3012-97-3

Basic information

• Product Name: S-methyl piperidine-1-carbothioate
• Synonyms: 1-Piperidinecarbothioic acid, S-methyl ester; S-Methyl 1-piperidinecarbothioate
• CAS NO: 3012-97-3
• Molecular Formula: C₇H₁₃NOS
• Molecular Weight: 159.2492
• Mol File: 3012-97-3.mol

Chemical Properties

• Boiling Point: 241.8°C at 760 mmHg
• Flash Point: 100°C
• Density: 1.115g/cm³
• Vapor Pressure: 0.0353mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: S-methyl piperidine-1-carbothioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-methyl piperidine-1-carbothioate(3012-97-3)
• EPA Substance Registry System: S-methyl piperidine-1-carbothioate(3012-97-3)

Safety Data

• Hazardous Substances Data: 3012-97-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
S-methyl piperidine-1-carbothioate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, S-methyl piperidine-1-carbothioate serves as a crucial component in the creation of agrochemicals, aiding in the production of effective and stable products for agricultural use.
Used in Organic Synthesis:
As a building block in organic synthesis, S-methyl piperidine-1-carbothioate is utilized for its reactivity, allowing chemists to construct a diverse array of chemical compounds for various applications, including the development of new materials and chemical entities.

Upstream product

• 110-89-4 piperidine 
• 6132-46-3 O-(2,4-dinitrophenyl) S-methyl thiocarbonate 
• 18369-83-0 methyl thiochloroformate 

Relevant articles and documents

Phenolysis and aminolysis of 4-nitrophenyl and 2,4-dinitrophenyl S-methyl thiocarbonates in aqueous ethanol

The reactions of S-methyl O-(4-nitrophenyl) thiocarbonate (1) and S-methyl O-(2,4-dinitrophenyl) thiocarbonate (2) with a series of secondary alicyclic (SA) amines and phenols are subjected to a kinetic investigation. Under nucleophile excess, pseudo-first-order rate coefficients (kobs) are obtained. Plots of kobs against the free nucleophile concentration at constant pH are linear with slopes kN. The Brnsted plots (log kN vs. nucleophile pKa) for the reactions are linear with slope (β) values in the 0.5-0.7 range, in accordance with concerted mechanisms. Comparison of the SA aminolysis of 1 with the same one carried out in water shows that the change of solvent from water to aqueous ethanol destabilizes the zwitterionic tetrahedral intermediate, changing the mechanism from stepwise to concerted. This destabilization is greater than that due to the change from SA amines to quinuclidines. For the phenolysis reactions, the kN values in aqueous ethanol are smaller than those for the same reactions in water. Considering that the nucleophile is an anion, this result is unexpected because the anion should be more stabilized in the more polar solvent. This result is explained by the facts that the phenoxide reactant has a negative charge that is delocalized in the aromatic ring and the transition state is highly polar.

Kinetics and mechanisms of the reactions of S-methyl chlorothioformate with pyridines and secondary alicyclic amines

The pyridinolysis of S-methyl chlorothioformate shows a biphasic Br?nsted-type plot, in agreement with a stepwise mechanism and a change in the rate-limiting step, from formation of a zwitterionic tetrahedral intermediate (T±) at high pKa to its breakdown at low pKa. The reaction of the same substrate with secondary alicyclic amines shows a linear Br?nsted-type plot of slope 0.23, which is in accordance with a stepwise mechanism where formation of T± is the rate-determining step for the whole pKa range examined.