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[ CAS No. 73841-32-4 ]

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2D
Chemical Structure| 73841-32-4
Chemical Structure| 73841-32-4
Structure of 73841-32-4 *Storage: {[proInfo.prStorage]}

Quality Control of [ 73841-32-4 ]

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Related Doc. of [ 73841-32-4 ]

SDS

Product Details of [ 73841-32-4 ]

CAS No. :73841-32-4MDL No. :MFCD01928487
Formula : C6H4INO2 Boiling Point : 350°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :249.01Pubchem ID :11253692
Synonyms :

Computed Properties of [ 73841-32-4 ]

TPSA : 50.2 H-Bond Acceptor Count : 3
XLogP3 : 1.4 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 73841-32-4 ]

Signal Word:WarningClassN/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 [ 73841-32-4 ]

  • Upstream synthesis route of [ 73841-32-4 ]
  • Downstream synthetic route of [ 73841-32-4 ]

[ 73841-32-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 98-98-6 ]
  • [ 73841-32-4 ]
YieldReaction ConditionsOperation in experiment
66%
Stage #1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran at -78 - 30℃; for 0.50 h;
Stage #2: With iodine In tetrahydrofuran at 20℃; for 1.00 h;
A solution of 2,2,6,6-tetramethylpiperidine (8.48 g, 60 mmol) in tetrahydrofuran (100 mL)Cooling to -78 deg C, N-butyllithium (2.5 mol / L, 16 mL, 40 mmol) was added dropwise, Slowly warmed to room temperature for 30 minutes. Cooling to -78 deg C, This was added dropwise to a suspension of pyridine-2-carboxylic acid (2.46 g, 20 mmol) in tetrahydrofuran, After completion of the dropwise addition, the reaction was allowed to proceed at room temperature for 30 minutes, Cooling to -30 deg C, A solution of iodine (15.23 g, 60 mmol) in tetrahydrofuran was added dropwise to the reaction flask, The mixture was stirred at room temperature for 1 hour, add water, Standing overnight Precipitation of solids, The target compound was filtered (3.3 g, yield 66percent).
41%
Stage #1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexanes at -78 - 0℃; for 0.92 h;
Stage #2: With iodine In tetrahydrofuran; hexanes at 0 - 25℃; for 1.25 h;
Stage #3: at 25℃; for 2.00 h;
Description 1; 3-Iodo-2-pyridinecarboxylic acid (D1); To a stirred solution of 2,2,6,6-tetramethylpiperidine (20 ml, 0.122 mol) in dry THF (100 ml) at -78° C., under argon was added n-butyllithium (52 ml, 0.163 mol, 2.5M solution in hexanes) dropwise, followed 15 min later by a solution of 2-pyridinecarboxylic acid (5.0 g, 0.0407 mol) in dry THF (30 ml). After 10 min at -78° C., the reaction mixture was warmed to 0° C. for 30 min. and then transferred to a solution of iodine (30.9 g, 0.243 mol) in dry THF (70 ml) at 0° C., under argon. After 15 min at 0° C. the reaction mixture was warmed to 25° C. and stirred for 1 h. After this period water (80 ml) was added and the reaction mixture concentrated in vacuo. The residue was re-dissolved in water (100 ml) and washed with EtOAc (100 ml). The aqueous layer was separated, concentrated in vacuo and the resulting residue triturated with diethyl ether. The solid material was filtered and dried in vacuo before being re-dissolved in MeOH (200 ml). To this solution was added Amberlyte IR-120 ion-exchange resin (100 g) and the reaction mixture stirred at 25° C. for 2 h. After this period the resin was filtered off and the solvents concentrated in vacuo to afford the title compound (4.15 g, 41percent). δH (DMSO-d6, 250 MHz) 6.79 (1H, bs) 7.28 (1H, dd), 8.37 (1H, dd), 8.58 (1H, dd). MS (ES): C6H41NO2 requires 249. found (M-H+) 248.
41%
Stage #1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.92 h;
Stage #2: With iodine In tetrahydrofuran; hexane at 0 - 25℃; for 1.25 h;
Stage #3: With water In tetrahydrofuran; hexane
Description 1; 3-lodo-2-pyridinecarboxylic acid (D1);To a stirred solution of 2,2,6,6-tetramethylpiperidine (20ml, 0.122mol) in dry THF (100ml) at -78 °C, under argon was added /7-butyllithium (52ml, 0.163mol, 2.5M EPO <DP n="40"/>solution in hexanes) dropwise, followed 15min later by a solution of 2- pyridinecarboxylic acid (5.Og, 0.0407mol) in dry THF (30ml). After 10min at -78 0C, the reaction mixture was warmed to 00C for 30 min. and then transferred to a solution of iodine (30.9g, 0.243mol) in dry THF (70ml) at 00C, under argon. After 15min at O0C the reaction mixture was warmed to 25°C and stirred for 1h. After this period water (80ml) was added and the reaction mixture concentrated in vacuo. The residue was re-dissolved in water (100ml) and washed with EtOAc (100ml). The aqueous layer was separated, concentrated in vacuo and the resulting residue triturated with diethyl ether. The solid material was filtered and dried in vacuo before being re- dissolved in MeOH (200ml). To this solution was added Amberlyte IR-120 ion- exchange resin (100g) and the reaction mixture stirred at 25°C for 2h. After this period the resin was filtered off and the solvents concentrated in vacuo to afford the title compound (4.15g, 41percent). δH (DMSO-d6, 250MHz) 6.79 (1H, bs) 7.28 (1H, dd), 8.37 (1 H, dd), 8.58 (1H, dd). MS (ES): C6H4INO2 requires 249; found (M-H+) 248.
Reference: [1] Patent: CN106317027, 2017, A. Location in patent: Paragraph 0246; 0247; 0248
[2] Patent: US2008/312209, 2008, A1. Location in patent: Page/Page column 13
[3] Patent: WO2007/7018, 2007, A1. Location in patent: Page/Page column 38-39
[4] Tetrahedron, 2002, vol. 58, # 33, p. 6723 - 6728
[5] Patent: WO2006/25783, 2006, A1. Location in patent: Page/Page column 120-121
[6] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4236 - 4238
  • 2
  • [ 57841-90-4 ]
  • [ 73841-32-4 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086
  • 3
  • [ 10354-53-7 ]
  • [ 73841-32-4 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086
  • 4
  • [ 1462-86-8 ]
  • [ 73841-32-4 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1937, vol. &lt;2&gt; 148, p. 13,16
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