58138-74-2

Usage

Uses

Used in Pharmaceutical Industry:
2-HYDROXY-3,4-DIMETHYL-BENZOIC ACID is used as a reagent for the synthesis of vadimezan, a tumor vascular disrupting agent. Vadimezan targets the tumor's blood supply, leading to the collapse of the tumor's vasculature and subsequently inhibiting tumor growth and progression. 2-HYDROXY-3,4-DIMETHYL-BENZOIC ACID's unique structure allows it to be a key intermediate in the development of this therapeutic agent.

InChI:InChI=1/C9H10O3/c1-5-3-4-7(9(11)12)8(10)6(5)2/h3-4,10H,1-2H3,(H,11,12)

Upstream product

• 124-38-9 carbon dioxide 
• 526-75-0 2,3-Dimethylphenol 
• 71321-28-3 2-Hydroxy-2-(2-hydroxy-3,4-dimethyl-phenyl)-indan-1,3-dione 
• 619-04-5 3,4-dimethylbenzoic acid 
• 95646-20-1 3-(2-Hydroxy-3,4-dimethyl-benzoyl)-2-p-tolyl-2,3-dihydro-isoindol-1-one 

Downstream Products

• 91061-57-3 methyl 2-hydroxy-3,4-dimethylbenzoate 

Relevant academic research and scientific papers

Carboxylation of Phenols with CO2 at Atmospheric Pressure

A convenient and efficient method for the ortho-carboxylation of phenols under atmospheric CO2 pressure has been developed. This method provides an alternative to the previously reported Kolbe-Schmitt method, which requires very high pressures of CO2. The addition of a trisubstituted phenol has proved essential for the successful carboxylation of phenols with CO2 at standard atmospheric pressure, allowing the efficient preparation of a broad variety of salicylic acids.

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).