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[ CAS No. 72914-19-3 ]

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Chemical Structure| 72914-19-3
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Product Details of [ 72914-19-3 ]

CAS No. :72914-19-3 MDL No. :MFCD01863731
Formula : C18H24N2 Boiling Point : 395.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :268.40 g/mol Pubchem ID :4249187
Synonyms :

Safety of [ 72914-19-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 72914-19-3 ]

  • Upstream synthesis route of [ 72914-19-3 ]
  • Downstream synthetic route of [ 72914-19-3 ]

[ 72914-19-3 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 3978-81-2 ]
  • [ 72914-19-3 ]
YieldReaction ConditionsOperation in experiment
80% With sodium In tetrahydrofuran; paraffin oil at 50℃; for 6 h; In this example, following Example 1, the synthesis of 4,4′-di-tert-butyl-2,2′-bipyridine was investigated. In this example, the synthesis was performed through the reaction of 4-tert-butylpyridine with SD at low concentrations in THF. 4-tert-Butylpyridine (0.5 mmol) was reacted with SD in an amount of molar equivalents with respect to 4-tert-butylpyridine as shown in FIG. 2 in THF. The usage amounts of THF, the reaction temperatures and the reaction times were set as shown in FIG. 2, and the synthesis was performed in the same manner as in Example 1. After the reaction, in the same manner as in Example 1, the production amounts of 4,4′-di-tert-butyl2,2′-bipyridine (Compound 2), which was the target reaction product, and 4-tert-butyl-1,4-dihydropyridine (Compound 1) and 4,4′,4″-tri-tert-butyl-2,2′:6′,2″-terpyridine (Compound 3), which were the possible reaction by-products, were measured, and their yields were calculated. The recovery rate of the unreacted 4-tert-butylpyridine was calculated in the same manner. The results are summarized in FIG. 2. It is found from these results that when 4-tert-butylpyridine (0.5 mmol) was reacted with SD in an amount of 1 to 2 mol equivalents with respect to the 4-tert-butylpyridine in 2 to 4 ml of THF at 25 to 50° C. for 1 to 24 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield in all of the cases. In particular, when 0.5 mmol 4-tert-butylpyridine was reacted with SD in an amount of 1 mol equivalent with respect to the 4-tert-butylpyridine in 2 ml of THF at 50° C. for 1 to 6 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield without the generation of reaction by-products. In addition, when 0.5 mmol 4-tert-butylpyridine was reacted with SD in an amount of 1 mol equivalent with respect to the 4-tert-butylpyridine in 4 ml of THF at 25° C. for 6 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield without the generation of reaction by-products. It was found that when SD in an amount of 2 mol equivalents was used, the yield decreased compared with the case of 1 mol equivalent, and the material balance also decreased. It was also found from comparison with Example 1 that the lower the concentrations of 4-tert-butylpyridine and SD were with respect to THF, the higher the yield was.
Reference: [1] Patent: US2018/282278, 2018, A1, . Location in patent: Paragraph 0057; 0127-0130
[2] Helvetica Chimica Acta, 1980, vol. 63, # 6, p. 1675 - 1702
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 2000, # 1, p. 63 - 68
[4] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 127 - 132
[5] Synthesis (Germany), 2013, vol. 45, # 22, p. 3099 - 3102
[6] Organometallics, 2016, vol. 35, # 14, p. 2348 - 2360
[7] Patent: US4177349, 1979, A,
[8] Patent: US4177349, 1979, A,
  • 2
  • [ 81167-60-4 ]
  • [ 72914-19-3 ]
YieldReaction ConditionsOperation in experiment
90% With manganese; nickel(II) bromide trihydrate In N,N-dimethyl-formamide at 20 - 60℃; for 20 h; Inert atmosphere General procedure: On the benchtop, a 50 mL round-bottomed flask equipped with a inch Teflon coated magnetic stir bar was charged with NiBr2·3H2O(401 mg, 1.47 mmol) and DMF (20.0 mL). The vessel was stopperedwith a rubber septum and heated to 60 °C until a green homogeneoussolution resulted (approx. 20 min). Once homogeneity wasachieved, the vessel was removed from the heat and allowed to coolto r.t. Once at r.t., 4-tert-butyl-2-chloropyridine (2a; 4.99 g, 29.4mmol) and Mn powder (–325 mesh, 3.30 g, 60.0 mmol) were added,and the vessel was resealed with the septum, purged with argon, andheated again to 60 °C for the duration of the reaction. Reactionprogress was monitored by GC analysis of aliquots of the crude reactionmixture. In general, the reaction turns very dark brown orblack in color when complete, and the color change is a reliable indicatorfor the reaction endpoint. Upon completion, the reactionmixture was cooled to r.t., diluted with Et2O (80 mL), and filteredthrough a short pad of Celite (approx. 2 in × 2 in × 2 in) that hadbeen wetted with Et2O to remove metal salts. The reaction vesselwas washed with Et2O (2 × 40 mL) and the washings were thenpassed through the filter. The combined filtrates were transferred toa separatory funnel and washed with aq 1 M NaOH (200 mL). Abrown emulsion formed in the separatory funnel during the workupthat slowly separated. Care was taken to keep the brown emulsion with the organics. Once separated, the aqueous layer was extractedwith additional Et2O (3 × 150 mL). The combined organic extracts and brown emulsion were washed with brine (500 mL). Again carewas taken to keep the brown emulsion with the organics. The organicswere dried with copious amounts of MgSO4. The solid dryingagent was removed by filtration, ground into a fine powder, andwashed with additional Et2O (3 × 150 mL). The filtrate was evaporated to dryness to give 3a (3.57 g) as faintly yellow crystals in 90percentyield. This material was judged analytically pure by NMR and combustion analysis. If necessary the product can be further purified bysublimation (140 °C/300 mtorr).
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 22, p. 3099 - 3102
  • 3
  • [ 3978-81-2 ]
  • [ 72914-19-3 ]
YieldReaction ConditionsOperation in experiment
78% With sodium In tetrahydrofuran; paraffin oil at 25℃; for 24 h; In this example, following Example 1, the synthesis of 4,4′-di-tert-butyl-2,2′-bipyridine was investigated. In this example, the synthesis was performed through the reaction of 4-tert-butylpyridine with SD at low concentrations in THF. 4-tert-Butylpyridine (0.5 mmol) was reacted with SD in an amount of molar equivalents with respect to 4-tert-butylpyridine as shown in FIG. 2 in THF. The usage amounts of THF, the reaction temperatures and the reaction times were set as shown in FIG. 2, and the synthesis was performed in the same manner as in Example 1. After the reaction, in the same manner as in Example 1, the production amounts of 4,4′-di-tert-butyl2,2′-bipyridine (Compound 2), which was the target reaction product, and 4-tert-butyl-1,4-dihydropyridine (Compound 1) and 4,4′,4″-tri-tert-butyl-2,2′:6′,2″-terpyridine (Compound 3), which were the possible reaction by-products, were measured, and their yields were calculated. The recovery rate of the unreacted 4-tert-butylpyridine was calculated in the same manner. The results are summarized in FIG. 2. It is found from these results that when 4-tert-butylpyridine (0.5 mmol) was reacted with SD in an amount of 1 to 2 mol equivalents with respect to the 4-tert-butylpyridine in 2 to 4 ml of THF at 25 to 50° C. for 1 to 24 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield in all of the cases. In particular, when 0.5 mmol 4-tert-butylpyridine was reacted with SD in an amount of 1 mol equivalent with respect to the 4-tert-butylpyridine in 2 ml of THF at 50° C. for 1 to 6 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield without the generation of reaction by-products. In addition, when 0.5 mmol 4-tert-butylpyridine was reacted with SD in an amount of 1 mol equivalent with respect to the 4-tert-butylpyridine in 4 ml of THF at 25° C. for 6 hours, the 4,4′-di-tert-butyl-2,2′-bipyridine compound was obtained with a high yield without the generation of reaction by-products. It was found that when SD in an amount of 2 mol equivalents was used, the yield decreased compared with the case of 1 mol equivalent, and the material balance also decreased. It was also found from comparison with Example 1 that the lower the concentrations of 4-tert-butylpyridine and SD were with respect to THF, the higher the yield was.
Reference: [1] Patent: US2018/282278, 2018, A1, . Location in patent: Paragraph 0057; 0127-0130
[2] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14830 - 14835
  • 4
  • [ 1187755-05-0 ]
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Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
  • 5
  • [ 1268488-94-3 ]
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Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
  • 6
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Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
  • 7
  • [ 1268488-94-3 ]
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Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
[2] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
  • 8
  • [ 1187755-05-0 ]
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Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
  • 9
  • [ 1268488-94-3 ]
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Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 7, p. 861 - 872
  • 10
  • [ 72914-19-3 ]
  • [ 676525-77-2 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: at 150℃; for 15 h; Inert atmosphere
A magnetically stirred suspension of 4,4’-di-tert-butyl-2,2’-dipyridyl (118 mg, 0.44 mmol) and tetrakis(2-phenylpyridine-C2,N’)(μ-dichloro)-diiridium (214 mg, 0.2 mmol) in 10 mL of 1,2-ethanediol under nitrogen was heated to 150 °C. The mixture was kept at this temperature for 15h. All the solids dissolved to yield a clear, yellow solution. After cooling the mixture to room temperature, 150 mL of water was added. The excess of bipyridine ligand was removed through three extractions with diethyl ether (50 mL), and the aqueous layer was subsequently heated to 60-70 °C. NH4PF6 (1 g) in 10 mL of water was added, and the PF6 salt of the chromophore immediately precipitated. After cooling the suspension to 5 °C, the yellow solid was separated through filtration, dried, and recrystallized through acetonitrile/ether diffusion. Yield: 280 mg (77percent).
66%
Stage #1: at 150℃; for 15 h; Inert atmosphere
Synthesis of [Ir(ppy)2(dtbbpy)](PF6) was adapted from literature procedures6 for the analogousunsubstituted complex. A stirred suspension of 4,4-di-tert-butyl-2,2-dipyridyl (0.44 g, 0.88mmol) and tetrakis(2-phenylpyridine-C,N)(µ-dichloro)diiridium, A (0.428g, 0.400 mmol) in 20mL of 1,2-ethanediol under nitrogen was heated to 150 °C for 15 h. All the solids dissolved toyield a clear, yellow solution. After cooling the mixture to room temperature, 200 mL of waterwere added. The excess of the bipyridine ligand was removed through three extractions withdiethyl ether (3 × 50 mL), and the aqueous layer was subsequently heated to 70 °C. NH4PF6 (2 g)in 20 mL of water was added, and the PF6 salt of the iridium complex immediately precipitated.After cooling the suspension to 5 °C, the yellow solid was separated through filtration, dried, andrecrystallized through acetonitrile/ether. Yield: 0.50 g (66percent). 1H NMR (acetone-d6, 400 MHz):δ 8.88 (d, J =2.0 Hz, dtb-bpy-H3, 2H), 8.24 (ppy-H6, pyridine, 2H, d, J = 8), 7.99-7.93 ( m,dtb-bpy-H6, 2H, ppy-H5, pyridine, 2H), 7.90 (ppy-H3, phenyl, 2H, dd, J = 7.2, 0.8 Hz), 7.79(ppy-H6, phenyl, 2H, d, J = 6 Hz), 7.71 (dtb-bpy-H5, 2H, dd, J = 6.0, 2.0 Hz), 7.14 (ppy-H4,pyridine, 2H, dt, J = 7.2, 1.6 Hz), 7.04 (ppy-H4, phenyl, 2H, dt, J= 7.6, 0.8 Hz), 6.91 (ppy-H5,phenyl, 2H, dt, J = 6.8, 1.2 Hz), 6.34 (ppy-H3, pyridine, 2H, d, J = 8), 1.42 (18H, s).HRMS (ESI) m/z calculated for C40H40N4Ir+ ([M - PF6]+) 769.2876, found 769.2866.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 21, p. 2046 - 2049
[2] Journal of the American Chemical Society, 2018,
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 2, p. 447 - 451
[4] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2636 - 2643
[5] Chemical Communications, 2015, vol. 51, # 89, p. 16033 - 16036
  • 11
  • [ 17084-13-8 ]
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  • [ 676525-77-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 9088 - 9092
  • 12
  • [ 870987-64-7 ]
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  • [ 676525-77-2 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11314 - 11318
  • 13
  • [ 72914-19-3 ]
  • [ 676525-77-2 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 43, p. 14129 - 14135
  • 14
  • [ 26042-63-7 ]
  • [ 72914-19-3 ]
  • [ 676525-77-2 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 20, p. 6340 - 6349
  • 15
  • [ 26042-63-7 ]
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  • [ 676525-77-2 ]
Reference: [1] Journal of Materials Chemistry C, 2018, vol. 6, # 24, p. 6385 - 6397
  • 16
  • [ 808142-69-0 ]
  • [ 72914-19-3 ]
  • [ 808142-80-5 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 43, p. 14129 - 14135
  • 17
  • [ 870987-64-7 ]
  • [ 72914-19-3 ]
  • [ 870987-63-6 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: for 15 h; Reflux; Inert atmosphere
Bis-(μ)-chlorotetrakis(2-(4,6-difluoromethylphenyl)-pyridinato-C2,N)diiridium(III) (0.09 mmol, 0.13 g) was heated to reflux with 4,4’-di-tert-butyl-2,2’-dipyridyl (0.20 mmol, 0.054g) in ethylene glycol (6.0 mL) under nitrogen with constant stirring for 15h. Upon cooling to room temperature, the mixture was transferred to a separatory funnel with water (60 mL) and washed with hexanes (3×30 mL). The aqueous layer was heated to 85 °C for 5 min to remove residual hexanes. A 10 mL aqueous ammonium hexafluorophosphate solution (1.0g in 10 mL deionized water) was added to the reaction mixture, producing a yellow-green amorphous powder. This precipitate was filtered, dried, and recrystallized by acetone:pentane vapor diffusion, giving the pure product, [Ir(dF(CF3)ppy)2(dtbbpy)]-(PF6). Yield: 0.15 g (75percent).
121 mg
Stage #1: at 150℃; for 15 h; Inert atmosphere
General procedure: Heteroleptic iridium 4xy were synthesized in a two-step procedure[42,43]. In the first step, chloro-bridged dimer was synthesized by charging a two-necked reaction flask with magnetic stir bar, iridium(III) chloride (1 equiv), ligand (2.26 equiv), and a 2:1 v:v mixture of 2-methoxyethanol/water. The mixture was degased with Ar (via Ar bubbling) and heated under reflux at 120 °C with constant stirring overnight. The reaction mixture cooled to room temperature and filtered. The precipitate was washed with water (3x10 mL), dried in air and taken onto the second step without further purification unless noted. In the second step, the chloro bridging dimer (1 equiv), bipyridyl ligand (2.2 equiv) and ethylene glycol were placed in a two-necked flask and then flushed with Ar. The mixture was heated at 150 °C for 15 h and then cooled. The cooled reaction mixture was washed hexane (3 10 mL) and mixture was heated to 85 °C for 5 min to remove residual hexane. Aqueous ammonium hexafluorophosphate (sat. solution) was added to the reaction mixture causing the iridium-PF6 salt to precipitate,which was filtered, dried and recrystallized (acetone/ether).
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 15, p. 7642 - 7651
[2] Tetrahedron Letters, 2018, vol. 59, # 21, p. 2046 - 2049
[3] Journal of Organometallic Chemistry, 2015, vol. 776, p. 51 - 59
  • 18
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  • [ 870987-63-6 ]
Reference: [1] Organic Letters, 2018,
  • 19
  • [ 387827-64-7 ]
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11314 - 11318
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