Name: 113305-56-9|4-Iodo-3-nitrophenol|98%
Brand: Ambeed
SKU: A672185
Price: 12.0 USD
Availability: InStock
Rating: 96 (30 reviews)

1
[ 610-81-1 ]
[ 113305-56-9 ]

Yield	Reaction Conditions	Operation in experiment
89%		A solution of NaNO2 (4.759 g, 68.982 mmol) in H2O (12 mL) was added dropwise to a mechanically stirred suspension of <strong>[610-81-1]4-amino-3-nitrophenol</strong> (5.316 g, 34.491 mmol) in concentrated HCl (12 mL) and H2O (2 mL) over 30 min at 0 ?. Subsequently, a solution of KI (11.451 g, 68.982 mmol) in H2O (10 mL) was added dropwise over 30 min at 0 ?. After the reaction mixture was stirred for 3 h at rt under dark, the precipitate was collected by filtration, washed with water and dried under vacuum. Silica gel column chromatography of crude product (n-hexane/Et2O = 4:1) afforded 6 (8.060 g, 30.414 mmol, 89 %) as orange crystalline solid.: Rf = 0.28 (n-hexane/Et2O = 2:1); IR (neat, cm-1) 3418, 1645, 1520, 1294, 1214; 1H NMR (400 MHz, CD3OD) delta 7.79 (d, 1H, J = 8.4 Hz), 7.26 (d, 1H, J = 2.8 Hz), 6.81 (dd, 1H, J = 8.4, 8.4 Hz), 4.69 (br s, OH); 13C NMR (100 MHz, CD3OD) delta 159.8, 155.5, 143.1, 122.2, 113.3, 72.5.

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 3794 - 3796
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 513 - 517
[3]European Journal of Organic Chemistry,2006,p. 3809 - 3825
[4]Journal of the American Chemical Society,2019,vol. 141,p. 17295 - 17304
[5]Journal fur praktische Chemie (Leipzig 1954),1891,vol. <2> 43,p. 74
[6]Tetrahedron Letters,1996,vol. 37,p. 7099 - 7102
[7]Organic Letters,2009,vol. 11,p. 4036 - 4039

2
[ 1878-94-0 ]
[ 113305-56-9 ]

Reference： [1]Gazzetta Chimica Italiana,1920,vol. 50 I,p. 183

3
[ 113305-56-9 ]
[ 108-24-7 ]
4-iodo-3-nitrophenyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With dmap; triethylamine In dichloromethane at 20℃; for 9.5h; Inert atmosphere; Cooling with ice;

Reference： [1]Maier, Martin S.; Hüll, Katharina; Reynders, Martin; Matsuura, Bryan S.; Leippe, Philipp; Ko, Tongil; Schäffer, Lukas; Trauner, Dirk [Journal of the American Chemical Society, 2019, vol. 141, # 43, p. 17295 - 17304]
[2]Haehle [Journal fur praktische Chemie (Leipzig 1954), 1891, vol. <2> 43, p. 74]

4
[ 113305-56-9 ]
[ 100-39-0 ]
[ 183007-32-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In acetone	4-benzyloxy-1-iodo-2-nitrobenzene (7) To a solution of compound 6 (8.060 g, 30.414 mmol) and K2CO3 (8.407 g, 60.828 mmol) in acetone (20 ml) was added benzyl bromide (4.161 g, 24.331 mmol), and stirred at rt for overnight. The reaction mixture was filtered, washed with ether and the filtrate was purified by silica gel column chromatography (n-hexane/EtOAc = 8:1) affored 7 (10.298g, 28.999 mmol, 95 %) as yellow crystalline solid.: Rf = 0.56 (n-hexane/EtOAc = 4:1); IR (neat, cm-1) 3090, 3033, 2874, 1597, 1532, 1472, 1352, 1298, 1268, 1231, 1010; 1H NMR (400 MHz, CDCl3) δ 7.85 (d, 1H, J = 8.4 Hz), 7.48 (d, 1H, J = 3.0 Hz), 7.38 (m, 5H), 6.91 (dd, 1H, J = 8.4, 3.0 Hz), 5.09 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 159.1, 142.1, 135.2, 128.8, 128.5, 127.5, 121.1 112.0, 74.8, 70.7; MS (FAB) m/z 356.0 (M+H)+.
94%	With potassium carbonate In acetone

Reference： [1]Gim, Hyo Jin; Li, Hua; Lee, Eun; Ryu, Jae-Ha; Jeon, Raok [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 2, p. 513 - 517]
[2]Shinada, Tetsuro; Miyachi, Miki; Itagaki, Yasuhiro; Naoki, Hideo; Yoshihara, Kazuo; Nakajima, Terumi [Tetrahedron Letters, 1996, vol. 37, # 39, p. 7099 - 7102]

5
[ 1878-94-0 ]
[ 7697-37-2 ]
[ 113305-56-9 ]

Reference： [1]Gazzetta Chimica Italiana,1920,vol. 50 I,p. 183

6
[ 1565-80-6 ]
[ 113305-56-9 ]
[ 604800-36-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;
94%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[2]Jiang, Jing; Slutsky, Morris M.; Jones, Ticora V.; Tew, Gregory N. [New Journal of Chemistry, 2010, vol. 34, # 2, p. 307 - 312]

7
[ 1111-97-3 ]
[ 113305-56-9 ]
[ 851857-15-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone at 65℃; for 18h;
91%	With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone at 23 - 65℃; for 18h;	2 3-Chloro-3-methyl-1-butyne (640 μL, 5.7 mmol, 3.0 equiv) was added to a stirred solution of 4-iodo-3-nitrophenol (500 mg, 1.89 mmol, 1 equiv), tetrabutylammonium iodide (2.10 g, 5.7 mmol, 3.0 equiv), and potassium carbonate (522 mg, 3.8 mmol, 2.0 equiv) in acetone (5.2 mL) at 23 °C. The reaction mixture was warmed to 65 °C and was heated at this temperature for 18 h. The product solution was allowed to cool to 23 °C, then was diluted with ethyl acetate (50 mL). The diluted product solution was washed with saturated aqueous sodium bicarbonate solution (5 mL) and saturated aqueous sodium chloride solution (5 mL). After washing, the organic layer was dried over sodium sulfate and the solids were filtered. The filtrate was concentrated. The residue obtained was dissolved in ethyl acetate (10 mL) and the resulting solution was filtered through a pad of Celite, eluting with ethyl acetate (50 mL). The eluent was concentrated and the residue obtained was purified by flash-column chromatography (4% acetone-hexanes) to furnish l-iodo-4-(2- methyl-3-butyn-2-yloxy)-2 -nitrobenzene as a pale yellow oil (569 mg, 91%).[00309] Rf= 0.55 (20% ethyl acetate-hexanes). 1H NMR (400 MHz, CDCl3), δ 7.88 (d, 1H, J = 8.8 Hz, H1), 7.78 (d, 1H, J = 2.8 Hz, H3), 7.14 (dd, 1H, J = 8.8, 2.8 Hz, H2), 2.67 (s, 1H, H4), 1.68 (s, 6H, CH3). 13C NMR (100 MHz, CDCl3), 8156.6, 153.3, 142.0, 126.1, 117.8, 84.6, 77.1, 75.9, 73.7, 29.6. IR (NaCl, thin film), cm-1 3290 (m), 2991 (w), 1532 (s). HRMS-EI (m/z): [M]+ calcd for C11H10INO3, 33θτ9706; found7330.9706:

Reference： [1]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]
[2]Current Patent Assignee: HARVARD UNIVERSITY - WO2006/102097, 2006, A2 Location in patent: Page/Page column 148; 32/33

8
[ 112-35-6 ]
[ 113305-56-9 ]
[ 835629-17-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

9
[ 113305-56-9 ]
[ 88-11-9 ]
[ 914673-75-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium hydroxide In tetrahydrofuran; water at 20℃; for 16h;

Reference： [1]Blaszczyk, Alfred; Chadim, Martin; Von Haenisch, Carsten; Mayor, Marcel [European Journal of Organic Chemistry, 2006, # 17, p. 3809 - 3825]

10
[ 910644-90-5 ]
[ 113305-56-9 ]
[ 910644-91-6 ]

Yield	Reaction Conditions	Operation in experiment
54%	With triethylamine; copper(l) chloride In acetonitrile at 0 - 23℃;
54%	With triethylamine; copper(l) chloride In acetonitrile

Reference： [1]Wulff, Jeremy E.; Herzon, Seth B.; Siegrist, Romain; Myers, Andrew G. [Journal of the American Chemical Society, 2007, vol. 129, # 16, p. 4898 - 4899]
[2]Current Patent Assignee: HARVARD UNIVERSITY - WO2006/102097, 2006, A2 Location in patent: Page/Page column 31/33

11
[ 113305-56-9 ]
[ 835629-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

12
[ 113305-56-9 ]
[ 835629-30-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

13
[ 113305-56-9 ]
3,3-diethyl-1-{2-iodo-5-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-phenyl}-1-triazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

14
[ 113305-56-9 ]
3,3-diethyl-1-(2-ethynyl-5-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-phenyl)-1-triazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: K₂CO₃; methanol

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

15
[ 113305-56-9 ]
3,3-diethyl-1-[2-trimethylsilylethynyl-5-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-phenyl]-1-triazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

16
[ 113305-56-9 ]
C₃₄H₄₇N₃O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol
	Multi-step reaction with 7 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: K₂CO₃; methanol 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[2]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

17
[ 113305-56-9 ]
C₃₇H₅₅N₃O₈Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating
	Multi-step reaction with 6 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: K₂CO₃; methanol 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[2]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

18
[ 113305-56-9 ]
C₄₉H₆₅N₃O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol 8.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 9.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran
	Multi-step reaction with 7 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran
	Multi-step reaction with 9 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: K₂CO₃; methanol 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol 8.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 9.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[2]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[3]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

19
[ 113305-56-9 ]
C₅₂H₇₃N₃O₁₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol 8.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating
	Multi-step reaction with 6 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating
	Multi-step reaction with 8 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: K₂CO₃; methanol 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol 8.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[2]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[3]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

20
[ 113305-56-9 ]
C₆₇H₉₁N₃O₁₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol 8.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 9.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran 10.1: 58 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / Heating
	Multi-step reaction with 8 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran 8.1: 58 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / Heating
	Multi-step reaction with 6 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 58 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / Heating

Multi-step reaction with 10 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: K₂CO₃; methanol 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol 8.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 9.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran 10.1: 58 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / Heating

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[2]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[3]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[4]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

21
[ 113305-56-9 ]
C₆₈H₉₁N₃O₁₇Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol 8.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 9.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran 10.1: 68 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / Heating
	Multi-step reaction with 8 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran 8.1: 68 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / Heating
	Multi-step reaction with 10 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl₃*6H₂₀; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO₂ / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K₂CO₃ / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 5.1: K₂CO₃; methanol 6.1: 87 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 7.1: 97 percent / K₂CO₃; methanol 8.1: 63 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / Heating 9.1: 97 percent / K₂CO₃; methanol / tetrahydrofuran 10.1: 68 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / Heating

Reference： [1]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[2]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]
[3]Jones, Ticora V.; Slutsky, Morris M.; Laos, Roberta; De Greef, Tom F. A.; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 49, p. 17235 - 17240]

22
[ 113305-56-9 ]
[ 851857-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 91 percent / tetrabutylammonium iodide; K₂CO₃ / acetone / 18 h / 65 °C 2.1: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3.1: PhMgCl / tetrahydrofuran / 0.17 h / -40 °C 3.2: 44 percent / tetrahydrofuran / 0.5 h / -40 - 23 °C

Reference： [1]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]

23
[ 113305-56-9 ]
[ 851959-12-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 91 percent / tetrabutylammonium iodide; K₂CO₃ / acetone / 18 h / 65 °C 2.1: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3.1: PhMgCl / tetrahydrofuran / 0.17 h / -40 °C 3.2: 44 percent / tetrahydrofuran / 0.5 h / -40 - 23 °C 4.1: 56 percent / aq. Ba(OH)2; 2-(di-tert-butylphosphino)biphenyl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 23 - 40 °C 5.1: 49 percent / Zn; 1,2-dibromoethane; chlorotrimethylsilane / aq. NH₄Cl / tetrahydrofuran; ethanol / 40 °C
	Multi-step reaction with 4 steps 1: 91 percent / tetrabutylammonium iodide; K₂CO₃ / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3: 72 percent / Cu; tris(dibenzylideneacetone)dipalladium / dimethylsulfoxide / 2 h / 70 °C 4: 49 percent / Zn; 1,2-dibromoethane; chlorotrimethylsilane / aq. NH₄Cl / tetrahydrofuran; ethanol / 40 °C

Reference： [1]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]
[2]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]

24
[ 113305-56-9 ]
C₂₆H₂₇N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 91 percent / tetrabutylammonium iodide; K₂CO₃ / acetone / 18 h / 65 °C 2.1: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3.1: PhMgCl / tetrahydrofuran / 0.17 h / -40 °C 3.2: 44 percent / tetrahydrofuran / 0.5 h / -40 - 23 °C 4.1: 56 percent / aq. Ba(OH)2; 2-(di-tert-butylphosphino)biphenyl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 23 - 40 °C
	Multi-step reaction with 3 steps 1: 91 percent / tetrabutylammonium iodide; K₂CO₃ / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3: 72 percent / Cu; tris(dibenzylideneacetone)dipalladium / dimethylsulfoxide / 2 h / 70 °C

Reference： [1]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]
[2]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]

25
[ 113305-56-9 ]
(-)-stephacidin B [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 91 percent / tetrabutylammonium iodide; K₂CO₃ / acetone / 18 h / 65 °C 2.1: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3.1: PhMgCl / tetrahydrofuran / 0.17 h / -40 °C 3.2: 44 percent / tetrahydrofuran / 0.5 h / -40 - 23 °C 4.1: 56 percent / aq. Ba(OH)2; 2-(di-tert-butylphosphino)biphenyl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 23 - 40 °C 5.1: 49 percent / Zn; 1,2-dibromoethane; chlorotrimethylsilane / aq. NH₄Cl / tetrahydrofuran; ethanol / 40 °C 6.1: 95 percent Spectr_. / Et₃N / acetonitrile / 3.5 h / 23 °C
	Multi-step reaction with 5 steps 1: 91 percent / tetrabutylammonium iodide; K₂CO₃ / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3: 72 percent / Cu; tris(dibenzylideneacetone)dipalladium / dimethylsulfoxide / 2 h / 70 °C 4: 49 percent / Zn; 1,2-dibromoethane; chlorotrimethylsilane / aq. NH₄Cl / tetrahydrofuran; ethanol / 40 °C 5: 95 percent Spectr_. / Et₃N / acetonitrile / 3.5 h / 23 °C

Reference： [1]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]
[2]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]

26
[ 113305-56-9 ]
[ 200814-22-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 91 percent / tetrabutylammonium iodide; K₂CO₃ / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C

Reference： [1]Herzon, Seth B.; Myers, Andrew G. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5342 - 5344]

27
[ 113305-56-9 ]
[ 604800-37-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

28
[ 113305-56-9 ]
[ 604800-40-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

29
[ 113305-56-9 ]
N,N-diethyl-N'-(2-iodo-5-((S)-2-methylbutoxy)phenyl)triazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

30
[ 113305-56-9 ]
N,N-diethyl-N'-[2-ethynyl-5-((S)-2-methylbutoxy)phenyl]triazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

31
[ 113305-56-9 ]
N,N-diethyl-N'-[2-trimethylsilylethynyl-5-((S)-2-methylbutoxy)phenyl]triazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

32
[ 113305-56-9 ]
C₃₀H₃₉N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C
	Multi-step reaction with 7 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[2]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

33
[ 113305-56-9 ]
C₃₃H₄₇N₃O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C
	Multi-step reaction with 6 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[2]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

34
[ 113305-56-9 ]
[ 604800-47-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 88 percent / CH₃I / 6 h / 110 °C
	Multi-step reaction with 7 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 7.1: 88 percent / CH₃I / 6 h / 110 °C
	Multi-step reaction with 9 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 88 percent / CH₃I / 6 h / 110 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[2]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[3]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

35
[ 113305-56-9 ]
C₄₃H₅₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C
	Multi-step reaction with 7 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 7.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C
	Multi-step reaction with 9 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[2]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[3]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

36
[ 113305-56-9 ]
C₄₆H₆₁N₃O₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C
	Multi-step reaction with 6 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C
	Multi-step reaction with 8 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[2]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[3]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

37
[ 113305-56-9 ]
C₅₉H₇₅N₃O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 10.1: 45 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C
	Multi-step reaction with 8 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 7.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 45 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C
	Multi-step reaction with 6 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 45 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C

Multi-step reaction with 10 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃*6H₂O; N₂H₄*H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 10.1: 45 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[2]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[3]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[4]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

38
[ 113305-56-9 ]
C₈₅H₁₀₃N₃O₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 88 percent / CH₃I / 6 h / 110 °C 10.1: 52 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C
	Multi-step reaction with 10 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 10.1: 52 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C
	Multi-step reaction with 8 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 7.1: 88 percent / CH₃I / 6 h / 110 °C 8.1: 52 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C

	Multi-step reaction with 8 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 72 percent / CH₃I / 12 h / 110 °C 6.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 7.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 52 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C
	Multi-step reaction with 10 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 88 percent / CH₃I / 6 h / 110 °C 10.1: 52 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C
	Multi-step reaction with 10 steps 1.1: 94 percent / PPh₃; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl₃6H₂O; N₂H₄H₂O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO₂ / acetonitrile; H₂O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K₂CO₃ / acetonitrile; H₂O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 5.1: 80 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 12 h / 45 °C 7.1: 82 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C 9.1: 100 percent / K₂CO₃ / methanol; tetrahydrofuran / 20 °C 10.1: 52 percent / CuI; Et₃N / PdCl₂(PPh₃)2 / 45 °C

Reference： [1]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[2]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[3]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[4]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[5]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]
[6]Jones, Ticora V.; Blatchly, Richard A.; Tew, Gregory N. [Organic Letters, 2003, vol. 5, # 18, p. 3297 - 3299]

39
[ 113305-56-9 ]
[ 443-31-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1: 94 percent / K₂CO₃ / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et₃N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH₂Cl₂ 5: 92 percent / triphosgene, Et₃N / CH₂Cl₂ 6: 1.) Bu₃SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H₂O; tetrahydrofuran 8: H₂ / Pd-C / methanol 9: DIBAL / CH₂Cl₂ / -78 °C 10: pyridine / CH₂Cl₂ / 0 °C 11: NaN₃ / dimethylformamide 12: H₂ / 10percent Pd-C / methanol

Reference： [1]Shinada, Tetsuro; Miyachi, Miki; Itagaki, Yasuhiro; Naoki, Hideo; Yoshihara, Kazuo; Nakajima, Terumi [Tetrahedron Letters, 1996, vol. 37, # 39, p. 7099 - 7102]

40
[ 113305-56-9 ]
[ 682802-86-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 94 percent / K₂CO₃ / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et₃N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH₂Cl₂ 5: 92 percent / triphosgene, Et₃N / CH₂Cl₂ 6: 1.) Bu₃SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H₂O; tetrahydrofuran 8: H₂ / Pd-C / methanol 9: DIBAL / CH₂Cl₂ / -78 °C

Reference： [1]Shinada, Tetsuro; Miyachi, Miki; Itagaki, Yasuhiro; Naoki, Hideo; Yoshihara, Kazuo; Nakajima, Terumi [Tetrahedron Letters, 1996, vol. 37, # 39, p. 7099 - 7102]

41
[ 113305-56-9 ]
[ 31031-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 94 percent / K₂CO₃ / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et₃N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH₂Cl₂ 5: 92 percent / triphosgene, Et₃N / CH₂Cl₂ 6: 1.) Bu₃SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H₂O; tetrahydrofuran 8: H₂ / Pd-C / methanol

Reference： [1]Shinada, Tetsuro; Miyachi, Miki; Itagaki, Yasuhiro; Naoki, Hideo; Yoshihara, Kazuo; Nakajima, Terumi [Tetrahedron Letters, 1996, vol. 37, # 39, p. 7099 - 7102]

42
[ 113305-56-9 ]
3-(2-Azido-ethyl)-1H-indol-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: 94 percent / K₂CO₃ / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et₃N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH₂Cl₂ 5: 92 percent / triphosgene, Et₃N / CH₂Cl₂ 6: 1.) Bu₃SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H₂O; tetrahydrofuran 8: H₂ / Pd-C / methanol 9: DIBAL / CH₂Cl₂ / -78 °C 10: pyridine / CH₂Cl₂ / 0 °C 11: NaN₃ / dimethylformamide

Reference： [1]Shinada, Tetsuro; Miyachi, Miki; Itagaki, Yasuhiro; Naoki, Hideo; Yoshihara, Kazuo; Nakajima, Terumi [Tetrahedron Letters, 1996, vol. 37, # 39, p. 7099 - 7102]

43
[ 2623-33-8 ]
[ 113305-56-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1891,vol. <2> 43,p. 74

44
[ 113305-56-9 ]
[ 6482-24-2 ]
[ 926297-19-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; sodium iodide In acetone for 20h; Heating / reflux;	200 To a solution of 4-iodo-3-nitrophenol (5.33 g) in acetone (60 ml) were added 2-bromoethyl methyl ether (11.1 g) , sodium iodide (3.65 g) and potassium carbonate (6.98 g) , and the mixture was heated under reflux for 20 hr. The reaction mixture was concentrated, water was poured into the obtained residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give l-iodo-4- (2-methoxyethoxy) - 2-nitrobenzene (5.59 g, yield: 86%) as pale-yellow crystals. 1H-NMR (300 MHz, CDCl3) δ-'3.44 (3 H, s) , 3.76 (2 H, t, J = 4.5 Hz), 4.15 (2.H, t, J = 4.5 Hz), 6.90 (1 H, dd, J = 9.0, 2.7 Hz), 7.46 (1 H, d, J = 2.7 Hz), 7.87 (1 H, d, J = 9.0 Hz) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2007/18314, 2007, A2 Location in patent: Page/Page column 191-192

45
[ 113305-56-9 ]
[ 161270-70-8 ]
[ 960307-34-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 23℃; for 16h;
73%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 23℃; for 16h;	[00221] Iodoarene 20. Diisopropyl azodicarboxylate (3.25 mL, 16.5 mmol, 1.1 equiv) was added dropwise to a solution of 4-iodo-3-nitrophenol (19) (3.98 g, 15.0 mmol, 1.0 equiv), the alcohol 18 (5.01 g, 16.5 mmol, 1.1 equiv), and triphenylphosphine (4.33 g, 16.5 mmol, 1.1 equiv) in tetrahydrofuran (37 mL). The orange solution was stirred at 23 0C for 16 hours. The product solution was concentrated in vacuo and the residue was recrystallized from chloroform, furnishing the iodoarene 20 (6.03 g, 73%) as a pale yellow solid. [00222] R/= 0.64 (hexanes-ethyl acetate 3 :2). 1H NMR (500 MHz, CDCl3), δ 7.86-7.83 (m, 3H), 7.71 (dd, 2H, J= 5.4, 2.9 Hz), 7.40 (d, IH, J= 2.4 Hz), 6.85 (dd, IH, J= 8.8, 2.9 Hz), 3.97 (t, 2H, J= 6.4 Hz), 3.68 (t, 2H, J= 7.3 Hz), 1.81-1.76 (m, 2H), 1.69-1.66 (m, 2H), 1.45-1.42 (m, 2H), 1.33-1.25 (m, 10H). 13C NMR (100 MHz, CDCl3), δ 168.7, 159.9, 153.7, 142.2, 134.1, 132.4, 123.4, 121.1, 111.7, 74.3, 69.1, 38.3, 29.6, 29.5, 29.4, 29.3, 29.1, 28.8, 27.0, 26.0. IR (NaCl, thin film), cm"1 2928(m), 2854(m), 1772(m), 1706(s). HRMS-ESI (m/z): [M + H]+ calcd for C24H28IN2O5+, 551.1037; found, 551.1039.

Reference： [1]Wulff, Jeremy E.; Siegrist, Romain; Myers, Andrew G. [Journal of the American Chemical Society, 2007, vol. 129, # 46, p. 14444 - 14451]
[2]Current Patent Assignee: HARVARD UNIVERSITY - WO2009/20768, 2009, A1 Location in patent: Page/Page column 134-135

46
[ 113305-56-9 ]
[ 824-94-2 ]
[ 1037305-13-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate In N,N-dimethyl-formamide
86%	With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;

Reference： [1]Okada, Masahiro; Matsubara, Akira; Ueda, Minoru [Tetrahedron Letters, 2008, vol. 49, # 23, p. 3794 - 3796]
[2]Hornberger, Keith R.; Badiang, Jennifer G.; Salovich, James M.; Kuntz, Kevin W.; Emmitte, Kyle A.; Cheung, Mui [Tetrahedron Letters, 2008, vol. 49, # 44, p. 6348 - 6351]

47
[ 113305-56-9 ]
[ 100-44-7 ]
[ 183007-32-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate In ethanol at 60℃; for 15h;

Reference： [1]Location in patent: experimental part Nepveu, Françoise; Kim, Sothea; Boyer, Jeremie; Chatriant, Olivier; Ibrahim, Hany; Reybier, Karine; Monje, Marie-Carmen; Chevalley, Severine; Perio, Pierre; Lajoie, Barbora H.; Bouajila, Jalloul; Deharo, Eric; Sauvain, Michel; Tahar, Rachida; Basco, Leonardo; Pantaleo, Antonella; Turini, Francesco; Arese, Paolo; Valentin, Alexis; Thompson, Eloise; Vivas, Livia; Petit, Serge; Nallet, Jean-Pierre [Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 699 - 714]

48
[ 113305-56-9 ]
[ 98-80-6 ]
[ 51264-59-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In 1,4-dioxane at 90℃; for 2h; Inert atmosphere;	Intermediate 165.2-nitrobiphenyl-4-oI To a solution of 4-iodo-3-nitrophenol (ig, 0.0037mo1) in dioxane (l0mL) was added potassium carbonate (2g, 0.014mo1) and phenyl boronic acid (0.6g, 0.0049mo1), the mixture was placed under nitrogen atmosphere and then norbornylphosphino Pd II (0.llg, 0.002mo1) was added into the reaction mixture, which was stirred for 2 hours at 90°C. The mixture was filtered through Celite and the solvent was removed under reduced pressure. The crude was partitioned between ethyl acetate and water, the organic layer was washed with brine, dried, filtered and the solvent was removed under reduced pressure giving the title compound as a solid (890mg, 95%), which was used in the next step without further purification.LRMS (mlz): 216 (M+1)+

Reference： [1]Current Patent Assignee: ALMIRALL SA - WO2014/95920, 2014, A1 Location in patent: Page/Page column 110; 111

49
[ 3143-02-0 ]
[ 113305-56-9 ]
3-[(4-Iodo-3-nitrophenoxy)methyl]-3-methyloxetane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
971 mg	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 18h;	17.1 Step 1: 3- [(4-Iodo-3 -nitrophenoxy)methyl] -3 -methyloxetane To a stirred mixture of 4-iodo-3-nitrophenol (1.02 g, 3.849 mmol), 3-methyl-3-oxetanemethanol (393 mg, 3.849 mmol) and triphenylphosphine (1.51 g, 5.773 mmol) in THF (20mL) was added a diethyl azadicaboxylate (DEAD) (0.91 mL, 5.773 mmol) at 0 °C. The reaction mixture was stirred at RT for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography to yield 971 mg of the title product as yellow solid. ‘H NIVIR (300 MHz, CDC13) ö 1.44 (s, 3H), 4.07 (s, 2H), 4.48 (d, J 6.0 Hz, 2H), 4.60 (d, J= 6.0 Hz, 2H), 6.89-6.93 (m, 1H), 7.45-7.47 (m, 1H), 7.91 (d, J 8.7 Hz, 1H).

Reference： [1]Current Patent Assignee: GLENMARK PHARMACEUTICALS LTD - WO2015/52675, 2015, A1 Location in patent: Page/Page column 52; 53

50
[ 113305-56-9 ]
[ 98-09-9 ]
4-iodo-3-nitrophenyl benzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine In dichloromethane for 16h;	2.a 4-Iodo-3-nitrophenylbenzenesulfonate (3E) a. 4-Iodo-3-nitrophenylbenzenesulfonate (3E) To a vial containing 4-iodo-3-nitrophenoli (1.03 g, 3.8 mmol, 1 equiv) in CH2Cl2 (8 mL) was added sequentially benzenesulphonyl chloride (0.73 mL, 5.7 mmol, 1.5 equiv), pyridine (0.9 mL, 11.4 mmol, 3 mmol), and the reaction was stirred for 16 hrs. After which the reaction was diluted with H2O (10 mL) and extracted with CH2Cl2 (2*10 mL). The combined organic layers were concentrated in vacuo and purified by column chromatography to afford the title compound as a yellow solid in 98% yield: Rf 0.47 (40:60, EtOAc/hex); 1H (CDCl3, 400 MHz) δ 8.00 (d, J=8.6 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.80-7.70 (m, 1H), 7.64-7.56 (m, 2H), 7.47 (d, J=2.4 Hz, 1H); 13C (CDCl3, 100 MHz) δ 149.5, 142.9, 135.0, 134.4, 129.6, 128.5, 127.7, 119.9, 105.0, 84.1.
98%	With pyridine In dichloromethane for 16h;	2.f f. 4-Iodo-3-nitrophenylbenzenesulfonate f. 4-Iodo-3-nitrophenylbenzenesulfonate (0158) To a vial containing 49 4-iodo-3-nitrophenol (1.03 g, 3.8 mmol, 1 equiv) in 11 CH2Cl2 (8 mL) was added sequentially 50 benzenesulphonyl chloride (0.73 mL, 5.7 mmol, 1.5 equiv), 51 pyridine (0.9 mL, 11.4 mmol, 3 mmol), and the reaction was stirred for 16 hrs. After which the reaction was diluted with H2O (10 mL) and extracted with CH2Cl2 (2×10 mL). The combined organic layers were concentrated in vacuo and purified by column chromatography to afford the 52 title compound as a yellow solid in 98% yield: Rf 0.47 (40:60, EtOAc/hex); 1H (CDCl3, 400 MHz) δ 8.00 (d, J=8.6 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.80-7.70 (m, 1H), 7.64-7.56 (m, 2H), 7.47 (d, J=2.4 Hz, 1H); 13C (CDCl3, 100 MHz) δ 149.5, 142.9, 135.0, 134.4, 129.6, 128.5, 127.7, 119.9, 105.0, 84.1

Reference： [1]Current Patent Assignee: UNIVERSITY OF MINNESOTA SYSTEM - US2016/68533, 2016, A1 Location in patent: Paragraph 0084
[2]Current Patent Assignee: UNIVERSITY OF MINNESOTA SYSTEM - US2017/217960, 2017, A1 Location in patent: Paragraph 0158

51
[ 113305-56-9 ]
[ 501-53-1 ]
[ 183007-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-iodo-3-nitrophenol With potassium carbonate In acetone for 0.0833333h; Stage #2: benzyl chloroformate In acetone for 4h; Reflux;	1 Step 1: Intermediate 38-b To a solution of 4-iodo-3-nitrophenol 38-a (3.0 g, 11.3 mmol) in acetone (113 ml) was added potassium carbonate (1.5 g, 11.3 mmol) and after stirring for 5 minutes, benzylbromide (1.3 ml, 11.3 mmol) was added. The reaction was stirred at reflux for 4 hours, then cooled to room temperature and filtered. Volatiles were removed under reduced pressure to provide Intermediate 38-b as a yellow solid.

Reference： [1]Current Patent Assignee: GOSSAMER BIO INC - WO2017/49401, 2017, A1 Location in patent: Page/Page column 106

52
[ 113305-56-9 ]
[ 107-30-2 ]
1-iodo-4-(methoxymethoxy)-2-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84g	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice; Inert atmosphere;	31 Reference Example 31: 1-iodo-4-(methoxymethoxy)-2-nitrobenzene Under a stream of nitrogen, to a solution of 4-iodo-3-nitrophenol (70.0 g) and N,N-diisopropylethylamine (68.2 g) in dichloromethane (370 mL), in the ice bath, chloromethyl methyl ether (31.8 g) was added dropwise. The resulting mixture was stirred at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction mixture, followed by separation. The water layer was extracted with ethyl acetate, and the organic layer was washed with hydrochloric acid aqueous solution (0.5 mol/L), water, saturated sodium hydrogencarbonate aqueous solution, and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (84.0 g) having the following physical property values. TLC: Rf 0.46 (hexane : ethyl acetate = 9:1); 1H-NMR (CDCl3): δ 3.47, 5.20, 6.98, 7.56, 7.87.

Reference： [1]Current Patent Assignee: ONO PHARMACEUTICAL CO LTD - EP3632898, 2020, A1 Location in patent: Paragraph 0543

53
[ 629-03-8 ]
[ 113305-56-9 ]
4-[(6-bromohexyl)oxy]-1-iodo-2-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 4-iodo-3-nitrophenol With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: 1 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Švec, Pavel; Nový, Zbyněk; Kučka, Jan; Petřík, Miloš; Sedláček, Ondřej; Kuchař, Martin; Lišková, Barbora; Medvedíková, Martina; Kolouchová, Kristýna; Groborz, Ondřej; Loukotová, Lenka; Konefał, Rafał Ł.; Hajdúch, Marián; Hrubý, Martin [Journal of Medicinal Chemistry, 2020, vol. 63, # 24, p. 15960 - 15978]

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CAS No. :	113305-56-9	MDL No. :	MFCD01320680
Formula :	C₆H₄INO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QCKXOEOOXJUACP-UHFFFAOYSA-N
M.W :	265.01	Pubchem ID :	2733454
Synonyms :

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501	UN#:	3077
Hazard Statements:	H302-H315-H317-H318-H410	Packing Group:	Ⅲ
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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 113305-56-9 ] {[proInfo.proName]}

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[ 113305-56-9 ] Synthesis Path-Downstream 1~53

Technical Information

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[ 113305-56-9 ]

Aryls

Iodides

Nitroes

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Inquiry

[ CAS No. 113305-56-9 ] {[proInfo.proName]}

Quality Control of [ 113305-56-9 ]

Related Doc. of [ 113305-56-9 ]

Product Details of [ 113305-56-9 ]

Safety of [ 113305-56-9 ]

Application In Synthesis of [ 113305-56-9 ]

[ 113305-56-9 ] Synthesis Path-Downstream 1~53

Technical Information

Related Functional Groups of [ 113305-56-9 ]

Aryls

Iodides

Nitroes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 113305-56-9 ]