79645-02-6

Basic information

• Product Name: 3-cyclohexyl-1-methyl-1-nitrosothiourea
• CAS NO: 79645-02-6
• Molecular Formula: C₈H₁₅N₃OS
• Molecular Weight: 201.2892
• Mol File: 79645-02-6.mol

Chemical Properties

• Boiling Point: 271.9°C at 760 mmHg
• Flash Point: 118.2°C
• Density: 1.27g/cm³
• Vapor Pressure: 0.00629mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 3-cyclohexyl-1-methyl-1-nitrosothiourea(CAS DataBase Reference)
• NIST Chemistry Reference: 3-cyclohexyl-1-methyl-1-nitrosothiourea(79645-02-6)
• EPA Substance Registry System: 3-cyclohexyl-1-methyl-1-nitrosothiourea(79645-02-6)

Safety Data

• Hazardous Substances Data: 79645-02-6(Hazardous Substances Data)

Upstream product

• 1122-82-3 isothiocyanatocyclohexane 
• 108-91-8 cyclohexylamine 
• 13120-04-2 methyl-1 cyclohexyl-3 thio-2 uree 

Downstream Products

• 13120-04-2 methyl-1 cyclohexyl-3 thio-2 uree 
• 39804-96-1 1-cyclohexyl-3-methylurea 
• 1122-82-3 isothiocyanatocyclohexane 

Relevant articles and documents

Electronic and Steric Effects of Alkyl Group on Denitrosation of 3-Alkyl-1-methyl-1-nitrosothioureas

A series of 3-alkyl-1-methyl-1-nitrosothioureas with R=CH3, C2H5, cyclo-C6H11 (3), (CH3)2CH (4), C2H5(CH3)CH, and (CH3)3C were synthesized and their rates of acid catalyzes (pHH:kD is 1.25 for 4.Except 3, a linear plot of log kR/kMe for the denitrosation of RNHCSN(NO)CH3 vs. ?* provides ρ*=-0.98(r=-0.997).The significant factor affecting the rate determining step of the denitrosation of these N-nitrosothioureas at pH 4.6 is the electronic effect of the substituent at the N3 position.

ACID CATALYSIS OF THE DENITROSATION OF N-METHYL-N prime -CYCLOHEXYL-N-NITROSOTHIOUREA.

The kinetics of denitrosation of N-methyl-N prime -cyclohexyl-N-nitrosothiourea has been studied in the range of pH 3. 45-3. 73 using four organic acids; acetic acid, formic acid, chloracetic acid, and cyanoacetic acid. Analyses of the kinetic data including the Bronsted plots have shown that the reaction is subject to a general acid catalysis.

Synthesis of Novel N-Nitrosothioureas and Examination of Their Mechanisms of Formation by High-Field Nitrogen-15 and Carbon-13 Nuclear Magnetic Resonance Spectra of Specifically Labeled Compounds

An examination by 15N NMR of Na15NO2 under various conditions of acidity led to the identification of several electrophilic nitrogen species.This permitted the selection of reaction conditions of low acidity which favor nitrosation at the nitrogen atom of thioureas rather than on the normally more reactive sulfur, leading to the isolation of novel N-nitrosothioureas.In contrast it was shown by employing 15N and 13C labeling that higher acidity conditions favor reaction via a detectable thionitrosyl intermediate.

Synthesis of Nitrosothioureas. 15N N.M.R. Evidence for the Formation of Thionitrosyl Compounds in the Nitrosation of Thioureas

Nitrosothioureas may be prepared by treatment of thioureas with NaNO2 in 0.1 N HCl at -5 deg C by direct N-nitrosation whereas 15N n.m.r. studies at -10 deg C which employed specifically 15N-enriched compounds revealed the intermediacy of a thionitrosyl compound under more acidic conditions which gave the urea by hydrolysis.