3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).COA of Formula: C8H9NO3
Researches concerning nitrofluoroaromatic compounds. Nitration of m-fluorotoluene was written by Ostaszynski, Abram. And the article was included in Bull. soc. sci. et lettres lódź, Classe III in 1952.COA of Formula: C8H9NO3 This article mentions the following:
The directive effect of F and Me in m-FC6H4Me (I) was determined upon entering NO2 groups. The reactivity of the F in the nitro derivatives was also determined I (1 part) and 4 parts concentrated HNO3 (d. 1.51) react, at less than -3°, to give mono- and 25-35% dinitro derivatives Similarly, 20% dinitro derivatives resulted from the reaction of 1 mole of I and a mixture of 1 mole of HNO3 (d. 1.49) and 2 moles of H2SO4 (d. 1.84). AcONO2 (2.4 moles) and 1 mole of I react in HOAc at less than -7° to give 97.4% of 2 isomeric mono derivatives 3,6-F(O2N)C6H3Me (II), m. 24.6-4.8°, b3 78.5-9.5°, b775 215.9-16°, d25 1.2760, nα25 1.51809, nD25 1.52398, nβ25 1.54006, and 3,4-F(O2N)C6H3Me (III), m. 53-3.2°, b3 97-8°. The dinitro compound, 3,4,6-F(O2N)2C6H2Me (IV), m. 78-8.5°, b0.5 129-30.5°, forms yellow prisms. II reacts with alc. NaOMe to give 3,6-MeO(O2N)C6H3Me (V). V and NH3 give, on heating, 3,6-H2N(O2N)C6H3Me, m. 134°. III and alc. NH3 gives 3,4-H2N(O2N)C6H3Me. IV was treated with NaOMe and NaOEt to give the corresponding alkoxy derivatives, and these with NH3 to give 3,4,6-H2N(O2N)2C6H2Me, m. 195°. Reduction of II and III with Fe-HCl gave 3,6-F(H2N)C6H3Me (VI), m. 14.1-14.2°, b3 64°, d18 1.1263, nα18 1.53080, nα18 1.53627, nβ18 1.55087 (Ac derivative, white needles, m. 113.2°, water solubility 7.31 g./l. at 20° and 35.2 g./l. at b.p.); and 3,4-F(H2N)C6H3Me (VII), m. 3.2-3.5°, b7 70-1°, d18 1.1084, nα18 1.52694, nα18 1.53243, nβ18 1.54700 (Ac derivative, yellow needles, m. 128.2-8.4°, water solubility 3.04 g./l. at 20° and 21.8 g./l. at b.p.). Nitration of VI gave 3,4,6-F(O2N)(H2N)C6H2Me, red needles, m. 96-7°. The rate (K) of reaction of the F in III with NaOMe is twice that of II and Kt+10°/Kt = 3. IV reacts so rapidly that no rate was determined. The nitration of I with AcONO2 gives 79.2% II and 20.8% III, while the nitration of PhMe gives 58% ortho, 38.1% para, and 3.9% meta derivatives; and of PhF, 12% ortho, 87.4% para, and 0.2% meta derivatives, which indicates that F exerts a greater effect than the Me group upon a group entering the benzene ring. (Directing effect of F)/(directing effect of Me) is greater than 2. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8COA of Formula: C8H9NO3).
3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).COA of Formula: C8H9NO3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem