| Identification | More | [Name]
Cyclohexylthiophthalimide | [CAS]
17796-82-6 | [Synonyms]
CTPI
CYCLOHEXYL N-PHTHALIMIDYL SULFIDE
cyclohexylthiophthalimide
N-(CYCLOHEXYLTHIO)PHTHALIMIDE
SANTOGARD(R) PVI
SANTOGARD(R) PVI 50
VANTARD PVI
2-(cyclohexylthio)-1h-isoindole-3(2h)-dione
3-(2H)-dione,2-(cyclohexylthio)-1H-Isoindole-1
cp29242
n-(cyclohexylthio)-phthalimid
n-cyclohexylsulfenylphthalimide
santogardpvi
santogardpvi-ds
N-(Cyclohexylthio)phtalimide
N-Cyclohexy(thio)phthalimide
Antiscorching Agent CTP
N-Cyclohexy(Thio)Phthalimide(Pvi)(Ctp)
N-(Cyclohexylthio)phthalimide, SANTOGARD PVI-100%
1H-Isoindole-1,3(2H)-dione, 2-(cyclohexylthio)- | [EINECS(EC#)]
241-774-1 | [Molecular Formula]
C14H15NO2S | [MDL Number]
MFCD00072247 | [Molecular Weight]
261.34 | [MOL File]
17796-82-6.mol |
| Chemical Properties | Back Directory | [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 | [form ]
powder to crystal | [pka]
-2.91±0.20(Predicted) | [color ]
White to Light yellow | [Henry's Law Constant]
1.5×102 mol/(m3Pa) at 25℃, HSDB (2015) | [Contact allergens]
N-Cyclohexyl-thiophthalimide is a rubber chemical, widely used as a vulcanization retarder. Sensitization sources are often protective gloves. | [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]
17796-82-6(EPA Substance) |
| Safety Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RTECS ]
TI4290000 | [TSCA ]
TSCA listed | [HS Code ]
2930.90.2400 | [REACH Registrations]
Active | [Hazardous Substances Data]
17796-82-6(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Description]
Cyelohexyl thiophtalimide is a rubber chemical widely
used as a vulcanization retarder. Sensitization sources
are perhaps protective gloves.
| [Uses]
N-(Cyclohexylthio)phthalimide is a vulcanization retarder widely used in various rubber products. | [Uses]
N-(Cyclohexylthio)phthalimide is used in preparation of high ortho-position Phenolic adhesive resin for improving steam aging-resistance of rubber. | [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 | [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 |
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