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[ CAS No. 51792-85-9 ]

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2D
Chemical Structure| 51792-85-9
Chemical Structure| 51792-85-9
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Quality Control of [ 51792-85-9 ]

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Product Details of [ 51792-85-9 ]

CAS No. :51792-85-9MDL No. :MFCD00082778
Formula :C20H17NO4Boiling Point :522.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :335.35Pubchem ID :350342
Synonyms :

Computed Properties of [ 51792-85-9 ]

TPSA : 64.3 H-Bond Acceptor Count : 4
XLogP3 : 4.7 H-Bond Donor Count : 0
SP3 : 0.10 Rotatable Bond Count : 6

Safety of [ 51792-85-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51792-85-9 ]

  • Upstream synthesis route of [ 51792-85-9 ]
  • Downstream synthetic route of [ 51792-85-9 ]

[ 51792-85-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 621-91-0 ]
  • [ 51792-85-9 ]
YieldReaction ConditionsOperation in experiment
100% at 0℃; for 3.00 h; Nitric acid (70percent) (19.5 ml, 437.4 mmol, 2.0 equiv) was added slowly to a suspensionof hydroquinol 2 (63.5 g, 218.7 mmol,1.0 equiv) in glacial acetic acid(400 ml) at 0 C. The solutionwas stirred at 0 C for 3 h, poured intowater (w1500 ml) and the resulting precipitate filtered off. Theprecipitate was washed with water (1500 ml), dissolved in CHCl3(300 ml), dried over magnesium sulfate and concentrated undervacuum to give nitro compound 3 as a yellow solid. (73.04 g, 100percent).mp 80e81 C (lit.: 80e81 C44). dH (400 MHz, CDCl3): 7.49 (1H, d,J3.0, H3), 7.46e7.30 (10H, m, OCH2Ph), 7.12 (1H, dd, J9.2, 3.1 Hz,H5), 7.05 (1H, d, J9.2 Hz, H6), 5.18 (2H, s, CH2), 5.05 (2H, s, CH2). 13CNMR (101 MHz, CDCl3) d 152.30 (C), 146.39 (C), 135.97 (C), 135.88(C), 128.75 (CH), 128.70 (CH), 128.37 (CH), 128.22 (CH), 127.59 (CH),127.15 (CH), 121.54 (CH), 117.24, 111.18 (CH), 72.10 (CH2), 70.94(CH2). IR (ATR cm1): 1520 (NO2), 1497 (CAr]CAr), 1341 (NO2). MS(ESI): 358 [(MNa), 100]. HRMS: 358.1034. C20H17NNaO4 requires358.1050. Spectroscopic data agree with lit.31
94% With silica supported Al(NO3)3*9H2O In acetone at 20℃; for 0.67 h; General procedure: To a solution of phenol (1 mmol) in acetone (5 mL) wasadded silica supported Al(NO3)3·9H2O (1 mmol) and theresulting mixture stirred at room temperature. After completionof the reaction, as indicated by TLC, the reaction masswas filtered and the residue (silica) was washed with ethylacetate (2 5 mL). The filtrate and the washing were collectivelyconcentrated under reduced pressure, and the crudecompound was purified by column chromatography oversilica gel (100-200 mesh) to afford the pure ortho-nitro phenol(95percent) and para- nitro phenol (3percent).
77% With tert.-butylnitrite In acetonitrile at 20℃; for 1.00 h; Add 1 mmol of 1,4-dibenzyloxybenzene to the reaction flask, dissolve in 2 mL of dichloromethane, add 145 uL of t-butyl nitrite, stir at room temperature for 1 hour, and after the reaction, remove with a rotary evaporator. Removal of organic solvent, column chromatography to obtain the product nitro product, reaction yield 77percent
Reference: [1] Tetrahedron, 2015, vol. 71, # 51, p. 9571 - 9578
[2] Letters in Organic Chemistry, 2015, vol. 12, # 2, p. 129 - 135
[3] Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2645 - 2667
[4] Chemical Communications, 2013, vol. 49, # 66, p. 7313 - 7315
[5] Patent: CN108530242, 2018, A. Location in patent: Paragraph 0063-0065
[6] Justus Liebigs Annalen der Chemie, 1883, vol. 221, p. 369
  • 2
  • [ 100-39-0 ]
  • [ 16090-33-8 ]
  • [ 51792-85-9 ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate In acetone at 20℃; for 10.00 h; To a 100-mL round-bottom flask was placed a solution of 2-nitrobenzene-1,4-diol (1 g,6.45 mmol) in acetone (15 mL) then K2C03 (4.45 g,32.20 mmol) and (bromomethyl)benzene (2.64 g,15.48mmol) were added. Thereaction was stirred for 10 h at rt,filtered,and concentrated under reduced pressure affording1.302 g (60percent) of the title compound as a yellow solid.
Reference: [1] Patent: WO2017/62581, 2017, A1. Location in patent: Paragraph 0297
  • 3
  • [ 123-31-9 ]
  • [ 51792-85-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1883, vol. 221, p. 369
[2] Tetrahedron, 2015, vol. 71, # 51, p. 9571 - 9578
[3] Chemical Communications, 2013, vol. 49, # 66, p. 7313 - 7315
  • 4
  • [ 100-44-7 ]
  • [ 51792-85-9 ]
Reference: [1] Tetrahedron, 2015, vol. 71, # 51, p. 9571 - 9578
[2] Chemical Communications, 2013, vol. 49, # 66, p. 7313 - 7315
  • 5
  • [ 100-39-0 ]
  • [ 51792-85-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1883, vol. 221, p. 369
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