266339-14-4

Basic information

• Product Name: 2(1H)-Pyridinethione,1-[(methoxycarbonyl)oxy]-(9CI)
• Synonyms: 2(1H)-Pyridinethione,1-[(methoxycarbonyl)oxy]-(9CI)
• CAS NO: 266339-14-4
• Molecular Formula: C₇H₇NO₃S
• Molecular Weight: 184.19244
• Product Categories: METHOXY
• Mol File: 266339-14-4.mol

Chemical Properties

• Boiling Point: 246.6±23.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• PKA: -2.42±0.70(Predicted)
• CAS DataBase Reference: 2(1H)-Pyridinethione,1-[(methoxycarbonyl)oxy]-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Pyridinethione,1-[(methoxycarbonyl)oxy]-(9CI)(266339-14-4)
• EPA Substance Registry System: 2(1H)-Pyridinethione,1-[(methoxycarbonyl)oxy]-(9CI)(266339-14-4)

Safety Data

• Hazardous Substances Data: 266339-14-4(Hazardous Substances Data)

Usage

Uses

Anti-dandruff shampoos and treatments for seborrheic dermatitis

Chemical properties

Derivative of pyridine, contains a thiocarbonyl group

Active properties

Antifungal and antibacterial

Mechanism of action

Inhibits the growth of the fungus Malassezia

Additional properties

Anti-inflammatory and antioxidant

Popularity

Common ingredient in skincare and hair care products

Safety

Generally considered safe for topical use, but may cause skin irritation in some individuals.

Upstream product

• 3811-73-2 2-mercaptopyridine-1-oxide sodium salt 
• 79-22-1 methyl chloroformate 

Downstream Products

• 103698-37-9 2-{[2-cyclohexyl-1-(phenylsulfonyl)ethyl]sulfanyl}pyridine 
• 119520-56-8 2-(cyclohexylsulfanyl)pyridine 
• 145144-82-7 3-Cyclohexyl-2-(pyridin-2-ylsulfanyl)-propionic acid methyl ester 
• 579488-78-1 methyl 5-(4-methylcyclohex-3-enyl)-2-(2-pyridylsulfanyl)hexanoate 
• 579488-74-7 methyl 3-(3-(tert-butyldimethylsilyloxy)cyclohexyl)-2-(2-pyridylsulfanyl)propanoate 
• 579488-71-4 methyl 3-(2-(tert-butyldimethylsilyloxy)cyclohexyl)-2-(2-pyridylsulfanyl)propanoate 

Relevant articles and documents

Organoboranes mediated radical cyclizations

Hydroboration of dienes with catecholborane followed by radical cyclization using pyridine-2-thione-N-methoxycarbonyloxy (= PTOC-OMe, a Barton carbonate) as chain transfer reagent is reported. A facile access to a bicyclic α-methylenelactone is described.

B-Alkylcatecholboranes as a Source of Radicals for Efficient Conjugate Additions and Allylations

B-Alkylcatecholboranes, easily prepared in situ by hydroboration of alkenes, are powerful radical precursors that can be used for carbon-carbon bond formation. Typical procedures for (a) conjugate addition to enones, (b) conjugate addition to activated al

One-pot rhodium(I)-catalyzed hydroboration of alkenes: Radical conjugate addition

B-Alkylcatecholboranes, prepared by rhodium-(I)-catalyzed hydroboration of alkenes, are suitable radical precursors for conjugate addition to activated olefins. This procedure proved to be particularly useful for the control of the regio- and chemoselectivity of such tandem processes. Enantioselective hydroboration has also been successfully coupled with radical chain reaction in a one-pot process.

Self-terminating, oxidative radical cyclizations of medium-sized cycloalkynones with inorganic and organic oxygen-centered radicals of type XO·: The reaction pathway depends on the nature of X

The reaction of various inorganic and organic oxygen-centered radicals of type XO· with cyclodec-5-ynone 6 can be used as a mechanistic probe to study the ease with which X· acts as a leaving group in self-terminating, oxidative radical cyclizations. It was observed that when X· has good leaving ability the reaction leads to formation of the bicyclic epoxy ketones 13 and 14, whereas in the other cases a competition between the individual reversible cyclization steps resulted in predominant formation of the spiro ketone 20. The experimental data obtained lead to the suggestion that vinyl radicals could rearrange through 1,2-group migrations.

A convenient and general tin-free procedure for radical conjugate addition

An environmentally friendly one-pot reaction for conjugate radical additions to activated olefins, with good to excellent yields, uses organoboranes generated in situ as radical precursors and the Barton carbonate PTOC-OMe as a radical-chain transfer reag