3-Methyl-4-nitrobenzoic acid
4-NITRO-M-TOLUIC ACID · 4-Nitro-m-toluylsure · Methyl-4-nitrobenzoic · 4-NITRO-3-METHYLBENZOIC ACID · RMA-109 · 4,3-NMBA · Fluralaner-027 · RARECHEM AL BO 0346
Identifiers & Physical Properties
| CAS No. | 3113-71-1 |
|---|---|
| Molecular formula | C8H7NO4 |
| Average molar mass | 181.15 g/mol |
| Monoisotopic mass | 181.0375077 g/mol |
| SMILES | Cc1cc(C(=O)O)ccc1[N+](=O)[O-] |
| InChIKey | XDTTUTIFWDAMIX-UHFFFAOYSA-N |
| PubChem CID | 18370 |
| ChEMBL | CHEMBL1329280 |
| EC No. | 221-479-4 |
| DTXSID | DTXSID1025641 |
Chemical & Physical Properties
| XLogP | 2.4 |
|---|---|
| Topological polar surface area | 83.1 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 1 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 223 |
| LogP (partition coefficient) | 2.42 |
| Solubility | less than 1 mg/mL at 72 °F (NTP, 1992)slightly sol. in Alcohol<0.1 g/100 mL at 22 ºC |
| Melting point | 421 to 424 °F (NTP, 1992)216-218 °C (lit.) |
| Physical Description | 3-methyl-4-nitrobenzoic acid appears as needles or off white powder. (NTP, 1992) |
| Boiling point | 314.24°C (rough estimate) |
| Density | 1.4283 (rough estimate) |
| Refractive index | 1.5468 (estimate) |
| Storage conditions | Sealed in dry,Room Temperature |
| pKa (acidity coefficient) | 3.49±0.10(Predicted) |
| Physical state | Amorphous Powder |
| Color | Yellow |
| BRN | 1959154 |
| Henry's law constant | 9.2×102 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| InChI | 1S/C8H7NO4/c1-5-4-6(8(10)11)2-3-7(5)9(12)13/h2-4H,1H3,(H,10,11) |
| InChIKey | XDTTUTIFWDAMIX-UHFFFAOYSA-N |
| SMILES | Cc1cc(ccc1[N+]([O-])=O)C(O)=O |
| CAS DataBase Reference | 3113-71-1(CAS DataBase Reference) |
| FDA UNII | ELP258JXH0 |
| NIST Chemistry Reference | 3-Methyl-4-nitrobenzoic acid(3113-71-1) |
| EPA Substance Registry System | 3-Methyl-4-nitrobenzoic acid (3113-71-1) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi,Xn |
| Risk statements (R) | 36/37/38-20/21/22 |
| Safety statements (S) | 26-36-36/37/39-22 |
| Water hazard class (WGK) | 3 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29163900 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 82 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| DOT label | Poison |
| Fire hazards | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Health hazards | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Reactive group | Acids, Carboxylic |
| Reactivity Profile | 3-METHYL-4-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 waterthose 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 and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Fire fighting | Fires involving this compound can be controlled with a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992) |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29163900 |
| Risk statements (R) | 36/37/38-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,Xn |
| hazard_note | Irritant |
| Safety statements (S) | 26-36-36/37/39-22 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
Description
In organic synthesis, 3-Methyl-4-nitrobenzoic acid (abbreviated as MNBA) is the fine chemical product that adds value is higher; many critical organic products are obtained for raw material can synthesize further with it, as 4-chloro-quinazoline-6-ethyl formate, 2-n-propyl-4-methyl-6-carboxy benzimidazole, 4-methyl-2-ethyl-1H-benzoglyoxaline-6-methyl-formiate, 3,4-dihydro-4-quinazoline is with-6-formic acid, 4-aminophenyl-1,3-dioctyl phthalate, 4-Amino-3-methylbenzoic acid methyl esters, 4-nitrophenyl-1,3-dioctyl phthalate etc. In medicine, it is an essential intermediate in the synthesis of telmisartan (via esterification, reduction, butyrylation, nitration, reduction and cyclization), which is used to treat essential hypertension. Telmisartan is a drug belonging to the group of antagonists of angiotensin II receptors. The active ingredient telmisartan counteracts the effect of angiotensin II, allowing the arteries to relax, thereby reducing blood pressure. As a precursor, pharmaceutical researchers have also synthesized anti-cancer substances and AIDS drugs with MNBA[1].
Uses
3-Methyl-4-nitrobenzoic Acid is used as a reagent in the synthesis of influenza neuraminidase inhibitors with pyrrolidinobenzoic acid scaffold containing lipophilic side chains.
General Description
Needles or off white powder.
Preparation & Synthesis
Preparation
3-Methyl-4-nitrobenzoic acid was synthesized via oxidation of 2,4-(dimethylnitrobenzene) with mole-(cular) oxygen catalyzed by cobalt acetate in acetic acid in the presence of an initiator.It was found that the yield of 3-methyl-4-nitrobenzoic acid increased remarkably with the addition of sodium bromide as a co-(catalyst).The reaction was carried out at 130 ℃ for 8 h at 0.8 MPa of oxygen in the presence of 0.017 mol of cobalt acetate,(0.017 mol) of sodium bromide,and 0.30 mol of 2-butanone with 1.00 mole of 2,4-dimethylnitrobenzene.(Under) these conditions 99% of the reactant converted with a selectivity of 52% to 3-methyl-4-(nitrobenzoic) acid,and the yield of 3methyl-4-(nitrobenzoic) acid was 51%.The reaction mechanism and the function of(sodium) bromide were discussed.According to the fact that the reaction could not proceed without the presence of an initiator,it was proposed that the reaction took place via a free radical mechanism,and(sodium) bromide reacted with Co(Ⅲ) to generate bromine radicals,which promoted the formation of benzyl radicals.Synthesis of 3-Methyl-4-nitrobenzoic Acid via Catalytic Oxidation with Molecular OxygenMethod for preparing 3-methyl-4-nitrobenzoic acid by oxidizing with nitric acid