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[ CAS No. 1517860-48-8 ] {[proInfo.proName]}

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Chemical Structure| 1517860-48-8
Chemical Structure| 1517860-48-8
Structure of 1517860-48-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1517860-48-8 ]

CAS No. :1517860-48-8 MDL No. :
Formula : C5H5N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 155.11 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1517860-48-8 ]

* 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 [ 1517860-48-8 ]

[ 1517860-48-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 4704-94-3 ]
  • [ 1517860-48-8 ]
  • (2-(1-methyl-4-nitro-1H-pyrazol-5-yl)-1,3-dioxan-5-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; Intermediate 68 (2-(1-Methyl-4-nitro-1H-pyrazol-5-yl)-1,3-dioxan-5-yl)methanol (trans isomer) To a solution of 2-methyl-4-nitro-pyrazole-3-carbaldehyde (718 mg, 4.63 mmol, intermediate 3) in toluene (100 mL) was added 2-(hydroxymethyl)propane-1,3-diol (700 mg, 6.73 mmol) followed by p-toluenesulfonic acid (88 mg, 0.463 mmol). The reaction mixture was heated at reflux for 18 hr whilst azeotropically removing the water. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with DCM (50 mL) and washed with a saturated aqueous NaHCO3 (50 mL). The organic layer was washed with water (20 mL) and brine (20 mL), separated, dried over Na2SO4 and concentrated under reduced pressure. Purification via silica gel column chromatography (0-100% EtOAc/isohexane) gave (2-(1-methyl-4-nitro-1H-pyrazol-5-yl)-1,3-dioxan-5-yl)methanol (trans isomer) as the first eluting isomer as a colourless solid (220 mg, 20%). 1H NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 6.42 (s, 1H), 4.34 (dd, J=11.6, 4.7 Hz, 2H), 4.12 (s, 3H), 3.81 (t, J=11.5 Hz, 2H), 3.56 (t, J=5.1 Hz, 2H), 2.53-2.38 (m, 1H), 1.67 (t, J=4.6 Hz, 1H).
  • 2
  • [ 42098-25-9 ]
  • potassium vinyltrifluoroborate [ No CAS ]
  • [ 1517860-48-8 ]
YieldReaction ConditionsOperation in experiment
With dimethylsulfide; nitrogen; caesium carbonate; ozone; In water; ethyl acetate; N,N-dimethyl-formamide; Intermediate 3 2-Methyl-4-nitro-pyrazole-3-carbaldehyde Nitrogen was bubbled through a solution of 3-chloro-2-methyl-4-nitro-pyrazole (16 g, 100 mmol), potassium vinyltrifluoroborate (18 g, 134 mmol) and cesium carbonate (3.7 M in water, 50 mL, 190 mmol) in DMF (100 mL). 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (900 mg, 1.10 mmol) was added and degassing continued for 30 min. The reaction mixture was heated at 110 C. for 18 hr. More 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (900 mg, 1.10 mmol) was added and heating continued for 24 hr. More 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (400 mg, 0.49 mmol) was added and heating continued for 4 hr. The reaction was cooled to room temperature and brine (200 mL) and EtOAc (500 mL) were added. The organic layer was washed with water (4*300 mL), separated, dried over Na2SO4 and concentrated under reduced pressure. Purification via silica gel column chromatography (0-40% EtOAc/isohexane) gave 1-methyl-4-nitro-5-vinyl-1H-pyrazole as a colourless solid (9.1 g). Through a solution of this solid (9.1 g, 59 mmol) in DCM (400 mL) cooled to -78 C. was bubbled ozone. When the solution turned blue, ozone addition was stopped. Nitrogen was passed through the solution until the blue colour was discharged. The mixture was allowed to warm to room temperature and flushed with nitrogen for 15 min Anhydrous dimethyl sulfide (5 mL) was added and the mixture warmed to room temperature. After stirring for 12 hr, the solvents were removed under reduced pressure. DCM (150 mL) was added and the mixture was washed with water (50 mL). The aqueous layer was extracted with DCM (3*100 mL) and the combined organic layers were washed with brine (100 mL), separated, dried over Na2SO4 and concentrated to give 2-methyl-4-nitro-pyrazole-3-carbaldehyde as a yellow-orange solid (6.6 g, 43% over two steps). 1H NMR (400 MHz, CDCl3) delta 10.51 (s, 1H), 8.11 (s, 1H), 4.23 (s, 3H).
  • 3
  • [ 4704-94-3 ]
  • [ 1517860-48-8 ]
  • trans-(2-(1-methyl-4-nitro-1H-pyrazol-5-yl)-1,3-dioxan-5-yl)methanol [ No CAS ]
  • cis-(2-(1-methyl-4-nitro-1H-pyrazol-5-yl)-1,3-dioxan-5-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
20%; 24% With toluene-4-sulfonic acid; In toluene; for 18h;Reflux; To a solution of 2-methyl-4-nitro-pyrazole-3-carbaldehyde (718 mg, 4.63 mmol, intermediate 3) in toluene (100 mL) was added 2-(hydroxymethyl)propane- l,3-diol (700 mg, 6.73 mmol) followed by /?-toluenesulfonic acid (88 mg, 0.463 mmol). The reaction mixture was heated at reflux for 18 hr whilst azeotropically removing the water. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with DCM (50 mL) and washed with a saturated aqueous NaHC03 (50 mL). The organic layer was washed with water (20 mL) and brine (20 mL), separated, dried over Na2S04 and concentrated under reduced pressure. Purification via silica gel column chromatography (0- 100% EtOAc/isohexane) gave (2-(l-methyl-4-nitro-lH-pyrazol-5-yl)-l,3- dioxan-5-yl)methanol (trans isomer) as the first eluting isomer as a colourless solid (220 mg, 20%). NMR (400 MHz, CDC13) delta 8.02 (s, 1H), 6.42 (s, 1H), 4.34 (dd, / = 11.6, 4.7 Hz, 2H), 4.12 (s, 3H), 3.81 (t, / = 11.5 Hz, 2H), 3.56 (t, / = 5.1 Hz, 2H), 2.53-2.38 (m, 1H), 1.67 (t, J = 4.6 Hz, 1H). Intermediate 77 (2-(l-Methyl-4-nitro- lH-pyrazol-5-yl)- l,3-dioxan-5- yl)methanol (cis isomer) Following the procedure for Intermediate 68 also gave (2-(l-methyl-4-nitro- lH- pyrazol-5-yl)- l,3-dioxan-5-yl)methanol (cis isomer) as a colourless solid (268 mg, 24%). NMR (400 MHz, CDC13) delta 8.02 (s, 1H), 6.49 (s, 1H), 4.28 (d, J = 11.9 Hz, 2H), 4.20 (d, / = 3.3 Hz, 2H), 4.12 (s, 3H), 4.06 (dd, / = 7.8, 3.7 Hz, 2H), 1.82 (t, / = 4.9 Hz, 1H), 1.78-1.71 (m, 1H).
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