538-74-9 Usage
Description
Dibenzyl sulphide is a colorless crystalline solid, which may appear as plates or pale beige in color. It is characterized by an unpleasant or crippling stench. This organic compound is known for its beige crystals or powder form and is utilized in various applications across different industries due to its unique chemical properties.
Uses
Used in Organic Synthesis:
Dibenzyl sulphide is used as an intermediate in the field of organic synthesis for the production of various organic compounds. Its chemical structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. Dibenzyl sulphide's reactivity and stability make it a valuable asset in creating a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Dibenzyl sulphide is used as a key component in the development of new drugs. Its unique properties enable it to interact with biological targets, potentially leading to the discovery of novel therapeutic agents. Additionally, it may be employed in the formulation of drug delivery systems to improve the bioavailability and efficacy of existing medications.
Used in Agrochemical Industry:
Dibenzyl sulphide also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various pesticides and insecticides. Its chemical properties make it suitable for the development of compounds that can effectively control pests and diseases in agriculture, thereby contributing to increased crop yields and food security.
Used in Fragrance Industry:
Given its distinct smell, Dibenzyl sulphide can be utilized in the fragrance industry as a component in the creation of various scent profiles. Its unique odor can be blended with other compounds to develop new and innovative fragrances for the perfume, cosmetics, and personal care markets.
Used in Chemical Research:
Dibenzyl sulphide serves as a valuable research tool in the field of chemistry. It is used in various experimental setups to study reaction mechanisms, test hypotheses, and develop new methodologies. Its availability and reactivity make it an attractive candidate for researchers looking to explore new avenues in chemical science.
Synthesis Reference(s)
Canadian Journal of Chemistry, 53, p. 1480, 1975 DOI: 10.1139/v75-205Tetrahedron Letters, 27, p. 1073, 1986 DOI: 10.1016/S0040-4039(86)80051-X
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Organosulfides, such as Dibenzyl sulphide, 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.
Fire Hazard
Dibenzyl sulphide is combustible.
Safety Profile
Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofSOx.
Purification Methods
Crystallise the sulfide from EtOH/water (10:1), or repeatedly from Et2O. It has also been purified by chromatography on Al2O3 (pentane as eluent), then recrystallised from EtOH [Kice & Bowers J Am Chem Soc 84 2390 1962]. Dry it in a vacuum at 30o over P2O5, fused under nitrogen and re-dried. [Beilstein 6 IV 2649.]
Check Digit Verification of cas no
The CAS Registry Mumber 538-74-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 8 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 538-74:
(5*5)+(4*3)+(3*8)+(2*7)+(1*4)=79
79 % 10 = 9
So 538-74-9 is a valid CAS Registry Number.
InChI:InChI=1/C14H14S/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2
538-74-9Relevant articles and documents
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
Scalable electrochemical reduction of sulfoxides to sulfides
Kong, Zhenshuo,Pan, Chao,Li, Ming,Wen, Lirong,Guo, Weisi
supporting information, p. 2773 - 2777 (2021/04/21)
A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.
Copper based on diaminonaphthalene-coated magnetic nanoparticles as robust catalysts for catalytic oxidation reactions and C-S cross-coupling reactions
Yarmohammadi, Nasrin,Ghadermazi, Mohammad,Mozafari, Roya
, p. 9366 - 9380 (2021/03/16)
In this work, the immobilization of copper(ii) on the surface of 1,8-diaminonaphthalene (DAN)-coated magnetic nanoparticles provides a highly active catalyst for the oxidation reaction of sulfides to sulfoxides and the oxidative coupling of thiols to disulfides using hydrogen peroxide (H2O2). This catalyst was also applied for the one-pot synthesis of symmetrical sulfidesviathe reaction of aryl halides with thiourea as the sulfur source in the presence of NaOH instead of former strongly basic and harsh reaction conditions. Under optimum conditions, the synthesis yields of sulfoxides, symmetrical sulfides, and disulfides were about 99%, 95%, and 96% respectively with highest selectivity. The heterogeneous copper-based catalyst has advantages such as the easy recyclability of the catalyst, the easy separation of the product and the less wastage of products during the separation of the catalyst. This heterogeneous nanocatalyst was characterized by FESEM, FT-IR, VSM, XRD, EDX, ICP and TGA. Furthermore, the recycled catalyst can be reused for several runs and is economically effective.
