Home Cart 0 Sign in  

[ CAS No. 24463-15-8 ]

{[proInfo.proName]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 24463-15-8
Chemical Structure| 24463-15-8
Structure of 24463-15-8 *Storage: {[proInfo.prStorage]}

Quality Control of [ 24463-15-8 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 24463-15-8 ]

SDS

Product Details of [ 24463-15-8 ]

CAS No. :24463-15-8MDL No. :MFCD00029252
Formula :C17H12OBoiling Point :455.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :232.28Pubchem ID :104977
Synonyms :

Computed Properties of [ 24463-15-8 ]

TPSA : 20.2 H-Bond Acceptor Count : 1
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.06 Rotatable Bond Count : 1

Safety of [ 24463-15-8 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24463-15-8 ]

  • Upstream synthesis route of [ 24463-15-8 ]
  • Downstream synthetic route of [ 24463-15-8 ]

[ 24463-15-8 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 3029-19-4 ]
  • [ 24463-15-8 ]
YieldReaction ConditionsOperation in experiment
88% With sodium tetrahydroborate In tetrahydrofuran; methanol Pyrene-aldehyde (1 g, 4.3 mmol) anddry tetrahydrofuran (20 mL) were placed in a round bottom flask.Sodium borohydride (165 mg, 4.3 mmol) was added in small portions,together with small portions of methanol to help the solubilization(total volume of added methanol = 10 mL). An orangesolution was obtained. The reaction was quenched with a 2percent concentratedhydrochloric acid solution. The solvent was removedunder reduced pressure. The white powder obtained was dissolvedin dichloromethane, washed with water and the organic phase wasdried with magnesium sulphate. The solvent was removed underreduce pressure. The resulting solid was subjected to silica gel columnchromatography (eluent = dichloromethane). Yield = 88percent.1H NMR (300 MHz, CDCl3, 300 K): d (ppm) = 1.87 (s, 1H); 5.39 (s,2H); 7.9–8.4 (m, 9H). 13C NMR {1H} (75 MHz, CDCl3, 300 K): d(ppm) = 6403; 123.15; 124.87; 124.93; 125.13; 125.42; 125.45;126.14; 126.19; 127.54; 127.63; 128.07; 128.97; 130.95; 131.42;131.44; 133.94. ESI-MS: m/z = 254.97 [M+Na]+, 214.99 [MOH]+(Calcd. for C17H12O:: 232.09 (exact mass); 232.28 (FW)). UV–Vis(DCM): kmax (nm) = 314; 327; 344.
81% With sodium tetrahydroborate In methanol at 0 - 20℃; 1-pyrenecarboxaldehyde (0.35 g, 1.50 mmol) was dissolved in15 mL methanol, and NaBH4 (0.08 g, 2.10 mmol) was added slowly into the reaction mixture at 0 °C for 30 min. After stirring at room temperature overnight, 20 mL 5percent HCl was added in the reaction to quench the excess NaBH4, and the solution changed to milk-white suspension. The organic solvent was removed and then the solid was extracted with ethyl acetate (3 × 15 mL). The organic fractions were washed with saturated NaHCO3 aqueous solution. The collected organic solution was dried with sodium sulfate and was concentrated to give compound 8 in an 81percent yield. 1H NMR (400MHz, CDCl3) δ 8.30–7.96 (m, 9 H, Ar–H),5.33 (s, 2 H, CH2). TOF-MS: m/z 231.1[M–H].
75% With sodium tetrahydroborate In tetrahydrofuran; ethanol at 0 - 20℃; for 5.00 h; To a solution of pyrene aldehyde 13 (1.0 g, 4.34 mmol) in THF/Ethanol (10 mL: 30 mL) at 0 °C, NaBH4 (0.83 g, 21.71 mmol) was slowly added in five portions. The reaction mixture was slowly raised to rt and stirred for 5 h. It was then poured into ice-water (100 mL) containing 10 mL of Conc. HCl. The reaction mixture was extracted with CHCl3 (3 x 25 mL). The combined organic layer was washed with water and dried (Na2SO4). Removal of solvent under reduced pressure afforded pyrenyl methanol 15 (0.76 g, 75percent) as a pale yellow solid. mp 124-125 °C (Lit. 123-124 °C); 1H-NMR (300 MHz, CDCl3): δ 8.24 (d, J = 9.3 Hz, 1 H, ArH), 8.13 (t, J = 7.5 Hz, 2 H, ArH), 8.06-8.01 (m, 2 H, ArH), 7.99-7.918 (m, 4 H, ArH), 5.28 (s, 2 H, OCH2), 2.03 (s, 1 H, OH) ppm. 13C-NMR (75 MHz, CDCl3): δ 133.7 (C), 131.2 (2C), 131.1 (C), 130.7 (C), 128.7 (C), 127.8 (C-H), 127.4 (C-H), 127.3 (C-H), 125.9 (C-H), 125.9 (2C-H), 125.2 (C-H), 125.2 (C-H), 124.6 (C), 122.9 (C-H), 63.7 (Ar-CH2) ppm.
54 %Chromat. With sodium hydroxide In isopropyl alcohol at 82℃; for 2.00 h; General procedure: In a typical procedure, a 5 mg (0.77 molpercent) of RuO2/MWCNT and 80 mg (2 mmol) of NaOH were stirred with 5 mL of i-PrOH taken in an ace pressure tube equipped with a stirring bar. Then the substrate (1 mmol) was added to the stirring solution and then the mixture was heated at 82°C. The completion of the reaction was monitored by GC. After the reaction, the catalyst was separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was alsocalculated. Finally, the separated RuO2/MWCNT was washed well with diethyl ether followed by drying in an oven at 60°C for 5 h and it was reused for the subsequent transfer hydrogenation of carbonyl compounds to investigate the reusability of the RuO2/MWCNT.

Reference: [1] Molecules, 2011, vol. 16, # 8, p. 6950 - 6968
[2] Journal of the American Chemical Society, [3] Journal of the American Chemical Society, 2008, vol. 130, p. 12846 - 12847
[4] Analytical Chemistry, 2018, vol. 90, # 2, p. 1402 - 1407
[5] Journal of Physical Chemistry A, 2003, vol. 107, # 40, p. 8363 - 8370
[6] Inorganic Chemistry, 2017, vol. 56, # 22, p. 13715 - 13731
[7] Chemistry - A European Journal, 2010, vol. 16, # 30, p. 9154 - 9163
[8] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 2, p. 413 - 420
[9] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2385 - 2393
[10] Organic Preparations and Procedures International, 1998, vol. 30, # 2, p. 203 - 210
[11] Chemical Communications, 2013, vol. 49, # 5, p. 478 - 480
[12] Tetrahedron Letters, 1991, vol. 32, # 44, p. 6347 - 6350
[13] Journal of the Chemical Society, Faraday Transactions, 1993, vol. 89, # 6, p. 891 - 904
[14] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2016, vol. 159, p. 209 - 218
[15] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 18883 - 18885
[16] Synthetic Communications, 2016, vol. 46, # 22, p. 1810 - 1819
[17] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 10, p. 2881 - 2890
[18] Journal of the American Chemical Society, 1941, vol. 63, p. 2494,2496
[19] Journal of the American Chemical Society, 1941, vol. 63, p. 2494,2496
[20] Journal of the Chemical Society, 1965, p. 5920 - 5926
[21] Helvetica Chimica Acta, 1955, vol. 38, p. 2009,2020
[22] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 5804 - 5810
[23] Journal fuer Praktische Chemie (Leipzig), 1958, vol. <4> 6, p. 80
[24] Bulletin de la Societe Chimique de France, 1954, p. 615,617
[25] Bulletin of the Chemical Society of Japan, 1973, vol. 46, p. 358 - 363
[26] Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 10, p. 535 - 548
[27] Nucleosides and Nucleotides, 1996, vol. 15, # 5, p. 1029 - 1039
[28] Journal of the Chemical Society. Perkin Transactions 2, 2001, # 10, p. 1927 - 1932
[29] Chemistry - A European Journal, 2007, vol. 13, # 11, p. 3169 - 3176
[30] Tetrahedron Letters, 1987, vol. 28, # 6, p. 679 - 682
[31] Organic Letters, 2009, vol. 11, # 19, p. 4294 - 4297
[32] Organic Letters, 2010, vol. 12, # 18, p. 4014 - 4017
[33] Chemical Communications, 2012, vol. 48, # 38, p. 4567 - 4569
[34] Tetrahedron, 2013, vol. 69, # 23, p. 4536 - 4540
[35] ChemPlusChem, 2014, vol. 79, # 7, p. 1059 - 1064
[36] Applied Catalysis A: General, 2014, vol. 484, p. 84 - 96
[37] Supramolecular Chemistry, 2013, vol. 25, # 2, p. 69 - 78
[38] Chemical Science, 2015, vol. 6, # 8, p. 4978 - 4985
[39] Dalton Transactions, 2018, vol. 47, # 7, p. 2352 - 2359
[40] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2018, vol. 204, p. 425 - 431
[41] Tetrahedron Letters, 2019, vol. 60, # 1, p. 59 - 62
  • 2
  • [ 76465-53-7 ]
  • [ 24463-15-8 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 6, p. 679 - 682
  • 3
  • [ 1373393-14-6 ]
  • [ 24463-15-8 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 38, p. 4567 - 4569
  • 4
  • [ 2595-90-6 ]
  • [ 24463-15-8 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846
  • 5
  • [ 1386958-83-3 ]
  • [ 24463-15-8 ]
  • [ 1086-00-6 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846
  • 6
  • [ 2595-90-6 ]
  • [ 24463-15-8 ]
  • [ 1086-00-6 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846
  • 7
  • [ 220196-58-7 ]
  • [ 3029-19-4 ]
  • [ 24463-15-8 ]
  • [ 91385-15-8 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750
  • 8
  • [ 220196-58-7 ]
  • [ 142-08-5 ]
  • [ 822-89-9 ]
  • [ 24463-15-8 ]
  • [ 91385-15-8 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750
  • 9
  • [ 78377-23-8 ]
  • [ 24463-15-8 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 6, p. 679 - 682
  • 10
  • [ 111077-41-9 ]
  • [ 24463-15-8 ]
  • [ 99-94-5 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 6, p. 679 - 682
  • 11
  • [ 220196-58-7 ]
  • [ 142-08-5 ]
  • [ 822-89-9 ]
  • [ 3029-19-4 ]
  • [ 24463-15-8 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750
  • 12
  • [ 1386958-83-3 ]
  • [ 24463-15-8 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3843 - 3846
  • 13
  • [ 3029-19-4 ]
  • [ 24463-15-8 ]
  • [ 19694-02-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 1,38
  • 14
  • [ 350498-58-7 ]
  • [ 24463-15-8 ]
  • [ 4064-06-6 ]
Reference: [1] Organic Letters, 2001, vol. 3, # 12, p. 1809 - 1812
[2] Organic Letters, 2001, vol. 3, # 12, p. 1809 - 1812
  • 15
  • [ 169268-03-5 ]
  • [ 2381-21-7 ]
  • [ 24463-15-8 ]
  • [ 61577-80-8 ]
  • [ 56-40-6 ]
Reference: [1] Photochemistry and Photobiology, 1995, vol. 61, # 5, p. 431 - 434
  • 16
  • [ 67-56-1 ]
  • [ 220196-58-7 ]
  • [ 3029-19-4 ]
  • [ 24463-15-8 ]
  • [ 91385-15-8 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2001, # 10, p. 1927 - 1932
Historical Records