1975-52-6

Basic information

• Product Name: 2-Methyl-5-nitrobenzoic acid
• Synonyms: Benzoic acid, 2-methyl-5-nitro-;5-NITRO-O-TOLUIC ACID;2-METHYL-5-NITROBENZOIC ACID;RARECHEM AL BO 0285;5-nitro-2-methyl benzoic acid;2-Methyl-5-nitro-benzoic Aci;2-Methyl-3-nitrobenzoic;2-Methyl-5-nitrobenzoic
• CAS NO: 1975-52-6
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• EINECS: 217-829-0
• Product Categories: blocks;Carboxes;NitroCompounds;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Aromatics Compounds;Aromatics;Pyridines
• Mol File: 1975-52-6.mol

Chemical Properties

• Melting Point: 177-180 °C(lit.)
• Boiling Point: 314.24°C (rough estimate)
• Flash Point: 163.5 °C
• Appearance: Yellow to beige/Crystalline Powder
• Density: 1.4283 (rough estimate)
• Vapor Pressure: 7.78E-06mmHg at 25°C
• Refractive Index: 1.5468 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform
• PKA: 3.12±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 22℃
• BRN: 2451300
• CAS DataBase Reference: 2-Methyl-5-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-5-nitrobenzoic acid(1975-52-6)
• EPA Substance Registry System: 2-Methyl-5-nitrobenzoic acid(1975-52-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-43-36/37/38-20/21/22
• Safety Statements: 37/39-36/37/39-26-22
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1975-52-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Methyl-5-nitrobenzoic acid is used as a key intermediate in the synthesis of various organic compounds. Its chemical structure allows it to participate in a range of reactions, making it a versatile building block for the creation of new molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methyl-5-nitrobenzoic acid is used as a starting material for the development of new drugs. Its unique chemical properties enable it to be modified and functionalized to create a variety of drug candidates with potential therapeutic applications.
Used in Chemical Research:
2-Methyl-5-nitrobenzoic acid is also used in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methods. Its reactivity and structural features make it an ideal candidate for exploring new chemical transformations and understanding fundamental reaction pathways.
Used in Dye Manufacturing:
In the dye manufacturing industry, 2-Methyl-5-nitrobenzoic acid is used as a precursor for the production of various dyes and pigments. Its chemical structure can be modified to create a range of colored compounds, which are then used in various applications such as textiles, plastics, and printing inks.
Used in Material Science:
2-Methyl-5-nitrobenzoic acid is also utilized in material science for the development of new materials with specific properties. Its chemical structure can be incorporated into polymers and other materials to impart unique characteristics, such as improved stability, enhanced color, or altered electronic properties.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Methyl-5-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-5-nitrobenzoic acid are not available; however, 2-Methyl-5-nitrobenzoic acid is probably combustible.

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

Upstream product

• 118-90-1 ortho-methylbenzoic acid 
• 939-83-3 2-cyano-4-nitrotoluene 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 99-51-4 4-nitro-o-xylene 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 872791-71-4 (2-methyl-5-nitro-benzoyl)-malonic acid diethyl ester 
• 64-19-7 acetic acid 
• 77324-87-9 methyl 2-methyl-5-nitrobenzoate 
• 529-19-1 2-Methylbenzonitrile 
• 95-47-6 o-xylene 
• 619-04-5 3,4-dimethylbenzoic acid 
• 7745-93-9 2-bromo-4-nitrotoluene 

Downstream Products

• 28169-46-2 3,5-dinitro-o-toluic acid 
• 13304-20-6 4,4'-dinitro-bibenzyl-2,2'-dicarboxylic acid 
• 2840-04-2 5-amino-2-methylbenzoic acid 
• 64688-68-2 2-methyl-5-nitrobenzoyl chloride 
• 5981-39-5 2,5-dihydroxy-3-methylbenzoic acid 
• 77324-87-9 methyl 2-methyl-5-nitrobenzoate 
• 143617-90-7 5-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methylbenzoic acid 
• 22474-47-1 (2-methyl-5-nitro-7-phenyl)methanol 
• 124358-24-3 ethyl 2-methyl-5-nitrobenzoate 
• 690243-02-8 2-(2-methyl-5-nitro-phenyl)-benzothiazole 
• 690243-08-4 5-chloro-2-(2-methyl-5-nitro-phenyl)-benzothiazole 
• 942605-68-7 N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methyl-5-nitro-benzamide 
• 1001340-67-5 N-(2-(3-(2-(pyrrolidin-1-yl)ethoxy)phenylamino)pyrimidin-5-yl)-5-amino-2-methylbenzamide 
• 1005499-46-6 3-iodo-2-methyl-5-nitrobenzoic acid 

Relevant articles and documents

Selective oxidation of substituted xylenes to toluic acids by hypochlorite-Ru system under phase transfer conditions

Instantaneous aqueous extraction of toluic acid salts is the basis for a novel selective process for the oxidation of a single methyl group of various xylenes; aqueous hypochlorite is inert towards methylbenzenes at pH higher than 9.0, however, in the presence of an organic solvent, a Ru catalyst and a phase transfer agent, rapid oxidation to benzoic acids is observed at 25°C.

Regioselectivity nitration of aromatics with N2O5 in PEG-based dicationic ionic liquid

Regioselective mononitration of simple aromatic compounds has been investigated with N2O5 as nitrating agent and a new PEG200-based dicationic acidic ionic liquid (PEG200-DAIL) as catalyst. The results of experiments show that this nitration system can significantly improve the para-selectivity of alkyl-benzenes and the ortho-selectivity of halogenated-benzenes. The PEG200-DAIL exhibits recyclable temperature-dependant phase behavior in CCl4 solvent, and it can be recycled without apparent loss of catalytic activity, and only 5% loss of weight is observed after six times recycling.

Discovery of N-(3-(morpholinomethyl)-phenyl)-amides as potent and selective CB2 agonists

Recently sulfamoyl benzamides were identified as a novel series of cannabinoid receptor ligands. Replacing the sulfonamide functionality and reversing the original carboxamide bond led to the discovery of N-(3-(morpholinomethyl)-phenyl)-amides as potent and selective CB2 agonists. Selective CB2 agonist 31 (Ki = 2.7; CB1/CB2 = 190) displayed robust activity in a rodent model of postoperative pain.

Dihydroxylphenyl amides as inhibitors of the Hsp90 molecular chaperone

Information from X-ray crystal structures were used to optimize the potency of a HTS hit in a Hsp90 competitive binding assay. A class of novel and potent small molecule Hsp90 inhibitors were thereby identified. Enantio-pure compounds 31 and 33 were potent in PGA-based competitive binding assay and inhibited proliferation of various human cancer cell lines in vitro, with IC50 values averaging 20 nM.

Aromatic nitration using nitroguanidine and EGDN

Acid catalyzed nitration has been examined using a variety of novel nitration agents: guanidine nitrate (GN) and nitroguanidine (NQ) as well as the simple nitrate ester, ethylene glycol dinitrate (EGDN). Reactions with either activated or deactivated aromatic substrates proceed rapidly and in high yield. Regioselectivity was similar for all nitrating agents examined. The synthetic advantages of liquid EGDN include high solubility in organic solvents, strong nitration activity and ease of preparation.

Imidazolylmethylbenzophenones as highly potent aromatase inhibitors

Suppression of tumor and plasma estrogen levels by inhibition of aromatase is one of the most effective treatments for post-menopausal breast cancer patients. Starting from an easy, synthetically accessible, benzophenone scaffold, a new class of potent aromatase inhibitors was synthesized, endowed with high selectivity with respect to 17α-hydroxylase/17,20-lyase (CYP17). Compounds 1b and 1d proved to be among the most potent inhibitors described so far.

AMIDE RESORCINOL COMPOUNDS

The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as HSP-90 inhibitors.

Counterion effects in indium-catalysed aromatic electrophilic substitution reactions

Indium(III) triflamide (In(NTf2)3) has been prepared in high yield and has been demonstrated to be an efficient, recoverable catalyst for a range of aromatic electrophilic substitution reactions. When compared to other indium(III) complexes, anomalous reactivities suggest a non-innocent role for the counterion in the studied processes.

Synthetic receptors for CG base pairs.

Hydrogen-bond-mediated complexation of a CG base pair by a hexylureido phthalimide and a hexylureido isoindolin-1-one was studied by (1)H NMR spectroscopy in an organic solvent. Chemical shift data indicate that both receptors effectively bind the CG base pair from the major groove side.

Process for the production of nitro derivatives of aromatic compounds

Nitroderivates of aromatic compounds which are difficult to nitrate, can readily be obtained by nitration providing that the aromatic compound is treated with nitric acid or another nitrating agent in the presence of aliphatic or cycloaliphatic hydrocarbons monosubstituted or polysubstituted by halogen, the nitro group or an alkyl sulphonyl group, and the nitro derivative formed subsequently isolated.