42841-31-6

Usage

Uses

Used in Pharmaceutical Industry:
3 3'-DITHIOBIS(PROPIONITRILE) 98 is used as a chemical intermediate for the preparation of inhibitors containing diazole or tetrazole structures of oxygen group elements. These inhibitors are specifically designed to target the allosteric site of kidney glutaminase, an enzyme that plays a crucial role in cellular metabolism and energy production. By inhibiting this enzyme, it may help in the development of new therapeutic strategies for various diseases and conditions related to abnormal cellular metabolism.

Upstream product

• 1001-58-7 3-mercaptopropionitrile 
• 6634-40-8 S‐(2‐cyanoethyl)isothiouronium chloride 
• 107-13-1 acrylonitrile 
• 2417-90-5 bromopropionitrile 

Downstream Products

• 59012-54-3 dimethyl dithiobispropionimidate 
• 1001-58-7 3-mercaptopropionitrile 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 

Relevant academic research and scientific papers

Rapid, Stoichiometric, Site-Specific Modification of Aldehyde-Containing Proteins Using a Tandem Knoevenagel-Intra Michael Addition Reaction

A site-specific modification of aldehyde-containing proteins using a tandem Knoevenagel-intra Michael addition reaction was developed. The reaction featured fast kinetics (50 M-1 s-1) and favorable stoichiometry. Various functionalities could be introduced into the protein with little impact on its function and conformation. The reaction was successfully applied in the labeling of living cells.

Photodisulfidation of alkenes with linear disulfides: Reaction scope and kinetics

Thiol-ene and thiol-yne photomediated conjugations have received substantial attention in research and in practice. Herein is presented the photodisulfidation of alkenes based on the radical-mediated 1:1 reaction of a disulfide and a vinyl ether, which provides an additional route for the formation of the types of sulfides seen in thiol-ene and thiol-yne polymers. Although similar linkages are formed, this approach starting with disulfides is expected to have benefits over the thiol-ene and thiol-yne reactions including extended shelf life of disulfides compared to thiols, reduced shrinkage stress, and increased refractive index of the resulting materials. It was determined that vinyl ethers were the only alkenes capable of undergoing photodisulfidation under ambient conditions and in reasonable timescales. The reaction between vinyl ethers and disulfides performed well in a variety of solvents providing modest to excellent yields (100% for bis(1-methylacetate) disulfide (DSMA)/triethyleneglycol divinylether (TEGDVE)) for numerous disulfide substrates evaluated. It was determined that the mechanism of the photodisulfidation reaction involves an auto-propagating cycle of thiyl radicals which add into either end of a vinyl ether to form thio-ether and thio-acetal linkages in the final product. Finally, although the reaction rate is slower than that of the thiol-ene reaction, the photodisulfidation reaction proceeds relatively rapidly under the explored conditions.

A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates

A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates, including those bearing low molecular weight S-alkyl side-chains, is presented. Application of the “caesium effect” in conjunction with the disulfide 3,3’-dithiobis(propionitrile), which acts as a shelf-stable sulfur source, avoids recourse to malodorous alkanethiols and toxic P?Cl precursors. A diverse range of sulfur-containing organophosphorus targets, including phosphorus-based heterocycles, may be prepared in consistently high yields. This chemistry also provides ready access to the corresponding DBU salts which are potential substrates for Pd-catalysed coupling reactions. (Figure presented.).

Method for producing high-purity 3-thiohydracrylic acid

The invention discloses a method for producing high-purity 3-thiohydracrylic acid. The method comprises the following steps that 1, an addition reaction is carried out, wherein acrylonitrile and sodium bisulfide are added to generate 3-mercapto propionic nitrile and sodium sulphide, sodium sulphide can react with acrylonitrile to generate disulfide generation malononitrile, and therefore an addition product is a mixture of 3-mercapto propionic nitrile and disulfide generation malononitrile; 2, a hydrolysis reaction is carried out, wherein in a hydrochloric acid system, the mixture of 3-mercapto propionic nitrile and disulfide generation malononitrile is hydrolyzed into a mixture of 3-thiohydracrylic acid and dithio malonic acid; 3, a reduction reaction is carried out, wherein in the hydrochloric acid system, dithio malonic acid is reduced into 3-thiohydracrylic acid through iron powder, and crude 3-thiohydracrylic acid is obtained after solvent extraction and solvent recovery; 4, a refining procedure is carried out, wherein crude 3-thiohydracrylic acid is rectified to obtain finished 3-thiohydracrylic acid. The defects in the prior art are overcome, the advantages of being low in cost and high in yield are achieved, all the reaction procedures are carried out under normal pressure, three wastes are reutilized, and almost no three wastes are discharged.

Facile solvent-free generation of disulfide dianion and its use for preparation of symmetrical disulfides

A variety of symmetrical dialkyl disulfides were prepared from the reaction of alkyl halides, sodium hydroxide and elemental sulfur under solvent free conditions. The reaction proceeded very fast and produced the desired products in moderate to excellent isolated yields.

Solution phase synthesis of oligonucleotides

A process for the synthesis in solution phase of a phosphorothioate triester is provided. The process comprises the solution phase coupling of an H-phosphonate with an alcohol in the presence of a coupling agent to form an H-phosphonate diester. The H-phosphonate diester is oxidized in situ with a sulfur transfer agent to produce the phosphorothioate triester. Preferably, the H-phosphonate and alcohol are protected nucleosides or oligonucleotides. Oligonucleotide H-phosphonates which can be used in the formation of phosphorothioate triesters are also provided.

Preparation of 2-(2-cyanoethyl)sulfanyl-1H-isoindole-1,3-(2H)-dione and related sulfur-transfer agents

The title compound 3 and 4-[(2-cyanoethyl)sulfanyl]morpholine-3,5-dione 12 are both conveniently prepared in good yield from 2-cyanoethyl disulfide, which itself is readily prepared in one step from S-(2-cyanoethyl)isothiouronium chloride 4. In the same way, dimethyl and diphenyl disulfides are converted, into 2-methylsulfanyl- and 2-phenylsulfanyl-1H-isoindole-1,3-(2H)-diones 8a and 8b, respectively, also in good yields.