydro-pyran-2-yloxy)-cyclopentyl]-4-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enone 
• 107172-27-0 (2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol 
• 107172-26-9 (2S,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol 
• 80564-71-2 3,4-Di-O-benzyl-D-arabinose-trimethylendithioacetal 
• 82313-68-6 14-(4-tert-Butylphenyl)-2,6-dithia<1.7>paracyclophan 
• 108275-13-4 (1R*,3R*,4R*)-N-benzyl-3<1'(S*)-hydroxyethyl>-4-<2-(1'',3''-dithiano)ethyl>piperidine-2-one 
• 82313-56-2 14-Phenyl-2,6-dithia<1.7>paracyclophan 
• 135720-60-4 Methanesulfonic acid (1R,2R)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-[1,3]dithian-2-yl-propyl ester 
• 135663-56-8 Methanesulfonic acid (1S,2R)-2-benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-[1,3]dithian-2-yl-propyl ester 
• 139025-21-1 (-)-(1R,5R,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)spiro<<3>azabicyclo<4.3.0>nonane-8,2''-<1.3>dithiane>-4-one 
• 140367-80-2 6β-acetoxy-N-demethyl-N-benzyl-3-(1',3'-propylenedithiano)tropane 
• 120927-71-1 Benzoic acid (1S,2R,3R,4R,5S,6R)-3,4-bis-benzyloxy-5-[1,3]dithian-2-yl-6-ethoxycarbonylmethyl-2-hydroxy-cyclohexyl ester 
• 124778-57-0 C₄₀H₄₉NO₃S₂Si 

Relevant articles and documents

Synthesis of thietane from sulfur and 1-bromo-3-chloropropane in hydrazine hydrate-alkali system

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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.

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.

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.