4-Nitro-m-toluylsure
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
Identifikatoren & physikalische Daten
| CAS No. | 3113-71-1 |
|---|---|
| Summenformel | C8H7NO4 |
| Durchschnittliche Molmasse | 181,15 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | 4-Nitro-m-toluylsure |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 83,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 223 |
| LogP (Verteilungskoeffizient) | 2.42 |
| Löslichkeit | less than 1 mg/mL at 72 °F (NTP, 1992)slightly sol. in Alcohol<0.1 g/100 mL at 22 ºC |
| Schmelzpunkt | 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) |
| Siedepunkt | 314.24°C (rough estimate) |
| Dichte | 1.4283 (rough estimate) |
| Brechungsindex | 1.5468 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | 3.49±0.10(Predicted) |
| Aggregatzustand | Amorphous Powder |
| Farbe | Yellow |
| BRN | 1959154 |
| Henry-Konstante | 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 Datenbank | 3113-71-1(CAS DataBase Reference) |
| NIST chemische Informationen | 3-Methyl-4-nitrobenzoic acid(3113-71-1) |
| EPA chemische Informationen | 3-Methyl-4-nitrobenzoic acid (3113-71-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Reaktive Gruppe | 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%) |
| Brandbekämpfung | Fires involving this compound can be controlled with a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992) |
Anwendungen & Verwendung
Beschreibung
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].
Verwenden
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.