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[ CAS No. 263398-16-9 ]

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2D
Chemical Structure| 263398-16-9
Chemical Structure| 263398-16-9
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Product Details of [ 263398-16-9 ]

CAS No. :263398-16-9MDL No. :MFCD24448806
Formula : C17H19F3O3S Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :360.39Pubchem ID :-
Synonyms :

Computed Properties of [ 263398-16-9 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

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Application In Synthesis of [ 263398-16-9 ]

  • Downstream synthetic route of [ 263398-16-9 ]

[ 263398-16-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 358-23-6 ]
  • [ 29799-07-3 ]
  • [ 263398-16-9 ]
YieldReaction ConditionsOperation in experiment
92.4% With pyridine; In dichloromethane; at 0 - 20℃; for 17h;Inert atmosphere; A stream of argon, 4- (1-adamantyl) phenol (3.77 g, 16.5 mmol), was suspended in dichloromethane (40 mL), was added pyridine (2.66 mL, 33.0 mmol).The resulting mixed solution was cooled to 0 , and was dropped slowly over a period of 15 minutes anhydrous trifluoromethanesulfonic acid (5.59g, 19.8mmol) and dichloromethane mixed solution of the (20mL).The resulting reaction solution, and the mixture was stirred for 2 hours at 0 , and the mixture was stirred for 15 hours at room temperature.After stirring, to the reaction solution, shaken in addition chloroform (30mL) and aqueous HCl 2M (30mL), it was taken out only the organic layer.Magnesium sulfate was added to the organic layer was dried and filtered.By distilling off the low-boiling components obtained organic layer to obtain the the target compound 4- (1-adamantyl) phenyl triflate yellowish white solid (yield 5.50 g, 92.4% yield).
85% With pyridine; In dichloromethane; at 0℃; for 3h; 91 g (0.40 mol) of 4-(adamantane-1-yl)phenol and63 g (0.80 mol) of pyridine were dissolved in 500 ml of dichloromethane and cooled to 0 C., and then 135 g (0.48 mol) of trifluoromethanesulfonic anhydride was slowly added. After the reaction was completed with stirring for 3 hours, 1 N hydrochloric acid and 300 ml of water were sequentially added to the resulting solution for extraction. Following dehydration of the organic layer with MgSO4, the remaining solution was distilled and subjected to column chromatography using n-hexane/dichloromethane, thereby obtaining 122 g of 4-(adamantane-1-yl)phenyl trifluoromethanesulfonate with a yield of 85%.
  • 2
  • [ 29799-07-3 ]
  • [ 145100-51-2 ]
  • [ 263398-16-9 ]
YieldReaction ConditionsOperation in experiment
73% With hydrogenchloride; triethylamine; In hexane; dichloromethane; 4-(1-Adamantyl)phenyltrifluoromethanesulfonate (Compound 37) A stirred, cooled (0 C.) solution of 4-(1-adamantyl)phenol (3.2 g, 14 mmol, obtainable in accordance with the chemical literature) and triethylamine (3.3 mL, 22.4 mmol) in 40 mL of anhydrous dichloromethane was treated with 2-[N,N-bis(trifluoromethanesulfonyl)amino]-5-chloropyridine (5.6 g, 14.2 mmol). The resulting solution was warmed to room temperature over 0.5 hour, then diluted with 20 mL of dichloromethane and washed with 30 mL of 3M HCl followed by 30 mL of brine. The organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to yield an orange solid which on flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent afforded the title compound as a white solid (3.72 g, 73%). 1H-NMR (300 MHz, CDCl3): d 1.78 (dd, J=10.0, 19.9 Hz, 6H), 1.91 (d, J=2.4 Hz, 6H), 2.12 (s, 3H), 7.21 (dd, J=2.3, 8.9 Hz, 2H), 7.43 (dd, J=8.9, 2.2 Hz, 2H).
73% With hydrogenchloride; triethylamine; In hexane; dichloromethane; 4-(1-Adamantyl)phenyltrifluoromethanesulfonate (Compound 37) A stirred, cooled (0 C.) solution of 4-(1-adamantyl)phenol (3.2 g, 14 mmol, obtainable in accordance with the chemical literature) and triethylamine (3.3 mL, 22.4 mmol) in 40 mL of anhydrous dichloromethane was treated with 2-[N,N-bis(trifluoromethanesulfonyl)amino]-5-chloropyridine (5.6 g, 14.2 mmol). The resulting solution was warmed to room temperature over 0.5 hour, then diluted with 20 mL of dichloromethane and washed with 30 mL of 3M HCl followed by 30 mL of brine. The organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to yield an orange solid which on flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent afforded the title compound as a white solid (3.72 g, 73%). 1 H-NMR (300 MHz, CDCl3): d 1.78(dd, J=10.0, 19.9 Hz, 6H), 1.91(d, J=2.4 Hz, 6H), 2.12(s, 3H), 7.21(dd, J=2.3, 8.9 Hz, 2H), 7.43(dd, J=8.9, 2.2 Hz, 2H).
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