13506-76-8

Basic information

• Product Name: 2-METHYL-6-NITROBENZOIC ACID
• Synonyms: Benzoic acid, 2-methyl-6-nitro-;6-NITRO-O-TOLUIC ACID;2-NITRO-6-METHYLBENZOIC ACID;2-METHYL-6-NITROBENZOIC ACID;RARECHEM AL BO 0232;2-METHYL-6-NITROBENZOIC ACID / 6-NITRO-O-TOLUIC ACID;6-Nitro-o-toluic acid (COOH=1);2-METHYL-6-NITROBENZOIC ACID 98+%
• CAS NO: 13506-76-8
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• EINECS: 236-833-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 13506-76-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 153-157 °C(lit.)
• Boiling Point: 314.24°C (rough estimate)
• Flash Point: 159.6 °C
• Appearance: light orange to yellow-brown crystalline powder
• Density: 1.4283 (rough estimate)
• Vapor Pressure: 1.38E-05mmHg at 25°C
• Refractive Index: 1.5468 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO, Methanol
• PKA: pK1:1.87 (25°C)
• BRN: 2050804
• CAS DataBase Reference: 2-METHYL-6-NITROBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-6-NITROBENZOIC ACID(13506-76-8)
• EPA Substance Registry System: 2-METHYL-6-NITROBENZOIC ACID(13506-76-8)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 13506-76-8(Hazardous Substances Data)

Usage

Chemical Properties

light orange to yellow-brown crystalline powder

Uses

2-Methyl-nitrobenzoic acid acts as herbicide due to the anthranilic acid moiety within the substructure.

General Description

Pale yellow needles or tan powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-METHYL-6-NITROBENZOIC ACID is a nitrated carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.

Fire Hazard

Flash point data for 2-METHYL-6-NITROBENZOIC ACID are not available; however, 2-METHYL-6-NITROBENZOIC ACID is probably combustible.

InChI:InChI=1/C8H7NO4/c1-5-3-2-4-6(9(12)13)7(5)8(10)11/h2-4H,1H3,(H,10,11)/p-1

Upstream product

• 83-41-0 2,3-dimethylnitrobenzene 
• 7664-93-9 sulfuric acid 
• 40637-78-3 2-methyl-6-nitro-benzoic acid amide 
• 67-56-1 methanol 
• 71-36-3 butan-1-ol 
• 570-24-1 2-Methyl-6-nitroaniline 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 544-92-3 copper(I) cyanide 
• 124-38-9 carbon dioxide 
• 41085-43-2 2-bromo-3-nitrotoluene 
• 1885-76-3 2-cyano-3-nitrotoluene 

Downstream Products

• 4389-50-8 2-amino-6-methylbenzoic acid 
• 434935-69-0 2-methyl-6-nitrobenzoic anhydride 
• 19500-95-9 Methoxyacetic anhydride 
• 61940-22-5 methyl 2-methyl-6-nitrobenzoate 
• 5434-20-8 3-aminophthalic acid 
• 54526-00-0 ethyl 2-methyl-6-nitrobenzoate 
• 861355-91-1 (2-methyl-6-nitro-benzoyl)-malonic acid diethyl ester 
• 1260071-69-9 6,6'-bis(2-methyl-6-nitrobenzoyl)-2,2',3,3',4,4'-(hexabenzyloxy)-α,α'-D-trehalose 
• 567-61-3 2-hydroxy-6-methylbenzoic acid 
• 79383-44-1 methyl 2-methyl-6-methoxybenzoate 
• 943595-13-9 methyl 2-(bromomethoxy)-6-methoxybenzoate 
• 42760-46-3 7-nitro-3H-isobenzofuran-1-one 

Relevant articles and documents

Method for co-production 2-methyl-6-nitrobenzoic acid and 3-nitro-2-methylbenzoic acid

The invention discloses a method for co-production of 2-methyl-6-nitrobenzoic acid and 3-nitro-2-methylbenzoic acid. The method is characterized by comprising the following steps: (1) feeding 3-nitro-o-xylene and dilute nitric acid into an oxidation reaction kettle, carrying out heating, and conducting reacting under certain pressure by using oxygen as an oxidant; (2) after the reaction is finished, discharging an oxidation reaction solution to obtain a crude product; (3) washing the crude product with water, conducting esterifying, and performing distilling to recover a solvent after the reaction is finished, thereby obtaining an esterified concentrated solution; (4) adding alkali into the esterification concentrated solution to adjust a pH value, carrying out layering, and distilling anorganic layer under reduced pressure to recover 3-nitro-2-nitrobenzoic acid; and (5) extracting a water layer with an organic solvent, adjusting an pH value with an acid, and performing filtering anddrying to obtain the 2-methyl-6-nitrobenzoic acid. In a low-concentration nitric acid environment, 3-nitro-2-nitrobenzoic acid is produced and 2-methyl-6-nitrobenzoic acid is co-produced with oxygen used as an oxidizing agent, so the problems of low selectivity of 3-nitro-o-xylene in an oxidation process and high risks in a concentrated nitric acid oxidation process are solved.

Metal-Free Aerobic Oxidation of Nitro-Substituted Alkylarenes to Carboxylic Acids or Benzyl Alcohols Promoted by NaOH

Efficient and selective aerobic oxidation of nitro-substituted alkylarenes to functional compounds is a fundamental process that remains a challenge. Here, we report a metal-free, efficient, and practical approach for the direct and selective aerobic oxidation of nitro-substituted alkylarenes to carboxylic acids or benzyl alcohols. This sustainable system uses O2 as clean oxidant in a cheap and green NaOH/EtOH mixture. The position and type of substituent critically affect the products. In addition, this sustainable protocol enabled gram-scale preparation of carboxylic acid and benzyl alcohol derivatives with high chemoselectivities. Finally, the reactions can be conducted in a pressure reactor, which can conserve oxygen and prevent solvent loss. The approach was conducive to environmental protection and potential industrial application.

OXIDATION OF SUBSTITUTED TOLUENES UNDER PHASE-TRANSFER CATALYSIS CONDITIONS

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