94-37-1

Usage

Uses

Used in Rubber Industry:
Dicyclopentamethylenethiuram disulfide is used as an accelerator and vulcanizing agent for latex (gloves) and butyl rubber. It plays a crucial role in the vulcanization process, which is essential for the production of rubber products with desired properties.
Used in Latex Glove Production:
Dicyclopentamethylenethiuram disulfide is used as a rubber accelerator in the production of latex gloves. It helps to speed up the vulcanization process, resulting in the formation of a stable and elastic rubber material that is suitable for manufacturing gloves.
Used in Butyl Rubber Production:
Dicyclopentamethylenethiuram disulfide is also used as a vulcanizing agent in the production of butyl rubber. It contributes to the formation of a durable and flexible rubber material that is ideal for various applications, including automotive and industrial products.

Contact allergens

A rubber chemical contained in “thiuram mix.” The most frequent occupational categories are the metal industry, homemakers, health services and laboratories, and the building industry

InChI:InChI=1/C12H20N2S4/c15-11(13-7-3-1-4-8-13)17-18-12(16)14-9-5-2-6-10-14/h1-10H2

Upstream product

• 75-15-0 carbon disulfide 
• 10220-20-9 1,1'-dithiobispiperidine 
• 71-43-2 benzene 
• 873-57-4 sodium piperidinedithiocarbamate 
• 98-99-7 piperidine-1-carbodithioic acid 
• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 60-29-7 diethyl ether 
• 66232-66-4 N-(N,N-dimethylthiocarbamoyldithioyl)piperidine 
• 110-85-0 piperazine 
• 110-89-4 piperidine 
• 887144-97-0 Togni's reagent 
• 136-04-9 potassium 1-piperidinecarbodithioate 
• 887144-94-7 Togni's reagent II 
• 26773-65-9 N-piperidin-2-benzothiazole sulfenamide 

Downstream Products

• 1013-92-9 di(piperidin-1-yl)methanethione 
• 873-57-4 sodium piperidinedithiocarbamate 
• 725-32-6 bis(1-piperidinylthiocarbonyl)sulfide 
• 2762-59-6 N-phenylpiperidine-1-carbothioamide 
• 110-89-4 piperidine 
• 7783-06-4 hydrogen sulfide 
• 7664-41-7 ammonia 
• 645-48-7 1-phenyl-3-thiosemicarbazide 
• 41025-57-4 cyclohexyl piperidine-1-carbo(dithioperoxo)thioate 
• 13939-69-0 piperidine carbamoyl chloride 
• 946069-71-2 [bis(triphenylphosphine)iminium]titanium⁽⁰⁾ tetracarbonyl(S₂CN(CH₂)5) 
• 147723-51-1 Piperidine-1-carbodithioic acid 2-oxo-cyclohexyl ester 

Relevant academic research and scientific papers

Continuous-flow step-economical synthesis of thiuram disulfidesviavisible-light photocatalytic aerobic oxidation

A continuous-flow photocatalytic synthesis of the industrially important thiuram disulfides has been developed, utilizing O2as the oxidant and Eosin Y as the photoredox catalyst. This highly atom- and step-economical method features much reduced reaction time as well as excellent product yield and purity, making it a sustainable and potentially scalable process for industrial production.

Development of disulfide-derived fructose-1,6-bisphosphatase (FBPase) covalent inhibitors for the treatment of type 2 diabetes

Fructose-1,6-bisphosphatase (FBPase), as a key rate-limiting enzyme in the gluconeogenesis (GNG) pathway, represents a practical therapeutic strategy for type 2 diabetes (T2D). Our previous work first identified cysteine residue 128 (C128) was an important allosteric site in the structure of FBPase, while pharmacologically targeting C128 attenuated the catalytic ability of FBPase. Herein, ten approved cysteine covalent drugs were selected for exploring FBPase inhibitory activities, and the alcohol deterrent disulfiram displayed superior inhibitory efficacy among those drugs. Based on the structure of lead compound disulfiram, 58 disulfide-derived compounds were designed and synthesized for investigating FBPase inhibitory activities. Optimal compound 3a exhibited significant FBPase inhibition and glucose-lowering efficacy in vitro and in vivo. Furthermore, 3a covalently modified the C128 site, and then regulated the N125–S124–S123 allosteric pathway of FBPase in mechanism. In summary, 3a has the potential to be a novel FBPase inhibitor for T2D therapy.

Iodine mediated direct coupling of benzylic alcohols with dithiocarbamate anions: An easy access of S-benzyl dithiocarbamate esters under neat reaction condition

An efficient, metal and solvent free synthesis of S-benzylic dithiocarbamate esters has been demonstrated via the iodine mediated direct C-S coupling of benzylic alcohols with dithiocarbamate anions generated in-situ by the reactions of amines and carbon disulphide. All the reactions were very fast (15–30 min) and performed under open air atmosphere. Cyclic and acyclic secondary amines, primary amine, aromatic amine actively participated in the one-pot coupling reactions with different benzylic alcohols. Non benzylic alcohols offer the synthesis of O-thiocarbamate compounds under the identical reaction condition.

Disulfiram as a potent metallo-β-lactamase inhibitor with dual functional mechanisms

We report a promising NDM-1 inhibitor, disulfiram, which can covalently bind to NDM-1 by forming an S-S bond with the Cys208 residue. Its copper-containing metabolite in vivo, Cu(DTC)2, also inactivated NDM-1 through oxidizing the Zn(ii) thiolate site of the enzyme, therefore exhibiting dual functional inhibitory potential against B1 and B2 subclass MβLs.

Pyruvate dehydrogenase kinase inhibitor and application thereof

The invention provides a pyruvate dehydrogenase kinase inhibitor and an application thereof, specifically a compound as shown in a formula I described in the specification or pharmaceutically acceptable salts thereof. The compound has excellent effects of inhibiting pyruvate dehydrogenase kinase activity and resisting tumors. The invention also provides a pharmaceutical composition containing the compound provided by the invention and the application thereof in the aspect of inhibiting pyruvate dehydrogenase kinase.

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni's reagent

A one-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni's reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C-N bond in the dithiocarbamate moiety of piperidine, pyrrolidine, and diethylamine adducts, respectively. In addition, the calculated barriers of rotation are in reasonable agreement with the experiments.

Role of disulfide linkage in action of bis(dialkylaminethiocarbonyl)disulfides as potent double-Edged microbicidal spermicide: Design, synthesis and biology

Trichomoniasis and candidiasis are amongst the most common morbidity-causing reproductive tract infections, generally treated by Metronidazole and Fluconazole respectively. Poor vaginal efficacy, drug-resistance and non-spermicidal nature limit their use as topical microbicidal contraceptives. Bis(dialkylaminethiocarbonyl)disulfides (4-38) were designed as dually active, non-surfactant molecules capable of eliminating Trichomonas vaginalis and Candida strains as well as irreversibly immobilizing 100% human sperm instantly, at doses non-cytotoxic to human cervical epithelial cells and vaginal microflora in vitro. Compounds 12, 16, 17 were fifty times more active than nonoxynol-9, OTC vaginal spermicide, and compounds 12 and 17 have shown remarkable in vivo activity in rabbit model. Most promising compound 17 has shown promise for further development as a double-edged vaginal microbicide due to their improved activity and safety along with notable in vivo trichomonicidal activity. Role of disulfide group was established by loss of spermicidal activity on chemical modifications (39-56). These disulfides might be targeting thiol groups present over cell membrane of human sperm and Trichomonas as shown by fluorescence labeling of free thiols.

Reduced graphene oxide as recyclable catalyst for synthesis of Bis(aminothiocarbonyl)disulfides from secondary amines and carbon disulfide

The reaction of secondary amines with CS2 under mild conditions using reduced graphene oxide (rGO) as a green catalyst was reported, which provided an efficient access to the one-pot synthesis of bis(aminothiocarbonyl) disulfides. The rGO can be recycled at least four times without any loss of catalytic activity. A plausible mechanism was proposed.

Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: Facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides

Diverse disubstituted and trisubstituted thioureas were synthesized by the condensation of dithiocarbamate TEA (or DABCO) salts and amines using cerium ammonium nitrate (CAN) as a catalyst in high yields at room temperature. It is a one-pot method and it is unnecessary to isolate isothiocyanates. This reaction probably took place through nucleophilic addition of amines to isothiocyanates, which were generated by oxidative coupling of dithiocarbamates and the following decomposition of bis(aminothiocarbonyl)disulfides. When secondary amines and CS2served as the reactants, bis(aminothiocarbonyl)disulfides were obtained via tandem nucleophilic addition/oxidative coupling reactions in moderate to excellent yields. In all the coupling reactions, the oxidant was air and CAN possibly acted as an SET catalyst.

Development of an improved method for conversion of thiuram disulfides into N,N-dialkylcarbamoyl halides and derivatives

A convenient procedure for preparing N,N-disubstituted carbamoyl halides is reported. It consists of two steps: (1) reaction of carbon disulfide and a secondary amine in the presence of a polar organic solvent and oxygen to produce the corresponding tetraalkyl thiuram disulfides and (2) reaction of tetraalkyl thiuram disulfide with a halide in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halide. Copyright Taylor & Francis Group, LLC.