2-Methyl-5-nitrobenzoic acid Chemical Properties

Melting point:

177-180 °C (lit.)

Boiling point:

314.24°C (rough estimate)

Density 

1.4283 (rough estimate)

refractive index 

1.5468 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform

pka

3.12±0.10(Predicted)

form 

Crystalline Powder

color 

Yellow to beige

Water Solubility 

<0.1 g/100 mL at 22 ºC

BRN 

2451300

InChI

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

InChIKey

DJRFJAVPROZZFL-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC([N+]([O-])=O)=CC=C1C

CAS DataBase Reference

1975-52-6(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 Information

Hazard Codes 

Xn,Xi

Risk 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

HS Code 

29163900

MSDS

• Language:English Provider:5-Nitro-o-toluic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Methyl-5-nitrobenzoic acid Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

2-Methyl-5-nitrobenzoic Acid (cas# 1975-52-6) is a compound useful in organic synthesis.

General Description

Needles or beige solid.

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.

Synthesis

General procedure for the synthesis of 2-methyl-5-nitrobenzoic acid from methyl 2-methyl-5-nitrobenzoate: To a solution of methyl 2-methyl-5-nitrobenzoate (75.0 g, 0.46 mol) in tetrahydrofuran (THF, 500 mL) was added a 1N aqueous solution of lithium hydroxide (LiOH) (1 L, 0.92 mol). The reaction mixture was stirred at 30 °C for 4 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding reagent ratio of petroleum ether: ethyl acetate = 10:1), and after confirming the completion of the reaction, the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate (200 mL x 2). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently concentrated under reduced pressure to afford 2-methyl-5-nitrobenzoic acid (67 g, 98% yield) as a brown solid, which could be used in subsequent steps without further purification. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 8.93 (s, 1H), 8.30-8.32 (d, J=8.0 Hz, 1H), 7.48-7.50 (d, J=8.0 Hz, 1H), 2.79 (s, 3H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6273 - 6278
[2] Patent: WO2006/117669, 2006, A1. Location in patent: Page/Page column 41; 114
[3] Organic letters, 2000, vol. 2, # 19, p. 2931 - 2934

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