4253-89-8

Basic information

• Product Name: ISOPROPYL DISULFIDE
• Synonyms: (i-C3H7S)2;2-(Isopropyldisulfanyl)propane;2,5-Dimethyl-3,4-dithiahexane;3,4-dithiahexane,2,5-dimethyl-;bis(1-methylethyl)disulfide;Diisopropyl disulphide;diisopropyldisulfide,2,5-dimethyl-3,4-dithiahexane;disulfide,bis(1-methylethyl)
• CAS NO: 4253-89-8
• Molecular Formula: C₆H₁₄S₂
• Molecular Weight: 150.31
• EINECS: 224-225-0
• Product Categories: sulfide Flavor;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds;Alphabetical Listings;Flavors and Fragrances;I-L;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
• Mol File: 4253-89-8.mol
• Article Data: 72

Chemical Properties

• Melting Point: -69°C
• Boiling Point: 175-176 °C(lit.)
• Flash Point: 65 °F
• Appearance: White to off-white to beige/Powder
• Density: 0.943 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.35mmHg at 25°C
• Refractive Index: n20/D 1.4906(lit.)
• Storage Temp.: Flammables area
• CAS DataBase Reference: ISOPROPYL DISULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPROPYL DISULFIDE(4253-89-8)
• EPA Substance Registry System: ISOPROPYL DISULFIDE(4253-89-8)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38-52-50
• Safety Statements: 9-16-29-33-36-26-61
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 4253-89-8(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
ISOPROPYL DISULFIDE is used as a flavoring agent for its characteristic odor and taste. It is commonly found in the natural aroma of various Allium species, contributing to the unique flavor profile of these plants.
Used in Pharmaceutical Industry:
ISOPROPYL DISULFIDE is used as a pharmaceutical compound due to its potential therapeutic properties. Studies have shown that it may have beneficial effects on human health, such as antioxidant and antimicrobial activities, making it a valuable component in the development of new drugs and treatments.
Used in Agricultural Industry:
ISOPROPYL DISULFIDE is used as a natural pesticide and fungicide in the agricultural industry. Its antimicrobial properties help protect crops from various diseases and pests, promoting healthier growth and increased yield.
Used in Environmental Science:
ISOPROPYL DISULFIDE is used in environmental science for its potential role in reducing harmful emissions and pollutants. Its volatile nature allows it to be used in air purification systems, helping to remove toxic substances from the atmosphere and improve air quality.

InChI:InChI=1/C6H14S2/c1-5(2)7-8-6(3)4/h5-6H,1-4H3

Upstream product

• 828-26-2 hexamethyl-[1,3,5]trithiane 
• 75-30-9 2-iodo-propane 
• 2438-90-6 N,N'-dimethylthioperoxydicarbamic acid 
• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 
• 75-33-2 2-propanethiol 
• 67-64-1 acetone 
• 38739-06-9 S-isopropyl isopropanethiosulfinate 
• 18068-25-2 Formaldehyde diisopropyl dithioacetal 
• 591-51-5 phenyllithium 
• 83511-37-9 bis(isopropylthio) selenide 
• 108-98-5 thiophenol 
• 6006-15-1 N,N-diethyl-N-isopropylamine 
• 75-26-3 isopropyl bromide 
• 6804-20-2 N,N-dicyclohexyl-O-(1'-methylethyl)isourea 

Downstream Products

• 53966-36-2 ethyl-isopropyl-disulfane 
• 43022-60-2 tert-butyl isopropyl disulfide 
• 52693-47-7 methyl i-propylsulfinate 
• 70398-84-4 1,2-Bisbenzene 
• 76757-65-8 C₂₄H₂₆PS⁽¹⁺⁾*BF₄^(1-) 
• 74542-66-8 1,2,3-tris(isopropylthio)benzene 
• 781-33-9 2-methyl-1,1-diphenylpropene 
• 35906-28-6 benzhydryl(isopropyl)sulfide 
• 101773-89-1 C₁₉H₂₄S₂ 
• 2386-41-6 triisopropyl tetrathiophosphate 
• 5728-82-5 1,2-bis(2,6-dimethoxyphenyl)disulfane 
• 26163-11-1 2,6-dimethoxybenzenethiol 
• 220648-35-1 2-amino-3-isopropylthio-6-benzoylimidazo<1,2-a>pyridine 
• 75-33-2 2-propanethiol 

Relevant articles and documents

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.

Condensation of Propan-2-one with Formaldehyde and Propane-2-thiol

Abstract: Three-component condensation of propan-2-one with formaldehyde and propane-2-thiol in the presence of sodium hydroxide afforded 3-{[(propan-2-yl)sulfanyl)]methyl}but-3-en-2-one or 4-[(propan-2-yl)sulfanyl]-3-{[(propan-2-yl)sulfanyl]methyl}butan-

A rapid, efficient and green procedure for transformation of alkyl halides/ tosylates to organochalcogens in water

A one-pot and efficient synthesis of dialkyl dichalcogenides (S, Se) in aqueous media under catalyst-free conditions using benzylic, allylic and primary halides with elemental sulfur and selenium has been developed. Also, this procedure was extended to preparation of trisulfides and triselenides from secondary and tertiary halides in same condition. In all cases, products can be obtained in good to excellent yield in short reactions time.

Dicationic Thiolate-Bridged Diruthenium Complexes for Catalytic Oxidation of Molecular Dihydrogen

Dicationic thiolate-bridged diruthenium complexes bearing sterically bulky alkane substituents on the thiolate ligands such as [Cp?Ru(μ-SiPr)2Ru(OH2)Cp?](OTf)2 have been found to work as effective catalysts toward oxidation of molecular dihydrogen into protons and electrons in protic solvents such as water and methanol. DFT calculations indicate that the sterically bulky alkane substituent in the complex plays an important role in facilitating the reaction step of the coordination of molecular dihydrogen.

Thiol Reactivity toward Atomic Oxygen Generated during the Photodeoxygenation of Dibenzothiophene S-Oxide

Aromatic heterocyclic oxides, such as dibenzothiophene S-oxide (DBTO), have been suggested to release ground state atomic oxygen [O(3P)] upon irradiation, and as such, they have been used to create a condensed phase reactivity profile for O(3P). However, thiols, which are highly reactive with O(3P) in the gas phase, were not previously investigated. An earlier study of O(3P) with proteins in solution indicated a preference for thiols. A further investigation of the apparent thiophilicity provided the subject for this study. DBTO was employed as a putative O(3P)-precursor. However, the effective rate of O(3P) formation was found to be dependent on reactant concentrations in certain cases. All reactants were found to increase the rate of deoxygenation to some extent, but in the presence of reactants containing an alcohol linked to a reactive functional group, deoxygenation occurred substantially more rapidly. The rate enhancement was quantified and attributed to the reaction of activated O atom within the solvent cage prior to escape into the bulk solution. Through competition experiments, the relative rate constants of O(3P) with thiols and other functional groups were found. A small preference for primary thiols was observed over other thiols, sulfides, and alkenes. A much larger preference was observed for thiols, sulfides, and alkenes over aromatic groups. In summary, DBTO was successfully used as an O(3P)-precursor, and the thiophilicity of O(3P) was confirmed and quantified.

Europhtal (8020) efficiently catalyzes the aerobic oxidation of in situ generated thiols to symmetric disulfides (disulfanes)

Efficient, odorless and scalable synthetic protocols have been introduced for the preparation of symmetric alkyl disulfides by treatment of the corresponding organic halides with thiourea and NaHCO3in the presence of commercially available Europhtal catalyst (8020) in both H2O and poly ethylene glycol (PEG-200) media at 80–90 °C. Structurally diverse primary, secondary, allylic and benzylic halides were examined successfully whereas, the result with tert-butyl bromide was not satisfactory. Also, another procedure has been introduced for achieving symmetric aryl disulfides in high yields by reacting aryl halides, thiourea and NaHCO3in PEG-200 at 115–120 °C using CuI along with Europhtal catalysts. The results showed that the aerobic oxidation of in situ generated thiols proceeded efficiently in the presence of Europhtal catalyst giving the symmetric disulfide without contamination by symmetric sulfide side-product.

A two in one approach: Renewable support and enhanced catalysis for sweetening using chicken feather bound cobalt(II) phthalocyanine under alkali free environment

Poultry waste chicken feathers, an inexpensive and abundantly available material has been used as a renewable support for immobilizing a cobalt phthalocyanine catalyst. The synthesized heterogeneous cobalt(ii) phthalocyanine catalyst was used for the aerobic oxidation of mercaptans to the corresponding disulfides using ultrasonic irradiation under alkali free conditions. The significantly higher catalytic activity of the heterogeneous catalyst as compared to a homogeneous one can be attributed to the synergistic effect of the support matrix. In addition, the catalyst could easily be recovered and recycled for several runs without loss of activity, which makes the process greener and more cost-effective.

The synthesis of symmetrical disulfides by reacting organic halides with Na2S2O3·5H2O in DMSO

A one-pot, and scalable method to prepare symmetric disulfides from their corresponding primary, secondary, allylic, and benzylic halides has been developed. In this method, a disulfide is synthesized by reacting an alkyl halide with Na2S2O3·5H2O at 60-70 °C in DMSO.

One-pot conversion of alkyl halides to organic disulfides (disulfanes) using thiourea and hexamethyldisilazane (HMDS) in DMSO

A practical method to synthesize symmetric disulfides from alkyl halides has been developed. Using this procedure primary, secondary, benzylic and allylic disulfides were prepared by treating the corresponding alkyl halides with thiourea and HMDS in DMSO at 50 °C within 10-24 h in high yields.

Magnetic Fe3O4@MgAl-LDH composite grafted with cobalt phthalocyanine as an efficient heterogeneous catalyst for the oxidation of mercaptans

Magnetically separable layered double hydroxide MgAl-LDH@Fe3O4 composite supported cobalt phthalocyanine catalyst was synthesized and used for the aerobic oxidation of mercaptans to corresponding disulfides under alkali free conditions. The catalyst exhibited excellent activity for the oxidation of mercaptans using molecular oxygen as an oxidant which can be effectively recovered by using an external magnetic field. In addition, the covalent immobilization of cobalt phthalocyanine to MgAl-LDH@Fe3O4 support prevents the leaching of the catalyst and improves its activity and stability.