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| | Cyclohexylthiophthalimide Basic information |
| | Cyclohexylthiophthalimide Chemical Properties |
| Melting point | 90°C | | Boiling point | 422.6±28.0 °C(Predicted) | | density | 1.25~1.35g/cm3 | | refractive index | 1.7500 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | Water Solubility | Insoluble in water | | pka | -2.91±0.20(Predicted) | | form | powder to crystal | | color | White to Light yellow | | Henry's Law Constant | 1.5×102 mol/(m3Pa) at 25℃, HSDB (2015) | | InChIKey | UEZWYKZHXASYJN-UHFFFAOYSA-N | | LogP | 2.82-3.56 at 25℃ and pH6.9 | | Dissociation constant | 7.83-8.75 at 22℃ | | CAS DataBase Reference | 17796-82-6(CAS DataBase Reference) | | EPA Substance Registry System | N-(Cyclohexylthio)phthalimide (17796-82-6) |
| | Cyclohexylthiophthalimide Usage And Synthesis |
| Description | Cyelohexyl thiophtalimide is a rubber chemical widely
used as a vulcanization retarder. Sensitization sources
are perhaps protective gloves. | | Description | Cyclohexylthiophthalimide, also known as scorch retarder, early vulcanization inhibitor, scorch retarder CTP, and scorch retarder PVI, is white, light yellow or light yellow-brown crystal at room temperature. The product recrystallized from n-heptane is white crystals. Soluble in acetone, benzene, toluene, ether, ethyl acetate and ethyl acetate, slightly soluble in gasoline, insoluble in kerosene and water, soluble in hot carbon tetrachloride, ethanol and heptane. | | Uses | N-(Cyclohexylthio)phthalimide is used in preparation of high ortho-position Phenolic adhesive resin for improving steam aging-resistance of rubber. | | Uses | N-(Cyclohexylthio)phthalimide is a vulcanization retarder widely used in various rubber products. | | Application | Cyclohexylthiophthalimide is a very effective scorch retarder for all sulfur vulcanized dienes and low unsaturation rubbers, such as natural rubber, styrene-butadiene rubber, nitrile rubber, butyl rubber, neoprene, isoprene Rubber, butadiene rubber, EPDM rubber, etc. all have good anti-scorch effect, and their activity is not affected when used in combination with other rubber additives. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 44, p. 1554, 1979 DOI: 10.1021/jo01323a039 | | Contact allergens | N-Cyclohexyl-thiophthalimide is a rubber chemical, widely used as a vulcanization retarder. Sensitization sources are often protective gloves. | | Synthesis | Example 1: Synthesis of 2-(cyclohexylthio)isoindoline-1,3-dione
1,2-Dicyclohexyl disulfide (0.51 g, 2.21 mmol) was dissolved in anhydrous acetonitrile (20 mL) with N-bromophthalimide (0.50 g, 2.21 mmol) in a microwave reactor. The microwave irradiation reaction was carried out at 100 °C and 1 bar pressure for 10 min. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by fast column chromatography with the eluent of hexane/ethyl acetate (2:1, v/v) to afford the target compound 2-(cyclohexylsulfanyl)isoindoline-1,3-dione as a light yellow solid (0.29 g, 52% yield).
1H NMR (CDCl3) δ: 7.95-7.91 (2H, dd, 3JHH = 5.46 Hz, 4JHH = 3.07 Hz), 7.81-7.76 (2H, dd, 3JHH = 5.46 Hz, 4JHH = 3.07 Hz), 3.22-3.15 (1H, tt, 3JHH = 3.63 Hz, 10.88 Hz), 1.95-1.88 (2H, m), 1.84-1.75 (2H, m), 1.65-1.57 (1H, m), 1.43-1.33 (2H, m), 1.32-1.18 (3H, m). | | References | [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4142 - 4148
[2] Patent: WO2010/100337, 2010, A1. Location in patent: Page/Page column 6-7 |
| | Cyclohexylthiophthalimide Preparation Products And Raw materials |
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