109514-84-3

Basic information

• Product Name: Carbamothioic acid, (4-methoxyphenyl)-, O-(4-methoxyphenyl) ester
• CAS NO: 109514-84-3
• Molecular Formula: C15H15NO3S
• Molecular Weight: 289.355
• Mol File: 109514-84-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Carbamothioic acid, (4-methoxyphenyl)-, O-(4-methoxyphenyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamothioic acid, (4-methoxyphenyl)-, O-(4-methoxyphenyl) ester(109514-84-3)
• EPA Substance Registry System: Carbamothioic acid, (4-methoxyphenyl)-, O-(4-methoxyphenyl) ester(109514-84-3)

Safety Data

• Hazardous Substances Data: 109514-84-3(Hazardous Substances Data)

Upstream product

• 940-58-9 4-methoxyphenyl chlorothionoformate 
• 104-94-9 4-methoxy-aniline 
• 45714-57-6 p-anisidine-ND2 
• 150-76-5 4-methoxy-phenol 

Relevant articles and documents

Aminolysis of aryl chlorothionoformates with anilines in acetonitrile: Effects of amine nature and solvent on the mechanism

The aminolysis of aryl chlorothionoformates (7, YC6H 4OC(=S)Cl) with anilines (XC6H4NH2) in acetonitrile at 5.0 °C has been investigated. The rates are slower than those for the corresponding reactions of aryl chloroformates (6, YC 6H4OC(=O)Cl). This rate sequence is a reverse of that for alkyl chloroformates (1 4) in water, for which rate-limiting formation of a tetrahedral intermediate, T±, is predicted. On the basis of the large negative cross-interaction constant, ρXY = -0.77, failure of the reactivity-selectivity principle, normal kH/k D values involving deuterated nucleophiles (XC6H 4ND2), and low ΔH≠ with large negative ΔS≠ values, a concerted mechanism with a four-membered hydrogen bonded cyclic transition state (11) is proposed for the title reaction series. It has been shown that the solvent change from water to acetonitrile for the aminolysis of 6 and 7 causes a mechanistic change from stepwise to concerted.