2-Nitroresorcinol

orange crystalline powder

General procedure: Reactants such as sodium nitrite (12 mmol), with aromatic or heteroaromatic compound (10 mmol), KHSO4 (1 mmol), and SPB (1 mmol), were thoroughly mixed with silica gel and placed in MW oven. Reaction progress was monitored by thin-layer chromatography (TLC) until completion. The reaction mixture was then treated with NaHCO3 solution and extracted with ethyl acetate (30 mL). Final product was obtained by using the same workup steps as detailed in the preceding section. Sodium perborate/NaNO2/KHSO4-initiated nitration reactions with several other compounds also afforded corresponding nitroderivatives (Scheme 1) via both conventional and MW-assisted reactions.At room temperature, 1 mmol of resorcinol was dissolved in 40 mL of phosphate buffer at pH = 7, Then, 60 mmol of sodium nitrite was added and 4 mmol of hydrogen peroxide was dissolved in 10 mL of phosphate buffer, in15 min into the reaction solution, at room temperature by adding 0.06g Fe-Al-MCM-41 molecular sieve to start the reaction, stirring reaction 80min. The filtrate was extracted with ethyl acetate (2 x 80 mL), concentrated under reduced pressure, Column chromatography (column packed with silica gel, eluted with petroleum ether and acetone as eluent, Petroleum ether and acetone volume ratio of 1: 1, that is, the target product 2 - nitroresorcinol, the yield of 27.4percentAnd 4 - nitroresorcinol, the yield was 23.5percent and the total yield was 50.9percent. Under the same conditions, In the absence of the use of molecular sieve but 0.06gThe reaction was initiated using a water-soluble tetrakis (sodium sulfonate-based) iron porphyrin.As a result, the yield of 2-nitroresorcin was 9.9percent, the yield of 4-nitroresorcin was 11.8percent, The total yield was 21.7percent.Room temperature, 1 mmol of resorcinol was dissolved in 40 mL of phosphate buffer pH = 7, Then add 60mmol of sodium nitrite, 4 mmol of hydrogen peroxide was dissolved in 10 mL of phosphate buffer, In 15min drip into the reaction solution, At room temperature add 0.06g water-soluble Tetrakis (p-carboxyphenyl) iron porphyrin with Tetra (sodium sulfonate phenyl) iron An equal mass mixture of porphyrins initiates the reaction, The reaction was stirred for 80 min. Extraction with ethyl acetate (2 x 80 mL) Concentrated under reduced pressure, Column chromatography (silica gel column, With petroleum ether and acetone as eluent, Petroleum ether and acetone volume ratio of 1: 1) to obtain the target product 2-nitro resorcinol, Yield 10.9percent And 4-nitro resorcinol, Yield 13.0percent.General procedure: To a solution contained phosphate sodium buffer (50 mL, 0.1 M, pH 7.0), phenols (1 mmol) and NaNO2 (50–60 mmol), H2O2 (30 percent aqueous solution, 3 mmol) was added dropwise in 80 min. The reaction was initiated by adding metalloporphyrin (50–60 mg) at room temperature. After stirring for 80 min, the reaction products were extracted several times with chloroform or ethyl acetate, and the organic phase was combined, dried with sodium sulfate. The organic solvent was removed under vacuum.The residue was dissolved in methanol and quantitatively analyzed by HPLC.

Molecular Weight:155.11
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:155.02185764
Monoisotopic Mass:155.02185764
Topological Polar Surface Area:86.3
Heavy Atom Count:11
Complexity:145
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes