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[ CAS No. 873107-98-3 ]

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2D
Chemical Structure| 873107-98-3
Chemical Structure| 873107-98-3
Structure of 873107-98-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 873107-98-3 ]

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Related Doc. of [ 873107-98-3 ]

SDS

Product Details of [ 873107-98-3 ]

CAS No. :873107-98-3MDL No. :MFCD11226772
Formula :C6H3F3INBoiling Point :-
Linear Structure Formula :-InChI Key :-
M.W :272.99Pubchem ID :45598118
Synonyms :

Computed Properties of [ 873107-98-3 ]

TPSA : 12.9 H-Bond Acceptor Count : 4
XLogP3 : 2.4 H-Bond Donor Count : 0
SP3 : 0.17 Rotatable Bond Count : 0

Safety of [ 873107-98-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P301 P312-P305 P351 P338UN#:N/A
Hazard Statements:H303 H313 H333-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 873107-98-3 ]

  • Upstream synthesis route of [ 873107-98-3 ]
  • Downstream synthetic route of [ 873107-98-3 ]

[ 873107-98-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 106877-33-2 ]
  • [ 873107-98-3 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With hydrogenchloride; sodium nitrite In water at -5 - 5℃; for 0.17 h;
Stage #2: With potassium iodide In water at -5 - 10℃;
Step 1: 5-iodo-2-(trifluoromethyl)pyridine [0251] A solution of 6-(trifluoromethyl)pyridin-3-amine (9.96 g, 0.062 mol) in 5N HC1 (70 mL) was cooled to -5°C and sodium nitrite (6.39 g, 0.093 mol) in 30 mL of water was added dropwise while maintaining the internal temperature below 5°C. After 10 min, KI (22.5 g, 0.136 mol) in 30 mL of water was added dropwise at -5°C while maintaining the internal temperature below 10°C over the course of the addition. The reaction mixture was warmed to rt and 250 mL of EtOAc was added. The pH of the aqueous layer was adjusted to 11 by the addition of 50 mL of 6N NaOH, the layers were separated, and the organic layer was washed with 120 mL of 0.3M Na2S203. The EtOAc layer was concentrated and the concentrate was purified by column chromatography over silica gel (hexane/ EtOAc =25/1) to afford the title compound as a white solid (14.6 g, 87percent). MS (ESI) calcd for C6H3F3IN: 273.0; found: 274.0[M+H]. 1H NMR (400 MHz, CDC13) δ 8.96 (s, 1H), 8.22 (d, J = 8.2 Hz, 1H), 7.47 (d, J = 8.2 Hz, 1H).
87%
Stage #1: With hydrogenchloride; sodium nitrite In water at -5 - 5℃; for 0.17 h;
Stage #2: With potassium iodide In water at -5 - 20℃;
A solution of 6—(triflucron’iethyi)pyridin—3—arnine (c.96 g. 0.062 moi) in sN HCI (70 mL) was cooled to -5°C and sodium nitrite (6.39 g, 0.093 mol) in 30 niL of water was added dtopwise \percent bile rnamtaanrng the internal temper ilure helms 5 C. \ftei 10 mm K (22 5 g 0 1 o mol) in 30 niL of water uac added dropi 1st at —5°C while inarntauung the inttrnaltemperature below 10 °C over the course of the addition. [he reaction mixture was warmed to rt and 250 mL of EtOAc was added. The pH of the aqueous layer was adjusted to 11 by the addition of So ml of ON ‘4aOH Ihe oiganic laser ws sepaiated and ashed ;kith 120 mL of 0 M \&S2O, Tin. EtOc laser was oncntrated and the onc,.entratc was purifitd b Lolumo chronwogiaphy O\ ei sdica gel he,.ane 1 ii) .c 2 I) to aifoid the title compound as a white solid (14.6 g, 87percent). MS (ES) ealcd for C6H3F31N: 273.0; found: 274.0 [M±HJ. ‘H NMR (400 MHz. CDCL) ii 8.96 (s. iS). 8.22 (d. J:::: 8.2 Hz, JHI, 7.47 (d. J 8.2 Hz, iii).
Reference: [1] Patent: WO2015/187845, 2015, A1. Location in patent: Paragraph 0251
[2] Patent: WO2016/44323, 2016, A1. Location in patent: Paragraph 0347
[3] Patent: WO2006/4533, 2006, A1. Location in patent: Page/Page column 25
  • 2
  • [ 436799-32-5 ]
  • [ 873107-98-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10480 - 10483
  • 3
  • [ 106877-33-2 ]
  • [ 873107-98-3 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With hydrogenchloride; sodium nitrite In water at -5 - 5℃; for 0.17 h;
Stage #2: With potassium iodide In water at -5 - 10℃;
Step 1: 5-iodo-2-(trifluoromethyl)pyridine [0251] A solution of 6-(trifluoromethyl)pyridin-3-amine (9.96 g, 0.062 mol) in 5N HC1 (70 mL) was cooled to -5°C and sodium nitrite (6.39 g, 0.093 mol) in 30 mL of water was added dropwise while maintaining the internal temperature below 5°C. After 10 min, KI (22.5 g, 0.136 mol) in 30 mL of water was added dropwise at -5°C while maintaining the internal temperature below 10°C over the course of the addition. The reaction mixture was warmed to rt and 250 mL of EtOAc was added. The pH of the aqueous layer was adjusted to 11 by the addition of 50 mL of 6N NaOH, the layers were separated, and the organic layer was washed with 120 mL of 0.3M Na2S203. The EtOAc layer was concentrated and the concentrate was purified by column chromatography over silica gel (hexane/ EtOAc =25/1) to afford the title compound as a white solid (14.6 g, 87percent). MS (ESI) calcd for C6H3F3IN: 273.0; found: 274.0[M+H]. 1H NMR (400 MHz, CDC13) δ 8.96 (s, 1H), 8.22 (d, J = 8.2 Hz, 1H), 7.47 (d, J = 8.2 Hz, 1H).
87%
Stage #1: With hydrogenchloride; sodium nitrite In water at -5 - 5℃; for 0.17 h;
Stage #2: With potassium iodide In water at -5 - 20℃;
A solution of 6—(triflucron’iethyi)pyridin—3—arnine (c.96 g. 0.062 moi) in sN HCI (70 mL) was cooled to -5°C and sodium nitrite (6.39 g, 0.093 mol) in 30 niL of water was added dtopwise \percent bile rnamtaanrng the internal temper ilure helms 5 C. \ftei 10 mm K (22 5 g 0 1 o mol) in 30 niL of water uac added dropi 1st at —5°C while inarntauung the inttrnaltemperature below 10 °C over the course of the addition. [he reaction mixture was warmed to rt and 250 mL of EtOAc was added. The pH of the aqueous layer was adjusted to 11 by the addition of So ml of ON ‘4aOH Ihe oiganic laser ws sepaiated and ashed ;kith 120 mL of 0 M \&S2O, Tin. EtOc laser was oncntrated and the onc,.entratc was purifitd b Lolumo chronwogiaphy O\ ei sdica gel he,.ane 1 ii) .c 2 I) to aifoid the title compound as a white solid (14.6 g, 87percent). MS (ES) ealcd for C6H3F31N: 273.0; found: 274.0 [M±HJ. ‘H NMR (400 MHz. CDCL) ii 8.96 (s. iS). 8.22 (d. J:::: 8.2 Hz, JHI, 7.47 (d. J 8.2 Hz, iii).
Reference: [1] Patent: WO2015/187845, 2015, A1. Location in patent: Paragraph 0251
[2] Patent: WO2016/44323, 2016, A1. Location in patent: Paragraph 0347
[3] Patent: WO2006/4533, 2006, A1. Location in patent: Page/Page column 25
  • 4
  • [ 436799-32-5 ]
  • [ 873107-98-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2019, [2] Angew. Chem., 2019, vol. 131, # 5, p. 1472 - 1476,5
[3] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10480 - 10483
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