65370-06-1

Upstream product

• 90-01-7 salicylic alcohol 
• 75-08-1 ethanethiol 
• 108-95-2 phenol 
• 120-65-0 ortho-dimethylaminomethylphenol 
• 625-60-5 ethyl thioacetate 
• 29973-13-5 ethiofencarb 
• 18885-85-3 2-phenyl-4H-benzo-1,3,2-dioxaborine 

Relevant academic research and scientific papers

In situ fluorescent labeling of highly volatile methylamine with 8-(4,6-dichloro-1,3,5-triazinoxy)quinoline

The first in situ fluorescent labeling probe for monitoring of highly volatile methylamine, 8-(4,6-dichloro-1,3,5-triazinoxy)quinoline, has been designed, synthesized and evaluated. The probe labels spectroscopically inert methylamine, causing a large change in fluorescence properties through suppression of the internal charge transfer, and thus can serve as an in situ labeling probe. This applicability has been demonstrated by measuring methylamine released during hydrolysis of N-methylcarbamates such as ethiofencarb.

Alkaline hydrolysis of ethiofencarb: Kinetic study and mechanism degradation

The present paper deals with the hydrolysis of ethiofencarb [2-ethylthiomethyl(phenyl)-N-methylcarbamate] in alkaline solution. The reaction kinetics has been investigated using spectrophotometric and liquid chromatographic techniques. The rate constants were determined following a proposed first-order kinetic model. The positive activation entropy ΔS≠ = +100.07 J mol-1 K-1 and the absence of general basic catalysis indicated an E1cB hydrolytic mechanism, involving the formation of methyl isocyanate. This result was confirmed by the fact that ethiofencarb fits well into Broensted and Hammett lines, obtained for a series of substituted N-methylcarbamate whose decomposition in aqueous media was established to follow an E1cB mechanism.

Iodine-Mediated Direct Generation of o-Quinone Methides at Room Temperature: A Facile Protocol for the Synthesis of ortho-Hydroxybenzyl Thioethers

An iodine-mediated preparation of ortho-quinone methides (o-QMs) from ortho-hydroxybenzyl alcohols by a C?O bond scission strategy is described. The in situ generated o-QMs were then employed for C?S bond formation by thio-Michael addition of thiols to provide the ortho-hydroxybenzyl thioethers (o-HBT) in moderate to excellent yields.

Photodegradation of the Carbamate Insecticide Ethiofencarb

In order to study the photoreactivity and possible photodegradation pathways of ethiofencarb (2-ethylthiomethylphenyl methylcarbamate) on plant surfaces, model experiments in the presence of cyclohexane, cyclohexene and isopropanol were performed. Both artificial light (λ > 280 nm) and natural sunlight were used. Half-lives of the ethiofencarb photodegradation were in the order cyclohexane isopropanol cyclohexene and ranged from 75 min to more than 20 h. Depending on the solvent and the light source chosen, different photoproducts were obtained. When ethiofencarb was irradiated in the presence of cyclohexane, photooxidation to the corresponding sulfoxide was the main degradation pathway, followed by a cyclization reaction. In the case of isopropanol as model solvent, numerous photoproducts were detected as a result of photooxidation, hydrolysis and the addition to ethiofencarb of the solvent molecule.

ortho-Specific alkylation of phenols via 1,3,2-benzodioxaborins

Reaction of a phenol with an aldehyde in the presence of phenylboronic acid gives a 1,3,2-benzodioxaborin.The latter could be reduced to the corresponding ortho-alkylphenol with tert-butylamine borane in the presence of aluminum chloride.Alternatively, the dioxaborin, when reacted with an alkylthiol or an alcohol in the presence of an acid, gave the corresponding ortho-alkylthiomethyl- or ortho-alkoxymethylphenol.Key words: phenol, alkylation, ortho-specific, 1,3,2-benzodioxaborin.

Process for the production of N-methylcarbamates

Process for the production of N-methylcarbamates: STR1 (wherein RO- is the radical of a substituted phenol or of a naphthol), wherein: in a first reaction step methylamine and diphenyl carbonate are reacted with each other, operating in the liquid phase and as a continuous process, in order to form phenol and phenyl-N-methylurethane; in a second reaction step phenyl-N-methylurethane, within the related reaction mixture outcoming from the first step, is thermally continuously decomposed, to yield a gaseous stream containing methyl isocyanate, from which the components different than methyl isocyanate are condensed off; in a third step the methyl isocyanate stream, outcoming from the second step, after an optional preliminary condensation, is continuously fed and contacted with a solution of a substituted phenol or of a naphthol in an inert organic solvent, containing a basic catalyst, to form N-methylcarbamate (I); N-methylcarbamate (I) is finally recovered from the reaction mixture outcoming from the third step.

Process for the preparation of alkylthiomethylphenols and arylthiomethylphenols

The present invention provides a process for the preparation of an alkylthiomethylphenol or arylthiomethylphenol of the general formula STR1 in which m, n, R and R1 have the meaning mentioned in the specification, in which a hydroxymethylphenol of the general formula STR2 is reacted with a mercaptan or thiophenol at a temperature of from 20° to 200° C., if appropriate in the presence of a diluent.

Preparation of 2-alkyl- and 2-aryl-thiomethylphenols

In the preparation of a 1-alkyl- and 2-aryl-thio-methylphenol of the formula STR1 in which R1 is, or the radicals R1 are, in the 3-, 5- and/or 6-positions relative to the hydroxyl group and each independently is a hydrogen or halogen atom, or an alkyl, cycloalkyl, aryl, aralkyl or alkoxy group, n is 1, 2, or 3, and R2 is an optionally substituted alkyl group having 1 to 12 carbon atoms, an optionally substituted cycloalkyl group having 3 to 6 carbon atoms, an optionally substituted phenyl radical or an optionally substituted aralkyl radical, by reacting a phenol of the formula STR2 with formaldehyde or an formaldehyde producing compound and with a mercaptan or a thiophenol of the formula the improvement which comprises effecting the reaction at a temperature of about 90° to 220° C. in the presence of at least one compound of lithium, magnesium, calcium, strontium, barium, zinc, cadmium, lead, manganese, cobalt, nickel, cooper, iron, chromium and aluminum as a catalyst. The products are obtained in high yield and selectivity.

Preparation of alkylthiomethylphenols

A process for the preparation of an alkylthiomethylphenol of the formula STR1 COMPRISING REACTING A DIALKYLAMINOMETHYLPHENOL OF THE FORMULA STR2 WITH A THIOCARBOXYLIC ACID S-ester of the formula STR3 in which R1 is optionally substituted alkyl with 1 to 12 carbon atoms or optionally substituted phenyl, R2 and R3 each independently is hydrogen, alkyl with 1 to 5 carbon atoms, halogen or nitro, or together form a benzene ring or cycloalkane ring with 3 to 5 carbon atoms which is fused to the phenyl ring, R4 and R5 each independently is alkyl with 1 to 6 carbon atoms, or together with the nitrogen atom form a five- or six-membered heterocyclic ring, R6 is hydrogen or alkyl with 1 to 6 carbon atoms, and n is 1, 2 or 3. The process may be carried out in a solvent, advantageously at a temperature from about 100° to 150° C, at about normal pressure using phenol as a catalyst with about 0.9 to 1.5 moles of thiocarboxylic acid S-ester per mole of dialkylaminomethylphenol.