| Identification | More | [Name]
2-Methyl-5-nitrobenzoic acid | [CAS]
1975-52-6 | [Synonyms]
2-METHYL-5-NITROBENZOIC ACID
5-NITRO-O-TOLUIC ACID
RARECHEM AL BO 0285
Benzoic acid, 2-methyl-5-nitro-
5-nitro-2-methyl benzoic acid
2-Methyl-5-nitro-benzoic Aci
2-Methyl-3-nitrobenzoic
2-Methyl-5-nitrobenzoic
2-METHYL-5-NITROBENZOIC ACID 99+%
2-Methyl-5-nitrobenzoic acid, 98+%
3-Nitro-6-methylbenzoic acid | [EINECS(EC#)]
217-829-0 | [Molecular Formula]
C8H7NO4 | [MDL Number]
MFCD00007371 | [Molecular Weight]
181.15 | [MOL File]
1975-52-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Solid | [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 | [form ]
Crystalline Powder | [pka]
3.12±0.10(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust . | [RIDADR ]
2811 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163900 |
| Hazard Information | Back Directory | [General Description]
Needles or beige solid. | [Reactivity Profile]
2-METHYL-5-NITROBENZOIC ACID(1975-52-6) 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. | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for this chemical are not available; however, 2-METHYL-5-NITROBENZOIC ACID is probably combustible. | [Chemical Properties]
Light Yellow Solid | [Uses]
2-Methyl-5-nitrobenzoic Acid (cas# 1975-52-6) is a compound useful in organic synthesis. | [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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