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Chemical Structure| 1758-68-5 Chemical Structure| 1758-68-5
Chemical Structure| 1758-68-5

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1,2-Diaminoanthraquinone is a highly sensitive and specific, non-toxic fluorescent probe for nitric oxide (NO), used to detect NO production in living cells and animals. Its maximum absorption wavelength is approximately 540 nm, with a minimum detection limit for NO of 5 μM.

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Product Details of 1,2-Diaminoanthraquinone

CAS No. :1758-68-5
Formula : C14H10N2O2
M.W : 238.24
SMILES Code : O=C1C2=C(C=CC=C2)C(C3=CC=C(N)C(N)=C13)=O
MDL No. :MFCD00001219
InChI Key :LRMDXTVKVHKWEK-UHFFFAOYSA-N
Pubchem ID :15652

Safety of 1,2-Diaminoanthraquinone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 1,2-Diaminoanthraquinone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1758-68-5 ]

[ 1758-68-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1758-68-5 ]
  • [ 117-78-2 ]
  • 2-(9,10-dioxo-9,10-dihydro-[2]anthryl)-3<i>H</i>-anthra[1,2-<i>d</i>]imidazole-6,11-dione [ No CAS ]
  • 3
  • [ 1758-68-5 ]
  • [ 128376-65-8 ]
  • [ 1400888-07-4 ]
  • 4
  • [ 1758-68-5 ]
  • [ 128376-65-8 ]
  • [ 1400888-14-3 ]
YieldReaction ConditionsOperation in experiment
60% In nitrobenzene; at 150℃; for 24h;Inert atmosphere; General procedure: Into a two-neck round bottom flask equipped with a magnetic bar, the corresponding formyl phenylboronate ester (1 mmol) in nitrobenzene (25 mL) was added dropwise to a solution of 1,2-diamino-1,4-anthraquinone (1 mmol) in nitrobenzene (75 mL). (0021) The reaction mixture was slowly heated to 150 C for 1 day under nitrogen atmosphere. The solution was cooled to room temperature and then the precipitate slowly formed. The precipitate was filtered and washed with diethylether to give a brown solid of the protecting products (Boc-oHAQB=45%, Boc-pHAQB=60%). 1H NMR (DMSO, 400 MHz) Boc-oHAQB, delta (ppm): 13.56 (s, 1H), 8.41 (d, 1H, J=6.4 Hz), 8.25-8.13 (m, 4H), 7.94-7.92 (m, 2H), 7.57-7.50 (m, 3H), 3.70 (s, 4H), 1.07 (s, 6H). Boc-pHAQB, delta (ppm): 10.18 (s, 1H), 8.40 (t, 1H, J=8.2 Hz), 8.29-8.21 (m, 4H), 8.13-8.05 (m, 2H), 7.97-7.93 (m, 3H), 3.78 (s, 2H), 3.11 (s, 2H), 0.97 (s, 3H) 0.72 (s, 3H).
  • 5
  • [ 54221-96-4 ]
  • [ 1758-68-5 ]
  • 2-(4-methoxy-2-pyridyl)-1H-anthra[1,2-d]imidazole-6,11-dione [ No CAS ]
  • 6
  • [ 1758-68-5 ]
  • [ 87220-68-6 ]
  • 2-(9-phenyl-9H-carbazol-3-yl)-3H-anthra[1,2-d]imidazole-6,11-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% 2-(9-Phenyl-9H-carbazol-3-yl)-3H-anthra[1,2-d]imidazole-611-dione (AQ CBZ) and 2-(4-(diphenylamino)phenyl)-3H-anthra[1,2-d]imidazole-611-dione (AQ TPA) were synthesized by heating aldehydes CBZ, TPA and 1,2-diaminoanthraquinone for 15h in ethanol at reflux using acetic acid as catalyst, to yield the corresponding imines that was consequently cyclized to the resultant imidazoanthraquinones i.e. AQ CBZ and AQ TPA in the existence of lead tetraacetate and acetic acid at room temperature (see Fig. 1). Both the dyes purified by recrystallization in ethanol and dried over air to give 87 and 82% yield respectively.The characterization spectra of AQ CBZ and AQ TPA (1H NMR, 13C NMR, FT-IR, and LC-MS analysis) are listed in the (SI) see (S1 to S4). (0010) AQ CBZ. m.p. 322-323C 1H NMR (500MHz, TFA) AQ CBZ was highly insoluble in most of the deuterated solvents. δ 9.82 (Q=s, 1H), 8.84-8.76 (B=m, 2H), δ 8.53-8.47 (A, C, F=m, 5H), δ 8.36 (A=s, 1H), δ 8.25 (Z=s, 1H), δ 8.16-8.07 (E, G, I, J=m, 4H), δ 7.91-7.68 (X, Y, H=m, 3H), δ 7.49 (D, K=s, 2H). FT-IR 3433 (imidazole N-H stretch), 1664 (C=O stretch), 1593 (imidazole C=N stretch), 1500 (imidazole N-H bend), 1434 (Ar-C=C stretch), 1290 (C-N stretch) cm-1. MS (m/z): Calculated 489.15, [M + H]+ for C33H19N3O2; obtained 490.1, [M + H]+. CHN analysis Anal. Calculated C33H19N3O2 C, 80.97, H, 3.91, N, 8.58 found C, 81.02, H, 3.92, N, 8.57.
 

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