94-37-1

Basic information

• Product Name: DICYCLOPENTAMETHYLENETHIURAM DISULFIDE
• Synonyms: 1,1’-(dithiodicarbonothioyl)bis-piperidin;1,1’-(dithiodicarbonothioyl)bispiperidine;1-piperidinethiocarbonyldisulfide;dipentamethylenethiuramdisulfide;disulfide,bis(piperidinothiocarbonyl);BIS(PENTAMETHYLENE)THIURAM DISULPHIDE;BIS(PIPERIDINOTHIOCARBONYL) DISULFIDE;DI-N-PENTAMETHYLENETHIURAM DISULFIDE
• CAS NO: 94-37-1
• Molecular Formula: C₁₂H₂₀N₂S₄
• Molecular Weight: 320.56
• EINECS: 202-328-1
• Mol File: 94-37-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 436.6°C at 760 mmHg
• Flash Point: 217.9°C
• Appearance: /
• Density: 1.3550 (rough estimate)
• Vapor Pressure: 7.97E-08mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 0.89±0.20(Predicted)
• CAS DataBase Reference: DICYCLOPENTAMETHYLENETHIURAM DISULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DICYCLOPENTAMETHYLENETHIURAM DISULFIDE(94-37-1)
• EPA Substance Registry System: DICYCLOPENTAMETHYLENETHIURAM DISULFIDE(94-37-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43-36/37/38
• Safety Statements: 37-26-24
• Hazardous Substances Data: 94-37-1(Hazardous Substances Data)

Usage

Description

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

Uses

Different sources of media describe the Uses of 94-37-1 differently. You can refer to the following data:
1. Dipentamethylenethiuram disulfide is an accelerator and vulcanizing agent for latex (gloves) and butyl rubber.
2. Dicyclopentamethylenethiuram Disulfide is a known rubber accelerator used during vulcanizing.

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 
• 136-04-9 potassium 1-piperidinecarbodithioate 
• 26773-65-9 N-piperidin-2-benzothiazole sulfenamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 98-09-9 benzenesulfonyl chloride 
• 14990-66-0 1-(1-phenylvinyl)piperidine 

Downstream Products

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

Relevant articles and documents

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.

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.