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[ CAS No. 25033-19-6 ]

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Chemical Structure| 25033-19-6
Chemical Structure| 25033-19-6
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CAS No. :25033-19-6 MDL No. :MFCD00760297
Formula : C13H12 Boiling Point : 296.4±7.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :168.23 g/mol Pubchem ID :14668693
Synonyms :

Safety of [ 25033-19-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25033-19-6 ]

  • Upstream synthesis route of [ 25033-19-6 ]
  • Downstream synthetic route of [ 25033-19-6 ]

[ 25033-19-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 90-11-9 ]
  • [ 23719-80-4 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: at 0 - 20℃; for 16 h;
Stage #2: With water; ammonium chloride In ethyl acetate
[00354] Cyclopropylmagnesium bromide (15OmL, 0.5M in tetrahydrofuran) was slowly added to a solution of 1 -bromonaphthalene (1Og, 50mmol) and [l ,3-bis(diphenylphosphino)ρroρane] dichloro nickel (II) in tetrahydrofuran (1OmL) stirred at 0°C, and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride were added- After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield l-cyclopropylnaphthalcne (6.4g, 76percent).
76% at 0 - 20℃; for 16 h; Cyclopropylmagnesium bromide (150 niL, 0.5 M in tetrahydrofuran) was slowly added to a solution of 1-bromo-naphthalene (10 g, 50 mmol) and [1,3- bis(diphenylphosphino)propane]dichloronickel(II) in tetrahydrofuran (10 niL) stirred at 0 0C. The reaction mixture was stirred at room temperature for 16 hours and the solvent was evaporated under reduced pressure. EtOAc and ammonium chloride in water were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1 -cyclopropyl-naphthalene (6.4 g, 76percent).
76% at 0 - 20℃; STEP A: 1-CyclopropylnaphthaleneCyclopropylmagnesium bromide (150 mL, 0.5M in tetrahydrofuran) was slowly added to a solution of 1-bromonaphthalene (10 g, 50 mmol) and [l,3-bis(diphenylphosphino)propane] dichloro nickel (II) in tetrahydrofuran (10 mL) stirred at 0 °C, and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-cyclopropylnaphthalene (6.4 g, 76percent).
Reference: [1] Patent: WO2009/70740, 2009, A2, . Location in patent: Page/Page column 89
[2] Patent: WO2006/26356, 2006, A2, . Location in patent: Page/Page column 20
[3] Patent: WO2011/85009, 2011, A2, . Location in patent: Page/Page column 36
[4] Patent: WO2014/8295, 2014, A1, . Location in patent: Paragraph 0345-0348
  • 2
  • [ 411235-57-9 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
89% With potassium phosphate monohydrate; palladium diacetate; XPhos In <i>tert</i>-butyl alcohol at 50℃; for 12 h; Schlenk technique; Inert atmosphere; Sealed tube General procedure: Procedure A: To a Schlenk tube equipped with a magnetic stiring bar and a teflon septum was charged K3PO4.H2O (1.5 mmol, 3 equiv), aryl pentafluorobenzene sulfonate (0.5 mmol, 1.0 equiv), aryl boronic acid (0.75 mmol, 1.5 equiv) and Pd(PPh3)2Cl2 (0.015 mmol, 3 molpercent). The tube was then capped with a rubber septum, evacuated and backfilled with nitrogen and this cycle was repeated twice. Under an inertatmosphere, tert - butanol (3 mL) was added via syringe. Under a positive pressure of nitrogen, the rubber septum was replaced with a Teflon screw cap and this was sealed. The Schlenk tube was stirred at room temperature for the time indicated. When the reaction was completed according to TLC or GCMS (FID), thereaction mixture was diluted with EtOAc (5 mL) and filtered through celite bed. The organic layer was concentrated under reduced pressure. The residue was purified through silica gel (230 - 400 mesh) column chromatography using 1-10percent ethyl acetate in petroleum ether to afford the product. Procedure B: Similar procedure as A except that Pd(OAc)2 (3 molpercent) and Xphos (5 molpercent) instead of Pd(PPh3)2Cl2 as catalyst system.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 36, p. 5106 - 5111
  • 3
  • [ 90-11-9 ]
  • [ 411235-57-9 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
57% With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd In water; toluene at 100℃; for 5 h; Inert atmosphere General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.
Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
[2] Tetrahedron, 2012, vol. 68, # 3, p. 900 - 905
  • 4
  • [ 5409-58-5 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide; hydrazine; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol In water for 5 h; Heating General procedure: 3-dimethylamino-1-(naphthalen-1-yl)propan-1-one hydrochloride (50g, El equivalents) andtriethylene glycol (100 ml) were charged to the reactor at room temperature. 50percent NaOH (E2equivalents) was added while keeping the internal temperature at room temperature. 64percent hydrazine solution in water (E3 equivalents) was added dropwise followed by heating the reaction mixture to a temperature of 80±5°C for a period of 5 hours. Thereafter, water was distilled off in a vacuum of 30-40mbar at a temperature of 80±5°C. The precipitated salt was separated from the reaction mixture by filtration at a temperature of approximately 80°C andsubsequently washed with triethylene glycol brought to a temperature of approximately 80°C (20 Volpercent of the total amount of triethylene glycol).Bringing the reaction mixture to a temperature of 200±10°C for a period of about 5 hours gave crude 1-cyclopropyl-napthalene which was isolated by azeotropic distillation at a temperature of 190±10°C in a vacuum of 30-40mbar. For further purification and isolation ofthe obtained product water was added to the distillate and the product extracted with methyl tert.-butyl ether. The organic phase was washed with water and distilled in a vacuum of 50- lOOmbar at a temperature of 80°C.The isolated pure 1-cyclopropyl-naphtalene was obtained as clear, colorless or pale yellow liquid with a boiling point of 152°C at 13 Torr.
Reference: [1] Patent: WO2017/1516, 2017, A1, . Location in patent: Page/Page column 9; 10
  • 5
  • [ 826-74-4 ]
  • [ 74-95-3 ]
  • [ 25033-19-6 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 36, p. 6405 - 6407
  • 6
  • [ 1065010-87-8 ]
  • [ 38262-42-9 ]
  • [ 25033-19-6 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 8126 - 8130
  • 7
  • [ 27650-86-8 ]
  • [ 25033-19-6 ]
Reference: [1] Journal of the American Chemical Society, 1969, vol. 91, # 13, p. 3558 - 3566
  • 8
  • [ 91954-77-7 ]
  • [ 25033-19-6 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 2065 - 2068[2] Zhurnal Obshchei Khimii, 1963, vol. 33, # 11, p. 2119 - 2123
  • 9
  • [ 90-15-3 ]
  • [ 25033-19-6 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 36, p. 5106 - 5111
  • 10
  • [ 25033-19-6 ]
  • [ 878671-94-4 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: CN105985295, 2016, A,
[4] Patent: CN106478531, 2017, A,
  • 11
  • [ 25033-19-6 ]
  • [ 878671-96-6 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
  • 12
  • [ 25033-19-6 ]
  • [ 1151516-14-1 ]
Reference: [1] Patent: WO2011/85009, 2011, A2,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
[4] Patent: WO2014/8295, 2014, A1,
[5] Patent: WO2014/8295, 2014, A1,
[6] Patent: WO2014/8295, 2014, A1,
[7] Patent: WO2014/8295, 2014, A1,
[8] Patent: CN105985295, 2016, A,
  • 13
  • [ 25033-19-6 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
  • 14
  • [ 25033-19-6 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
[4] Patent: CN105985295, 2016, A,
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