339274-33-8

Usage

Uses

Used in Pharmaceutical Industry:
(S)-AMINO-O-TOLYL-ACETIC ACID is used as a building block for the synthesis of various pharmaceuticals. Its chiral nature allows for the development of enantiomer-specific drugs, which can have different biological activities and reduce potential side effects.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-AMINO-O-TOLYL-ACETIC ACID is utilized as a precursor for the synthesis of agrochemicals, such as pesticides and herbicides. Its ability to form different enantiomers enables the creation of more effective and targeted agrochemicals with reduced environmental impact.
Used in Dye and Pigment Production:
(S)-AMINO-O-TOLYL-ACETIC ACID is used as a precursor in the production of dyes and pigments. Its unique chemical properties contribute to the development of new and improved colorants for various applications, including textiles, plastics, and printing inks.
Used in Specialty Chemicals:
(S)-AMINO-O-TOLYL-ACETIC ACID is also employed in the synthesis of specialty chemicals, such as fragrances, flavorings, and other fine chemicals. Its versatility and chiral nature make it a valuable component in the development of innovative and high-quality specialty products.

InChI:InChI=1/C9H11NO2/c1-6-4-2-3-5-7(6)8(10)9(11)12/h2-5,8H,10H2,1H3,(H,11,12)/t8-/m0/s1

Upstream product

• 203314-21-0 2-(o-methylphenyl)malonic acid 
• 129592-94-5 methyl N-(trifluoroacetyl)-2-amino-2-(2-methylphenyl)acetate 
• 271583-29-0 benzylamino-o-tolyl-acetic acid 
• 271583-70-1 N-benzyl amino-(2-methylphenyl)acetonitrile 
• 529-20-4 2-methylphenyl aldehyde 
• 271583-48-3 2-benzylamino-2-o-tolyl-acetamide 
• 129592-87-6 methyl 2-bromo-2-(2-methylphenyl)acetate 
• 70484-46-7 diethyl (2-methylphenyl)propanedioate 
• 40291-39-2 ethyl 2-(2-methylphenyl)acetate 
• 92876-67-0 1-(2-methylphenyl)ethane-1,2-diol 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 56464-73-4 DL-2-methylphenylglycine nitrile 
• 203065-98-9 (+/-)-2-methylphenylglycine amide 

Relevant academic research and scientific papers

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine

The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.

A remarkable titanium-catalyzed asymmetric strecker reaction using hydrogen cyanide at room temperature

Close to perfect enantioselectivity (up to 98% ee) is obtained for the formation of amino nitrites using hydrogen cyanide (HCN) as the cyanide source at room temperature for the first time. In an operationally simple process, the catalyst generated from a partially hydrolyzed titanium alkoxide (PHTA) and (S)-N-salicyl-ss-amino alcohol ligand, catalyzes the cyanation of imines in a short reaction time.

Practical and convenient enzymatic synthesis of enantiopure α-amino acids and amides

Catalyzed by the nitrile hydratase and the amidease in Rhodococcus sp. AJ270 cells under very mild conditions, a number of α-aryl- and α-alkyl-substituted DL-glycine nitriles 1 rapidly underwent a highly enantioselective hydrolysis to afford D-(-)-α-amino acid amides 2 and L-(+)-α-amino acids 3 in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of a high L-enantioselective amidase and a low enantioselective nitrile hydratase. The influence of the substrates on both reaction efficiency and enantioselectivity was also discussed in terms of steric and electronic effects. Coupled with chemical hydrolysis of D-(-)-α-phenylglycine amide, biotransformation of DL-phenylglycine nitrile was applied in practical scale to produce both D- and L-phenylglycines in high optical purity.

Highly efficient and enantioselective synthesis of L-arylglycines and D-arylglycine amides from biotransformations of nitriles

Under very mild conditions, the Rhodococcus sp. AJ270-catalysed biotransformation of arylglycine nitriles 1, prepared easily from the reaction of substituted benzaldehydes, ammonium chloride and potassium cyanide, proceeded efficiently to produce optically active D-arylglycine amides 2 and L-arylglycines 3 in excellent yields with enantiomeric excesses higher than 99%.

A practical asymmetric synthesis of homochiral α-arylglycines

Enantioselective reduction of a series of substituted aryl trichloromethyl ketones with the CBS-catecholborane reagent afforded homochiral aryl trichloromethyl carbinols which have been elaborated to give homochiral α-arylglycines in high e.e.

A facile synthesis of substituted phenylglycines

A convenient scaleable process for the preparation of substituted phenylglycines 2 by a modified Strecker reaction is described. Bisulfite- mediated addition of benzylamine and cyanide anion to substituted benzaldehydes 3 gave the aminonitriles 4 which were hydrolysed in two steps to the N-protected amino acid 1. Debenzylation using catalytic transfer hydrogenation gave the title compounds in good yield.