110097-28-4

Basic information

• Product Name: phenyl (1Z)-N-hydroxy-2-oxobutanimidothioate
• CAS NO: 110097-28-4
• Molecular Formula: C₁₀H₁₁NO₂S
• Molecular Weight: 209.2648
• Mol File: 110097-28-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 367.48°C at 760 mmHg
• Flash Point: 176.046°C
• Density: 1.176g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: phenyl (1Z)-N-hydroxy-2-oxobutanimidothioate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl (1Z)-N-hydroxy-2-oxobutanimidothioate(110097-28-4)
• EPA Substance Registry System: phenyl (1Z)-N-hydroxy-2-oxobutanimidothioate(110097-28-4)

Safety Data

• Hazardous Substances Data: 110097-28-4(Hazardous Substances Data)

Upstream product

• 22920-77-0 1-nitrobutan-2-one 
• 108-98-5 thiophenol 
• 110097-30-8 N-hydroxy-2-oxobutanimidoyl chloride 

Relevant articles and documents

Simple Preparation of α-Acyl α-Arylthio Oximes (N-Hydroxy-2-oxoalkanimidothioates): Ambident Reactivity of α-Nitro Ketones

A one-step synthesis of α-acyl α-phenylthio oximes by nucleophilic dehydration of α-nitro ketones is described.Treatment of the α-nitro ketones 7a-c (prepared by reaction of the sodium salt of nitromethane 6 with the acylimidazoles 5a-c) with thiophenol and titanium tetrachloride in the presence of triethylamine gave the phenyl N-hydroxy-2-oxoalkanimidothioates 4a-c in good yield.These products are potentially useful intermediates for the synthesis of analogues of the well known pesticides, methomyl, thiodicarb, and oxamyl.Interestingly, when the α-nitro ketones 7a-c are treated with thiophenol in the presence of boron trifluoride, only thioketalization is observed and the thioketals 8a-c are produced.The stereochemistry of the oxime hydroxyl in the crystal was shown to be syn to the phenylthio group, i.e., Z stereochemistry, by a single-crystal X-ray structure determination.A reasonable mechanistic explanation is presented to explain the reaction pathway.