2- Nitrobenzoic acid methyl ester

Preparation of 2-(l-methoxynaphthalen-2-yl)-3-nitrobenzoic acid, methyl ester... 

Synonyms 3-Nitrobenzoic acid methyl ester Methyl 3-nitrobenzoate Source Chang, H. Morrell, D. G. 

C21HJ0O2 22034-63-5) see Promestriene 2-propoxy-4-nitrobenzoic acid methyl ester (CiiHijNO,) see Propoxycaine propylamine... 

C8H6CIN04 2-chloro-5-nitrobenzoic acid methyl ester 6307-82-0 18.00 1.4875 2 12911 C8H6N405 nitrofurantoin 67-20-9 25.00 1.6123 2... 

Benzoic acid, 5-(2,4-dichlorophenoxy)-2-nitro-, methyl ester Bifenox BRN 2170169 Caswell No. 561AA CCRIS 7158 5-(2,4-Diohlorophenoxy)-2-nitrobenzoic acid methyl ester MC-4379 Modown Modown 4 Flowable EPA Pesticide Chemical Code 104301 MC-4379 Methyl 5-(2,4-dichlorophenoxy)-2-nltrobenz-oate Modown, Selective herbicide used for control of annual broad-leaved weeds and some grasses in cereals, maize, sorghum, soybeans, rice and some other crops. Registered by EPA as a herbicide (cancelled). Yellow crystals mp = 84-86 poorly soluble in H2O (0.000035 g/100 ml), more soluble in MezCO (31.5 g/100 ml), chlorobenzene (44,3 g/100 ml), xylene (25.8 g/100 ml), EtOH (< 4 g/100 ml) slightly soluble in aliphatic hydrocarbons LDso (rat orl) > 6400 mg/kg, (mus orl) = 4556 mg/kg, (rbt der) > 20000 mg/kg LC50 (rat ihl) > 200 mg/l air, (duck, pheasant 8 day dietary) > 5000 mg/kg diet, (rainbow trout 96 hr.) = 0.87 mg/l, (bluegill sunfish 96 hr.) = 0.64 mg/l. Aventis Crop Science. 

Hydrolysis of methyl m-nitrobenzoate to m-nitrobenzoic acid. Place 90 -5 g. of methyl m-nitrobenzoate and a solution of 40 g. of sodium hydroxide in 160 ml. of water in a 1-htre round-bottomed flask equipped with a reflux condenser. Heat the mixture to boiling during 5-10 minutes or until the ester has disappeared. Dilute the reaction mixture with an equal volume of water. When cold pour the diluted reaction product, with vigorous stirring, into 125 ml. of concentrated hydrochloric acid. Allow to cool to room temperature, filter the crude acid at the pump and wash it with a httle water. Upon drying at 100°, the crude m-nitrobenzoic acid, which has a pale brownish colour, weighs 80 g. and melts at 140°, Recrystalhsation from 1 per cent, hydrochloric acid afibrds the pure acid, m.p. 141°, as a pale cream sohd the loss of material is about 5 per cent. 

Etbyl-3-nitrobenzoate, monoclinic prisms, mp 47°, bp 296° It may be prepd by saturating an ale soln of the acid with. HCl gas from the acid salt of 3 nitrobenziminoethylether from the 3-nitro acid and diazoethane and from the >nitro benz in bulling abs ale and HCl gas Ref Beil 9, 378, (151), (154) [248] Etbyl 4-nitrobenzoate, pi tits (from ale), mp 57°. It may.be prepd from the acid in ale in the presence of HCl, from the methyl ester and excess ale in the presence of KOCH3 Ref Beil 9, 390 [258]... 

If we compare the acid strengths Ka) of a series of substituted benzoic acids with the strength of benzoic acid itself (Table 26-4), we see that there are considerable variations with the nature of the substituent and its ring position, ortho, meta, or para. Thus all three nitrobenzoic acids are appreciably stronger than benzoic acid in the order ortho para > meta. A methoxy substituent in the ortho or meta position has a smaller acid-strengthening effect, and in the para position decreases the acid strength relative to benzoic acid. Rate effects also are produced by different substituents, as is evident from the data in Table 26-5 for basic hydrolysis of some substituted ethyl benzoates. A nitro substituent increases the rate, whereas methyl and methoxy substituents decrease the rate relative to that of the unsubstituted ester. 

Chemical Name benzoic acid, 5-(2,4-dichlorophenoxy)-2-nitro-, methyl ester methyl-5-(2,4-dichlorophenoxy)-2-nitrobenzoate... 

Smith and Lieber (36) reported that, although the use of alkali activated Raney nickel for the hydrogenation of carbonyl groups, it had a deterring effect on the reduction of aromatic nitro compounds. In particular, alkali retarded the reduction of nitrobenzene and the three isomeric sodium nitrobenzoates, whereas it increased the velocity of reduction of the methyl and ethyl esters of nitrobenzoic acid. 

Nitro is the most electron-withdrawing of these groups and some of the other compounds are nearly as reactive (in the meta position, of course) as benzene itself. It is easy to nitrate methyl benzoate and the m-nitro ester can then be hydrolysed to m-nitrobenzoic acid very easily. 

Low-molecular-weight a- and /3-amino esters are easily hydrolyzed merely by boiling with water. Also, aqueous barium hydroxide is employed in the preparation of several amino acids, e.g., /3-aminopropionic acid (72%) and a-methyl-y-dimethylaminobutyric acid (90%). m-Nitrobenzoic acid (96%) is best prepared from the corresponding methyl ester by boiling for 10 minutes with 20% sodium hydroxide. Longer heating gives a colored product, and the use of a more dilute base is unsatisfactory. y-Nitrovaleric acid is obtained from its methyl ester by hydrolysis with concentrated hydrochloric acid. ... 

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