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Usage

Uses

Used in Rubber and Plastic Industry:
2-Thioxohexamethyleneimine is used as a key ingredient in the production of rubber and plastic products for its ability to enhance the properties of these materials, such as flexibility and durability.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Thioxohexamethyleneimine is used as a starting material for the synthesis of certain drugs, contributing to the development of new medicinal compounds.
Used in Agricultural Chemical Production:
2-Thioxohexamethyleneimine is also utilized in the production of agricultural chemicals, where it plays a role in the synthesis of various agrochemicals to improve crop protection and yield.
Used as a Catalyst in Organic Reactions:
Furthermore, 2-Thioxohexamethyleneimine serves as a catalyst in organic reactions, facilitating and speeding up chemical processes, which is crucial for the synthesis of a range of organic compounds.
Safety Precautions:
It is important to handle and store 2-Thioxohexamethyleneimine with caution, as it may cause skin and eye irritation. Additionally, it should be kept away from heat and open flames to prevent potential hazards.

Upstream product

• 105-60-2 caprolactam 
• 507-09-5 thioacetic acid 
• 100-64-1 cyclohexanone-oxime 
• 110-86-1 pyridine 
• 98-09-9 benzenesulfonyl chloride 
• 108-94-1 cyclohexanone 
• 2432-74-8 1-amino-5-cyanopentane 

Downstream Products

• 111-49-9 hexamethylene imine 
• 54-95-5 pentetrazole 
• 19214-08-5 perhydro-2-azepinone oxime 
• 56929-67-0 tetramethylenethieno<2,3-d>tetrahydroazepino<1,2-a>pyrimidin-4-one 
• 94892-43-0 3-phenyl-6,7,8,9-tetrahydro-5H-thiazolo[3,2-a]azepinium; iodide 
• 34845-36-8 2,3-diphenyl-2,3,6,7,8,9-hexahydro-[1,3]thiazino[3,2-a]azepin-4-one 
• 99999-84-5 2,3-diphenyl-6,7,8,9-tetrahydro-5H-thiazolo[3,2-a]azepinium; iodide 
• 80815-09-4 C₁₄H₁₄N₂O₃S 
• 121003-13-2 N-methoxyacetyl-ε-thiocaprolactam 
• 125880-11-7 1-(3'-Methyl-3'-butenoyl)-ε-thiocaprolactam 
• 882-33-7 diphenyldisulfane 
• 75121-60-7 1-Phenyl-2-(2-thioxo-azepan-1-ylmethyl)-propenone 
• 20169-57-7 7-Benzylsulfanyl-3,4,5,6-tetrahydro-2H-azepine; hydrochloride 
• 121003-24-5 1-(2-Thioxo-azepan-1-yl)-ethanone 

Relevant academic research and scientific papers

Ring Expansion of Thiolactams via Imide Intermediates: An Amino Acid Insertion Strategy

The AgI-promoted reaction of thiolactams with N-Boc amino acids yields an N-(α-aminoacyl) lactam that can rearrange through an acyl transfer process. Boc-deprotection results in convergence to the ring-expanded adduct, thereby facilitating an overall insertion of an amino acid into the thioamide bond to generate medium-sized heterocycles. Application to the site-specific insertion of amino acids into cyclic peptides is demonstrated.

Amide (A)–thioamide (T) interconversions using Ph3SiSH (A to T) and Ph3SnOH (T to A) reagents

Ph3SiSH transforms amides to thioamides and Ph3SnOH performs the reverse process, with the concomitant formation of Ph3SiOH (or Ph3SiOSiPh3) and Ph3SnSSnPh3, respectively. The chemistry is a delightful illustration of the oxophilicity of silicon compared to the thiophilicity of tin and occurs under relatively mild conditions, and for amide to thioamide transformation requires no amide activation. The chemistry is in accord with available data for Si?(S)(O), Sn?(O)(S) and C?(O)(S) bond energies. Copyright

An Aluminum(III)-Catalyzed Thioamide-Aldehyde-Styrene Condensation: Direct Synthesis of Allylic Thioamide Derivatives

An aluminum(III) triflate catalyzed three-component synthesis of allylic thioamide derivatives by condensation of a thioamide, paraformaldehyde and a styrene is reported.

A THIONATION PROCESS AND A THIONATING AGENT

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N

A thionation process and a thionating agent

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.

Facile synthesis of thioamides via P2S5-mediated beckmann rearrangement of oximes

A facile and efficient approach to the synthesis of secondary thioamides from ketoximes via Beckmann rearrangement has been established, using phosphorus pentasulfide as a dehydrating and thiating agent. It is also efficient for the preparation of primary thiobenzamide from benzaldoxime. This approach features simple-operation, easy-control and good to excellent yields.

O,O-Diethyl dithiophosphoric acid mediated direct synthesis of thioamides from aldehydes and ketones

A general and convenient method for a one-pot conversion of aldehydes and ketones into thioamides has been developed. The protocol involves oximation of aldehydes and ketones followed by deoxygenative thioamidation of oximes with O,O-diethyl dithiophosphoric acid which acts as an acid as well a source of sulfur. The method is operationally simple, high yielding, and also applicable to the conversion of amides and nitriles into the corresponding thioamides.

Facile and odorless one-pot process for the synthesis of N-substituted thioamides via TsCl-mediated Beckmann rearrangement of ketoximes

A facile and odorless one-pot thionation process for the synthesis of N-substituted thioamides using chemically stable and inexpensive thiourea reagent via the Beckmann rearrangement of ketoximes, has been described. Georg Thieme Verlag Stuttgart · New York.

Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone

Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.

Targeting the polyamine transport system with benzazepine- and azepine-polyamine conjugates

The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.