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Chemical Structure| 92874-17-4 Chemical Structure| 92874-17-4

Structure of 92874-17-4

Chemical Structure| 92874-17-4

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Product Details of [ 92874-17-4 ]

CAS No. :92874-17-4
Formula : C16H14BrNO2
M.W : 332.19
SMILES Code : O=C(C1=C2C3=CC=CC2=C(Br)C=C1)N(CCCC)C3=O
MDL No. :MFCD28033162

Safety of [ 92874-17-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 92874-17-4 ]

* 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 [ 92874-17-4 ]

[ 92874-17-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 92874-17-4 ]
  • [ 189178-09-4 ]
  • 4,4',4''-tri(N-butyl-4-ethynyl)-1,8-naphthalimide-triphenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In flame dried Schlenk flask (100 mL), <strong>[189178-09-4]tris(4-ethynylphenyl)amine</strong> (105.8 mg, 0.33 mmol), Pd(PPh3)4 (62.4mg, 0.054 mol), CuI (3.4mg, 0.018mmol), and anhydrous THF (10 mL) were charged under N2 atmosphere. After 30 min stirring, 4-bromo-1,8-napthalimide (328.9 mg,0.99 mmol) in anhydrous THF (20 mL) and Et3N (6 mL) were added. The mixture was stirred at room temperature overnight. After the starting materials were full reacted, as confirmed by TLC, the mixture was poured to distilled water 50mL. Then, it was extracted by dichloromethane (25 mL × 3). The organic phase dried over Mg2SO4 and evaporated in vacuum. The residue was loaded to the column. Column separation (silica gel 200-300 mesh,eluent: dichloromethane/petroleum = 2/1) produced 286 mg yellow powder (80%).Mp: 281-284C; IR (KBr, υ, cm-1): 780, 1085, 1235, 1274, 1319, 1353, 1503, 1511, 1587,1660, 1697, 2196, 2960. 1H NMR(400 MHz, CDCl3): δ (ppm): 8.73 (3H, d, J = 8.0 Hz), 8.65(3H, d, J = 8.0 Hz), 8.56 (3H, d, J = 8.0 Hz), 7.95 (3H, d, J = 8.0 Hz), 7.84 (3H, t, J = 8.0Hz), 7.64 (6H, d, J = 8.0 Hz), 7.23 (6H, d, J = 8.0 Hz), 4.20 (6H, t, J = 8.0 Hz), 1.73 (6H, m), 1.53-1.44 (6H, m), 0.99 (9H, t, J = 8.0 Hz). 13C NMR (100 MHz, CDCl3): δ (ppm): 164.1,163.9, 147.4, 133.5, 132.4, 131.73, 131.67, 130.7, 130.5, 128.2, 127.7, 127.6, 124.5, 123.2, 122.2,118.1, 117.5, 99.1, 86.8, 40.5, 30.4, 29.8, 20.6, 14.0.Maldi-Tof: [M+H]+ C72H56N4O5 requires1071.412; found [M+H]+ 1071.501; and [M+2H]+ C72H57N4O5 requires 1072.420; found1072.508 (Base).
  • 2
  • [ 92874-17-4 ]
  • [ 137215-27-1 ]
  • 2–butyl–6–((4–methyl–2–oxo–2H–chromen–7–yl)thio)–1H–benzo[de]isoquinoline–1,3(2H)–dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.38% With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3h; 6-Bromo-2-butyl-benzo [de]isoquinoline-1,3-dione 7 (0.2 g,0.604 mmol), 7-mercapto-4-methylcoumarin (0.11 g, 0.604 mmol)and potassium carbonate (0.24 g, 1.81 mmol) were taken in dry N,N-dimethylformamide (15 mL) and stirred at 90 C for 3 h. Upon completion of the reaction, the mixture was cooled and N,N-dimethylformamide was evaporated under vacuum and the obtainedcrude solid was extracted with chloroform (50×2) and dried on sodiumsulphate and chloroform was evaporated under vacuum to obtainthe residue. Then the residue was purified on silica gel column chromatographyemploying hexane: ethyl acetate (8:2, V/V). Yield, 74.38%(0.21 g), m. p. 208 C, IR (KBr): numax/cm-1 1720 (nuCO), 1691 (nuCO). 1HNMR (400 MHz, CDCl3) delta 8.66 (d, 1H, J=7.6 Hz, aromatic), 8.61 (d,1H, J=8.4 Hz, aromatic), 8.51 (d, 1H, J=7.6 Hz, aromatic),7.80-7.76 (m, 2H, aromatic), 7.53 (d, 1H, J=8.4 Hz, aromatic), 7.19(dd, J1-2=1.6 Hz, J1-3=8.4 Hz,1H, aromatic), 7.11 (d, 1H,J=1.6 Hz, aromatic), 6.27 (s, 1H), 4.20 (t, 2H, J=7.6 Hz, CH2), 2.45(s, 3H, CH3), 1.77-1.69 (m, 2H, CH2), 1.50-1.41 (m, 2H, CH2), 0.98 (t,3H, J=7.6 Hz, CH3). 13C (150 MHz, CDCl3) delta163.73, 163.59, 160.02,153.92, 151.73, 139.59, 139.01, 131.87, 131.63, 131.27, 130.95,130.72, 128.86, 127.83, 123.48, 122.97, 119.04, 117.90, 115.15,40.37, 30.18, 20.37, 18.62, 13.85. HRMS (m/z): [M+H] calculated forC26H22NO4S: 444.1270; Found: 444.1275.
  • 3
  • [ 21563-29-1 ]
  • [ 109-73-9 ]
  • [ 92874-17-4 ]
YieldReaction ConditionsOperation in experiment
90% In ethanol; for 5.0h;Reflux; 4-Bromo-1,8-naphthalic anhydride (1.385?g, 5?mmol) and n-butylamine(0.438?g, 6?mmol) were dissolved in ethanol (30?ml) and refluxed for about 5?h. The reaction was monitored by TCL until the end of the reaction. After cooling to room temperature, white product was obtained by recrystallization, 1.494?g. Yield: 90percent. 1H NMR (600?MHz, CDCl3) delta 8.68 (dd, J?=?7.3, 0.8?Hz, 1H), 8.58 (dd, J?=?8.5, 0.8?Hz, 1H), 8.43 (d, J?=?7.8?Hz, 1H), 8.06 (d, J?=?7.8?Hz, 1H), 7.87 (dd, J?=?8.3, 7.4?Hz, 1H), 4.30-4.06 (m, 2H), 1.74 (tt, J?=?7.7, 6.7?Hz, 2H), 1.52-1.41 (m, 2H), 1.00 (t, J?=?7.4?Hz, 3H). 13C NMR (151?MHz, CDCl3) delta 163.65 (d, J?=?3.5?Hz), 133.23 (s), 132.03 (s), 131.22 (s), 131.10 (s), 130.64 (s), 130.20 (s), 129.02 (s), 128.09 (s), 123.18 (s), 122.31 (s), 40.40 (s), 30.18 (s), 20.39 (s), 13.86 (s). TOF-MS (ESI) m/z calcd. For C16H14BrNO2 [M?+?H]+: 332.0208, found: 332.0200.
 

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