Name: 2226-96-2|2,2,6,6-Tetramethyl-4-hydroxy-1-piperidinyloxy radical|95%
Brand: Ambeed
SKU: A137942
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1
[ 2226-96-2 ]
[ 2351-36-2 ]
[ 112987-97-0 ]
[ 112987-99-2 ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 7337 - 7346

2
[ 45985-24-8 ]
[ 74-88-4 ]
[ 95407-69-5 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 1332 - 1334
[2]Organic Letters,2017,vol. 19,p. 1690 - 1693
[3]Journal of the American Chemical Society,1984,vol. 106,p. 3877 - 3878
[4]Journal of general chemistry of the USSR,1986,vol. 56,p. 753 - 758
Zhurnal Obshchei Khimii,1986,vol. 56,p. 855 - 860

3
[ 110-52-1 ]
[ 2226-96-2 ]
[ 184946-34-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: TEMPOL With sodium hydride In benzene for 24h; Heating / reflux; Stage #2: 1,4-dibromo-butane In benzene at 0℃; for 24h; Heating / reflux;	1 Tempol (3.44 g. or 20 mmole; Sigma-Aldrich Chemical Co.; Milwaukee, Wis.) was added to a 3-neck (250 ml) flask containing dry benzene (100 ml; Sigma-Aldrich). The flask was evacuated and filled with dry nitrogen (Sigma-Aldrich) three times. Sodium hydride (0.72 g or 30 mmole; Sigma-Aldrich) was added to the flask, under stirring, and refluxed for 24 hours. After cooling the flask in ice-cold water, 1,4-dibromobutane (8.6 g or 40 mmole; Sigma-Aldrich) was added and refluxed under nitrogen for 24 hours. The flask was again cooled in ice-cold water and 50 ml of cold water was added to the flask. The contents were transferred to a separatory funnel and gently shaken. A colored upper layer was collected, dried over magnesium sulfate (Sigma-Aldrich) and solvent removed by rotary evaporation. The residual oil was purified by column chromatography on a Silica gel-60 (Sigma-Aldrich). Unreacted dibromobutane was eluted with hexane (Sigma-Aldrich). The desired product (a colored band) was eluted with an ether/hexane (1:1) solvent mixture. An orange oil (5 g, 82% yield) was obtained by removing the solvent from the relevant fractions. Thin-layer chromatography in hexane/ether (1:1 mixture) using a Silica gel-60 was used to verify the purity of the product (one spot at an Rf of 0.75). The bromobutyl ether of Tempol (5 g) was added to a 200 ml flask containing 50 ml dioxane (Sigma-Aldrich) and 8 g triphenylphosphine (Sigma-Aldrich). The flask was partially evacuated and filled with dry nitrogen three times. The contents were heated again under reflux for 24 hours and further cooled down in an ice bath. The solvent was removed in a rotary evaporator to obtain a syrupy liquid. The reaction mixture was added to ether (200 ml; Sigma-Aldrich), stirred and decanted off the solvent. The precipitate was dissolved in dichloromethane (20 ml; Sigma-Aldrich) and added to ether (100 ml). The resulting precipitate was collected by decantation and further purified by dissolving in dichloromethane and precipitating by adding ether. This procedure was repeated three times. The final residue was dried on vacuum to get a fluffy brown solid that was hygroscopic. The purity of the final product was ascertained by HPLC using a C-16 column, LC-MS (mass weight, 489.5), and by EPR spectroscopy. The overall yield was 6.5 g (60%).
82%	Stage #1: TEMPOL With sodium hydride In benzene for 24h; Reflux; Inert atmosphere; Stage #2: 1,4-dibromo-butane In benzene for 24h; Cooling with ice; Reflux;	2; III.a To a 250-mL 3-neck flask equipped with a reflux condenser and nitrogen inlet line was charged 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy, free radical [tempol] (3.44 g, 20 mmol) and dry benzene (100 mL). Sodium hydride (0.72 g, 30 mmol) was slowly added. Once the addition was complete, the reaction was brought to reflux for 24 hours. The resulting suspension was cooled in an ice bath and 1,4-dibromobutane (8.6 g, 40 mmol) was added and the solution was again brought to reflux for 24 hours. After the reaction was complete the reaction solution was cooled and water (50 mL) was added. The contents of the reaction vessel were transferred to a separatory funnel and extracted with diethyl ether (100 mL). The organic layer was decanted and dried over MgSO4 then concentrated under reduced pressure to afford the crude product containing unreacted di-bromide. The product was purified over silica [gradient eluetion:100% hexane to 1:1 hexane/diethyl ether]. The solvent was removed in vacuo to afford 5.0 g (82% yield) of the desired product as a red oil. TLC (hexane/diethyl ether 1:1) one spot at Rf 0.75).
82%	Stage #1: TEMPOL With sodium hydride In benzene for 24h; Heating / reflux; Stage #2: 1,4-dibromo-butane In benzene at 0℃; for 24h; Heating / reflux;	2 To a 250-mL 3 -neck flask equipped with a reflux condenser and nitrogen inlet line was charged 4-hydroxy-2,2,,6-tetramethylpiperidinyloxy, free radical [tempol] (3.44 g, 20 mmol) and dry benzene (100 mL). Sodium hydride (0.72 g, 30 mmol) was slowly added. Once the addition was complete, the reaction was brought to reflux for 24 hours. The resulting suspension was cooled in an ice bath and 1 ,4-dibromobutane (8.6 g, 40 mmol) was added and the solution was again brought to reflux for 24 hours. After the reaction was complete the reaction solution was cooled and water (50 mL) was added. The contents of the reaction vessel were transferred to a separatory funnel and extracted with diethyl ether (100 mL). The organic layer was decanted and dried over MgSO4 then concentrated under reduced pressure to afford the crude product containing unreacted di-bromide. The product was purified over silica [gradient eluetion: 100% hexane to 1:1 hexane/diethyl ether]. The solvent was removed in vacuo to afford 5.0 g (82% yield) of the desired product as a red oil. TLC (hexane/diethyl ether 1 :1) one spot at Rf 0.75).

77%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 50℃;
25%	With sodium hydride In acetone at 20℃; for 3h;
25%	Stage #1: TEMPOL With sodium hydride In acetone at 20℃; for 0.166667h; Stage #2: 1,4-dibromo-butane at 20℃; for 3h;
	With sodium hydride 1.) DMF, 10 deg C, 1 h, 2.) DMF, 50 deg C, 1 h; Yield given. Multistep reaction;
	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In tetrahydrofuran; water at 20℃;

Reference： [1]Current Patent Assignee: NORTH DAKOTA UNIVERSITY SYSTEM - US2007/66572, 2007, A1 Location in patent: Page/Page column 4
[2]Current Patent Assignee: MEDICAL COLLEGE OF WISCONSIN; COLBY PHARMACEUTICAL COMPANY - US2011/59922, 2011, A1 Location in patent: Page/Page column 16
[3]Current Patent Assignee: MEDICAL COLLEGE OF WISCONSIN; COLBY PHARMACEUTICAL COMPANY - WO2008/109740, 2008, A2 Location in patent: Page/Page column 32-33
[4]Dessolin, Jean; Schuler, Marie; Quinart, Alice; De Giorgi, Francesca; Ghosez, Leon; Ichas, François [European Journal of Pharmacology, 2002, vol. 447, # 2-3, p. 155 - 161]
[5]Qian, Weixing; Jin, Erlei; Bao, Weiliang; Zhang, Yongmin [Tetrahedron, 2006, vol. 62, # 4, p. 556 - 562]
[6]Zhang, Yuecheng; Lü, Fenglian; Cao, Xiaohui; Zhao, Jiquan [RSC Advances, 2014, vol. 4, # 76, p. 40161 - 40169]
[7]Bossmann, Stefan H.; Ghatlia, Naresh D.; Francesca Ottaviani; Turro, Claudia; Duerr, Heinz; Turro, Nicholas J. [Synthesis, 1996, # 11, p. 1313 - 1319]
[8]Zheng, Zhi; Wang, Jianli; Chen, Hualiang; Feng, Linbin; Jing, Ren; Lu, Meizhen; Hu, Bao; Ji, Jianbing [ChemCatChem, 2014, vol. 6, # 6, p. 1626 - 1634]

4
[ 2226-96-2 ]
[ 51762-52-8 ]
C₂₃H₂₄NO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 10h;

Reference： [1]Jockusch, Steffen; Dedola, Giuseppe; Lem, George; Turro, Nicholas J. [Journal of Physical Chemistry B, 1999, vol. 103, # 43, p. 9126 - 9129]

5
[ 2226-96-2 ]
[ 2351-37-3 ]
C₃₂H₄₂N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine In toluene at 20℃; for 48h;

Reference： [1]Griesar; Soto-Bustamante; Haase [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2000, vol. 55, # 7, p. 567 - 575]

6
[ 89059-06-3 ]
[ 2226-96-2 ]
[ 320350-41-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: N-(2-carboxyethyl)pyrrole; TEMPOL With dmap In dichloromethane at 0℃; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	2.1. Synthesis of the monomer Py-TEMPO The 4-(3-(pyrrol-1-yl)propionyloxy)-2,2,6,6-tetramethylpi-peridin-1-yloxy (Py-TEMPO) was synthesized according to theprocedures shown in Scheme 1. 3-(Pyrrol-1-yl)propanoic acid wasobtained as described in the literatures [18].4-Hydroxy-TEMPO (8.6 g, 50.0 mmol), 3-(pyrrol-1-yl)propionic acid (7.0 g, 50.0 mmol) and a small quantityof 4-dimethylaminopyridine (DMAP) were stirred in 200 mLof dichloromethane at 0C. Then a solution of N,N’-dicyclohexylcarbodiimide (DCC, 10.3 g, 50.0 mmol) indichloromethane (100 mL) was added slowly to the above mixture.After addition, the mixture was warmed to room temperatureand stirred overnight. The reaction mixture was filtered and thefiltrate was concentrated under reduced pressure. The residuewas purified by column chromatography on silica gel to affordPy-TEMPO in 86% yield.
	With dicyclohexyl-carbodiimide In ethyl acetate at 0 - 20℃;

Reference： [1]Lu, Jin-Jin; Ma, Jia-Qi; Yi, Jing-Miao; Shen, Zhen-Lu; Zhong, Yi-Jun; Ma, Chun-An; Li, Mei-Chao [Electrochimica Acta, 2014, vol. 130, p. 412 - 417]
[2]Siu; Yekta; Yudin [Journal of the American Chemical Society, 2000, vol. 122, # 48, p. 11787 - 11790]

7
[ 2226-96-2 ]
[ 760-93-0 ]
[ 15051-46-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; triethylamine In dichloromethane at 20℃; for 13.5h;

Reference： [1]Anderson, Christopher D.; Shea, Kenneth J.; Rychnovsky, Scott D. [Organic Letters, 2005, vol. 7, # 22, p. 4879 - 4882]

8
[ 2226-96-2 ]
[ 106-96-7 ]
[ 147045-24-7 ]

Yield	Reaction Conditions	Operation in experiment
89.3%	Stage #1: TEMPOL With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 24.75h;
86%	Stage #1: TEMPOL In N,N-dimethyl-formamide at 0℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #3: propargyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 22h;
84%	With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran; toluene Heating;

83%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.833333h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h;
78%	With sodium hydride In N,N-dimethyl-formamide at 20℃;
71%	Stage #1: TEMPOL With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran; toluene; mineral oil at 20℃; for 24h; Inert atmosphere; Schlenk technique;
70%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.833333h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃;
69%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h;
69%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h;	12; 36 NIR-based MitoProbe 18. To a stirring suspension of NaH (600 mg, 15 mmol, 60 % dispersion in mineral oil) in dry DMF (30 mL) was added 4-hydroxytempo (2 g, 1 1.6mmol) in 30 ml DMF at 0°C followed by stirring at room temperature for 30 min. Propargyl bromide (1.4 mL) was added dropwise at 0°C. The resulting mixture was stirred for 3 h at room temperature. The reaction mixture was washed with brine and extracted with EtOAc (30 mL x 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (EtOAc:Hexane, 1 :5) to yield propargyl ether TEMPO as an orange solid (1.63 g, 69 %). XH NMR (400 MHz, CDC13) δ: 1.15 (s, 6H), 1.20 (s, 6H), 1.43 (t, J=11.7 Hz, 2H), 1.91 (dd, J=0.6 Hz, J=3.8 Hz, 2H), 2.42 (s, 1H), 3.83 (tt, J=1.2 Hz, J=3.8 Hz, 1H), 4.16 (s, 2H). 13C NMR (100 MHz, CDC13)5: 20.7, 32.6, 44.7, 55.5, 59.3, 70.0, 74.5, 80.4.
68%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 3h;
68%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 0 - 20℃;
66%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene; mineral oil at 20℃; Inert atmosphere;
65%	Stage #1: TEMPOL With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran; toluene at 0 - 20℃; Inert atmosphere;
65%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h;
65%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 0 - 20℃; for 3h; Inert atmosphere;
63%	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 0 - 25℃; for 3h;	4.2 Under an argon atmosphere was NaH (2.72 g, 67.9 mmol) added to dry DMF (300 mL) and cooled to 0 °C. To this suspension TEMPOL (9.00 g, 52.2 mmol) was added in portions. The reaction mixture was stirred 30 min at 25 °C and then cooled again to 0 °C before propargyl bromide (80 wt% in toluene, 10.1 g, 67.9 mmol) was added dropwise. The resulting reaction mixture was then stirred for 3 h at 25 °C. Then H2O (300 mL) was added and the product was extracted with EtOAc (3 x 150 mL). The combined organic layers were dried with brine and Na2SO4 and fully concentrated in vacuo. Column chromatography (heptane→ 10% EtOAc in heptane) yielded O-propargyl TEMPO (6.93 g, 63%) as an orange solid.
60%	With sodium hydride In N,N-dimethyl-formamide
Ca. 800 mg	Stage #1: TEMPOL With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 3h;

Reference： [1]Wang, Xuepu; Huang, Jian; Chen, Lingdi; Liu, Yujie; Wang, Guowei [Macromolecules, 2014, vol. 47, # 22, p. 7812 - 7822]
[2]Schachtschneider, Andreas; Wessig, Martin; Spitzbarth, Martin; Donner, Adrian; Fischer, Christian; Drescher, Malte; Polarz, Sebastian [Angewandte Chemie - International Edition, 2015, vol. 54, # 36, p. 10465 - 10469][Angew. Chem., 2015, vol. 127, # 36, p. 10611 - 10615,5]
[3]Luo, Juntao; Pardin, Christophe; Lubell, William D.; Zhu [Chemical Communications, 2007, # 21, p. 2136 - 2138]
[4]Guo, Ying; Wang, Wei David; Li, Shengyu; Zhu, Yin; Wang, Xiaoyu; Liu, Xiao; Zhang, Yuan [Chemistry - An Asian Journal, 2021, vol. 16, # 22, p. 3689 - 3694]
[5]Gheorghe, Alexandru; Cuevas-Yañez, Erick; Horn, Joachim; Bannwarth, Willi; Narsaiah, Banda; Reiser, Oliver [Synlett, 2006, # 17, p. 2767 - 2770]
[6]Hoffmann, Justus F.; Roos, Andreas H.; Schmitt, Franz-Josef; Hinderberger, Dariush; Binder, Wolfgang H. [Angewandte Chemie - International Edition, 2021, vol. 60, # 14, p. 7820 - 7827][Angew. Chem., 2021, vol. 133, # 14, p. 7899 - 7906,8]
[7]Yu, Wei; Zhou, Minghong; Wang, Tianqi; He, Zidong; Shi, Buyin; Xu, Yang; Huang, Kun [Organic Letters, 2017, vol. 19, # 21, p. 5776 - 5779]
[8]Yapici, Nazmiye B.; Jockusch, Steffen; Moscatelli, Alberto; Mandalapu, Srinivas Rao; Itagaki, Yasuhiro; Bates, Dallas K.; Wiseman, Sherri; Gibson, K. Michael; Turro, Nicholas J.; Bi, Lanrong [Organic Letters, 2012, vol. 14, # 1, p. 50 - 53]
[9]Current Patent Assignee: MICHIGAN TECHNOLOGICAL UNIVERSITY - WO2014/63033, 2014, A2 Location in patent: Paragraph 00206
[10]Gheorghe, Alexandru; Matsuno, Ai; Reiser, Oliver [Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1016 - 1020]
[11]Bogdan, Andrew; McQuade, D. Tyler [Beilstein Journal of Organic Chemistry, 2009, vol. 5]
[12]Griffiths, Rhys C.; Smith, Frances R.; Long, Jed E.; Williams, Huw E. L.; Layfield, Robert; Mitchell, Nicholas J. [Angewandte Chemie - International Edition, 2020, vol. 59, # 52, p. 23659 - 23667][Angewandte Chemie, 2020, vol. 132, # 52, p. 23867 - 23875,9]
[13]Location in patent: experimental part Tucker-Schwartz, Alexander K.; Garrell, Robin L. [Chemistry - A European Journal, 2010, vol. 16, # 42, p. 12718 - 12726]
[14]Wang, Zhijia; Zhao, Jianzhang; Barbon, Antonio; Toffoletti, Antonio; Liu, Yan; An, Yonglin; Xu, Liang; Karatay, Ahmet; Yaglioglu, Halime Gul; Yildiz, Elif Akhüseyin; Hayvali, Mustafa [Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7831 - 7842]
[15]Becker, Maximilian; Migenda, Julia; Schreiner, Peter R.; Schuler, Sören M. M.; Schulze, Julia S.; Smarsly, Bernd M.; Wende, Raffael C. [Journal of Materials Chemistry A, 2020, vol. 8, # 7, p. 4107 - 4117]
[16]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; EIDGENÖSSISCHE TECHNISCHE HOCHSCHULE ZÜRICH; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE; UNIVERSITY OF LYON - WO2016/38131, 2016, A1 Location in patent: Page/Page column 40
[17]Location in patent: scheme or table Fall, Alioune; Sene, Massene; Gaye, Mohamed; Gómez, Generosa; Fall, Yagamare [Tetrahedron Letters, 2010, vol. 51, # 34, p. 4501 - 4504]
[18]Romanova, Ekaterina E.; Akiel, Rana; Cho, Franklin H.; Takahashi, Susumu [Journal of Physical Chemistry A, 2013, vol. 117, # 46, p. 11933 - 11939]

9
[ 2226-96-2 ]
[ 112-54-9 ]
[ 863984-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In ethanol; water; toluene at 20 - 45℃;	84 Example 84: Preparation of 1-Undecyloxy-2,2,6,6-tetramethyl-piperidin-4-ol, compound 108; 10.0 g 1-oxy-2,2,6,6-tetramethyl-piperidin-4-ol (Prostab 5198, commercial product of Ciba Specialty Chemicals Inc.) are added to a mixture consisting of 40 ml water/ethanol (1 :2) and 14.6 g dodecanal. 78 mg CuCI2 are added, and 5.1g 50 % aqueous hydrogen peroxide are added at RT. When a white precipitate starts to form, 40 ml of a mixture 30 ml ethanol and 10 ml toluene are added and the temperature is raised to 45 °C. After 6 h another 2.5 g 50% H2O2e added and stirring is continued until TLC shows complete consumption of the starting material. 100 ml tert. butylmethylether are added. The two phases are separated and the organic one is washed twice with 1 M NaOH, then with water, 10% ascorbic acid solution, water, and saturated sodium chloride sol. The organic phase is dried over sodium sulfate and finally dried to complete dryness under vacuum to afford 15.1 g product; tan oil. The product can be purified by means of column chromatography (hexane/acetone 49:1 ). Yield 9.9g; colorless oil.1H-NMR (CDCI3), δ (ppm): 0.86 (t, 3H), 1.14 (s, 3 H), 1.18 (s, 3H), 1.26 (2s, 6H), 1.14-1.52 (m, 20H), 1.79 (dd, 2H), 3.72 (t, 2H), 3.95 (dddd, 1 H).13C-NMR (CDCI3), δ (ppm): 14.0, 21.0, 22.7, 26.4, 28.7, 29.4, 29.6, 29.65, 29.7, 31.9, 33.3, 48.3, 59.9, 63.2, 77.0.

Reference： [1]Current Patent Assignee: BASF SE - WO2008/3602, 2008, A1 Location in patent: Page/Page column 42-43

10
[ 2226-96-2 ]
[ 505-73-7 ]
bis(2,2,6,6-tetramethyl-1-piperidine oxyl) dithiodiglycolate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Heating;

Reference： [1]Billone, Paul S.; Maretti, Luca; Maurel, Vincent; Scaiano, Juan C. [Journal of the American Chemical Society, 2007, vol. 129, # 46, p. 14150 - 14151]

11
[ 2226-96-2 ]
[ 3245-23-6 ]
[ 319457-95-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	With di-tert-butyl peroxide at 20 - 25℃; Irradiation;	A1 Example A1: (Compound 101) A photoreactor is charged with 120 g (0.73 mol) of 4-ethylphenylacetate, 5 g (0.029 mol) of 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl and 16.9 g (0.115 mol) of t-butylperoxide. The red solution is flushed with nitrogen and is then irradiated at 20-25C using a mercury dipping lamp (Pyrex jacket). Subsequently, the reaction mixture is concentrated in a rotary evaporator and the residue is chromatographed over silica gel with hexane / ethyl acetate (6 : 4), affording 6.2 g (64% of theory) of compound 101 in the form of colourless crystals. m.p.: 65-67 C Analysis calculated for C19H29NO4: C 68.03%, H 8.71%, N 4.18%; found C 67.96%, H 8.85%, N 3.77%.

Reference： [1]Current Patent Assignee: BASF SE - EP1189875, 2004, B1 Location in patent: Page 20

12
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With phosphoric acid; acetic anhydride; sodium hydrogencarbonate In hexane; water	1 (Synthesis of Methacrylic Anhydride) Example 1 (Synthesis of Methacrylic Anhydride) A glass flask equipped with a stirrer, a dropping funnel, a thermometer, a Liebig condenser and a receiver was charged with 8.61 g (0.1 mol) of methacrylic acid, 7.66 g (0.075 mol) of acetic anhydride, 0.037 g (3.8*10-4 mol) of phosphoric acid and 0.009 g of 4-hydroxy-2,2,6,6-tetramethyl-piperdine-N-oxyl (hereinafter referred to as HO-TEMPO), and the mixture was heated and stirred at 60° C. for 20 hours. After cooling the reaction mixture, 75 ml of n-hexane was added, and the mixture was washed with 75 ml of water twice, neutralized and washed with 75 ml of saturated aqueous solution of sodium hydrogencarbonate (pH=7.81) 5 times, washed with 75 ml of water once, and the hexane layer of the mixture was concentrated to obtain 1.67 g of methacrylic anhydride of 97% purity. The isolation yield of methacrylic anhydride was 21% on the basis of methacrylic acid as the material.

Reference： [1]Current Patent Assignee: Mitsubishi Chemical Corp (in: MCG Group); MITSUBISHI CHEMICAL GROUP CORPORATION - US2003/181763, 2003, A1

13
[ 2226-96-2 ]
[ 4219-46-9 ]
[ 136831-95-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hypochlorite; sodium bromide In dichloromethane; water	2 2-n-Butyryloxyacetaldehyde EXAMPLE 2 2-n-Butyryloxyacetaldehyde The following solutions were prepared: Solution 1: 494 g (3.74 mol) of 2-n-butyryloxyethanol and 35.4 g (0.205 mol) of 4-hydroxy-TEMPO in 7.27 l of methylene chloride. Solution 2: 4.20 l of sodium hypochlorite solution (technical-grade) was brought to a pH of 9.5 by means of gaseous CO2. Concentration: about 2.1 M. Solution 3: 84.9 g of NaBr in 313 ml of water. The solutions 1, 2 and 3 were pumped from reservoirs by means of metering pumps via a static mixing element into a helically wound 20 m long titanium tube (internal diameter: 3 mm, external diameter: 4.1 mm) cooled in an ice bath. The pumping rate was 48 l/h for solution 1, 13 l/h for solution 2 and 0.5 l/h for solution 3. The reaction mixture was collected in a 20 l container, the methylene chloride solution was drained off, washed with 0.5 l of 10 percent strength HCl, 0.5 l of 10 percent strength sodium thiosulfate solution and 0.5 l of water and fractionally distilled. Yield: 80% of 2-n-butyryloxyacetaldehyde.

Reference： [1]Current Patent Assignee: WACKER CHEMIE AG - US2003/73871, 2003, A1

14
[ 2226-96-2 ]
[ 96-21-9 ]
1,3-Bis(4-hydroxy-2,2,6,6-tetramethyl piperidin-1-yloxy)-2-propanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tri-n-butyl-tin hydride In chlorobenzene	63 1,3-Bis(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-propanol EXAMPLE 63 1,3-Bis(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-propanol Tributyltin hydride is added dropwise to a solution of 1,3-dibromo-2-propanol and excess 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperdine in chlorobenzene. The mixture is heated to facilitate the reaction. The crude reaction mixture is passed through silica gel with heptane and then heptane/ethyl acetate to afford the title compound.
	With tri-n-butyl-tin hydride In chlorobenzene	63 1,3-Bis(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-propanol EXAMPLE 63 1,3-Bis(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-propanol Tributyltin hydride is added dropwise to a solution of 1,3-dibromo-2-propanol and excess 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine in chlorobenzene. The mixture is heated to facilitate the reaction. The crude reaction mixture is passed through silica gel with heptane and then heptane/ethyl acetate to afford the title compound.
	With tri-n-butyl-tin hydride In chlorobenzene	63 1,3-Bis(4-hydroxy-2,2,6,6-tetramethyl piperidin-1-yloxy)-2-propanol EXAMPLE 63 1,3-Bis(4-hydroxy-2,2,6,6-tetramethyl piperidin-1-yloxy)-2-propanol Tributyltin hydride is added dropwise to a solution of 1,3-dibromo-2-propanol and excess 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine in chlorobenzene. The mixture is heated to facilitate the reaction. The crude reaction mixture is passed through silica gel with heptane and then heptane/ethyl acetate to afford the tite compound.

Reference： [1]Current Patent Assignee: BASF SE - US6376584, 2002, B1
[2]Current Patent Assignee: BASF SE - US6392041, 2002, B1
[3]Current Patent Assignee: BASF SE - US6271377, 2001, B1

15
[ 2226-96-2 ]
[ 150-76-5 ]
[ 9011-14-7 ]
[ CAS Unavailable ]
[ 16868-12-5 ]

Yield	Reaction Conditions	Operation in experiment
96.7%	With LiOH; calcium oxide In methanol	2 Example 2 Example 2 The procedure was the same as in Example 1, but without N2 inflow. Using a 2-liter reaction vessel, 521 g (2.5 mol) of isobornyl acetate, 600 g (18 mol) of methanol, 3.36 g of LiOH, 7.85 g of CaO, 1.25 kg (12.5 mol) of MMA, 0.083 g of hydroquinone monomethyl ether and 0.006 g of 4-hydroxy-2,2,6,6-tetramethylpiperidyl-N-oxyl were reacted. There was obtained 443 g (80% of theory) of isobornyl (meth)acrylate with a purity of 96.7% as determined by gas chromatography.

Reference： [1]Current Patent Assignee: Roehm (in: Advent International); ADVENT INTERNATIONAL CORPORATION - US6479696, 2002, B1

16
[ 2403-88-5 ]
sodium 2,2'-((2-(bis(carboxymethyl)amino)ethyl)imino)diacetate dihydrate [ No CAS ]
[ 2226-96-2 ]

Yield	Reaction Conditions	Operation in experiment
99.2%	With dihydrogen peroxide; sodium carbonate; In water;	EXAMPLE 1 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl To a solution of 100 g (0.636 mol) of <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>, 0.29 g of ethylenediaminetetraacetic acid disodium salt dihydrate and 0.14 g (1.3 mmol) of anhydrous sodium carbonate in 80 g of deionized water at 60 C. is added over a four-hour period using a syringe pump 130 g (1.91 mol) of 50% hydrogen peroxide. The reaction mixture is stirred for 18 hours. The conversion to 4-hydroxy-2,2,6,6-tetramethyl-piperidine-N-oxyl is 99.2% as determined by GLC analysis.
	With dihydrogen peroxide; sodium hydrogencarbonate; In water;	EXAMPLE 2 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl A solution of 126.17 g (0.80 mol) of <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>, 0.74 g of ethylenediaminetetraacetic acid disodium salt dihydrate and 0.09 g (1.0 mmol) of anhydrous sodium bicarbonate in 100 mL of distilled water is heated to 70 C. To the resultant mixture is added over a two-hour period using a syringe pump 160 mL (2.61 mol) of 50% hydrogen peroxide. The temperature of the reaction mixture is raised to 95-98 C. over the first 25 minutes of the addition of the hydrogen peroxide and then the reaction mixture is maintained at that temperature. Upon completion of the slow addition of the hydrogen peroxide, the conversion to <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>-N-oxyl is 99.1% as determined by GLC analysis.
	With dihydrogen peroxide; sodium carbonate; In water;	EXAMPLE 4 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl A solution of 126.17 g (0.80 mol) of <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>, 0.77 g of ethylenediaminetetraacetic acid disodium salt dihydrate and 0.12 g (1.0 mmol) of anhydrous sodium carbonate in 100 mL of distilled water is heated to 70 C. To the resultant mixture is added over a two-hour period using a syringe pump 240 mL (3.92 tool) of 50% hydrogen peroxide. The temperature of the reaction mixture is raised to 95-98 C. over the first 25 minutes of the addition of the hydrogen peroxide and then the reaction mixture is maintained at that temperature. Upon completion of the slow addition of the hydrogen peroxide, the conversion to <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>-N-oxyl is 98.8% as determined by GLC analysis.

	With dihydrogen peroxide; sodium carbonate; In water;	EXAMPLE 5 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl A solution of 126.17 g (0.80 mol) of <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>, 0.77 g of ethylenediaminetetraacetic acid disodium salt dihydrate and 0.12 g (1.0 mmol) of anhydrous sodium carbonate in 100 mL of distilled water is heated to 75 C. To the resultant mixture is added over a five-hour period using a syringe pump 480 mL (4.70 mol) of 30% hydrogen peroxide. The temperature of the reaction mixture is raised to 91 C. over the first 25 minutes of the addition of the hydrogen peroxide and then the reaction mixture is maintained at 85-90 C. Upon completion of the slow addition of the hydrogen peroxide, the conversion to <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>-N-oxyl is 98.9% as determined by GLC analysis.
	With dihydrogen peroxide; sodium carbonate; In water;	EXAMPLE 6 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl A solution of 126.75 g (0.81 mol) of <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>, 0.73 g of ethylenediaminetetraacetic acid disodium salt dihydrate and 0.12 g (1.0 mmol) of anhydrous sodium carbonate in 100 mL of distilled water is heated to 68 C. To the resultant mixture is added over a six-hour period using a syringe pump 480 mL (4.70 mol) of 30% hydrogen peroxide. The temperature of the reaction mixture is raised to 80 C. over the first 20 minutes of the addition of the hydrogen peroxide and then the reaction mixture is maintained at 80 C. Upon completion of the slow addition of the hydrogen peroxide, the conversion to <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>-N-oxyl is 90.8% as determined by GLC analysis.
	With dihydrogen peroxide; lithium carbonate; In water;	EXAMPLE 3 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl A solution of 126.91 g (0.81 mol) of <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>, 0.72 g of ethylenediaminetetraacetic acid disodium salt dihydrate and 0.09 g (1.0 mmol) of lithium carbonate in 100 mL of distilled water is heated to 70 C. To the resultant mixture is added over a two-hour period using a syringe pump 240 mL (2.35 mol) of 30% hydrogen peroxide. The temperature of the reaction mixture is raised to 90-94 C. over the first 25 minutes of the addition of the hydrogen peroxide and then the reaction mixture is maintained at that temperature. Upon completion of the slow addition of the hydrogen peroxide, the conversion to <strong>[2403-88-5]4-hydroxy-2,2,6,6-tetramethylpiperidine</strong>-N-oxyl is 91.2% as determined by GLC analysis.

Reference： [1]Patent: US5629426,1997,A
[2]Patent: US5629426,1997,A
[3]Patent: US5629426,1997,A
[4]Patent: US5629426,1997,A
[5]Patent: US5629426,1997,A
[6]Patent: US5629426,1997,A

17
[ 2403-88-5 ]
[ 2226-96-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tert.-butylhydroperoxide;molybdenum hexacarbonyl; In 1,2-dichloro-ethane;	EXAMPLE 1 Preparation of 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl A reactor is charged with 50 ml of reagent-grade 1,2-dichloroethane, 8.5 g (0.054 mole) of 2,2,6,6-tetramethylpiperidin-4-ol and 0.10 g of molybdenum hexacarbonyl, Mo(CO)6. The mixture is brought to reflux to give a clear solution. A dropping funnel is charged with 27 ml of 4M tert-butyl hydroperoxide in 1,2-dichloroethane and this solution is then added dropwise into the reactor, at a rate sufficient to maintain a gentle reflux without external heat. The addition requires about 0.5 hour after which heat is applied for 4 hours. At this point gas chromatography (GC) showed <2% of unreacted amine. The reaction mixture is cooled, washed with 5% aqueous sodium sulfite. The aqueous phase is extracted with 50 ml of chloroform and the combined organic phases are dried over anhydrous magnesium sulfate. After evaporation of the solvents, the residue is crystallized from hexane, yielding 8.0 g (86% yield) of orange crystals, m.p. 69-71 (lit. 71 C.) (H. Lemaire, et al, Bull. Soc. Chim. France 1968, 886.).

Reference： [1]Patent: US4665185,1987,A
[2]Beilstein Journal of Organic Chemistry,2012,vol. 8,p. 1515 - 1522
[3]Molecular Diversity,2020
[4]Journal of Physical Chemistry B,2012,vol. 116,p. 5542 - 5550

18
[ 7758-89-6 ]
[ 2226-96-2 ]
[ 309752-65-6 ]
[ 78119-82-1 ]

Yield	Reaction Conditions	Operation in experiment
99.5%	In N,N-dimethyl-formamide;	Example 17 2.56 g (25.86 mmol) of copper (I) chloride, 4.46 g (25.89 mmol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, 90.1 g (0.517 mol) of 6-hydroxy-2-naphthylcarbinol and 0.6 L of N,N-dimethylformamide were introduced into a 1-L four-neckflask equipped with a stirrer, a gas bubbling pipe, a thermometer and a condenser, and then stirred at room temperature by bubbling with an oxygen gas diluted with an approximately equivalent volume of nitrogen at a rate of 100 to 110 mL/min. After bubbling for 10 hours, the reaction mixture was analyzed by liquid chromatography. As a result, it was found that the conversion of the 6-hydroxy-2-naphthylcarbinol was 99.5% and the yield of the 6-hydroxy-2-naphthaldehyde was 90.1%.

Reference： [1]Patent: EP1186588,2002,A1

19
[ 2226-96-2 ]
[ 920-46-7 ]
[ 15051-46-4 ]

Reference： [1]Yonekuta, Yasunori; Susuki, Kentaro; Oyaizu, Kenichi; Honda, Kenji; Nishide, Hiroyuki [Journal of the American Chemical Society, 2007, vol. 129, # 46, p. 14128 - 14129]

20
[ 615-20-3 ]
[ 2226-96-2 ]
4-(benzothiazole-2'-yloxy)-1-oxyl-2,2,6,6-tetramethylpiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydride In N,N-dimethyl-formamide at 20℃;	3.110 To a solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-l-oxyl (1.12 g, 6.5 mmol) in DMF (5 rnL), sodium hydride (0.28 g, 6 mmol) was added and 2-chlorobenzothiazole (1.02 g, 6 mmol) was followed slowly. The mixture was magnetically stirred at room temperature overnight. To the mixture, ethyl acetate (80 mL) was added. The organic phase was washed five times with distilled water. After dried with sodium sulfate, ethyl acetate was removed under vacuum. Further purification through column using hexane and combination with ethyl acetate afforded 4-(Benzothiazole-2'-yloxy)-l- oxyl-2,2,6,6-tetramethylpiperidine (1.4 g). Yield was76%. Anal. Calcd for C16H21N2O2S: C, 62.92; H, 6.93; N, 9.17. Found: C, 62.76; H, 6.98; N, 9.13. mp 109.0 - 110.0 0C.
76%	With sodium hydride In N,N-dimethyl-formamide at 20℃;	3 To a solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl) (1.12 g, 6.5 mmol) in DMF (5 mL), sodium hydride (0.28 g, 6 mmol) was added and 2-chlorobenzothiazole (1.02 g, 6 mmol) was followed slowly. The mixture was magnetically stirred at room temperature overnight. To the mixture, ethyl acetate (80 mL) was added. The organic phase was washed five times with distilled water. After dried with sodium sulfate, ethyl acetate was removed under vacuum. Further purification through column using hexane and combination with ethyl acetate afforded 4-(Benzothiazole-2'-yloxy)-1-oxyl-2,2,6,6-tetramethylpiperidine (1.4 g). Yield was 76%. Anal. Calcd for C16H21N2O2S: C, 62.92; H, 6.93; N, 9.17. Found: C, 62.76; H, 6.98; N, 9.13. mp 109.0-110.0° C.

Reference： [1]Current Patent Assignee: COLBY PHARMACEUTICAL COMPANY - WO2008/103613, 2008, A2 Location in patent: Page/Page column 112
[2]Current Patent Assignee: COLBY PHARMACEUTICAL COMPANY - US2008/200405, 2008, A1 Location in patent: Page/Page column 50

21
[ 2226-96-2 ]
[ 818-88-2 ]
[ 2516-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate In n-heptane Heating / reflux;	2.1; 2.2; 2.3 Example 2-1 and Comparative Examples 2-1 to 2-3; Comparative Compound 2 (bis(1-oxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate) was synthesized as described below.; The following compounds were mixed together: 4 ml of 1-oxy-2,2,6,6-tetramethyl-4-hydroxypiperidine, 1 ml of methyl sebacate, 0.06 g of sodium methoxide, and 30 ml of heptane. Methanol was removed from the mixture under reflux. After the absence of methyl sebacate in the reaction liquid was confirmed by gas chromatography, the reaction liquid was washed with water such that sodium methoxide and 1-oxy-2,2,6,6-tetramethyl-4-hydroxypiperidine were removed from the reaction liquid. The solvent was removed from the reaction liquid washed with water, whereby a solid was obtained. The solid was recrystallized from hexane, whereby 1.5 g of bis(1-oxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate was obtained. In 25 ml of n-hexadecane, 10 mg of each polymerization inhibitor shown in Table 2 was dissolved, whereby a solution was prepared. A mixture of 1 µl of the solution and 5 µl of stearyl methacrylate was heated from room temperature to 150°C at 15°C/minute in a differential scanning calorimeter. The time from the moment of reaching 150°C to an exothermic peak due to polymerization was thereby measured and defined as polymerization inhibitory activity (hours). The measurement results are summarized in Table 2. As is clear from Table 2, the compound according to the present invention is suitable for the long-term stabilization of a monomer and exhibits a stabilizing effect higher than that of Comparative Compound 1, which has a low molecular weight, and that of Comparative Compound 2, which has a high molecular weight. As a polymerization inhibitor, the compound according to the present invention is clearly superior to a known hindered amine compound having a nitroxyl structure.

Reference： [1]Current Patent Assignee: ADEKA CORP. - EP1978017, 2008, A1 Location in patent: Page/Page column 9

22
[ 2226-96-2 ]
[ 119-60-8 ]
[ 122586-79-2 ]
[ 87018-00-6 ]

Reference： [1]Synlett,2008,p. 1877 - 1881

23
[ 2226-96-2 ]
[ 3019-25-8 ]
[ 122586-72-5 ]
[ 1072455-14-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 31% 2: 10%	With dihydrogen peroxide; copper(l) chloride In water; butanone at 20 - 35℃; for 56h;

Reference： [1]Location in patent: experimental part Dichtl, Alexander; Seyfried, Martin; Schoening, Kai-Uwe [Synlett, 2008, # 12, p. 1877 - 1881]

24
[ 2226-96-2 ]
[ 129-64-6 ]
bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis(2,2,6,6-tetramethylpiperidin-1-oxyl-4-yl) ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: TEMPOL; 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride With dmap; triethylamine In benzene at 80℃; for 15h; Inert atmosphere; Stage #2: With 2-chloro-1-methyl-pyridinium iodide In benzene at 20℃; for 20h; Inert atmosphere;

Reference： [1]Oyaizu, Kenichi; Ando, Yuko; Konishi, Hiroaki; Nishide, Hiroyuki [Journal of the American Chemical Society, 2008, vol. 130, # 44, p. 14459 - 14461]

25
[ 2226-96-2 ]
[ 4509-90-4 ]
[ 1025769-20-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Franchi, Paola; Fani, Michela; Mezzina, Elisabetta; Lucarini, Marco [Organic Letters, 2008, vol. 10, # 10, p. 1901 - 1904]

26
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
71%	With dihydrogen peroxide; copper(l) chloride In water; <i>tert</i>-butyl alcohol at 40℃; for 17h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

27
[ 2226-96-2 ]
[ 5497-67-6 ]
[ 1110726-99-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dihydrogen peroxide; copper(l) chloride In water; <i>tert</i>-butyl alcohol at 20℃; for 28h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

28
[ 2226-96-2 ]
[ 123-05-7 ]
[ 1001081-26-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dihydrogen peroxide; copper(l) chloride In water; isopropyl alcohol at 30℃; for 16h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

29
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
63%	With dihydrogen peroxide; copper(l) chloride In water; <i>tert</i>-butyl alcohol at 30℃; for 26h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

30
[ 2226-96-2 ]
[ 533-67-5 ]
[ 1110727-11-1 ]

Yield	Reaction Conditions	Operation in experiment
38%	With dihydrogen peroxide; copper(l) chloride In water; acetic acid at 30℃; for 16h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

31
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
69%	With dihydrogen peroxide; copper(l) chloride In water; <i>tert</i>-butyl alcohol at 20℃; for 13h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

32
[ 2226-96-2 ]
[ CAS Unavailable ]
[ 1110727-10-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dihydrogen peroxide; copper(l) chloride In water; <i>tert</i>-butyl alcohol at 20℃; for 72h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

33
[ 2226-96-2 ]
[ CAS Unavailable ]
[ 1001081-12-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With dihydrogen peroxide; copper(l) chloride In toluene at 20℃; for 14h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

34
[ 2226-96-2 ]
[ 2938-69-4 ]
[ 1110727-08-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With dihydrogen peroxide; copper(l) chloride In water; <i>tert</i>-butyl alcohol at 20 - 40℃; for 43h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

35
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
64%	With dihydrogen peroxide; copper(l) chloride In water; <i>tert</i>-butyl alcohol at 20℃; for 22h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

36
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
68%	With dihydrogen peroxide; copper(l) chloride In <i>tert</i>-butyl alcohol at 20℃; for 13h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

37
[ 2226-96-2 ]
[ CAS Unavailable ]
[ 1110727-04-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	With dihydrogen peroxide; copper(l) chloride In water at 20℃; for 13h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

38
[ 2226-96-2 ]
[ 21662-09-9 ]
[ 1110727-01-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With dihydrogen peroxide; copper(l) chloride In toluene; <i>tert</i>-butyl alcohol at 20 - 40℃; for 29h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

39
[ 2226-96-2 ]
[ CAS Unavailable ]
[ 122586-72-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With dihydrogen peroxide; copper(l) chloride In water at 65 - 70℃; for 5h;
	With dihydrogen peroxide; copper(l) chloride In water for 4h; Reflux;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]
[2]Porel, Mintu; Ottaviani, M. Francesca; Jockusch, Steffen; Jayaraj, Nithyanandhan; Turro, Nicholas J.; Ramamurthy [Chemical Communications, 2010, vol. 46, # 41, p. 7736 - 7738]

40
[ 2226-96-2 ]
[ 630-19-3 ]
[ 140641-03-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dihydrogen peroxide; copper(l) chloride In ethanol; water at 20℃; for 17h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

41
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
84%	With dihydrogen peroxide; copper(l) chloride In water; butan-1-ol at 35℃; for 15h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

42
[ 2226-96-2 ]
[ 78-84-2 ]
[ 1001080-97-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dihydrogen peroxide; copper(l) chloride In water; isopropyl alcohol at 20℃; for 12h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

43
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
72%	With dihydrogen peroxide; copper(l) chloride In water; <i>tert</i>-butyl alcohol at 30℃; for 13h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

44
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
62%	With dihydrogen peroxide; copper dichloride In water; <i>tert</i>-butyl alcohol at 30℃; for 23h;

Reference： [1]Schoening, Kai-Uwe; Fischer, Walter; Hauck, Stefan; Dichtl, Alexander; Kuepfert, Michael [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1567 - 1573]

45
[ 2226-96-2 ]
[ 197775-45-4 ]
[ 1158203-75-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 12h;	1.d Example 1 : Synthesis of Compound 1 fTAPPl)[0189] As presented in Scheme I (below), the synthesis begins with a Claisen condensation between 4- acetylpyridine and ethyl oxalate to afford the diketone. Condensation of the diketone with hydrazine hydrate provides the substituted pyrazole. Hydrolysis of the ester followed by coupling of the resulting acid to 4- hydroxy-1-oxyl-2,2,6,6-tetramethylρiperidine yields the desired product 1-oxyl-2,2,6,6-tetramethylpiperidin- 4-yl 3-(pyridin-4-yl)-1H-ρyrazole-5-carboxylate. Reagents and conditions: a. diethyl oxylate, NaOEt, THF, rt, 3 h; b. hydrazine hydrate, EtOH, 75 °C, 12 h; c. 3 N HCl, 1,4-dioxane, 80 °C, 12 h; d. CDI, DMF, 4- hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine, DBU, 12 h.

Reference： [1]Current Patent Assignee: REVISION THERAPEUTICS - WO2009/70693, 2009, A2 Location in patent: Page/Page column 27; 43

46
[ 2226-96-2 ]
[ 112-16-3 ]
[ 22491-89-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With pyridine In diethyl ether at 0 - 20℃; for 3.08333h;	2.2.1. General procedure for the preparation of 4-acyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl radicals 1-6 General procedure: To a stirred solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (Aldrich) (0.8 g, 4.65 mmol) and pyridine (0.37 g,4.65 mmol) dissolved in Et2O (15 mL) was added dropwise the corresponding acyl chloride (5.12 mmol) in Et2O (5 mL) at 0 °C. Once the addition was completed the stirring was continued for 5 min and then the mixture was allowed to warm to room temperature, stirring for an additional 3 h. The red solution was washed with an aqueous solution of NaHCO3 5% (6 x 20 mL) and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated under vacuum to afford a crude red oil, which was purified by column chromatography (n-hexane/ethyl acetate = 9/1). With the exception of compound 1, all other TEMPO derivatives were isolated as oils. Characterization of all compounds was achieved by their IR and NMR spectra. The latter (1H and 13C) revealed only the presence of the 4-acyloxy substituent in the TEMPO derivatives, due to the paramagnetic nature of the piperidine-N-oxyl moiety. All signals in the 1H NMR spectra of these compounds appeared as uncoupled singlets, integrating normally. In a few instances, signal superpositions were observed in the 13C NMR spectra of the TEMPO derivatives, easily detected by their larger intensities.
60%	With pyridine In dichloromethane at 20℃; for 24h;

Reference： [1]Aliaga, Carolina; Bravo-Moraga, Felipe; Gonzalez-Nilo, Danilo; Márquez, Sebastián; Lühr, Susan; Mena, Geraldine; Rezende, Marcos Caroli [Food Chemistry, 2016, vol. 192, p. 395 - 401]
[2]Location in patent: experimental part Ionita, Gabriela; Caragheorgheopol, Agneta; Caldararu, Horia; Jones, Leonie; Chechik, Victor [Organic and Biomolecular Chemistry, 2009, vol. 7, # 3, p. 598 - 602]

47
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;

Reference： [1]Porel, Mintu; Ottaviani, M. Francesca; Jockusch, Steffen; Jayaraj, Nithyanandhan; Turro, Nicholas J.; Ramamurthy [Chemical Communications, 2010, vol. 46, # 41, p. 7736 - 7738]

48
[ 2226-96-2 ]
[ 144701-48-4 ]
[ 1276682-49-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 48h;Cooling with ice;	To an ice bath cooled solution of telmisartan (0.8 g, 1.55 mmol) in DMF (50 mL) was added 1-hydroxybenzotriazole (HOBt, 0.25 g, 1.87 mmol), 4-dimethylamino pyridine (DMAP, 0.23 g, 1.87 mmol), and l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 0.39 g, 2.02 mmol), followed by tempol (0.29 g, 1.712 mmol). The mixture was stirred at room temperature for 48 h. Water (15 mL) was added to the mixture and stirred at room temperature for 10 minutes. The mixture was extracted with ethyl Atty Docket No. GUX-024.25 acetate (3 x l5 mL). The organic layer was washed with sat. LiCl (15 mL), sat. NaHC03 (15 mL), water (15 mL) and brine (15 mL), dried over Na2S04. The solvent was evaporated and the residue was purified by flash chromatography using CH2Cl2-MeOH to afford YK-4-250 as a pink soft solid (0.81 g, 78%). LC-MS (ESI): m/z 669 (M+H)+; HRMS (TOF): calculated for C42H47N503 (M+H)+: 669.3679; Found: 669.3578.
78%	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 48h;Cooling with ice;	Conjugation of <strong>[144701-48-4]Telmisartan</strong> with Tempol (YK-4-250). (0206) (0207) To an ice bath cooled solution of telmisartan (0.8 g, 1.55 mmol) in DMF (50 mL) was added 1-hydroxybenzotriazole (HOBt, 0.25 g, 1.87 mmol), 4-dimethylamino pyridine (DMAP, 0.23 g, 1.87 mmol), and l -(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 0.39 g, 2.02 mmol), followed by tempol (0.29 g, 1.712 mmol). The mixture was stirred at room temperature for 48 h. Water (15 mL) was added to the mixture and stirred at room temperature for 10 minutes. The mixture was extracted with ethyl acetate (3 x 15 mL). The organic layer was washed with sat. LiCl (15 mL), sat. NaHCCb (15 mL), water (15 mL) and brine (15 mL), dried over Na2S04. The solvent was evaporated and the residue was purified by flash chromatography using CH2Cl2-MeOH to afford YK-4-250 as a pink soft solid (0.81 g, 78%). LC-MS (ESI): m/z 669 (M+H)+; HRMS (TOF): calculated for C42H47N5O3 (M+H)+: 669.3679; Found: 669.3578.

Reference： [1]Patent: WO2011/35110,2011,A2 .Location in patent: Page/Page column 40-41
[2]Patent: WO2017/173308,2017,A1 .Location in patent: Page/Page column 32

49
[ 2226-96-2 ]
[ 53-86-1 ]
2,2,6,6-tetramethylpiperidine-1-oxyl-4-yl 2-[1-(4-chlorbenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;
84%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	1 Dicyclohexyl carbodiimide (DCC, 1.32 g, 6.4 mmol) was added to a solution of indomethacin (2.08 g, 5.8 mmol), 4-hydroxy-TEMPO (1 g, 5.8 mmol) and DMAP (0.16 g, 5.8 mmol) in CH2Cl2 (45 mL) at 0° C. The mixture was allowed to warm to room temperature (rt) and stirred overnight. The solvent was evaporated in vacuum and the residue was purified by silica gel chromatography (hexanes:EtOAc 7:3, Rf=0.36) to give an orange solid (2.3 g, 84%). 1H NMR (CDCl3 with 2 drops of TFA-d) 7.69 (d, 2H, J=8.7 Hz), 7.55 (d, 2H, J=8.4 Hz), 6.8-7.4 (m, 3H), 5.32 (bt, 1H, J=11.4), 3.95 (s, 3H), 3.82 (s, 2H), 2.38 (s, 3H), 2.35-2.1 (m, 4H), 1.56 (s, 6H), 1.49 (s, 6H); 13C NMR 174.08, 172.13, 155.83, 141.34, 137.83, 132.81, 132.06, 130.18, 120.74, 116.97, 116.20, 113.41, 113.03, 109.42, 69.81, 66.18, 57.29, 41.65, 30.56, 28.14, 20.47, 13.60; MS: m/z 512 [M+]; Anal. Calcd. For C28H32ClN2O5: C, 65.68; H, 6.30; N, 5.47. Found: C, 66.28; H, 6.52; N, 5.38.
73%	With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 26h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Flores-Santana, Wilmarie; Moody, Terry; Chen, Weibin; Gorczynski, Michael J.; Shoman, Mai E.; Velazquez, Carlos; Thetford, Angela; Mitchell, James B.; Cherukuri, Murali K.; King, S Bruce; Wink, David A. [British Journal of Pharmacology, 2012, vol. 165, # 4 B, p. 1058 - 1067]
[2]Current Patent Assignee: WAKE FOREST UNIVERSITY; GOVERNMENT OF THE UNITED STATES - US2012/263650, 2012, A1 Location in patent: Page/Page column 10-11
[3]Hauenschild, Till; Reichenwallner, Jörg; Enkelmann, Volker; Hinderberger, Dariush [Chemistry - A European Journal, 2016, vol. 22, # 36, p. 12825 - 12838]

50
[ 2226-96-2 ]
[ 5538-51-2 ]
2,2,6,6-tetramethylpiperidine-1-oxyl-4-yl 2-(acetyloxy) benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
48%	With pyridine In dichloromethane at 0 - 20℃;	1 Pyridine (0.45 mL, 5.50 mmol) was added to a solution of 4-hydroxy-TEMPO (0.86 g, 5.00 mmol), and acetylsalicyloyl chloride (1.09 g, 5.50 mmol) in CH2Cl2 (6 mL) at 0° C. The solution was stirred at room temperature overnight and the precipitate was removed by filtration. The filtrate was washed with water (6 mL), 10% aq. NaHCO3 (10 mL), 2 M aq. HCl (10 mL), and water (6 mL). The CH2Cl2 was dried, filtered, concentrated, and purified by silica gel chromatography (7:3 hexanes:EtOAc, Rf=0.39) to give an orange oil (0.8 g, 48%). 1H NMR (CDCl3 with 2 drops of TFA-d) 7.96 (d, 1H, J=7.0 Hz), 7.60 (t, 1H, J=7.1 Hz), 7.33 (d, 1H, J=7.5), 7.19 (d, 1H, J=7.5 Hz), 5.44 (bt, 1H, J=11.7 Hz), 2.37 (s, 3H), 2.42-2.00 (m, 4H), 1.54 (s, 6H), 1.46 (s, 6H); 13C NMR 169.8, 163.36, 150.96, 134.59, 131.66, 126.25, 123.98, 122.68, 67.37, 63.94, 41.74, 27.77, 20.7; MS: m/z, 335 [M+1]; Anal. Calcd. For C18H24NO5: C, 64.65; H, 7.23; N, 4.19. Found: C, 64.73; H, 7.35; N, 4.20.

Reference： [1]Location in patent: experimental part Flores-Santana, Wilmarie; Moody, Terry; Chen, Weibin; Gorczynski, Michael J.; Shoman, Mai E.; Velazquez, Carlos; Thetford, Angela; Mitchell, James B.; Cherukuri, Murali K.; King, S Bruce; Wink, David A. [British Journal of Pharmacology, 2012, vol. 165, # 4 B, p. 1058 - 1067]
[2]Current Patent Assignee: WAKE FOREST UNIVERSITY; GOVERNMENT OF THE UNITED STATES - US2012/263650, 2012, A1 Location in patent: Page/Page column 10

51
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
49%	With triethylamine In toluene at 20 - 70℃; for 20h;
	With triethylamine In toluene

Reference： [1]Hyslop, David K.; Parent, J. Scott [Macromolecules, 2012, vol. 45, # 20, p. 8147 - 8154]
[2]Location in patent: experimental part Lopez-Penna, Hugo A.; Hernandez-Munnoz, Lindsay S.; Frontana-Uribe, Bernardo A.; Gonzalez, Felipe J.; Gonzalez, Ignacio; Frontana, Carlos; Cardoso, Judith [Journal of Physical Chemistry B, 2012, vol. 116, # 18, p. 5542 - 5550]

52
[ 2226-96-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; dmap; triethylamine In dichloromethane; water; acetonitrile	S.2 Synthesis of bis(2,2,6,6-tetramethylpiperidin-1-oxyl-4-yl)decanedioate (Substance Example 4) Synthesis Example 2 Synthesis of bis(2,2,6,6-tetramethylpiperidin-1-oxyl-4-yl)decanedioate (Substance Example 4) 28.5 g (166 mmol) of 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl (free radical) and 250 mg (2.05 mmol) of 4-(dimethylamino)pyridine are dissolved in 300 ml of degassed dichloromethane, and 50.0 ml (361 mmol) of triethylamine are added. The mixture is subsequently degassed and cooled to 0° C., and 10 g (41.4 mmol) of sebacoyl chloride dissolved in 100 ml of degassed dichloromethane are added dropwise at 0-5° C., and the mixture is stirred at room temperature for 18 h. When the reaction is complete, water and HCl (pH=4-5) are added with ice-cooling, and the mixture is stirred for a further 30 min. The organic phase is separated off, and the water phase is subsequently extracted with dichloromethane, and the combined phases are washed with saturated NaCl solution and dried over Na2SO4, filtered and evaporated, giving 24.4 g of a red liquid, which together are passed through 100 g of basic Al2O3 and 500 g of silica gel on a frit with dichloromethane/methyl tert-butyl ether (95/5), giving orange crystals, which are dissolved in degassed acetonitrile at 50° C. and crystallized at -25° C., giving the product as orange crystals having an HPLC purity of 99.9%.

Reference： [1]Current Patent Assignee: MERCK KGAA - US2012/268706, 2012, A1

53
[ 2226-96-2 ]
[ 814-68-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In benzene at 20℃;
	With triethylamine In toluene at 20℃; for 16h;

Reference： [1]Zakrzewski, Jerzy [Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1515 - 1522]
[2]Hyslop, David K.; Parent, J. Scott [Macromolecules, 2012, vol. 45, # 20, p. 8147 - 8154]

54
[ 2226-96-2 ]
[ 10487-71-5 ]
[ 116446-54-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine In toluene at 70℃; for 3h;

Reference： [1]Hyslop, David K.; Parent, J. Scott [Macromolecules, 2012, vol. 45, # 20, p. 8147 - 8154]

55
[ 2226-96-2 ]
[ 106-89-8 ]
[ 122413-85-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 30℃; for 4h;	2.3 Synthesis of GTEMPO General procedure: A mixture of 90% (w/w) aqueous sodium hydroxide (1.856 g NaOH/2.1 mL H2O), ECH (18 mL), 4-OH-TEMPO (2 g, 11.63 mmol) and TBAHS (0.23 g, 0.68 mmol) was added to a 150 mL flask. After stirring at 30 °C for 4 h, the mixture was poured into ice water (100 mL), and the aqueous phase was extracted with diethyl ether (3×50 mL). The organic phase was washed with cooled water to neutrality, dried with NaSO4, and filtered. Then, diethyl ether was concentrated under vacuum and purified by column chromatography (silica gel) eluting with 4:5 hexane-ethyl acetate (v/v) to obtain primrose red-orange liquid with a yield of 80.0%. 1H NMR (400 MHz, MeOD4, 25 °C, in the presence of calculated amount of HCOONH4 and Pd/C, Electronic Supplementary Material, Fig.S1): 1.16, 1.19, 1.42, 1.96, and 3.12 (complex, 17H, CH3, CH2, and CH of the TEMPO group), 2.62 (dd, 1H methylene CH of the oxirane ring), 2.80 (t, 1H methylene CH of the oxirane ring), 3.34 (MeOD4), 3.39 (m, 1H methylene CH of the oxirane ring), 3.67-3.76 (m, 1H methylene CH of the glycidyl ring), 3.79-3.83 (m, 1H methylene CH of the glycidyl ring), 4.89 (assigned to water in MeOD4 and Pd/C), 8.56 (HCOO- of HCOONH4). FTIR (KBr/cm-1, Electronic Supplementary Material, Fig.S2): 2996, 2976, 2939, 2901, 2869, 2833, 1462, 1376, 1364, 1242, 1177, 1095, 991, 914, 857, 767. Mass spectrum (Electronic Supplementary Material, Fig.S3) for C12H22O3N [M+1]+ 229.16; found 229.2. Element analysis: Anal. Calcd. for C12H22O3N: C, 63.2%; H, 9.6%; N, 6.1%. Found: C, 62.6%; H, 9.6%; N, 6.0%
	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 20℃;

Reference： [1]Zhang, Ze Ping; Rong, Min Zhi; Zhang, Ming Qiu [Polymer, 2014, vol. 55, # 16, p. 3936 - 3943]
[2]Yau, Wai-Ming; Thurber, Kent R.; Tycko, Robert [Journal of Magnetic Resonance, 2014, vol. 244, p. 98 - 106]

56
[ 2226-96-2 ]
[ 536-74-3 ]
[ 1639016-00-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tert.-butylnitrite In tetrahydrofuran at 70℃; for 24h; stereoselective reaction;

Reference： [1]Yan, Hong; Rong, Guangwei; Liu, Defu; Zheng, Yang; Chen, Jie; Mao, Jincheng [Organic Letters, 2014, vol. 16, # 24, p. 6306 - 6309]

57
[ 2226-96-2 ]
[ 614-27-7 ]
C₁₉H₂₇NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With copper dichloride In acetonitrile at 80℃; for 23h;	4.2. General procedure for preparation of compounds 2, 4,and 6 General procedure: TEMPO or its derivative (0.65 mmol) was added to a solution of carbonyl compounds 1 or 3 (0.5 mmol) and CuCl2 (0.05 mmol) in CH3CN (1.0 mL) at room temperature, and the mixture was stirred at 80 °C until the reaction was complete as judged by TLC.The resulting mixture was then purified by column chromatography on 100-200 mesh silica gel to afford pure compounds 2, 4 or 6.

Reference： [1]Luo, Xiaoyan; Wang, Zheng-Lin; Jin, Jing-Hai; An, Xing-Lan; Shen, Zhenlu; Deng, Wei-Ping [Tetrahedron, 2014, vol. 70, # 44, p. 8226 - 8230]

58
[ 2226-96-2 ]
[ 5089-70-3 ]
3-(4-oxy-TEMPO)propyl-triethoxysilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tempol With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: (3-chloropropyl)triethoxysilane In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	2 2.2.2 Synthesis of 3-(4-oxy-TEMPO)propyl-triethoxysilane The reactions were carried out in nitrogen (N2) atmosphere. Sodium hydride (0.2758 g, 6.9 mmol) was suspended in dry THF (20 mL) cooled in an ice-bath. A separately prepared 4-hydroxy-TEMPO (1.0 g, 5.8 mmol) solution in 5 mL dry THF was added dropwise in the cold NaH slurry. The mixture was brought to room temperature (RT) and stirred to facilitate the reaction. After complete gas evolution, the mixture was re-cooled at 0 °C and CPTES (1.6615 g, 6.9 mmol) was added dropwise. The reaction was continued at room temperature for another 48 h (Scheme 1). The crude product was retrieved by solvent evaporation under reduced pressure. To precipitate the impurities, the oily product was dissolved in diethyl ether. The filtered diethyl ether was dried over sodium sulfateand then re-filtered. The solvent was removed in a rotary evaporator to obtain the pure dark oily orange 3-(4-oxy-TEMPO)propyl-triethoxysilane (denoted as PTES-TEMPO).

Reference： [1]Mittal, Neha; Nisola, Grace M.; Seo, Jeong Gil; Lee, Seong-Poong; Chung, Wook-Jin [Journal of Molecular Catalysis A: Chemical, 2015, vol. 404-405, p. 106 - 114]

59
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With 1-butyl-3-methylimidazolium Tetrafluoroborate at 110℃; for 72h;	Synthesis of Nap-(CH2)2-O-TEMPO 4-HydroxyTEMPO (4.3 g, 25 mmol) and 6 (235 mg, 1 mmol) wereadded to a reaction vessel containing 2 ml 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid([Bmim] [BF4]). The resulting mixture was then heatedat 110 ° C for 3 days. The solution was then cooled toroom temperature and diluted with water (30 ml) andextracted with ethyl acetate (3×50 ml). The combinedorganic layers were dried with anhydrous sodium sulphate(15 g), filtered, concentrated and purified by columnchromatography using 0 to 10 % ethyl acetate/hexane as the eluent to yield an orange solid (<1 %). 1HNMR δ (CD3OD): 7.78 (m, 4H), 7.44 (m, 3H), 3.73 (t,2H), 3.58 (m, 1H), 3.03 (t, 2H), 1.93 (br-d, 2H), 1.52 (t,2H), 1.23 (m, 6H), 1.13 (m, 6H).

Reference： [1]Rane, Vinayak; Kundu, Sushma; Das, Ranjan [Journal of Fluorescence, 2015, vol. 25, # 5, p. 1351 - 1361]

60
[ 2226-96-2 ]
[ 939-26-4 ]
[ 1627678-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tempol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-bromomethylnaphthyl bromide In tetrahydrofuran at 20℃; for 24h;	Synthesis of Nap-CH2-O-TEMPO This moleculewas synthesized by following the protocol developed byDr Amol Deorukhkar in our laboratory. 4-hydroxy TEMPO(1.72 g, 10 mmol) was dissolved in 10 ml of dry THFand cooled to 0 °C. Sodium hydride (0.29 g, 12 mmol)was added gradually with constant stirring. The reactionwas stirred for 30 min at low temperature, followed byaddition of 2-bromo methylnaphthalene (2.2 g, 10mmol).The reaction mixture was then warmed to room temperatureand stirred until completion (1 day), as monitoredby TLC. The reaction mixture was diluted with water(30 ml). The resulting solution was extracted with ethylacetate (3×50 ml). The combined organic layers weredried with anhydrous sodium sulphate (15 g), filtered,concentrated and purified by column chromatographyusing 0 to 10 % ethyl acetate/hexane as the eluent toprovide an orange solid powder of Nap-CH2-O-TEMPO(m.p. 82-85 °C). 1H NMR δ (CD3OD): 7.85 (m, 4H),7.48 (br-s, 3H), 4.71 (s, 1H), 3.82 (br-s, 1H), 2.12 (d,2H), 1.80 (m, 2H), 1.36 (m, 6H), 1.25 (m, 6H).

Reference： [1]Rane, Vinayak; Kundu, Sushma; Das, Ranjan [Journal of Fluorescence, 2015, vol. 25, # 5, p. 1351 - 1361]

61
[ 2226-96-2 ]
[ CAS Unavailable ]
[ 1782096-26-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tempol With tetrabutylammomium bromide; potassium hydroxide In acetonitrile at 20℃; for 1h; Stage #2: C₁₇H₂₁BrO In acetonitrile for 24h; Inert atmosphere;	Synthesis of Nap-CH2-O-(CH2)6-O-TEMPO 4-hydroxy TEMPO (0.86 g, 5 mmol) was dissolved in12 ml acetonitrile. Tetrabutylammonium bromide(0.1 g) was then added followed by the addition of potassiumhydroxide (1.4 g, 25 mmol) at room temperature.The resulting mixture was stirred for 1 h and then 2 (1.6 g,5 mmol) was added. The solution was stirred under nitrogenatmosphere for 1 day. The reaction mixture wasthen diluted with water (30 ml) and extracted with ethylacetate (3×50 ml). The combined organic layers weredried with anhydrous sodium sulphate, filtered, concentratedand purified by column chromatography using 0 to10%ethyl acetate/hexane as the eluent to yield an orange solid powder of Nap-CH2-O-(CH2)6-O-TEMPO. 1HNMR δ (CD3OD): 7.80 (m, 4H), 7.47 (br-s, 3H), 4.66(s, 2H), 3.56 (s, 1H), 3.51 (t, 2H), 3.41 (t, 2H), 1.93 (d,2H), 1.66 (m, 2H), 1.57 (m, 2H), 1.50 (m, 2H), 1.40 (m,4H), 1.23 (m, 6H), 1.18 (m, 6H).

Reference： [1]Rane, Vinayak; Kundu, Sushma; Das, Ranjan [Journal of Fluorescence, 2015, vol. 25, # 5, p. 1351 - 1361]

62
[ 2226-96-2 ]
[ CAS Unavailable ]
[ 1782096-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tempol With potassium <i>tert</i>-butylate In acetonitrile at 0℃; for 1h; Stage #2: C₁₅H₁₇BrO In acetonitrile at 20℃; for 24h;	Synthesis of Nap-CH2-O-(CH2)4-O-TEMPO 4-hydroxy TEMPO (1.7 g, 10 mmol) was dissolved in25 ml acetonitrile and cooled to 0 °C. Potassium tertbutoxide(2 g, 18 mmol) was added to it over a periodof 10 min. The reaction mixture was stirred for furtherone hour and then 4 was added. The solution was warmedto room temperature and was stirred under nitrogen atmospherefor 1 day. The reaction mixture was then dilutedwith water (30 ml) and extracted with ethyl acetate(3×50 ml). The combined organic layers were dried withanhydrous sodium sulphate (15 g), filtered, concentratedand purified by column chromatography using 0 to 10 %ethyl acetate/hexane as the eluent to yield an oily orangeliquid. 1H NMR δ (CD3OD): 7.82 (m, 4H), 7.48 (br-s,3H), 4.71 (s, 2H), 3.59 (s, 1H), 3.54 (t, 2H), 3.45 (t, 2H),1.94 (d, 2H), 1.69 (m, 4H), 1.52 (m, 2H), 1.24 (m, 6H),1.18 (m, 6H).

Reference： [1]Rane, Vinayak; Kundu, Sushma; Das, Ranjan [Journal of Fluorescence, 2015, vol. 25, # 5, p. 1351 - 1361]

63
[ 2226-96-2 ]
[ 141-75-3 ]
[ 21270-96-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With pyridine In diethyl ether at 0 - 20℃; for 3.08333h;	2.2.1. General procedure for the preparation of 4-acyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl radicals 1-6 General procedure: To a stirred solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (Aldrich) (0.8 g, 4.65 mmol) and pyridine (0.37 g,4.65 mmol) dissolved in Et2O (15 mL) was added dropwise the corresponding acyl chloride (5.12 mmol) in Et2O (5 mL) at 0 °C. Once the addition was completed the stirring was continued for 5 min and then the mixture was allowed to warm to room temperature, stirring for an additional 3 h. The red solution was washed with an aqueous solution of NaHCO3 5% (6 x 20 mL) and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated under vacuum to afford a crude red oil, which was purified by column chromatography (n-hexane/ethyl acetate = 9/1). With the exception of compound 1, all other TEMPO derivatives were isolated as oils. Characterization of all compounds was achieved by their IR and NMR spectra. The latter (1H and 13C) revealed only the presence of the 4-acyloxy substituent in the TEMPO derivatives, due to the paramagnetic nature of the piperidine-N-oxyl moiety. All signals in the 1H NMR spectra of these compounds appeared as uncoupled singlets, integrating normally. In a few instances, signal superpositions were observed in the 13C NMR spectra of the TEMPO derivatives, easily detected by their larger intensities.

Reference： [1]Aliaga, Carolina; Bravo-Moraga, Felipe; Gonzalez-Nilo, Danilo; Márquez, Sebastián; Lühr, Susan; Mena, Geraldine; Rezende, Marcos Caroli [Food Chemistry, 2016, vol. 192, p. 395 - 401]

64
[ 2226-96-2 ]
[ 142-61-0 ]
[ 56240-96-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With pyridine In diethyl ether at 0 - 20℃; for 3.08333h;	2.2.1. General procedure for the preparation of 4-acyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl radicals 1-6 General procedure: To a stirred solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (Aldrich) (0.8 g, 4.65 mmol) and pyridine (0.37 g,4.65 mmol) dissolved in Et2O (15 mL) was added dropwise the corresponding acyl chloride (5.12 mmol) in Et2O (5 mL) at 0 °C. Once the addition was completed the stirring was continued for 5 min and then the mixture was allowed to warm to room temperature, stirring for an additional 3 h. The red solution was washed with an aqueous solution of NaHCO3 5% (6 x 20 mL) and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated under vacuum to afford a crude red oil, which was purified by column chromatography (n-hexane/ethyl acetate = 9/1). With the exception of compound 1, all other TEMPO derivatives were isolated as oils. Characterization of all compounds was achieved by their IR and NMR spectra. The latter (1H and 13C) revealed only the presence of the 4-acyloxy substituent in the TEMPO derivatives, due to the paramagnetic nature of the piperidine-N-oxyl moiety. All signals in the 1H NMR spectra of these compounds appeared as uncoupled singlets, integrating normally. In a few instances, signal superpositions were observed in the 13C NMR spectra of the TEMPO derivatives, easily detected by their larger intensities.

Reference： [1]Aliaga, Carolina; Bravo-Moraga, Felipe; Gonzalez-Nilo, Danilo; Márquez, Sebastián; Lühr, Susan; Mena, Geraldine; Rezende, Marcos Caroli [Food Chemistry, 2016, vol. 192, p. 395 - 401]

65
[ 2226-96-2 ]
[ 111-64-8 ]
[ 22491-88-9 ]

Yield	Reaction Conditions	Operation in experiment
59%	With pyridine In diethyl ether at 0 - 20℃; for 3.08333h;	2.2.1. General procedure for the preparation of 4-acyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl radicals 1-6 General procedure: To a stirred solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (Aldrich) (0.8 g, 4.65 mmol) and pyridine (0.37 g,4.65 mmol) dissolved in Et2O (15 mL) was added dropwise the corresponding acyl chloride (5.12 mmol) in Et2O (5 mL) at 0 °C. Once the addition was completed the stirring was continued for 5 min and then the mixture was allowed to warm to room temperature, stirring for an additional 3 h. The red solution was washed with an aqueous solution of NaHCO3 5% (6 x 20 mL) and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated under vacuum to afford a crude red oil, which was purified by column chromatography (n-hexane/ethyl acetate = 9/1). With the exception of compound 1, all other TEMPO derivatives were isolated as oils. Characterization of all compounds was achieved by their IR and NMR spectra. The latter (1H and 13C) revealed only the presence of the 4-acyloxy substituent in the TEMPO derivatives, due to the paramagnetic nature of the piperidine-N-oxyl moiety. All signals in the 1H NMR spectra of these compounds appeared as uncoupled singlets, integrating normally. In a few instances, signal superpositions were observed in the 13C NMR spectra of the TEMPO derivatives, easily detected by their larger intensities.

Reference： [1]Aliaga, Carolina; Bravo-Moraga, Felipe; Gonzalez-Nilo, Danilo; Márquez, Sebastián; Lühr, Susan; Mena, Geraldine; Rezende, Marcos Caroli [Food Chemistry, 2016, vol. 192, p. 395 - 401]

66
[ 2226-96-2 ]
[ 112-13-0 ]
[ 35203-69-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine In diethyl ether at 0 - 20℃; for 3.08333h;	2.2.1. General procedure for the preparation of 4-acyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl radicals 1-6 General procedure: To a stirred solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (Aldrich) (0.8 g, 4.65 mmol) and pyridine (0.37 g,4.65 mmol) dissolved in Et2O (15 mL) was added dropwise the corresponding acyl chloride (5.12 mmol) in Et2O (5 mL) at 0 °C. Once the addition was completed the stirring was continued for 5 min and then the mixture was allowed to warm to room temperature, stirring for an additional 3 h. The red solution was washed with an aqueous solution of NaHCO3 5% (6 x 20 mL) and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated under vacuum to afford a crude red oil, which was purified by column chromatography (n-hexane/ethyl acetate = 9/1). With the exception of compound 1, all other TEMPO derivatives were isolated as oils. Characterization of all compounds was achieved by their IR and NMR spectra. The latter (1H and 13C) revealed only the presence of the 4-acyloxy substituent in the TEMPO derivatives, due to the paramagnetic nature of the piperidine-N-oxyl moiety. All signals in the 1H NMR spectra of these compounds appeared as uncoupled singlets, integrating normally. In a few instances, signal superpositions were observed in the 13C NMR spectra of the TEMPO derivatives, easily detected by their larger intensities.

Reference： [1]Aliaga, Carolina; Bravo-Moraga, Felipe; Gonzalez-Nilo, Danilo; Márquez, Sebastián; Lühr, Susan; Mena, Geraldine; Rezende, Marcos Caroli [Food Chemistry, 2016, vol. 192, p. 395 - 401]

67
[ 2226-96-2 ]
[ 75-36-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
65%	With pyridine In diethyl ether at 0 - 20℃; for 3.08333h;	2.2.1. General procedure for the preparation of 4-acyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl radicals 1-6 General procedure: To a stirred solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (Aldrich) (0.8 g, 4.65 mmol) and pyridine (0.37 g,4.65 mmol) dissolved in Et2O (15 mL) was added dropwise the corresponding acyl chloride (5.12 mmol) in Et2O (5 mL) at 0 °C. Once the addition was completed the stirring was continued for 5 min and then the mixture was allowed to warm to room temperature, stirring for an additional 3 h. The red solution was washed with an aqueous solution of NaHCO3 5% (6 x 20 mL) and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated under vacuum to afford a crude red oil, which was purified by column chromatography (n-hexane/ethyl acetate = 9/1). With the exception of compound 1, all other TEMPO derivatives were isolated as oils. Characterization of all compounds was achieved by their IR and NMR spectra. The latter (1H and 13C) revealed only the presence of the 4-acyloxy substituent in the TEMPO derivatives, due to the paramagnetic nature of the piperidine-N-oxyl moiety. All signals in the 1H NMR spectra of these compounds appeared as uncoupled singlets, integrating normally. In a few instances, signal superpositions were observed in the 13C NMR spectra of the TEMPO derivatives, easily detected by their larger intensities.

Reference： [1]Aliaga, Carolina; Bravo-Moraga, Felipe; Gonzalez-Nilo, Danilo; Márquez, Sebastián; Lühr, Susan; Mena, Geraldine; Rezende, Marcos Caroli [Food Chemistry, 2016, vol. 192, p. 395 - 401]

68
[ 2226-96-2 ]
[ 1860843-59-9 ]
[ 1860888-39-6 ]

Yield	Reaction Conditions	Operation in experiment
1.36 g	With triethylamine In toluene at 70℃; for 8h;	2.2. Synthesis of adamantyl nitroxide derivatives (4) To a solution of compound 2 (2.70 g, 11 mmol) in THF (20 mL)was added thionyl chloride (3.6 mL, 50 mmol) and two drops ofN,N-dimethylformamide as catalyst. The reaction mixture wasrefluxed for 3 h and solvents were evaporated. Subsequently theacyl chloride intermediate 3 was added to a stirred solution of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (Tempol, 2.07 g,12 mmol) and triethylamine (1.6 mL, 12 mmol) in toluene (50 mL).The resulting mixture was stirred for 8 h at 70 C. After consumptionof the starting material the mixture was washed with water(6 50 mL), dried over MgSO4, concentrated. The crude materialwas purified by flash column chromatography (petroleum ether/EtOAc) to yield the title compound 4 as an orange solid 1.36 g. M.p.56e58 C; UV/vis (MeOH), lmax: 240 nm; IR (KBr, cm1): 3128(CeH), 1717 (C]O), 1400 (NeO), 1104 (CeO); MS (ESI) m/z (%):407.64 [MH]; Anal. calc. for C23H36NO5: C, 67.95; H, 8.93; N, 3.45.Found: C, 68.13; H, 8.91; N, 3.44.

Reference： [1]Zhu, Xiao-He; Sun, Jin; Wang, Shan; Bu, Wei; Yao, Min-Na; Gao, Kai; Song, Ying; Zhao, Jin-Yi; Lu, Cheng-Tao; Zhang, En-Hu; Yang, Zhi-Fu; Wen, Ai-Dong [Journal of Molecular Structure, 2016, vol. 1108, p. 611 - 617]

69
[ 2226-96-2 ]
[ 5089-70-3 ]
3-(4-oxy-TEMPO)propyltriethoxysilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 48h; Inert atmosphere;	Preparation of 3- (4-oxy-TEMPO) propyl-triethoxysilane The reaction was carried out in a nitrogen atmosphere. Sodium hydride (0.2758 g, 6.9 mmol) was added to the ice- (20 mL) cooled in an ice-bath. A solution of 4-hydroxy-TEMPO (1.0 g, 5.8 mmol) in 5 mL dry THF was prepared and added dropwise to a cold NaH slurry. The mixture was stirred at room temperature to promote the reaction. After completing the gas evolution, the mixture was re-cooled at 0 ° C and CPTES (3- (chloro) propyl-triethoxysilane, 1.6615 g, 6.9 mmol) was added dropwise. The reaction was further allowed to proceed at room temperature for 48 hours. The crude product was recovered by evaporating the solvent under reduced pressure. The oily product precipitating the impurities was dissolved in diethyl ether. The filtered diethyl ether was dried over sodium sulfate and filtered again. The solvent was removed from the rotary evaporator to obtain pure 3- (4-oxy-TEMPO) propyl-triethoxysilane (hereinafter PTESTEMPO) (oily, dark orange).

Reference： [1]Current Patent Assignee: MYONGJI UNIVERSITY - KR2015/6800, 2015, A Location in patent: Paragraph 0062; 0094; 0095

70
[ 2226-96-2 ]
[ 2277-19-2 ]
(Z)-2,2,6,6-tetramethyl-1-(oct-5-en-1-yloxy)piperidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With dihydrogen peroxide; copper(l) chloride In ethanol at 20℃; for 17h;

Reference： [1]Kipke, Andreas; Schöning, Kai-Uwe; Yusubov, Mekhman; Kirschning, Andreas [European Journal of Organic Chemistry, 2017, vol. 2017, # 46, p. 6906 - 6913]

71
[ 2226-96-2 ]
[ 2182588-05-0 ]
[ 2182588-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tempol With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 40℃; Stage #2: 3-{3-ethyl-4-[3-(methanesulphonyloxy)propyl]phenyl}propyl methanesulphonate In N,N-dimethyl-formamide; paraffin oil at 5 - 30℃; for 48.17h;	I-1.iii Synthesis of 4-[3-(3-ethyl-4-{3-[(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)oxy]propyl}phenyl)propoxy]-2,2,6,6-tetramethylpiperidin-1-oxyl (free radical) (4) To 6.20 g (155 mmol) of sodium hydride (60% in paraffin oil) at room temperature (RT) are cautiously added 50 ml of N,N-dimethylformamide (DMF), and the mixture is heated to 40° C. At this temperature, a solution of 27.0 g (157 mmol) of 4-hydroxy-TEMPO (free-radical) is added dropwise (gentle evolution of hydrogen gas). On completion of addition and after evolution of gas has ended, the mixture is stirred at 40° C. for another 2 hours and then cooled down to room temperature. Then a solution of 23.6 g (62.4 mmol) of mesylate 3 in 100 ml of DMF is added within 10 min (the temperature rises here by 5° C. to 30° C.) and then the mixture is stirred at room temperature for 48 h. The reaction solution is cautiously poured onto ice-water and extracted with MTB ether. The phases are separated and the water phase is extracted with MTB ether. The organic phases are combined, dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product is obtained as a red oil and is filtered through 1.3 l of silica gel with a mixture of heptane (H)/ethyl acetate (EA) (2:1). The product fractions are concentrated under reduced pressure and the product is obtained as a red solid. The mixture is filtered once again through 1 l of silica gel with H:EA (3:1 to 2:1), and the product obtained is crystallized from 250 ml of heptane and 10 ml of ethanol at -20° C. The product is obtained as an orange solid.

Reference： [1]Current Patent Assignee: MERCK KGAA - US2018/37820, 2018, A1 Location in patent: Paragraph 0287-0289

72
[ 2226-96-2 ]
[ 97410-02-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
91%	In hexane; dichloromethane at 60℃; for 0.333333h;	Preparation of [(1)Cu(hfac)2]n (4) General procedure: A solution of radical 1 (17.0 mg, 1 mmol) in CH2Cl2(2 mL) was added to a stirred solution of cis-CuII(hfac)2(H2O)2 (51.3 mg, 1 mmol) in hot n-hexane(20 mL). The mixture was stirred at 50-60 °C for 20 min,then cooled to room temperature and filtered. The filtratewas kept under air at room temperature for several daysto give crystals which were suitable for X-ray analysis.Green crystals of complex 4 in 57.7 mg (89%) yield wereobtained.

Reference： [1]Gao, Yan-Li; Inoue, Katsuya [Transition Metal Chemistry, 2019]

73
[ 4480-83-5 ]
[ 2226-96-2 ]
2-(2-((1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)oxy)-2-oxoethoxy)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	8 2.3.8. synthesis of digly-TEMPO (2-(2-((1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)oxy)-2-oxoethoxy)acetic acid) A solution of 4-hydroxy-TEMPO (1.0 g, 5.80 mmol), diglycolic anhydride (1.68 g, 14.5 mmol) and triethylamine (4.04 mL, 29.0 mmol) in DCM (20 mL) was stirred 4 h at room temperature under argon atmosphere. The mixture was then washed with 1 M HCl and brine before being dried over MgSO4. The residue was concentrated under reduced pressure to give 1.30 g of Digly-AMA-SG1 as a sticky solid. Yield = 77%. 1H NMR (300 MHz, CDCl3): δ 5.20 (m, 1H), 4.18 (s, 2H), 4.11 (s, 2H), 2.18 (d, 2H), 1.99 (t, 2H), 1.41 (s, 6H), 1.37 (s, 6H). MS (ESI-): m/z = 288.2 (M)+. Calc. for C13H22NO6: 288.1.

Reference： [1]Vinciguerra, Daniele; Jacobs, Merel; Denis, Stéphanie; Mougin, Julie; Guillaneuf, Yohann; Lazzari, Gianpiero; Zhu, Chen; Mura, Simona; Couvreur, Patrick; Nicolas, Julien [Journal of Controlled Release, 2019, vol. 295, p. 223 - 236]

74
[ 2226-96-2 ]
[ 15486-96-1 ]
[ 15051-46-4 ]

Yield	Reaction Conditions	Operation in experiment
4.2 g	With dmap; triethylamine In dichloromethane at 2 - 20℃;	Synthesis Example Compound RH-2 was prepared as follows. 4-hydroxy TEMPO (8.00 g, 45.5 mmol)And 4-(dimethylamino)pyridine (0.30 g, 2.46 mmol) was added to 100 ml DCM.After cooling to 2 ° C,Add triethylamine (25.00 ml, 180.35 mmol) to the above solution,3-Bromo-propionyl chloride (6.00 ml, 50.6 mmol) was then added dropwise to 50 ml DCM. After the addition was completed, the reaction mixture was allowed to warm to room temperature.After completion of the conversion indicated by TLC, an aqueous ammonium chloride solution was added.The aqueous phase was extracted with DCM. The organics were combined and dried over anhydrous sodium sulfate and filtered.After removing the solvent in a vacuum,Purification of the solid residue by gel column chromatography using DCM/methyl tert-butyl ether (MTBE) 95:5 as the dissolving agent.And further recrystallized from heptane/MTBE to obtain 3 crystals in red(4.2 g).

Reference： [1]Current Patent Assignee: MERCK KGAA - TW2018/40535, 2018, A Location in patent: Page/Page column 93

75
[ 2226-96-2 ]
[ 31643-49-9 ]
[ 1863947-45-8 ]

Yield	Reaction Conditions	Operation in experiment
4.85 g	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.666667h; Inert atmosphere;	Synthesis of 4-TEMPO-phthalonitrile In one iteration, 50 mL of dry DMF was degassed vigorously by bubbling nitrogen for 20minutes. Under nitrogen atmosphere the reagents of 4-nitrophthalonitrel (3.001 g) and 4-hydroxy-TEMPO (3.401 g) were added followed by 10 grams of K2CO3. TEMPO is easier toremove in the end of the reaction and is recommended to be in an excess. The mixture wascontinued to be degassed for an additional 40 minutes at room temperature and then held underpositive nitrogen pressure and room temperature with stirring. The reaction proceeds slowly andwas monitored over the course of 2 days via TLC using a 50:50 hexane:ethylacetate mixtureuntil complete. Once finished, 100 mL of DI water was added to the DMF which caused theproduct to precipitate. The mixture was left to sit for 3 hours, and then vacuum filtered. The offwhitesolid was washed with 2 liters of DI water in aliquots to remove the DMF and potassiumcarbonate. The solid was then dissolved in chloroform and passed through a clean fritted filterand the solvent was removed with rotary evaporation. The recovered light reddish solid wasdried in a vacuum oven for 24 hours at 35 Celsius. The recovered mass was 4.85 g.

Reference： [1]Anderson, Scott L.; Cass, Ashley C.; Klunder, Kevin J.; Minteer, Shelley D. [Synlett, 2019, vol. 30, # 10, p. 1187 - 1193]

76
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
47.4 g	With tert.-butylhydroperoxide; copper(II) choride dihydrate In ethanol at 65℃; for 9h;	1 This comparative example provides a method for preparing N-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidinol, which is specifically: Put 0.25mol (43.1g) 4-hydroxy-2,2,6,6-tetramethylpiperidine nitroxide radical, 3.24mol (273g) cyclohexane, 400g absolute ethanol, 10.8g CuCl2·2H2O in sequence Into a 1000mL three-necked flask with mechanical stirring, slowly add 2.4mol (216.3g) tert-butyl hydroperoxide dropwise, after the dropwise addition, heat to 65 and react for 9h. After the reaction is over, distill out ethanol and cyclohexane , Add 200mL deionized water and 350mL chloroform and stir at 30 for 20min, pour it into a separatory funnel and let stand to separate the water phase, wash the oil phase with 150mL×3 deionized water 3 times, and then distill the chloroform to obtain 47.4g product, N- The content of cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidinol is 78.6%

Reference： [1]Current Patent Assignee: RIANLON TIANJIN NEW MATERIAL TECH; RIANLON KAIYA HEBEI NEW MAT - CN112225687, 2021, A Location in patent: Paragraph 0083-0085

77
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
6.3 g	With dihydrogen peroxide; copper dichloride In water; <i>tert</i>-butyl alcohol at 20 - 30℃; for 12.5h;	2 This comparative example provides a method for preparing N-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidinol, which is specifically: 6.8g (39.5mmol) of ZJ-701, 25mL of tert-butanol/water (volume ratio 2:1), 39mg of CuCl2 and 4.42g (39.5mmol) of cyclohexanecarboxaldehyde, keeping the temperature below 30, add 8.9g ( 78.9mmol) After the 30% aqueous hydrogen peroxide solution was added dropwise for about 30 minutes, the reaction was completed by stirring at room temperature for 12 hours, the mixture was extracted with methyl tert-butyl ether, and then the organic phase obtained was sequentially used with 10% ascorbic acid solution and 1N hydroxide Washed with sodium, water and brine, then dried with MgSO4, concentrated in vacuo to obtain 6.9 g of bright green oil with a purity of 90%, and then purified by column chromatography (80g silica gel, hexane/acetone=9:1) to obtain N-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidinol 6.3g, purity 99%.

Reference： [1]Current Patent Assignee: RIANLON TIANJIN NEW MATERIAL TECH; RIANLON KAIYA HEBEI NEW MAT - CN112225687, 2021, A Location in patent: Paragraph 0087-0089

78
[ 2226-96-2 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
6.10 g	Stage #1: tempol; cyclohexene With tetrabutylammomium bromide; 2,2'-bipyridine copper In water at 20℃; for 0.333333h; Stage #2: With dihydrogen peroxide In water at 20 - 40℃; for 10h; Cooling with ice; Stage #3: With 5%-palladium/activated carbon; hydrogen In methanol at 80℃; for 8h;	1.a-5.b This embodiment provides a method for preparing N-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidinol, which is specifically: a. Take 5.00g (29.1mmol) of ZJ-701 and add it to a dry 100mL two-necked round bottom flask with a thermometer at the side and a constant pressure dropping funnel in the middle. Add 30mL water as a solvent, 50mg 2,2'-two Copper bipyridine complex (II) and0.7g tetrabutylammonium bromide (10wt%) is used as a catalyst,Add 9.56g (117mmol) of cyclohexene,Stir at room temperature for 20 minutes, then set up an ice water bath, and slowly add 10 mL of 30% hydrogen peroxide aqueous solution dropwise. After dripping in 1h, continue to stir at room temperature for 1h, slowly warm to 40, and react for 8h; TLC detects the progress of the reaction. After the reaction, it is cooled to room temperature. The reaction solution is diluted with 20mL aqueous solution and extracted with dichloromethane. The phases are washed with saturated sodium carbonate aqueous solution, water, saturated brine in sequence; after drying with anhydrous sodium sulfate; using cyclohexane to recrystallize and filter, the filter cake is dried and recovered, and the mother liquor is vacuumed to remove the solvent to obtain an intermediate. The yield is 6.28 g, the yield was 85.44%.b. Take 5.00g of the intermediate and add it to a 200mL autoclave, add 100mg of 5% Pd/C as a catalyst, 50mL of methanol as the reaction solvent, replace with nitrogen three times, replace with hydrogen three times, and pressurize 3MPa H2, react at 80 4h, maintain the hydrogen pressure during the reaction; after the reaction, after the autoclave is cooled to room temperature, the reaction solution is filtered and concentrated to obtain 6.10g of foamy white solid.The content of N-cyclohexyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidinol is 98%.

Reference： [1]Current Patent Assignee: RIANLON TIANJIN NEW MATERIAL TECH; RIANLON KAIYA HEBEI NEW MAT - CN112225687, 2021, A Location in patent: Paragraph 0040-0058

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	2226-96-2	MDL No. :	MFCD00006478
Formula :	C₉H₁₈NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UZFMOKQJFYMBGY-UHFFFAOYSA-N
M.W :	172.24	Pubchem ID :	137994
Synonyms :	4-Hydroxy-TEMPO	Chemical Name :	2,2,6,6-Tetramethyl-4-hydroxy-1-piperidinyloxy radical

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.94
TPSA :	23.47 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.77 cm/s

Log Po/w (iLOGP) :	-4.26
Log Po/w (XLOGP3) :	0.82
Log Po/w (WLOGP) :	0.96
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	0.47
Consensus Log Po/w :	-0.17

[ CAS No. 2226-96-2 ] {[proInfo.proName]}

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[ 2226-96-2 ] Synthesis Path-Upstream 1~2

[ 2226-96-2 ] Synthesis Path-Downstream 1~78

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.42
Solubility :	6.48 mg/ml ; 0.0376 mol/l
Class :	Very soluble
Log S (Ali) :	-0.89
Solubility :	21.9 mg/ml ; 0.127 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.75
Solubility :	30.9 mg/ml ; 0.179 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 2226-96-2 ] {[proInfo.proName]}

Quality Control of [ 2226-96-2 ]

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Product Details of [ 2226-96-2 ]

Calculated chemistry of [ 2226-96-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 2226-96-2 ]

[ 2226-96-2 ] Synthesis Path-Upstream 1~2

[ 2226-96-2 ] Synthesis Path-Downstream 1~78

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Precautionary Statements-General

Prevention

Response

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[ 2226-96-2 ]