Methyl 3-nitrobenzoate (other names: m-nitrobenzoic acid methyl ester, 3-nitrobenzoic acid methyl ester, etc.)
| methyl 3-nitrobenzoate | |
|---|---|
 | |
| Are common | |
| Systematic name | methyl 3-nitrobenzoate |
| Chem. formula | CβHβNOβ |
| Rat formula | C 8 H 7 NO 4 -> |
| Physical properties | |
| condition | solid |
| Molar mass | 181.04 g / mol |
| Classification | |
| Reg. CAS number | |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| ChemSpider | |
General information
Methyl 3-nitrobenzoate belongs to the class of esters of aromatic nitro compounds .
Physical and biological properties
Not explosive as the oxygen balance is negative. Less toxic than most nitro compounds, since a carbomethyl group is present in one of the substituents on the benzene ring .
Retrieval Methods
The main production method is nitration of methyl benzoate with a nitrating mixture of sulfuric and nitric acids. Methylbenzoate can be obtained by esterification of benzoic acid or isolated from dimethyl terephthalate production waste. Direct drain of reagents is applied. The main byproduct is the o-isomer. Purification is carried out by washing with methanol or ethanol , or by recrystallization from these solvents in which the orthoisomer is better soluble. In case of non-compliance with the thermal regime and insufficiently clean sources, the dinitro derivative and nitrophenol are also obtained.
Chemical Properties
Application
It is used for laboratory preparation of m-nitrobenzoic acid (obtained in industry by nitration of benzoic acid with a mixture of potassium nitrate and sulfuric acid) by alkaline hydrolysis, or reduced to methyl 3-aminobenzoate (reduction can be carried out according to the Zinin method with sulfides, hydrochloric acid -sawdust system ( the mechanism is probably based not on hydrogen at the moment of release, but on the action of the transition metal) Raney nickel, hydrogen over catalysts made of palladium or platinum oxide, etc.). Meta-aminobenzoic acid methyl ester can be used in the synthesis of thrombin inhibitors.
Literature
Agronomov A.E. Selected chapters of organic chemistry. - M.: Chemistry, 1990.560 s.