629-19-6

Basic information

• Product Name: Propyl disulfide
• Synonyms: N-PROPYL DISULFIDE;PROPYL DISULFIDE;PROPYL DISULPHIDE;PROPYLDITHIOPROPANE;(n-C3H7S)2;1-(Propyldisulfanyl)propane;4,5-Dithiaoctane;Disulfide,dipropyl
• CAS NO: 629-19-6
• Molecular Formula: C₆H₁₄S₂
• Molecular Weight: 150.31
• EINECS: 211-079-8
• Product Categories: Pyridines;pyrazine Flavor
• Mol File: 629-19-6.mol

Chemical Properties

• Melting Point: −86 °C(lit.)
• Boiling Point: 195-196 °C(lit.)
• Flash Point: 151 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.96 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.735mmHg at 25°C
• Refractive Index: n20/D 1.497(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 0.04g/l
• BRN: 969200
• CAS DataBase Reference: Propyl disulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Propyl disulfide(629-19-6)
• EPA Substance Registry System: Propyl disulfide(629-19-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26
• RIDADR: 2810
• WGK Germany: 3
• RTECS: JO1955000
• F: 13
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 629-19-6(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Propyl disulfide is used as a flavoring agent for its alliaceous, sulfurous, green, vegetative, and asefetida nuances. It is commonly found in various food items, such as cabbage, onion, garlic, shallot, roasted onion, raw leek, heated leek, chive, nobiru, caucas, Welsh onion, scallion, grilled and roasted beef, and roasted peanut.
Used in Pharmaceutical Industry:
Propyl disulfide is used as an antioxidant and a scavenger of reactive oxygen species (ROS) in the pharmaceutical industry. It helps prevent oxidative DNA damage caused by N-nitrosopiperidine (NPIP) and N-nitrosodibutylamine (NDBA), making it a potential candidate for applications in cancer prevention and treatment.
Used in Chemical Industry:
Propyl disulfide is used as a chemical intermediate in the synthesis of various organic compounds, particularly those with sulfur-containing functional groups. Its unique chemical properties make it a valuable building block for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

Preparation

By boiling propyl bromide and Na2S2 in propyl alcohol; from iodine and n-propyl mercaptan; from propyl iodide and sodium thiosulfate by way of sodium propyl thiosulfate, followed by heating.

InChI:InChI=1/C6H14S2/c1-3-5-7-8-6-4-2/h3-6H2,1-2H3

Upstream product

• 56-23-5 tetrachloromethane 
• 107-03-9 1-thiopropane 
• 141-52-6 sodium ethanolate 
• 6898-84-6 sodium 1-propanethiolate 
• 86808-17-5 dipropyl pentasulfide 
• 10147-36-1 n-propanesulfonyl chloride 
• 17891-56-4 tris-propylsulfanyl-silane 
• 106-94-5 propyl bromide 
• 594-42-3 chlorothio-trichloro-methane 
• 98-91-9 thiobenzoic acid 
• 136852-78-3 2-n-propyldithiopyridine-N-oxide 
• 869-56-7 tripropyl phosphorotrithioite 
• 4251-16-5 propyl thiocyanate 
• 127-18-4 1,1,2,2-tetrachloroethylene 

Downstream Products

• 1948-52-3 propyl propylthiosulfinate 
• 2280-26-4 S-propylmercapto-L-cysteine 
• 2179-60-4 methyl n-propyl disulfide 
• 17619-36-2 methyl propyl trisulfide 
• 6028-61-1 dipropyl trisulfide 
• 107-03-9 1-thiopropane 
• 3877-15-4 1-(methylthio)-propane 
• 79-05-0 Propionamid 
• 20195-06-6 O,O-diethyl-S-n-propyl phosporothiolate 
• 4110-50-3 ethyl propyl sulfide 
• 30453-31-7 ethyl propyl disulfide 
• 110-81-6 diethyldisulfane radical cation 
• 20614-39-5 1-propylthio-3-buten-2-ol 
• 791-28-6 Triphenylphosphine oxide 

Relevant articles and documents

Nucleophile-induced intramolecular dipole 1,5-transfer and 1,6-cyclization: Experimental and ab initio studies of formation, thermolysis, and molecular and electronic structures of 3,6-diphenyl-1-propanesulfenimido-1,2,4,5-tetrazine

Reaction of dichlorobenzaldazine (2) with sodium azide followed by 1-propanethiol/Et3N furnished tetrazine ylide 1 as the main product. The structure of this unprecedented ylide was confirmed with single-crystal X-ray analysis [C17H17N5S, monoclinic P21/n a = 6.8294(4) A, b = 13.6781(9) A, c = 17.5898(12) A, β = 90.666(1)°, Z = 4] and favorably compared with the results of ab initio calculations. The mechanisms of formation of the ylide and its thermal decomposition to 2,5-diphenyltetrazine (5) were investigated using ab initio methods and correlated with the experimental observations. The results suggest that formation of 1 involves intramolecular cyclization of a nitrile imine and thermolysis of 1 might generate a sulfenylnitrene. The formation of 1 is considered to be the first example of a potentially more general reaction.

A coordination network that catalyzes O2-based oxidations

Reaction of Tb(III) and two bridging ligands, a redox-active benzoic acid-terminated hexavandate ([V6O13{(OCH2)3C(4-CONHC6H4CO2H)}2]2- (1) and 4,4′-bis(pyridine-N-dioxide) (bpdo) produces a catalytically active open-framework pillared layer-type coordination polymer, Tb1. The network material catalyzes aerobic oxidation of PrSH to PrSSPr and the oxidation tetrahydrothiophene (THT) to tetrahydrothiophene oxide (THTO) by tert-butylhydroperoxide under ambient conditions. Tb(III) ions and bpdo units form two-dimensional (2D) coordination layers, and the 2D layers are connected by 1 to produce a three-dimensional coordination network. IR and powder X-ray diffraction of Tb1 before and after catalysis indicate the catalyst maintains an open framework structure during the catalytic reactions. Copyright

Application of Bulky NHC-Rhodium Complexes in Efficient S-Si and S-S Bond Forming Reactions

The efficient and straightforward syntheses of silylthioethers and disulfides are presented. The synthetic methodologies are based on new rhodium complexes containing bulky N-heterocyclic carbene (NHC) ligands that turned out to be efficient catalysts in thiol and thiol-silane coupling reactions. These green protocols, which use easily accessible reagents, allow obtaining compounds containing S-Si and S-S bonds in solvent-free conditions. Additionally, preliminary tests on coupling of mono- and octahydro-substituted spherosilicates with selected thiols have proved to be very promising and showed that these catalytic systems can be used for the synthesis of a novel class of functionalized silsesquioxane derivatives.

Substituted o-Aminophenols as Redox-Mediators in the Thiol Oxidation to Unsymmetrical Disulfides

A number of substituted o-aminophenols has been investigated as redox mediators of the thiol oxidation to disulfides. The electrooxidation of o-aminophenols leads to the corresponding o-iminobenzoquinones. These compounds react with thiols in the solution with a formation of disulfides. It was established that the use of 4,6-di-tert-butyl-2-(tert-butylamino)phenol as a redox mediator can reduce the overpotential of the thiol oxidation by 0.2-1.4 V depending on the nature of the coupling thiols. The unsymmetrical disulfides with alkyl, aryl, and heteroaryl substituents were obtained as the result of the indirect electrosynthesis.

Copper-catalyzedortho-selective direct sulfenylation ofN-aryl-7-azaindoles with disulfides

A copper-catalyzed direct C-H chalcogenation ofN-aryl-azaindoles with disulfides is described. This transformation was performed using Earth abundant Cu(OAc)2as a catalyst, benzoic acid as an additive, air as a terminal oxidant, and readily available diaryl and dialkyldisulfides (or diselenide) as chalcogenation reagents. High functional group tolerance and excellent regioselectivity are demonstrated by the efficient preparation of a wide range ofortho-sulfenylation-7-azaindoles.

METHOD FOR OXIDATION OF SULFUR-CONTAINING COMPOUNDS

Various embodiments disclosed relate to a method of oxidizing sulfur-containing compounds. The method involves contacting a sulfur-containing compound with a helmet phthalocyaninato-type catalyst in the presence of an oxidant. The present invention also provides a method of removing undesired sulfur-containing compounds from a fluid, such as natural gas, crude oil or an aqueous waste stream.

Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst

Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.

Key Odor-Active Compounds in Raw Green and Red Toona sinensis (A. Juss.) Roem. And Their Changes during Blanching

Application of aroma extract dilution analysis and headspace aroma dilution analysis revealed 51 odorants in raw green Toona sinensis and 54 odorants in raw red T. sinensis in the flavor dilution factor range of 8-4096. (E,E)-2,4-Decadienal, nonanal, 2,3,5-trimethylpyrazine, (E,Z)- and (Z,Z)-di-1-propenyl trisulfide, 2-methoxyphenol, and 4-ethylphenol were first identified as key odorants of T. sinensis. Clear differences between green and red T. sinensis in aroma profiles, flavor dilution factors, quantitative data, and odor activity values verified that (E,E)-, (E,Z)-, and (Z,Z)-di-1-propenyl disulfide, (E,E)-, (E,Z)- and (Z,Z)-di-1-propenyl trisulfide, cis- and trans-2-mercapto-3,4-dimethyl-2,3-dihydrothiophene, and dimethyl sulfide caused the distinct sulfury odor note of each variety. Further, hexanal, (E)-2-hexenal, (E)-2-hexen-1-ol, and (E,Z)-2,6-nonadienal led to the green odor note in green T. sinensis, while 2-methoxyphenol and 4-ethylphenol contributed to the intense phenolic aroma note in red T. sinensis. Quantitation experiments and triangle tests in blanched T. sinensis verified that the quick loss of the abovementioned sulfur-containing compounds, aldehydes, the alcohol (E)-2-hexen-1-ol, and phenols was responsible for the changes in the overall aroma profile during blanching.

Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides

Oxidative coupling of two different thiols bearing aliphatic, alicyclic, aromatic, and hetero-aromatic moieties promoted by mild oxidizing agents, viz., sterically hindered o-benzo(imino)-quinones, carried out in N-methylpyrrolidone at room temperature led to unsymmetrical disulfides. Among the studied oxidizers, the most active was 3,6-di-tert-butyl-o-benzoquinone, which, in contrast to 3,5-di-tert-butyl-o-benzoquinone, was not involved in the Michael addition. Under the optimal reaction conditions, the yields of the target unsymmetrical disulfides reach 81%.

Trisulfides over disulfides: Highly selective synthetic strategies, anti-proliferative activities and sustained H2S release profiles

Temperature-and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-Transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.