17796-82-6

Basic information

• Product Name: Cyclohexylthiophthalimide
• Synonyms: 2-(cyclohexylthio)-1h-isoindole-3(2h)-dione;3-(2H)-dione,2-(cyclohexylthio)-1H-Isoindole-1;cp29242;n-(cyclohexylthio)-phthalimid;n-cyclohexylsulfenylphthalimide;santogardpvi;santogardpvi-ds;SANTOGARD(R) PVI
• CAS NO: 17796-82-6
• Molecular Formula: C₁₄H₁₅NO₂S
• Molecular Weight: 261.34
• EINECS: 241-774-1
• Product Categories: Rubber Chemicals;Pharmaceutical Intermediates;PRE VULCANISATION INHIBITOR;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;masterbatch rubber antiscorching agent
• Mol File: 17796-82-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 90°C
• Boiling Point: 422.6 ºC at 760 mmHg
• Flash Point: 209.4 ºC
• Appearance: White or light yellow powder crystal
• Density: 1.25~1.35g/cm3
• Vapor Pressure: 0.000308mmHg at 25°C
• Refractive Index: 1.7500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.91±0.20(Predicted)
• Water Solubility: Insoluble in water
• CAS DataBase Reference: Cyclohexylthiophthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexylthiophthalimide(17796-82-6)
• EPA Substance Registry System: Cyclohexylthiophthalimide(17796-82-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: TI4290000
• Hazardous Substances Data: 17796-82-6(Hazardous Substances Data)

Usage

Description

Cyclohexylthiophthalimide, also known as scorch retarder, early vulcanization inhibitor, scorch retarder CTP, and scorch retarder PVI, is a rubber chemical widely used as a vulcanization retarder. It is a white, light yellow, or light yellow-brown crystal at room temperature. The product recrystallized from n-heptane is white crystals. It is soluble in acetone, benzene, toluene, ether, ethyl acetate, and slightly soluble in gasoline, insoluble in kerosene and water, and soluble in hot carbon tetrachloride, ethanol, and heptane.

Uses

Used in Rubber Industry:
Cyclohexylthiophthalimide is used as a vulcanization retarder for improving the steam aging-resistance of rubber. It 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. It provides a good anti-scorch effect, and its activity is not affected when used in combination with other rubber additives.
Additionally, N-(Cyclohexylthio)phthalimide is used in the preparation of high ortho-position Phenolic adhesive resin, which further enhances the steam aging-resistance of rubber products.

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.

InChI:InChI=1/C16H19ClOSi/c1-16(2,3)18-19(17,14-10-6-4-7-11-14)15-12-8-5-9-13-15/h4-13H,1-3H3

Upstream product

• 136918-14-4 phthalimide 
• 17797-03-4 cyclohexane sulphenyl chloride 
• 2439-85-2 N-bromophthalimide 
• 2550-40-5 1,2-dicyclohexyl disulfide 
• 1569-69-3 Cyclohexanethiol 
• 103-83-3 N,N'-dimethylbenzylamine 

Downstream Products

• 1170667-82-9 N₁,N₁-dimethyl-S-cyclohexyl-N₄-thiohydroxybiguanidine 
• 288588-24-9 4-cyanophenyl cyclohexyl sulfide 
• 59693-94-6 cyclohexyl-4-methoxyphenyl sulfide 
• 42267-53-8 4-(cyclohexylthio)morpholine 

Relevant articles and documents

RECOVERY METHOD OF SYNTHETIC SOLVENT

PROBLEM TO BE SOLVED: To provide a method for recovering a solvent industrially advantageously in order to reutilize the solvent, after synthesizing N-(cyclohexylthio)phthalimide in the solvent of a saturated hydrocarbon. SOLUTION: In a recovery method of

NOVEL PRODRUGS OF METFORMIN

The present invention relates to novel prodrugs of metformin, their pharmaceutically acceptable salts, pharmaceutical compositions containing the prodrugs, and methods of using the prodrugs. In particular, the present invention relates to prodrugs wherein sulfur-containing promoieties are attached to metformin to form novel bioreversible sulfenyl guanidine (N-S) prodrugs of metformin with improved oral absorption, and consequently promoted bioavailability.

N-Thiolated β-lactam antibacterials: Effects of the N-organothio substituent on anti-MRSA activity

A study on the structure-activity profiles of N-thiolated β-lactams 1 is reported which demonstrates the importance of the N-organothio moiety on antibacterial activity. Our results indicate that elongation of the N-alkylthio residue beyond two carbons, or extensive branching within the organothio substituent, diminishes antibacterial effects. Of the derivatives we examined, the N-sec-butylthio β-lactam derivative 5g possesses the strongest growth inhibitory activity against methicillin-resistant Staphylococcus aureus strains. Sulfur oxidation state is important, as the N-sulfenyl and N-sulfinyl groups provide for the best antibacterial activity, while lactams bearing the N-sulfonyl or N-sulfonic acid functionalities have much weaker or no anti-MRSA properties. Stereochemistry within the organothio chain does not seem to be a significant factor, although for N-sec-butylthio β-lactams 15a-d, the 3R,4S-lactams 15c, d are more active than the 3S,4R-stereoisomers 15a, b in agar diffusion experiments. The N-methylthio lactams are the most sensitive to the presence of glutathione, followed by N-ethylthio and N-sec-butylthio lactams, which indicates that bioactivity and perhaps bacterial selectivity of the lactams may be related to the amount of organothiols in the bacterial cell. These results support the empirical model for the mechanism of action of the compounds in which the lactam transverses the bacterial membrane to deliver the organothio moiety to its cellular target.