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[ CAS No. 87661-19-6 ] {[proInfo.proName]}

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Chemical Structure| 87661-19-6
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Product Details of [ 87661-19-6 ]

CAS No. :87661-19-6 MDL No. :MFCD16036940
Formula : C9H16O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SAUZLDCYUIYVRN-UHFFFAOYSA-N
M.W : 156.22 Pubchem ID :15444481
Synonyms :

Safety of [ 87661-19-6 ]

Signal Word:Danger Class:3
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235 UN#:3272
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 87661-19-6 ]

* 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 [ 87661-19-6 ]

[ 87661-19-6 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 75-65-0 ]
  • [ 5006-22-4 ]
  • [ 87661-19-6 ]
  • 2
  • [ 87661-19-6 ]
  • [ 224824-16-2 ]
  • [ 224824-05-9 ]
  • [ 224824-17-3 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; diisopropylamine 1) hexane, THF, -78 deg C, 30 min; 2) THF, hexane, pentane, rt, 1 h; Yield given; Multistep reaction. Yields of byproduct given;
  • 3
  • [ 87661-19-6 ]
  • 1-(1-<1,1';1',1''>tercyclobut-1-yl-vinyl)-cyclobutanecarboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-butyllithium, diisopropylamine / 1) hexane, THF, -78 deg C, 30 min; 2) THF, hexane, pentane, rt, 1 h 2: 1.) potassium-tert-butoxide / 1) benzene, reflux, 2 h; 2) 110 deg C, 48 h, 120 deg C, 96 h
  • 4
  • [ 98946-18-0 ]
  • [ 3721-95-7 ]
  • [ 87661-19-6 ]
YieldReaction ConditionsOperation in experiment
64% With boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; Inert atmosphere; 36A Example 36Atert-Butyl cyclobutanecarboxylate; Under argon, 99 μl (0.78 mmol) of boron trifluoride/diethyl ether complex were added to 5.2 g (52.3 mmol) of cyclobutanecarboxylic acid in 100 ml of THF. A little at a time, 13.7 g (62.75 mmol) of tert-butyl 2,2,2-trichloroethaneimidoate were then added, and the mixture was subsequently stirred at room temperature overnight. 5 g of sodium bicarbonate were then added, and the reaction mixture was stirred for 15 min. After filtration, the solution was concentrated to dryness under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 4:1). This gave 5.2 g (64% of theory) of the title compound as a yellow oil.GC-MS (Method 1): Rt=2.08 min; m/z=101 (M-C4H7)+.
  • 5
  • [ 86265-88-5 ]
  • [ 87661-19-6 ]
  • [ 1380606-20-1 ]
YieldReaction ConditionsOperation in experiment
56% Example 198Atert-Butyl]-[(3-bromo-4-chlorophenyl)(hydroxy)methyl]cyclobutanecarboxylate; 21.65 ml (54.12 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution, cooled to from -20 C. to -30 C., of 7.6 ml (54.12 mmol) of diisopropylamine in 30 ml of abs. THF. After the addition had ended, the mixture was stirred at from -20 C. to -30 C. for another 30 min. The mixture was then cooled to -78 C., and a solution of 6.2 g (39.7 mmol) of tert-butyl cyclobutanecarboxylate in 10 ml of abs. THF was added dropwise at this temperature. After 4 h at -78 C., a solution of 7.9 g (36.1 mmol) of <strong>[86265-88-5]3-bromo-4-chlorobenzaldehyde</strong> in 10 ml of abs. THF was then added. The reaction mixture was slowly warmed to RT overnight, saturated aqueous ammonium chloride solution was then added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1?10:1). This gave 7.77 g of the target compound (56% of theory).1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.33 (s, 9H), 1.55-1.77 (m, 2H), 1.98-2.11 (m, 2H), 2.21-2.35 (m, 1H), 2.35-2.47 (m, 1H), 4.70 (d, 1H), 5.89 (d, 1H), 7.31 (dd, 1H), 7.53-7.60 (m, 2H).
  • 6
  • [ 3721-95-7 ]
  • [ 87661-19-6 ]
YieldReaction ConditionsOperation in experiment
77% With 4-dimethylaminopyridine; dicyclohexyl-carbodiimide In dichloromethane; <i>tert</i>-butyl alcohol at 20℃; for 16h; 46.1 first step: Dissolve cyclobutanecarboxylic acid (I-46-a) (5.0 g, 50.0 mmol) in dichloromethane (40 mL), add dicyclohexylcarbodiimide (11.0 g, 55.5 mmol) to the reaction solution, 4 - Dimethylaminopyridine (0.61 g, 5.0 mmol) and tert-butanol (7.4 g, 100.0 mmol), the reaction solution was stirred at room temperature for 16 hours.The reaction solution was concentrated and separated by silica gel column chromatography (petroleum ether/ethyl acetate=0-10%) to obtain the target compound cyclobutyl tert-butyl ester (I-46-b) (6.0 g, 77%)
  • 7
  • [ 87661-19-6 ]
  • (1-(pyridin-2-yl)cyclobutyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium bis-(trimethyl-silyl)amide / tetrahydrofuran; toluene / 16 h / 20 °C 2: lithium aluminium hydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere
  • 8
  • [ 87661-19-6 ]
  • 1-(pyridin-2-yl)cyclobutane-1-formaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium bis-(trimethyl-silyl)amide / tetrahydrofuran; toluene / 16 h / 20 °C 2: lithium aluminium hydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
  • 9
  • [ 87661-19-6 ]
  • (6-(hydroxy(1-(pyridin-2-yl)cyclobutyl)methyl)pyridin-3-yl)tert-butyl carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium bis-(trimethyl-silyl)amide / tetrahydrofuran; toluene / 16 h / 20 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 16 h / 20 °C / Inert atmosphere
  • 10
  • [ 87661-19-6 ]
  • tert-butyl (6-(1-(pyridin-2-yl)cyclobutane-1-carbonyl)pyridin-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium bis-(trimethyl-silyl)amide / tetrahydrofuran; toluene / 16 h / 20 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 16 h / 20 °C / Inert atmosphere 5.1: 2-Iodobenzoic acid / ethyl acetate / Reflux
  • 11
  • [ 87661-19-6 ]
  • (5-aminopyridin-2-yl)(1-(pyridin-2-yl)cyclobutyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium bis-(trimethyl-silyl)amide / tetrahydrofuran; toluene / 16 h / 20 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 16 h / 20 °C / Inert atmosphere 5.1: 2-Iodobenzoic acid / ethyl acetate / Reflux 6.1: trifluoroacetic acid / dichloromethane
  • 12
  • [ 87661-19-6 ]
  • 2-(4-(ethylsulfonyl)phenyl)-N-(6-(1-(pyridin-2-yl)cyclobutane-1-carbonyl)pyridin-3-yl)ethanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium bis-(trimethyl-silyl)amide / tetrahydrofuran; toluene / 16 h / 20 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 16 h / 20 °C / Inert atmosphere 5.1: 2-Iodobenzoic acid / ethyl acetate / Reflux 6.1: trifluoroacetic acid / dichloromethane 7.1: 1-propanephosphonic acid cyclic anhydride; N-ethyl-N-isopropyl-2-propylamine / dichloromethane / 20 °C
  • 13
  • [ 372-48-5 ]
  • [ 87661-19-6 ]
  • 1-(pyridin-2-yl)cyclobutane-1-carboxylate tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With sodium bis-(trimethyl-silyl)amide In tetrahydrofuran; toluene at 20℃; for 16h; 46.2 Step 2: Cyclobutyl tert-butyl ester (I-46-b) (1.6 g, 10.0 mmol) and 2-fluoropyridine (1.0 g, 10.0 mmol) were dissolved in toluene (20 mL), and added to the reaction solution under nitrogen protection The solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (11.0 mL, 1.0 mol/L) was stirred at room temperature for 16 hours.Saturated aqueous ammonium chloride solution (100 mL) was added to the reaction solution to quench the reaction, the system was extracted with ethyl acetate (50 mL×3), washed with saturated brine, the organic phase was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness to obtain the crude product. The target compound 1-(pyridin-2-yl)cyclobutane-1-carboxylate tert-butyl ester (I-46-c)( 1.55 g, 65%).
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