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[ CAS No. 34461-00-2 ] {[proInfo.proName]}

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Chemical Structure| 34461-00-2
Chemical Structure| 34461-00-2
Structure of 34461-00-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 34461-00-2 ]

CAS No. :34461-00-2 MDL No. :MFCD05665630
Formula : C3H2NNaO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 139.04 Pubchem ID :-
Synonyms :

Safety of [ 34461-00-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P271-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338-P337+P313-P362+P364-P405-P501 UN#:1759
Hazard Statements:H302+H312+H332-H314-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 34461-00-2 ]

* 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.

  • Upstream synthesis route of [ 34461-00-2 ]
  • Downstream synthetic route of [ 34461-00-2 ]

[ 34461-00-2 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 623-33-6 ]
  • [ 34461-00-2 ]
  • [ 5930-92-7 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 1855 - 1859
  • 2
  • [ 623-33-6 ]
  • [ 34461-00-2 ]
  • [ 5930-92-7 ]
Reference: [1] Journal of the Chemical Society, 1951, p. 3155,3172
  • 3
  • [ 34461-00-2 ]
  • [ 626-34-6 ]
  • [ 51984-71-5 ]
Reference: [1] Patent: WO2007/56016, 2007, A2, . Location in patent: Page/Page column 105
  • 4
  • [ 34461-00-2 ]
  • [ 626-34-6 ]
  • [ 51984-71-5 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 737
  • 5
  • [ 34461-00-2 ]
  • [ 1225387-53-0 ]
  • [ 63572-73-6 ]
YieldReaction ConditionsOperation in experiment
84% at 90℃; A suspension of lH-pyrazol-5-amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 9O0C overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3 X 20 mL) and dried in vacuo to give 5-nitro-l H-pyrazolo [3 ,4-b]pyridine (1.40 g, 84percent) as a solid.
84% at 90℃; A suspension of lH-pyrazol-5 -amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 90°C overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3 X 20 mL) and dried in vacuo to give 5-nitro-lH-pyrazolo[3,4-b]pyridine (1.40 g, 84percent) as a solid.
Reference: [1] Patent: WO2011/25968, 2011, A1, . Location in patent: Page/Page column 49
[2] Patent: WO2009/111279, 2009, A1, . Location in patent: Page/Page column 96
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1992, vol. 28, # 11, p. 1335 - 1339[4] Khimiya Geterotsiklicheskikh Soedinenii, 1992, # 11, p. 1560 - 1564
[5] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 5, p. 342 - 347
  • 6
  • [ 1820-80-0 ]
  • [ 34461-00-2 ]
  • [ 63572-73-6 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With hydrogenchloride; zinc(II) chloride In ethanolReflux
Stage #2: for 1 h;
1H-pyrazol-3-amine (427 mg, 5.139 mmol) was dissolved in ethanol (10 mL) and 12M HCl (0.5 mL) was added to the stirred solution, followed by granulated zinc chloride (300 mg). The mixture was heated to reflux, and to the mixture was added a solution of 5.139 mmol of the source of the appropriate 1,3-dicarbonyl compound (sodium 2-nitro-1,3-dioxopropan-2-ide) in ethanol (5 mL). After 1 h the reaction mixture was poured into ice-cold water (15 mL), the resultant solution was made alkaline with concentrated aqueous ammonia, and the product was isolated by trichloromethane extraction. The product 5-nitro-1H-pyrazolo[3,4-b]pyridine (279 mg, 33percent) ( A) was isolated and purified by column chromatography.
27% at 90℃; for 16 h; To a solution of sodium nitromalonaldehyde monohydrate(1.23 g, 7.81 mmol) in water was added 1H-pyrazol-3-amine(0.84 g, 7.43 mmol). The mixture was stirred at 90 °C for 16 h andthen cooled to room temperature. The reaction solution wasadjusted to pH 5 and extracted by ethyl acetate (200 mL). Theorganic layer was dried over Na2SO4 and evaporated. The residuewas purified by silica gel chromatography (1percent MeOH in dichloromethane)to give 5-nitro-1H-pyrazolo [4,3-b]pyridine as a whitesolid (118 mg, 27percent). Rf: 0.23 (DCM/MeOH, 100/1, v/v). Mp:206-208 °C. 1H NMR (DMSO-d6, 400 MHz) d 14.40 (s, 1H), 9.35 (d,J 2.5 Hz, 1H), 9.21 (d, J 2.5 Hz, 1H), 8.46 (s, 1H). MS (ESI) m/z:162.8 [MH]-.
Reference: [1] Patent: US2013/29995, 2013, A1, . Location in patent: Paragraph 0372-0373
[2] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 1 - 13
  • 7
  • [ 1820-80-0 ]
  • [ 34461-00-2 ]
  • [ 63572-73-6 ]
YieldReaction ConditionsOperation in experiment
33% With hydrogenchloride; zinc(II) chloride In ethanol for 1 h; Reflux 1H-pyrazol-3-amine (427 mg, 5.139 mmol) was dissolved in ethanol (10 mL) and 12M HCl (0.5 mL) was added to the stirred solution, followed by granulated zinc chloride (300 mg). The mixture was heated to reflux, and to the mixture was added a solution of 5.139 mmol of the source of the appropriate 1,3-dicarbonyl compound (sodium 2-nitro-1,3-dioxopropan-2-ide) in ethanol (5 mL). After 1 h the reaction mixture was poured into ice-cold water (15 mL), the resultant solution was made alkaline with concentrated aqueous ammonia, and the product was isolated by trichloromethane extraction. The product 5-nitro-1H-pyrazolo[3,4-b]pyridine (279 mg, 33 percent) (A) was isolated and purified by column chromatography.
Reference: [1] Patent: WO2013/13816, 2013, A1, . Location in patent: Page/Page column 73
  • 8
  • [ 34461-00-2 ]
  • [ 1225387-53-0 ]
  • [ 63572-73-6 ]
  • [ 116835-08-6 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428
  • 9
  • [ 34461-00-2 ]
  • [ 60-34-4 ]
  • [ 3994-50-1 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 7, p. 2906 - 2915
  • 10
  • [ 34461-00-2 ]
  • [ 96-22-0 ]
  • [ 2423-71-4 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 1842,1850
  • 11
  • [ 34461-00-2 ]
  • [ 108-10-1 ]
  • [ 60515-72-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1963, vol. 6, p. 554 - 560
[2] Patent: US2007/49610, 2007, A1, . Location in patent: Page/Page column 25
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