4315-14-4

Basic information

• Product Name: 3,4-DIMETHYL-6-NITROBENZOIC ACID
• Synonyms: 3,4-DIMETHYL-6-NITROBENZOIC ACID;Benzoic acid, 4,5-diMethyl-2-nitro-
• CAS NO: 4315-14-4
• Molecular Formula: C₉H₉NO₄
• Molecular Weight: 195.17
• Mol File: 4315-14-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-DIMETHYL-6-NITROBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHYL-6-NITROBENZOIC ACID(4315-14-4)
• EPA Substance Registry System: 3,4-DIMETHYL-6-NITROBENZOIC ACID(4315-14-4)

Safety Data

• Hazardous Substances Data: 4315-14-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-DIMETHYL-6-NITROBENZOIC ACID is used as a reactant for the synthesis of mono-acylated derivatives containing bergenin. These derivatives have been tested for their potential as antiglycation agents, which can help in the development of treatments for diabetes and its associated complications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3,4-DIMETHYL-6-NITROBENZOIC ACID serves as a valuable building block for the creation of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile compound for the synthesis of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
3,4-DIMETHYL-6-NITROBENZOIC ACID is also utilized in research and development laboratories for studying its chemical properties, reactivity, and potential applications in various fields. Researchers can use 3,4-DIMETHYL-6-NITROBENZOIC ACID to explore new reaction pathways, develop novel synthetic methods, and gain insights into the structure-activity relationships of related compounds.

Upstream product

• 619-04-5 3,4-dimethylbenzoic acid 
• 2198-54-1 N-(3,4-dimethylphenyl)acetamide 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 
• 15089-77-7 2,3-dimethyl-6-nitrobenzonitrile 

Downstream Products

• 15089-51-7 2-amino-4,5-dimethylbenzoic acid 

Relevant articles and documents

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).

Zur Synthese sulfonierter Derivate von 2,3-Dimethylanilin und 3,4-Dimethylanilin

Baking the hydrogensulfate salt of 2,3-dimethylaniline (1) or of 3,4-dimethylaniline (2) led to 4-amino-2,3-dimethylbenzenesulfonic acid (4) and 2-amino-4,5-dimethylbenzenesulfonic acid (5), respectively (Scheme 1).The sulfonic acid 5 was also obtained by treatment of 2 with sulfuric acid or by reaction of 2 with amido-sulfuric acid. 3-Amino-4,5-dimethylbenzenesulfonic acid (3) and 5-amino-2,3-dimethylbenzenesulfonic acid (6) were prepared by sulfonation of 1,2-dimethyl-3-nitrobenzene (9) to 3,4-dimethyl-5-nitrobenzenesulfonic acid (11) and of 1,2-dimethyl-4-nitrobenzene (10) to 2,3-dimethyl-5-nitrobenzenesulfonic acid (12), respectively, with subsequent Bechamp reduction (Scheme 1).Preparations of 2-amino-3,4-dimethylbenzenesulfonic acid (7) and of 6-amino-2,3-dimethylbenzenesulfonic acid (8) were achieved by the sulfur dioxide treatment of the diazonium chlorides derived from 3,4-dimethyl-2-nitroaniline (24) and from 2,3-dimethyl-6-nitroaniline (31) to 3,4-dimethyl-2-nitrobenzenesulfonyl chloride (29) and 2,3-dimethyl-6-nitrobenzenesulfonyl chloride (32), respectively, followed by hydrolysis to 3,4-dimethyl-2-nitrobenzenesulfonic acid (30) and 2,3-dimethyl-6-nitrobenzenesulfonic acid (33), and final reduction (Scheme 3).Compound 7 was also synthesized by reaction of 4-chloro-2,3-dimethylaniline (23) with amidosulfuric acid to 2-amino-5-chloro-3,4-dimethylbenzenesulfonic acid (20) and subsequent hydrogenolysis (Scheme 2). 4'-Bromo-2',3'-dimethyl-acetanilide (13) and 4'-chloro-2',3'-dimethyl-acetanilide (14) on treatment with oleum yielded 5-acetylamino-2-bromo-3,4-dimethylbenzenesulfonic acid (17) and 5-acetylamino-2-chloro-3,4-dimethylbenzenesulfonic acid (18), respectively.Their structures were proven by hydrolysis to 5-amino-2-bromo-3,4-dimethylbenzenesulfonic acid (21) and 5-amino-2-chloro-3,4-dimethylbenzenesulfonic acid (22), followed by reductive dehalogenation to 3.Reaction of 1 with sulfuric acid gave a mixture of 3,4 and 7, whereas sulfonation of 2',3'-dimethyl-acetanilide with subsequent hydrolysis led to a mixture of 3 and 4.Treatment of 3',4'-dimethyl-acetanilide with oleum followed by hydrolysis resulted in the formation of mainly 5 and a small amount of unknown product.