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[ CAS No. 39835-28-4 ]

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2D
Chemical Structure| 39835-28-4
Chemical Structure| 39835-28-4
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Product Details of [ 39835-28-4 ]

CAS No. :39835-28-4MDL No. :MFCD06659648
Formula : C7H4N2O3 Boiling Point : 321.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :164.12Pubchem ID :142385
Synonyms :

Computed Properties of [ 39835-28-4 ]

TPSA : 71.8 H-Bond Acceptor Count : 4
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 39835-28-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 39835-28-4 ]

  • Upstream synthesis route of [ 39835-28-4 ]
  • Downstream synthetic route of [ 39835-28-4 ]

[ 39835-28-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 39835-28-4 ]
  • [ 239097-74-6 ]
YieldReaction ConditionsOperation in experiment
95% at 0 - 20℃; for 3.08333 h; To an ice cold stirred solution of SnCl4 (1.828 g, 7.02 mmol) in 12M HCl (0.5 mL) was added 5-nitro-1,2-benzoxazole (140 mg, 0.86 mmol) in one portion at 0 C. Then, 5 minutes later, a solution of SnCl2.2H2O (792 mg, 3.51 mmol) in 12M HCl (0.5 mL) was added dropwise at 0 C to the reaction mixture, followed by the addition of another 1.0 mL of 12M HCl. Then, the reaction mixture was stirred at room temperature for 3 hours, and extracted with Et2O. The aqueous layer was basified to pH ~8 with saturated NaHCO3, and extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4, filtered, concentrated and dried in vacuo to give 1,2-benzoxazol-5-amine as a colorless solid (110 mg, 95percent).1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 7.42 (d, J = 8.4 Hz, 1H), 6.94 (dd, J = 8.4 Hz, 2.0 Hz, 1H), 6.91 (d, J = 2.0 Hz, 1H) ES-MS m/z: 135.1 [M+H]+. LC-MS Purity (214 nm): 90percent; tR = 1.32 min.
95% With hydrogenchloride; tin(II) chloride dihdyrate; tin(IV) chloride In water at 0 - 20℃; for 3 h; To an ice cold stirred solution of SnCl4(1.828 g, 7.02 mmol) in 12M HC1 (0.5 mL) was added 5-nitro-l,2-benzoxazol (140 mg, 0.86 mmol) in one portion at 0 °C. 5 minutes later, a solution of SnCl2.2H20 (792 mg, 3.51 mmol) in 12M HC1 (0.5 mL) was added dropwise at 0 °C, followed by the addition of another 1.0 mL of 12M HC1. Then the reaction mixture was stirred at room temperature for 3 hours, and extracted with Et20. The aqueous layer was basified to pH ~8 with saturated NaHCC^, and extracted with EtOAc. The organic phase was dried over anhydrous Na2S04, filtered, concentrated and dried in vacuo to give 1,2-benzoxazol- 5-amine as a colorless solid (110 mg, 95percent).XH NMR (400 MHz, CDC13) δ 8.54 (s, 1H), 7.42 (d, J= 8.4 Hz, 1H), 6.94 (dd, J= 8.4 Hz, 2.0 Hz, 1H), 6.91 (d, J= 2.0 Hz, 1H) ES-MS m/z: 135.1 [M+H]+. LC-MS Purity (214 nm): 90percent; tR= 1.32 min.
Reference: [1] Patent: WO2016/73889, 2016, A1, . Location in patent: Paragraph 00229
[2] Patent: WO2016/73895, 2016, A1, . Location in patent: Paragraph 00286
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 18, p. 6189 - 6196
  • 2
  • [ 271-95-4 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 6, p. 1147 - 1150
[2] Journal of the American Chemical Society, 2000, vol. 122, # 6, p. 1022 - 1029
[3] Tetrahedron, 1967, vol. 23, p. 2001 - 2015
  • 3
  • [ 1595-15-9 ]
  • [ 39835-28-4 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 15, p. 2613 - 2615
[2] Australian Journal of Chemistry, 1977, vol. 30, p. 1847 - 1850
  • 4
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  • [ 39835-09-1 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8657 - 8667
  • 5
  • [ 97-51-8 ]
  • [ 39835-28-4 ]
  • [ 64037-16-7 ]
Reference: [1] Gazzetta Chimica Italiana, 1959, vol. 89, p. 1009,1013
  • 6
  • [ 97-51-8 ]
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  • [ 64037-16-7 ]
Reference: [1] Gazzetta Chimica Italiana, 1959, vol. 89, p. 1009,1013
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