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Chemical Structure| 92988-08-4 Chemical Structure| 92988-08-4

Structure of 92988-08-4

Chemical Structure| 92988-08-4

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Product Details of [ 92988-08-4 ]

CAS No. :92988-08-4
Formula : C6H9B3O3
M.W : 161.57
SMILES Code : C=CB1OB(C=C)OB(C=C)O1

Safety of [ 92988-08-4 ]

Application In Synthesis of [ 92988-08-4 ]

* 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 [ 92988-08-4 ]

[ 92988-08-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 3510-66-5 ]
  • [ 92988-08-4 ]
  • [ 3883-39-4 ]
YieldReaction ConditionsOperation in experiment
75.6% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 100℃;Inert atmosphere; Step 1; To a stirred mixture of 2-bromo-5-methyl-pyridine (1.7 g, 10 mmol), 2,4,6- trivinyl-cyclotriboroxanein (1.20 g, 5 mmol) and Na2CO3 (3.73 g, 35.2 mmol) in toluene (15 mL) / EtOH (10 mL) / H2O (5 mL) was added Pd(PPh3)4 (300 mg, 0.25 mmol) under N2. The mixture was stirred at 100 0C overnight. The resulting mixture was quenched with water (20 mL) and extracted with EtOAc (30 mL x 3).The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography column (PE:EA=50:1 ) to afford 5-methyl-2-vinyl-pyridine (900 mg, 75.6%) as a yellow oil.
  • 2
  • [ 92988-08-4 ]
  • [ 3998-88-7 ]
  • [ 1186513-02-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; In 1,2-dimethoxyethane; water; at 100℃; for 15h; b) To a solution of <strong>[3998-88-7]2-chloro-6-methyl-isonicotinic acid ethyl ester</strong> (15 g, 75.1 mmol) in DME (100 mL), vinylboroxine (18.1 g, 75.1 mmol) is added, followed by 2M aq. K2CO3 (15 mL), Pd(PPh3)4 (750 mg, 0.65 mmol), and PPh3 (1.0 g, 6.17 mmol). The mixture is stirred at 100 C. for 15 h before it is cooled to rt, diluted with diethyl ether (300 mL) and washed with 1N aq. NaOH and brine. The org. extract is dried over MgSO4, filtered and evaporated. The crude product is purified by CC on silica gel eluding with heptane:EA 4:1 to give 6-methyl-2-vinylisonicotinic acid ethyl ester (10.1 g) as a yellow oil; LC-MS: tR=0.67 min, [M+1]+=192.07.
  • 3
  • [ 92988-08-4 ]
  • [ 89942-77-8 ]
  • [ 1584139-70-7 ]
YieldReaction ConditionsOperation in experiment
50.4% With pyridine; copper diacetate; In dichloromethane; at 20℃; for 120h; [00189] A mixture of copper (II) acetate (11.98 g, 65.9 mmol) and dichloromethane(80 mL) were stirred at room temperature for 10 minutes, before the addition of2,4,6-trivinyl-1 ,3,5,2,4,6-trioxatriborinane with pyridine (1: 1) (1 0.63 g, 44.2 mmol, 0.67 eq),10 methyl<strong>[89942-77-8]3-hydroxy-2-nitrobenzoate</strong> (U.S. Publication No. 2012/0035194 AI [0202]) (13 g,65.9 mmol), pyridine (26.7 mL, 330 mmol), and molecular sieves (1 g). The resultingdeep blue mixture was stirred at room temperature for 5 days, with the reaction opened tothe air. The reaction solution was filtered through a pad of CELITE, washing withsome dichloromethane. The filtrate was washed with 3M aqueous ammonium acetate15 (2x), water, and brine, and then dried and concentrated in vacuo. The crude productmixture was purified via silica gel chromatography (0% to 20% EtOAC in DCM over 15minutes, 120g column) to give Intermediate A-lA (7.42 g, 33.2 mmol, 50.4% yield).HPLC: RT= 2.487 min (H20/MeOH with TFA, SunFire C18 3.5)lm, 2.1 x 30 mm,gradient= 4 min, wavelength= 220 nm); MS(ES):m/z = 246 [M+Nat; 1H NMR20 (400MHz, chloroform-d) 8 7.77 (dd, 1=7.8, 1.2 Hz, IH), 7.55 (t, 1=8.1 Hz, IH), 7.38 (dd,1=8.4, 1.3 Hz, IH), 6.61 (dd, 1=13.6, 5.9 Hz, IH), 4.95 (dd, 1=13.6, 2.4 Hz, IH), 4.69 (dd,1=5.9, 2.4 Hz, IH), 3.93 (s, 3H), 1.56 (s, IH), 0.03 (s, IH).
 

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