52888-49-0

Usage

Uses

Used in Agricultural Industry:
Methyl N-(2,6-dimethylphenyl)-DL-alaninate is used as an intermediate in the synthesis of Benalaxyl-d5 (B131902), which is an acylamino acid fungicide. This fungicide is effective in controlling a wide range of fungal diseases in crops, thus contributing to increased agricultural productivity and crop protection. methyl N-(2,6-dimethylphenyl)-DL-alaninate's role in the synthesis process is essential, as it helps in the development of a product that can protect plants from harmful fungal infections, ensuring a healthy and sustainable agricultural ecosystem.

Synthesis Reference(s)

Tetrahedron, 52, p. 9777, 1996 DOI: 10.1016/0040-4020(96)00503-0

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H17NO2/c1-8-6-5-7-9(2)11(8)13-10(3)12(14)15-4/h5-7,10,13H,1-4H3/t10-/m0/s1

Upstream product

• 600-22-6 pyruvic acid methyl ester 
• 81-20-9 2,6-dimethylnitrobenzene 
• 87-62-7 2,6-dimethylaniline 
• 67617-63-4 (S)-methyl 2-(2,6-dimethylphenylamino)propanoate 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 56905-18-1 methyl 2-iodopropionate 
• 5445-17-0 Methyl 2-bromopropionate 

Downstream Products

• 58234-85-8 2-[Cyclopentanecarbonyl-(2,6-dimethyl-phenyl)-amino]-propionic acid methyl ester 
• 58234-43-8 2-[(2,6-Dimethyl-phenyl)-(3-methyl-but-2-enoyl)-amino]-propionic acid methyl ester 
• 57837-20-4 N-(1'-methoxycarbonyl-ethyl)-N-ethoxyacetyl-2,6-dimethylaniline 
• 68482-80-4 2-[(2,6-Dimethyl-phenyl)-(3-methoxy-propionyl)-amino]-propionic acid methyl ester 
• 58234-25-6 2-[(2,6-Dimethyl-phenyl)-(2-ethyl-butyryl)-amino]-propionic acid methyl ester 
• 58234-17-6 2-[(2,6-Dimethyl-phenyl)-propionyl-amino]-propionic acid methyl ester 
• 58234-11-0 2-[(2,6-Dimethyl-phenyl)-(2,2-dimethyl-propionyl)-amino]-propionic acid methyl ester 
• 58234-16-5 2-[Acetyl-(2,6-dimethyl-phenyl)-amino]-propionic acid methyl ester 
• 58234-19-8 2-[(2,6-Dimethyl-phenyl)-isobutyryl-amino]-propionic acid methyl ester 
• 58234-18-7 2-[Butyryl-(2,6-dimethyl-phenyl)-amino]-propionic acid methyl ester 
• 58234-08-5 2-[Acryloyl-(2,6-dimethyl-phenyl)-amino]-propionic acid methyl ester 
• 58234-87-0 2-[Cyclohexanecarbonyl-(2,6-dimethyl-phenyl)-amino]-propionic acid methyl ester 
• 68482-85-9 2-[(2,6-Dimethyl-phenyl)-(3-ethoxy-propionyl)-amino]-propionic acid methyl ester 
• 58234-84-7 2-[Cyclobutanecarbonyl-(2,6-dimethyl-phenyl)-amino]-propionic acid methyl ester 

Relevant academic research and scientific papers

Two-Step Continuous-Flow Synthesis of Fungicide Metalaxyl through Catalytic C?N Bond-Formation Processes

Metalaxyl, an acylalanine fungicide, was synthesized through catalytic continuous sequential-flow reactions. Commonly used syntheses of this compound use batch systems and suffer from problems such as coproduction of halogen-containing by-products derived from acyl and alkyl halides in the substitution reactions of 2,6-dimethylaniline. To minimize waste and enhance efficiency, a halide-free approach including two continuous-flow catalytic processes, heterogeneous Pt-catalyzed reductive alkylation and homogeneous acid-catalyzed amidation with an acid anhydride, was developed. Systematic examination of the two reactions in flow mode enabled a high-yielding, two-step sequential continuous-flow process to be achieved. (Figure presented.).

Method for synthesizing 2-(2,6-dimethylphenyl) amino methyl propionate from recyclable catalyst

The invention discloses a method for synthesizing 2-(2,6-dimethylphenyl) amino methyl propionate from recyclable catalyst. The process for synthesizing 2-(2,6-dimethylphenyl) amino methyl propionate from recyclable catalyst includes synthesize of esters, filtration, absolute ethanol filtration and desolvation. The invention discloses a method for synthesizing 2-(2,6-dimethylphenyl) amino methyl propionate from recyclable catalyst has the advantages of simple step, one-time feeding of reactants, strong controllability and no process waste water. The solid material separated in step 3 can be directly sent to the desalination treatment section to be treated to obtain by-product industrial salt, thus reducing the process of evaporating water and obviously reducing the process energy consumption.

Compound of bisamide structure and preparing method and application thereof

The invention discloses a compound of a bisamide structure in the technical field of agricultural chemistry and a preparing method and application thereof. The preparing method includes the steps that monomethyl malonate acyl chloride is used as a raw material and reacts with arylamine in anhydrous dichloromethane to obtain an intermediate product III; the intermediate product III reacts with lithium hydroxide and then reacts with oxalyl chloride in tetrahydrofuran to obtain an intermediate product IV; 2,6-dimethylaniline is used as a raw material and reacts with 2-methyl bromopropionate to obtain an intermediate product VI; finally the intermediate product IV and the intermediate product VI react in a methylbenzene solution to obtain the compound of the bisamide structure shown in the final product I. The compound and a preparation have good bactericidal activity, have a good growth inhibiting function on phytophthora capsici, alternaria solani, rhizoctonia solani, cotton rhizoctonia solani, phytophthora infestans, and botrytis cinerea and have high pesticide research value.

Enzyme-catalyzed preparation of methyl (R)-N-(2,6-dimethylphenyl)alaninate: A key intermediate for (R)-metalaxyl

A biocatalytic approach for the production of (R)-metalaxyl, mefenoxam, has been developed. A practical synthesis of methyl (R)-N-(2,6-dimethylphenyl) alaninate, a key intermediate for (R)-metalaxyl, has been developed by the use of lipase-catalyzed hydrolytic kinetic resolution and chemical racemization of the remaining ester. At high concentrations in aqueous media (300 g/L) lipases were stable and gave moderate to good conversions and excellent enantioselectivities (>98% ee). A simple extraction procedure was used to separate the acid product from the remaining ester and the acid was esterified with methanol to give methyl (R)-N-(2,6-dimethylphenyl)alaninate without any reduction in enantiomeric excess (>98% ee). Subsequent chemical coupling with methoxyacetyl chloride provided enantiomerically pure (R)-metalaxyl (>98% ee) without racemization.

Catalytic reductive N-alkylation of anilines. Application to the synthesis of N-aryl aminoacid precursors

Different anilines have been monoalkylated by reductive alkylation using ketones and α-ketoesters as alkylating agents with good isolated yields. This provided access to aminoacid derivatives. Diastereoselective experiments were also performed.

Process for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula STR1 in which R1 and R2 are each methyl or ethyl and R3 is an alkyl group having 1-4 carbon atoms. According to this process, a 2-chloropropionic acid ester having 1-4 carbon atoms in the alkyl group is reacted in the presence of water and of a quaternary ammonium or phosphonium salt with an alkali metal iodide to give a mixture of the 2-chloropropionic acid ester and the 2-iodopropionic acid ester, and this mixture is subsequently reacted, after separating off the aqueous phase, at 110-130° C., in the presence of an alkali metal carbonate or alkali metal bicarbonate as an acid-binding agent, with excess 2,6-dialkylaniline, the reaction mixture is extracted with water and the mixture of the 2,6-dialkylaniline of the formula IV and the N-(1'-alkoxycarbonylethyl)-2,6-dialkylaniline of the formula I, which is obtained after separating off the aqueous extract, is separated by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

Process for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula STR1 in which R1 and R2 are each methyl or ethyl and R3 is an alkyl group having 1 to 4 carbon atoms, this process being based on the reaction of a corresponding 2,6-dialkylaniline with a corresponding alkyl 2-chloropropionate or alkyl 2-bromopropionate. The process is carried out by carrying out the reaction of the 2,6-dialkylaniline with the 2-halogenopropionic acid ester at 110°-130° C. in the presence of an alkali metal iodide as the catalyst, and of an alkali metal carbonate or alkali metal bicarbonate as an acid acceptor, in excess 2,6-dialkylaniline as the solvent, removing, by distillation, the water formed during the reaction and working up the organic phase, which is obtained after adding water and separating the phases, by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

N-(1'-alkoxycarbonyl-ethyl)-N-haloacetyl-2,6-dialkylanilines for the control of phytopathogenic fungi

N-(1'-Alkoxycarbonyl-ethyl)-N-haloacetyl-2,6-dialkylanilines possess microbicidal properties and may be used to combat plant-pathogenic fungi.