50419-58-4

Usage

Uses

Used in Organic Synthesis:
2-Amino-3,4-dimethylbenzoic acid is used as a building block in organic synthesis for the creation of a wide range of chemical compounds. Its unique structure allows for various chemical modifications, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceuticals:
In the pharmaceutical industry, 2-Amino-3,4-dimethylbenzoic acid is utilized as an intermediate in the development of new drugs. Its ability to form different chemical entities makes it a crucial component in the synthesis of potential therapeutic agents.
Used in Agrochemicals:
2-Amino-3,4-dimethylbenzoic acid is employed as a key intermediate in the production of agrochemicals, such as pesticides and herbicides. Its involvement in the synthesis of these compounds contributes to the development of effective solutions for agricultural applications.
Used in Dye Stuff:
In the dye industry, 2-Amino-3,4-dimethylbenzoic acid is used as a raw material for the production of various dyes. Its chemical properties enable the creation of a diverse array of colorants, which are essential for coloring textiles, plastics, and other materials.

InChI:InChI=1/C9H11NO2/c1-5-3-4-7(9(11)12)8(10)6(5)2/h3-4H,10H2,1-2H3,(H,11,12)

Upstream product

• 20205-43-0 6,7-dimethylisatin 
• 87-59-2 2,3-Dimethylaniline 
• 3637-01-2 3,4-dimethylacetophenone 
• 49666-83-3 1-(3,4-dimethyl-2-nitro-phenyl)-ethanone 
• 6579-44-8 2,3-dimethyl-α-isonitrosoacetanilide 
• 619-04-5 3,4-dimethylbenzoic acid 
• 4315-13-3 3,4-Dimethyl-2-nitrobenzoesaeure 

Downstream Products

• 31928-20-8 methyl 2-amino-3,4-dimethylbenzoate 
• 129833-31-4 3,4-dimethyl-2-iodobenzoic acid 

Relevant academic research and scientific papers

2-Amino-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxylic acid (FlAib), a completely rigidified, fluoren-9-one-based α-amino acid

The synthesis, optical resolution, determination of absolute configuration and conformational preference, and spectroscopic characteristics of terminally protected (blocked) derivatives and short peptides of 2-amino-1,2,3,6- tetrahydro-6-oxocyclopenta[c]f

CRYSTALLINE FORMS OF DMXAA SODIUM SALT

The present invention relates to pharmaceutically stable crystalline forms of (5, 6-Dimethyl-9- oxo-9H-xanthene-4-yl) acetic acid (DMXAA) sodium salt,- processes for preparing those stable crystalline forms; pharmaceutical compositions comprising at least one of those crystalline forms in solid form or in dissolved form and a pharmaceutically acceptable carrier. Disclosed are methods of using those pharmaceutical compositions to treat tumours, optionally in combination with other active pharmaceutical agents.

An improved synthesis of 5,6-dimethylxanthenone-4-acetic acid (DMXAA)

5,6-Dimethylxanthenone-4-acetic acid (DMXAA) is a novel anticancer agent with a number of unique activities, and is in clinical trial. The current synthesis of DMXAA involves six steps, beginning with a heterogeneous reaction to form an isonitrosoacetanilide, and gives an overall yield of 11% from 2,3-dimethylaniline. We report an alternative synthesis of the key intermediate 3,4-dimethylanthranilic acid via nitration of 3,4-dimethylbenzoic acid and separation of the key desired isomer by ready crystallisation. This, together with improvements in the rest of the synthesis, provide a shorter and higher-yielding route to DMXAA (22% overall from 3,4-dimethylbenzoic acid).

Syntheses, Enrichment of Enantiomers, and Barriers to Racemization of Twisted 9,10-Phenanthrenquinones

The known syntheses of the 9,10-phenanthrenequinones 10a-c were improved by the chlorotrimethylsilane modification of the acyloin condensation of biaryl diesters.The novel quinones 4a, 4b, and 12 were prepared.For the first time, enantiomers (M and P) of this class of compounds were enriched semipreparatively by liquid chromatography on optically active sorbents.The barriers to thermal racemization amount to 90-130 kJ mol-1 (Table 2) and are thus higher than the barriers for the corresponding phenanthrene hydrocarbons by roughly 20 kJ mol -1.The reasons for this increase are discussed in terms of repulsive interactions in the trans ition state of helix inversion.

Potential Antitumor Agents. 61. Structure-Activity Relationships for in Vivo Colon 38 Activity among Disubstituted 9-Oxo-9H-xanthene-4-acetic Acids

Analogues of 9-oxo-9H-xanthene-4-acetic acid (XAA) bearing small, lipophilic 5-substituents are among the most dose-potent compounds yet reported with the capability of causing hemorrhagic necrosis of implanted colon 38 tumors in mice.To further extend structure-activity relationships among this class of compound, a series of XAA derivatives bearing two small lipophilic groups at various positions have been prepared and evaluated.The 5,6-disubstituted compounds in particular show consistently high levels of both dose potency and activity, suggesting this is the optimal configuration among substituted 9-oxo-9H-xanthene-4-acetic acids.The 5,6-dimethyl and 5-methyl-6-methoxy are the most effective analogues, showing in vivo colon 38 activity comparable to that of FAA at 10-15-fold lower doses and superior activity to FAA at the respective optimal doses, and the former has been selected for detailed evaluation.