Atkinson, Jeffrey et al. published their research in Journal of Organic Chemistry in 1991 | CAS: 5367-32-8

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).Name: 3-Methyl-4-nitroanisole

Analogs of the cyclic hydroxamic acid 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one (DIMBOA): decomposition to benzoxazolinones and reaction with β-mercaptoethanol was written by Atkinson, Jeffrey;Morand, Peter;Arnason, John T.;Niemeyer, Hermann M.;Bravo, Hector R.. And the article was included in Journal of Organic Chemistry in 1991.Name: 3-Methyl-4-nitroanisole This article mentions the following:

Analogs I (R = OH, OMe, H; R1 = OH, H; R2 = H, 5-Me, 6-OMe, 8-OMe; R3 = OMe, CMe3, Me, H, Cl, F, CO2Me, CO2Et, NO2, CF3, cyano; R2R3 = 6,7-OCH2O) of the aglycons of naturally occurring cyclic hydroxamic acids from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the α-(O-nitrophenoxy)-α-methoxyacetates II, followed by demethylation of the C-2 methoxy group. A structure-activity series was produced, i.e., I (R = R1 = OH, R2 = H, R3 = OMe, CMe3, Me, H, Cl, F, CO2Me). The pKa values for the hydroxamic acid and the phenol moieties were determined for each member of this series. They correlated well with σ in a linear free energy relationship (LFER) yielding values of ρ = 0.71 (with σp) for pKa1 (the hydroxamic acid) and ρ = 1.6 (with σm) for pKa2 (the phenol). A LFER also existed between the rate constants for the unimol. decomposition of these hydroxamic acids to benzoxazolinones and σ+ (ρ = -1.1). The rates of hydroxamic acid reduction to lactams by β-mercaptoethanol were also investigated. Only I (R = R1 = OH; R2 = H, 6-OMe, 8-OMe, R3 = OMe; R2R3 = 6,7-OCH2O) had measurable rates of reduction 1H NMR spectra recorded during this reaction in D2O buffers (pD 9), however, showed that I (R = R1 = OH, R2 = H, R3 = OMe, CMe3, Me, H, Cl) formed a hemithioacetal at C-2 even though only I (R = R1 = OH, R2 = H, R3 = OMe) has a measurable rate of reduction by the same thiol. The remarkable rate enhancement provided by an oxa functionality suggests that reduction occurs by direct attack of thiolate on the hydroxamic N of a resonance-stabilized ion pair. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Name: 3-Methyl-4-nitroanisole).

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).Name: 3-Methyl-4-nitroanisole

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem