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[ CAS No. 5315-79-7 ]

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Chemical Structure| 5315-79-7
Chemical Structure| 5315-79-7
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CAS No. :5315-79-7 MDL No. :MFCD00044543
Formula : C16H10O Boiling Point : 437.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :218.25 g/mol Pubchem ID :21387
Synonyms :

Safety of [ 5315-79-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5315-79-7 ]

  • Downstream synthetic route of [ 5315-79-7 ]

[ 5315-79-7 ] Synthesis Path-Downstream   1~17

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  • [ 78751-40-3 ]
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  • [ 77-78-1 ]
  • [ 34246-96-3 ]
YieldReaction ConditionsOperation in experiment
45% With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 12h; A mixture of 1-formylpyrene (see preparation of 4, 0.69 g,3.0 mmol) and m-CPBA (1.04 g, 6.0 mmol) in CH2Cl2 (50 mL) wasstirred at reflux for 24 h under an argon atmosphere. To the solutionwere added THF (5 mL), MeOH (10 mL), and 25 % KOH aq (0.6 mL),and the resulting solution was stirred at room temperature for 3 h. Thesolution was concentrated in vacuo to give a black residue. The residuewas extracted with CH2Cl2 (100 mL) and sat. NaCl aq (50 mL). Theorganic layer was separated, dried over Na2SO4, filtered, and concentratedin vacuo, giving a residue that was subjected to silica gelcolumn chromatography (eluent: CHCl3) to give <strong>[5315-79-7]1-hydroxypyrene</strong>(0.36 g, 55 % yield, pink solid). Lit [96].A mixture of <strong>[5315-79-7]1-hydroxypyrene</strong> (0.17 g, 0.77 mmol), NaOH (0.5 g,5.0 mmol), Me2SO4 (0.26 g, 2.1 mmol) in H2O (15 mL) and THF (10 mL)was stirred at room temperature for 12 h. The mixture was extractedwith AcOEt (100 mL) and then Et2O (100 mL). The combined organiclayers were washed with sat. NaCl aq (50 mL), dried over Na2SO4, filtered,and concentrated in vacuo, giving a residue that was subjected tosilica gel column chromatography (eluent: CHCl3) to give 1-methoxypyrene(0.080 g, 45 % yield, brown solid). Lit [97].To a stirred nitrobenzene (120 mL) solution of 1-methoxypyrene(0.46 g, 2.0 mmol) was added dropwise nitrobenzene (40 mL) solutionof Br2 (0.4 mL, 7.2 mmol), and the resulting solution was stirred at 80 Cfor 12 h. After cooling to room temperature, conc. NaOH aq (10 mL)was added to quench excess Br2. The formed solid was washed withCHCl3 (100 mL) and collected by filtration to give 1,3,6-tribromo-8-methoxypyrene (0.85 g, 91 % yield, yellow solid).A mixture of 1,3,6-tribromo-8-methoxypyrene (0.93 g, 2.0 mmol),trimethylsilylacetylene (0.844 g, 8.6 mmol), PdCl2(PPh3)2 (0.071 g,0.10 mmol), CuI (0.033 g, 0.17 mmol), and PPh3 (0.068 g, 0.26 mmol)in THF (30 mL) and i-Pr2NH (25 mL) was stirred at 80 C for 12 h underan argon atmosphere. The resulting mixture was concentrated in vacuo,giving a residue that was subjected to silica gel column chromatography(eluent: hexane) followed by recycling preparative HPLC (GPC, eluent:CHCl3) to give 1-methoxy-3,6,8-tris(trimethylsilylethynyl)pyrene 0.24 g, 23 % yield). Yellow solid; mp 288 C; 1H NMR (400 MHz, CDCl3)8 0.37 (s, 9 H), 0.38 (s, 9 H), 0.40 (s, 9 H), 4.18 (s, 3 H), 7.66 (s, 1 H),8.27 (s, 1 H), 8.42 (d, J =9.3 Hz, 1 H), 8.48 (d, J =9.3 Hz, 1 H), 8.52 (d,J =9.3 Hz, 1 H), 8.53 (d, J =9.3 Hz, 1 H) ppm; 13C NMR (100 MHz,CDCl3) 8 0.0, 0.0, 0.0, 56.2, 100.3, 101.0, 103.0, 103.0, 103.5, 111.8,111.8, 116.8, 117.0, 119.2, 121.1, 122.5, 123.8, 123.9, 124.7, 125.0,126.6, 127.0, 132.5, 132.5, 134.3, 134.3, 153.5 ppm; IR (KBr) 887,1119, 1250, 2152, 2360, 2959 cm-1; MS (CI) m/z (relative intensity,%)=75 (100), 245 (12), 448 (14), 520 (M+, 85); HRMS (EI) calcd forC32H36OSi3: 520.1316, found: 520.2074.
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  • C16H8O(1+) [ No CAS ]
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  • [ 111843-54-0 ]
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  • [ 5522-43-0 ]
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  • 1-hydroxy-2-nitropyrene [ No CAS ]
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  • [ 78751-40-3 ]
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YieldReaction ConditionsOperation in experiment
95.4% With water; sodium hydroxide; at 60℃; 1000 ml of water,80 g of sodium hydroxide (2 mol) and 245 g of acetoxypyrene obtained in Step 2 were added to a 2000 ml reaction flask,After the mixture is fully dissolved,The mixture was warmed to 60 C,After sufficient reaction (approximately 6 hours for this example)Cooling to about 30 C, and then dropping 500ml concentration of 35% concentrated hydrochloric acid,To be fully reacted,It will produce a large number of white solid,The mixture was filtered,dry,To give 196 g of solid 1-hydroxyprene as a white solid,The HPLC chromatogram of 1-hydroxypyrene shown in Figure 3 shows that the content of 1-hydroxypyrene is 99.28%The yield of 1-hydroxypyrene was 95.4%.
94% With water; sodium hydroxide; In ethanol; for 2.5h;Reflux; A solution of 0.19 g (0.73 mmol) of 1-acetoxypyrene 5 and 0.19 g (4.75 mmol) of NaOH in a mixture of 8.1 ml of EtOH and 5.4 ml of H2O was heated under reflux for 2.5 h. EtOH was distilled off in vacuo and the small portions of 2.7 ml of conc. HCl were added dropwise on cooling and stirring. The precipitate of 3 was filtered, washed with an excess of H2O and dried in a dessicator over NaOH. Yield 0.15 g (94%), mp 180-182 C (crystals from the reaction mass) (lit.,9(a),(b)179-181 C). IR (CHCl3, n/cm-1): 3594 (OH). MS, m/z (%): 218 (100,M+), 189 (82), 163 (6), 109 (9), 94 (32), 82 (4).
80% With sodium hydroxide; In water; at 60℃; for 10h; The 1-acetoxyphosphonium (6.6 g, 25.16 mmol) obtained in the previous step was dissolved in 50 mL of a 1 M aqueous sodium hydroxide solution (2 g, 50 mmol) and reacted at 60 C. After the reaction was completed (about 10 hours), cooled to 0 C, Add about 20mL of 6M concentrated hydrochloric acid, precipitate a white solid, filter it, collect the solid, recrystallize with toluene, and add 1-hydroxypyrene seed crystals to induce crystallization during recrystallization to obtain high purity1-Hydroxyphosphonium (4.4 g, white solid, yield 80%, purity 99.87%)
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  • Formic acid pyren-1-yl ester [ No CAS ]
  • [ 5315-79-7 ]
YieldReaction ConditionsOperation in experiment
0.7 g With potassium hydroxide; In tetrahydrofuran; methanol; for 2h;Inert atmosphere; 1-hydroxypyrene was prepared from pyrene-1-carboxaldehyde 2 according to a known procedure by making changes in the purification procedure (Sehgal and Kumar, 1989). To a stirred solution of commercially available pyrene-1-carboxaldehyde 2(2.0 g, 8.6 mmol) in anhydrous CH2Cl2 (80 mL) m-chloroperbenzoic acid (m-CPBA, 2.2 g, 13 mmol) was added under an atmosphere of Ar. The resulting solution was refluxed under Ar atmosphere until TLC monitoring (SiO2, AcOEt/n-hexane 1/9, x2) showed the complete disappearance of the starting material (24 h). The reaction mixture was treated with 10% NaHCO3 until effervescence ceased and the organic solvent was evaporated under reduced pressure. The resulting brown residue was dissolved in a mixture of THF (20 mL) and MeOH (20 mL) and then 25% KOH solution (6 mL) was added. The solution was stirred under Ar until TLC monitoring (SiO2, AcOEt/n-hexane 1/9, x2) showed the complete disappearance of pyrene-1-carboxaldehyde 2 (2 h). Organic solvents were evaporated under reduced pressure and theresidue was taken up with 2% KOH solution and extracted with Et2O (320 mL) to remove unreacted aldehyde. The resulting aqueous phase was acidified (HCl 2 M) to pH = 2 at 0 C and extracted with CHCl3 (320 mL). The combined organic extracts were then dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by chromatography (Neutral Aluminium Oxide; MeOH/CHCl3 from 0.1/9.9 to 2.0/8.0) to afford compound 3 as a white solid with 37% yield (0.7 g, 3.2 mmol).1H NMR (CD3OD): 8.36 (d, J = 9.2, 1H), 8.00-7.73 (m, 7H), 7.48 (d,J = 8.4, 1H).
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  • [ 121633-88-3 ]
  • C80H76O8 [ No CAS ]
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