ChemicalBook CAS DataBase List 2,2'-DINITRODIBENZYL

2,2'-DINITRODIBENZYL synthesis

11synthesis methods

Product Name:2,2'-DINITRODIBENZYL
CAS Number:16968-19-7
Molecular formula:C14H12N2O4
Molecular Weight:272.26

88-72-2
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$15.00/25g

16968-19-7
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$10.00/5g

Yield: 95%

Reaction Conditions:

Stage #1:1-methyl-2-nitrobenzene with potassium tert-butylate in tetrahydrofuran at 0; for 0.0333333 h;Inert atmosphere;
Stage #2: with bromine in tetrahydrofuran at 20; for 0.0833333 h;Inert atmosphere;

Steps:

2,2'-Dinitrobibenzyl [CAS Reg. No. 16968-19-7]
Under a nitrogen atmosphere, 2-nitrotoluene (2.00 g, 15.0 mmol) wa sdissolved in dry THF (90 mL), cooled to 0 °C, followed by addition of potassium t-butoxide. The reaction was stirred for 2 min before addition of bromine (3.12 g, 19.5 mmol). After further stirring for 5 min, the reaction was added to 500 mL of ice/water. The precipitate was filtered and the filtrate extracted with CH₂Cl₂ (3 × 100 mL). The combined organic layers were washed with saturated sodium thiosulfate solution and saturated sodium chloride solution, then dried over MgSO₄ and concentrated under reduced pressure. The crude product was purified by crystallization (H₂O/EtOH, 1:2) to give 2,2′-dinitrodibenzyl as a white solid (1.94 g, 7.13 mmol, 95%); mp 121 °C; Rf = 0.33 (n-pentane/CH₂Cl₂, 1:1). IR (ATR): 2962, 2854, 2343, 1608, 1576, 1509, 1443, 1344, 1310, 1262,1201, 1164, 1126, 1073, 1041, 959, 859, 787, 749, 704, 666, 567, 531, 421 cm^-1. ¹H NMR (500.1 MHz, CDCl₃, 300 K): δ = 7.96 (dd, J = 8.2 Hz, J = 1.2 Hz,2 H, H-3), 7.54 (pseudo t, 2 H, H-5), 7.42 (dd, J = 7.7 Hz, J = 1.3 Hz, 2 H,H-6), 7.38 (pseudo t, 2 H, H-4), 3.25 (s, 4 H, CH₂). ¹³C NMR (125.8 MHz, CDCl₃, 300 K): δ = 149.37, 136.01, 133.30,132.49, 127.56, 124.84, 34.44. MS (EI, 70 eV): m/z (%) = 273 (1) [M + H]⁺, 255 (8), 237 (9), 178 (21), 136 (100), 120 (70), 92 (85).