Name: 5892-99-9|4-Bromo-N,N-diethylbenzamide|95%
Brand: Ambeed
SKU: A500655
Price: 11.0 USD
Availability: InStock
Rating: 99 (30 reviews)

1
[ 109-89-7 ]
[ 586-75-4 ]
[ 5892-99-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In dichloromethane at -10 - 20℃; for 0.5h;	General Procedure for the Preparation of N,N-Diethyl Benzamide Precursors to Ketopyrrole Ligands, Method A: To a stirred CH2Cl2 solution (20 mL) of the benzoyl chloride at -10° C. was added triethylamine (4 mL), followed by the dropwise addition of diethylamine (1.4 equivalents). The heterogeneous reaction mixture was allowed to warm to room temperature and stirring was continued for 30 minutes. The reaction mixture was then transferred to a separatory funnel containing H2O (20 mL). The organic layer was separated and washed with 5% HCl (2*25 mL), H2O (25 ml), and dried over Na2SO4. Removal of the CH2Cl2 solvent afforded the product.
	In benzene
	In 1,2-dichloro-ethane at 0℃;	134.134A Oxalyl chloride (3.5 mL, 40.1 mmol) was added dropwise to a solution of 4-bromobenzoic acid (4.08 g, 20.3 mmol) and dimethyl formamide (0.04 mL) in anhydrous DCE (50 mL) at 0° C. The mixture was stirred for 2 h at rt, concentrated in vacuo and coevaporated with toluene twice. The residue was dissolved in anhydrous DCE (25 mL) and cooled in an ice bath. Diethyl amine (5 mL, 48.3 mmol) in DCE (25 mL) was added dropwise. The reaction was stirred overnight and then concentrated in vacuo. The residue was treated with 1N hydrochloric acid solution and extracted twice with dichloromethane. The organic layer was washed with water and saturated sodium chloride solution, dried (MgSO4), and concentrated in vacuo to give 134A (4.87 g, 94%) as a pink solid. LC-MS m/z: 588.19 (M+H)+.

	With triethylamine In dichloromethane at 0 - 20℃;
	With triethylamine Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Current Patent Assignee: BOE TECHNOLOGY GROUP CO., LTD. - US2008/27028, 2008, A1 Location in patent: Page/Page column 35-36
[2]Gryf-Keller, Adam; Terpinski, Jacek; Zajaczkowska-Terpinska, Ewa [Polish Journal of Chemistry, 1980, vol. 54, # 7/8, p. 1465 - 1471]
[3]Kikukawa, Kiyoshi; Kono, Kiyoshi; Nagira, Kazuhiko; Wada, Fumio; Matsuda, Tsutomu [Journal of Organic Chemistry, 1981, vol. 46, p. 4413 - 4416]
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/3539, 2007, A1 Location in patent: Page/Page column 105
[5]Zhao, Yigang; Snieckus, Victor [Organic Letters, 2014, vol. 16, # 2, p. 390 - 393]
[6]Zhuang, Zhe; Hu, Zhi-Peng; Liao, Wei-Wei [Organic Letters, 2014, vol. 16, # 12, p. 3380 - 3383]
[7]Crisenza, Giacomo E. M.; McCreanor, Niall G.; Bower, John F. [Journal of the American Chemical Society, 2014, vol. 136, # 29, p. 10258 - 10261]

2
[ 78-81-9 ]
[ 5892-99-9 ]
N,N-Diethyl-4-isobutylamino-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis(diphenylphosphino)ferrocene/Pd; sodium t-butanolate In tetrahydrofuran at 100℃; for 3h;
82%

Reference： [1]Driver, Michael S.; Hartwig, John F. [Journal of the American Chemical Society, 1996, vol. 118, # 30, p. 7217 - 7218]
[2]Hartwig, John F. [Synlett, 1997, vol. 1997, # 4, p. 329 - 340]

3
[ 120-72-9 ]
[ 5892-99-9 ]
N,N-Diethyl-4-indol-1-yl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate In toluene at 100℃; for 12h;

Reference： [1]Mann, Grace; Hartwig, John F.; Driver, Michael S.; Fernández-Rivas, Carolina [Journal of the American Chemical Society, 1998, vol. 120, # 4, p. 827 - 828]

4
[ 781-35-1 ]
[ 5892-99-9 ]
N,N-Diethyl-4-(2-oxo-3,3-diphenyl-propyl)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With tol-BINAP; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate In tetrahydrofuran at 70℃;

Reference： [1]Palucki; Buchwald [Journal of the American Chemical Society, 1997, vol. 119, # 45, p. 11108 - 11109]

5
[ 5892-99-9 ]
[ 4885-19-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 20℃; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;
99%	With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 80℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;
85%	With diphenylsilane In tetrahydrofuran for 20h;

Reference： [1]Yao, Wubing; Fang, Huaquan; He, Qiaoxing; Peng, Dongjie; Liu, Guixia; Huang, Zheng [Journal of Organic Chemistry, 2019]
[2]Yao, Wubing; Fang, Huaquan; He, Qiaoxing; Peng, Dongjie; Liu, Guixia; Huang, Zheng [Journal of Organic Chemistry, 2019, vol. 84, # 10, p. 6084 - 6093]
[3]Kuwano, Ryoichi; Takahashi, Masatoshi; Ito, Yoshihiko [Tetrahedron Letters, 1998, vol. 39, # 9, p. 1017 - 1020]

6
[ 5892-99-9 ]
[ 95-48-7 ]
N,N-diethyl-4-(2'-methylphenoxy)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; sodium hydride; johnphos 1.) toluene, 100 deg C, 15 min, 2.) toluene, 100 deg C, 22 h; Yield given; Multistep reaction;

Reference： [1]Aranyos, Attila; Old, David W.; Kiyomori, Ayumu; Wolfe, John P.; Sadighi, Joseph P.; Buchwald, Stephen L. [Journal of the American Chemical Society, 1999, vol. 121, # 18, p. 4369 - 4378]

7
[ 4612-26-4 ]
[ 5892-99-9 ]
N,N,N',N'-tetraethyl-p-terphenyl-4,4''-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; ethanol; water for 19h; Heating;

Reference： [1]Jeong, Kyu-Sung; Cho, Young Lag; Chang, Sung-Youn; Park, Tae-Yoon; Song, Jung Uk [Journal of Organic Chemistry, 1999, vol. 64, # 26, p. 9459 - 9466]

8
[ 565-69-5 ]
[ 5892-99-9 ]
2-(4-N,N-diethylcarbamoylphenyl)-4-methyl-3-pentanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 80℃; for 24h;

Reference： [1]Fox, Joseph M.; Huang, Xiaohua; Chieffi, Andre; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 7, p. 1360 - 1370]

9
[ 5892-99-9 ]
N,N,N',N'-tetraethylbiphenyl-4,4'-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 4-bromo-N,N-diethylbenzamide With n-butyl magnesium bromide; n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.5h; Stage #2: With titanium tetrachloride In tetrahydrofuran; hexane at -40 - 0℃;

Reference： [1]Inoue, Atsushi; Kitagawa, Kazuya; Shinokubo, Hiroshi; Oshima, Koichiro [Tetrahedron, 2000, vol. 56, # 49, p. 9601 - 9605]

10
[ 5892-99-9 ]
[ 106-95-6 ]
4-allyl-N,N-diethylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 4-bromo-N,N-diethylbenzamide With lithium dibutyl(isopropyl)magnesate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: allyl bromide In tetrahydrofuran; hexane at -78℃; for 1h;

Reference： [1]Kitagawa, Kazuya; Inoue, Atsushi; Shinokubo, Hiroshi; Oshima, Koichiro [Angewandte Chemie - International Edition, 2000, vol. 39, # 14, p. 2481 - 2483]

11
[ 5720-07-0 ]
[ 5892-99-9 ]
[ 331816-27-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In methanol; benzene at 80℃; for 17h;
99%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In methanol; water; benzene at 80℃; for 17h;

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

12
[ 5892-99-9 ]
[ 123-38-6 ]
lithium dibutyl(isopropyl)magnesate [ No CAS ]
N,N-diethyl-4-(1-hydroxypropyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	Stage #1: 4-bromo-N,N-diethylbenzamide; lithium dibutyl(isopropyl)magnesate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: propionaldehyde In tetrahydrofuran; hexane at -78℃; Further stages.;

Reference： [1]Inoue; Kitagawa; Shinokubo; Oshima [Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4333 - 4339]

13
[ 5892-99-9 ]
[ 106-95-6 ]
lithium dibutyl(isopropyl)magnesate [ No CAS ]
4-allyl-N,N-diethylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 4-bromo-N,N-diethylbenzamide; lithium dibutyl(isopropyl)magnesate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: allyl bromide With CuCN*2LiCl In tetrahydrofuran; hexane at -78℃; Further stages.;

Reference： [1]Inoue; Kitagawa; Shinokubo; Oshima [Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4333 - 4339]

14
[ 5892-99-9 ]
[ 51207-85-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; lithium hexamethyldisilazane; CyJohnPhos In 1,4-dioxane at 80℃; for 15h;
94%	With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C₅₀H₇₀NO₄PPdS; C₅₀H₇₀NO₄PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; for 36h; Inert atmosphere;

Reference： [1]Huang; Buchwald [Organic letters, 2001, vol. 3, # 21, p. 3417 - 3419]
[2]Cheung, Chi Wai; Surry, David S.; Buchwald, Stephen L. [Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737]

15
[ 5892-99-9 ]
[ 101-97-3 ]
ethyl α-phenyl-α-(4-N,N-diethylcarbamoylphenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With palladium diacetate; lithium hexamethyldisilazane; DavePhos In toluene at 80℃; for 1h;

Reference： [1]Moradi; Buchwald [Journal of the American Chemical Society, 2001, vol. 123, # 33, p. 7996 - 8002]

16
[ 5892-99-9 ]
[ 331816-28-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating
	Multi-step reaction with 3 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

17
[ 5892-99-9 ]
3-(3-benzyl-4'-methoxy-biphenyl-4-yl)-propionyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C
	Multi-step reaction with 7 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

18
[ 5892-99-9 ]
[ 395681-97-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C
	Multi-step reaction with 6 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

19
[ 5892-99-9 ]
[ 331816-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C
	Multi-step reaction with 8 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

20
[ 5892-99-9 ]
[ 391864-70-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C
	Multi-step reaction with 5 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

21
[ 5892-99-9 ]
[ 331816-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H₂ / Pt₂O / ethanol; ethyl acetate / 15 h / 20 °C
	Multi-step reaction with 10 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C 10.1: 70 percent / H₂ / PtO₂ / ethanol; ethyl acetate / 15 h / 20 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

22
[ 5892-99-9 ]
4-benzyl-2-(4-hydroxy-benzyl)-6-(4-hydroxy-phenyl)-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H₂ / Pt₂O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C
	Multi-step reaction with 11 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C 10.1: 70 percent / H₂ / PtO₂ / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

23
[ 5892-99-9 ]
(S)-4-benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H₂ / Pt₂O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 11.1: HPLC DIACEL OC column / hexane; ethanol
	Multi-step reaction with 12 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C 10.1: 70 percent / H₂ / PtO₂ / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 12.1: chiral HPLC

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

24
[ 5892-99-9 ]
(R)-4-benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H₂ / Pt₂O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 11.1: HPLC DIACEL OC column / hexane; ethanol
	Multi-step reaction with 12 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C 10.1: 70 percent / H₂ / PtO₂ / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 12.1: chiral HPLC

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

25
[ 5892-99-9 ]
[ 391864-73-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C
	Multi-step reaction with 9 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

26
[ 5892-99-9 ]
(R)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H₂ / Pt₂O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 11.1: 60 percent / 2.5M aq. NaOH / ethanol / 2 h / 20 °C 12.1: HPLC DIACEL OC column / hexane; ethanol
	Multi-step reaction with 13 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C 10.1: 70 percent / H₂ / PtO₂ / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 12.1: NaOH / ethanol; H₂O / 2 h / 20 °C 13.1: chiral HPLC

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

27
[ 5892-99-9 ]
(S)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H₂ / Pt₂O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 11.1: 60 percent / 2.5M aq. NaOH / ethanol / 2 h / 20 °C 12.1: HPLC DIACEL OC column / hexane; ethanol
	Multi-step reaction with 13 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C 10.1: 70 percent / H₂ / PtO₂ / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 12.1: NaOH / ethanol; H₂O / 2 h / 20 °C 13.1: chiral HPLC

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

28
[ 5892-99-9 ]
[ 331816-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C
	Multi-step reaction with 4 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

29
[ 5892-99-9 ]
[ 331816-26-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: 99 percent / Pd(PPh₃)4; 2M aq. Na₂CO₃ / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H₂ / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 7.1: TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H₂ / Pt₂O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 11.1: 60 percent / 2.5M aq. NaOH / ethanol / 2 h / 20 °C
	Multi-step reaction with 12 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C 10.1: 70 percent / H₂ / PtO₂ / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr₃ / CH₂Cl₂ / 53 h / -78 - 20 °C 12.1: NaOH / ethanol; H₂O / 2 h / 20 °C

Reference： [1]Wu, Chun; Nakamura, Hideshi; Murai, Akio; Inouye, Satoshi [Tetrahedron, 2001, vol. 57, # 47, p. 9575 - 9583]
[2]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

30
[ 5892-99-9 ]
3-(hydroxy-phenyl-methyl)-4'-methoxy-biphenyl-4-carboxylic acid diethylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C

Reference： [1]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

31
[ 5892-99-9 ]
4-Benzyl-6-(4-hydroxy-phenyl)-2-[1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 99 percent / Na₂CO₃; Pd(PPh₃)4 / benzene; methanol; H₂O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H₂ / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl₂ / CH₂Cl₂ / 3 h / 60 °C 8.1: 85 mg / TiCl₄ / CH₂Cl₂ / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H₂O / 24 h / 20 °C 10.1: 50 percent / BBr₃ / CH₂Cl₂ / 29 h / -78 - 20 °C

Reference： [1]Nakamura; Wu; Inouye; Murai [Journal of the American Chemical Society, 2001, vol. 123, # 7, p. 1523 - 1524]

32
[ 5892-99-9 ]
[ 255850-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diethylamine; CuI; (PPh₃)4Pd / 11 h / Heating 2: 0.65 g / potassium hydroxide / toluene / 1 h / Heating

Reference： [1]Jeong, Kyu-Sung; Cho, Young Lag; Chang, Sung-Youn; Park, Tae-Yoon; Song, Jung Uk [Journal of Organic Chemistry, 1999, vol. 64, # 26, p. 9459 - 9466]

33
[ 5892-99-9 ]
p-(4-(p-diethylcarbamoylphenyl)-1,3-butadiynyl)-N,N-diethylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: diethylamine; CuI; (PPh₃)4Pd / 11 h / Heating 2: 0.65 g / potassium hydroxide / toluene / 1 h / Heating 3: 53 percent / tetramethylethylenediamine; CuCl; oxygen / acetone / 20 h

Reference： [1]Jeong, Kyu-Sung; Cho, Young Lag; Chang, Sung-Youn; Park, Tae-Yoon; Song, Jung Uk [Journal of Organic Chemistry, 1999, vol. 64, # 26, p. 9459 - 9466]

34
[ 5892-99-9 ]
[ 6238-20-6 ]
[ 682777-61-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100 - 150℃; for 16h;	1 Example 1; [N, N-DIETHYL-4- [PHENYL- (1-AZABICYCLO] [2.2. 2] octan-3-amino) ] benzamide Fumarate [1: 1]; (Compound 1) (Method [1A)] To a mixture of 9.3 g (0.1 mol) of aniline and 16.1 g (0.1 mol) of 1-azabicyclo [2.2. 2] octan-3-one hydrochloride in 250 mL of dichloroethane (DCE) was added 31.8 g (0.15 mol) of Na [(OAC)] 3BH and the mixture was stirred overnight at room temperature. The reaction was quenched with 3 N [NAOH.] The layers were separated and the aqueous layer was extracted with an additional portion of CHCi3. The organic layers were combined, dried over [NAS04,] and then filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica (95/5 [CHCI3/10] % NH40H in MeOH) to give [N-PHENYL-1-AZABICYCLO] [2.2. 2] [OCTAN-3-AMINE] (6.0 g 30 %) as an off-white solid. MH+ = [203.'H] NMR [(CDCI3)] 1.46 (m, [1 H),] 1.75 (m, [3H),] 2.0 (m, 1 H), 2.55 (m, 1 H), 2.95 (m, 4H), 3.4 (m, [2H),] 3.8 (s, 1 H), 6.6 (d, [2H),] [6.] 75 (t, 1H), 7.2 (t, [2H).] (Method 1 B) A mixture of 1.26 g of 1-azabicyclo [2.2. 2] octan-3-one and 0.93 g of aniline and 4.4 mL of Ti [(/PRO)] 4 was stirred overnight at room temperature. The reaction mixture was diluted with [ETOH] and then NaBH4 pellets (0.8 g) were added until reaction was judged complete by TLC. The solvent was evaporated in vacuo. The residue was diluted with 3N [NAOH,] water and EtOAc and the mixture was filtered through dicalite. The filter pad was washed with additional EtOAc. The filtrate was transferred to a separatory funnel and the aqueous layer was extracted with an additional portion of EtOAc. The combined organic extracts were washed with water and then brine and then dried over [K2CO3.] The solution was filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica [(90/7.] [5/2.] 5 [CHCI3/MEOH/7.] 0 M [NH3] in [MEOH)] to give N-Phenyl-1-azabicyclo [2.2. 2] [OCTAN-3-AMINE] (1.5 g, 75 %) as a white [SOLID.'H] NMR [(CDC13)] is consistent with the one from Method 1A. A solution of 0.5 g (2.5 [MMOL)] of [N-PHENYL-1-AZABICYCLO] [2.2. 2] octan-3-amine, 0.64 g (2.5 [MMOL)] of [NN-DIETHYL-4-BROMOBENZAMIDE,] 23 mg (0.025 [MMOL)] of tris [(DIBENZYLIDENEACETONE)-DIPALLADIUM (0)] (Pd2 (dba) 3), and 47 mg (0.075 [MMOL)] of BINAP and 0.36 g (3.75 [MMOL)] of NaOtBu in 5 mL of dry toluene was heated at 100-150° C for 16 hrs. The reaction mixture was cooled and diluted with water and EtOAc. The aqueous layer was extracted with a second portion of EtOAc and the combined extracts were washed with water and then with brine and then dried over [K2C03.] The solution was filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica (96/4 CHCl3/10% NH40H in [MEOH).] The appropriate fractions were combined and the solvent was evaporated in vacuo. The residue was combined with 1 eq. of fumaric acid in [2-PROH.'THE SOLVENT] was evaporated in vacuo and the residue recrystallized from acetone to give Compound 1 (0.45 [G,] 37%) as a white solid mp 181-183°C. MH+ = 378. 1H NMR [(DMSO-D6)] 1.05 (t, 6H), 1.35 (m, [1H),] 1.65 (m, [1H),] 1.8 [(M,] [2H),] 2.05 (br s, 1H). 2.7 (m, [1 H),] 3.0 (m, 4H), 3.3 (br s, 4H), 3.55 (t, [1H),] 4.3 (t, [1H),] 6.45 (s, 2H), 6.8 (d, 2H), 7. 2 (m, [5H),] 7.4 (t, 2H). Anal. Calcd for [C24H3N3O C4H404] : C, 68.13 ; H, 7.15 ; N, 8.51. Found C, 67.81 ; H, 7.03 ; [N,] 8.40.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2004/35574, 2004, A2 Location in patent: Page 19

35
[ 109-89-7 ]
[ 589-17-3 ]
[ 5892-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane	i I. (i) Preparation of 4-bromo-N,N-diethyl Benzamide (Compound 1). To an ice cooled solution of 4-bromobenzyl chloride (19.5 g, 86.8 mmol) in 150 ml of CH2Cl2 was added dropwise (13.5 ml, 130 mmol) of diethylamine. The reaction is stirred overnight then concentrated. The mixture is taken into ether and 1 HCl and the aqueous layer separated. The organic layer was extracted a further two times with ether then washed with brine and dried over Na2SO4. The resulting oil was taken into ethyl acetate and allowed to crystallize. 2 more crystallizations of the mother liquor yielded 18.6 g, 83.6%.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/36552, 2003, A1

36
[ 229479-46-3 ]
CH₂Cl₂:MeOH [ No CAS ]
[ 5892-99-9 ]
N,N-diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide [ No CAS ]
[ 229479-39-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With ammonium hydroxide In toluene	1 N,N-Diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide Fumarate [1:1], C1 Example 1 N,N-Diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide Fumarate [1:1], C1 A solution of 3.5 g (14.1 mmol) of N-(3-methoxyphenyl)-1-propyl-4-piperidinamine, 3.61 g (14.1 mmol) of N,N-diethyl-4-bromobenzamide, 129 mg (0.141 mmol) tris(dibenzylideneacetone)-dipalladium(0) (Pd2dba3), 263 mg (0.423 mmol) of (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (+BINAP) and 1.89 g (19.7 mmol) of sodium t-butoxide in 25 mL of dry toluene was heated at 110° C. under Ar in a pressure vessel for 16 h. The mixture was cooled and partitioned between CH2Cl2 and H2O. The organic layer was washed with brine, dried (K2CO3) and the solvent was evaporated. The residue was chromatographed on a Biotage Flash 75 unit using CH2Cl2:MeOH:NH4OH, 92:8:0.8 as eluent. There was obtained 3.2 g (53% yield) of N,N-diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4yl)amino]benzamide as a solid. A fumarate salt was prepared out of 2-PrOH: mp 168-169° C. MS m/z=424 (M++H). 300 MHz 1H NMR (DMSO-d6) δ7.3 (t, 1H); 7.2 (d, 2H); 6.8 (d, 1H); 6.6 (m, 4H); 6.5 (s, 2H); 4.0 (m, 1H); 3.75 (s, 3H); 3.3 (q, 4H); 3.1 (d, 2H); 2.4 (m, 4H); 1.9 (d, 2H); 1.4 (m, 4H); 1.1 (t, 6H); 0.8 (t, 3H). Anal calcd. for C26H37N3O2.C4H4O4: C, 66.77; H, 7.65; N, 7.78. Found: C, 66.69; H, 7.76; N 7.68.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US6436959, 2002, B1

37
[ 584-08-7 ]
[ 5892-99-9 ]
[ 588-16-9 ]
N,N-diethyl-4-[N-(3-methoxyphenyl)amino]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With CuI In dichloromethane; water	1 N,N-Diethyl-4-[N-(3-methoxyphenyl)amino]benzamide PREPARATION 1 N,N-Diethyl-4-[N-(3-methoxyphenyl)amino]benzamide 3.7 g (2.3 mmol) of N-acetyl-m-anisidine, 10.6 g (41.4 mmol) of 4-bromo-N,N-diethylbenzamide and 0.42 g of CuI were heated to 1000° C.; 3 g (22.3 mmol) of K2 CO3 were added and the resulting mixture was heated to 250° C. for 2 hours. The residue was dissolved in CH2 Cl2 and washed with H2 O, the organic layer was dried over Na2 SO4 and the solvent was removed in vacuo. The resulting residue was dissolved in 20 ml of absolute EtOH and refluxed for 2 h. The solvent was removed in vacuo, the residue was taken up in H2 O and the aqueous layer extracted with AcOEt. The organic layer was dried over Na2 SO4 and the solvent removed in vacuo. The resulting residue was purified by flash chromatography (AcOEt/Hexane 6:4), yielding 3 g of the title compound. IR cm- (neat): 3300, 1595, 1535. MS (EI) m/z: 297.6 (M-1)

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5922887, 1999, A

38
PD₂ [ No CAS ]
[ 5892-99-9 ]
[ 206273-87-2 ]
N,N-diethyl-4-[phenyl(1-(tert-butoxycarbonyl)piperidin-4-yl)amino]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; water; toluene	4 N,N-Diethyl-4-[benzyl(piperidin-4-yl)amino]benzamide (Compound 8) A solution of 4-benzylamino-1-(tert-butoxycarbonyl)piperidine (2.63 g, 9.06 mmol), N,N-diethyl-4-bromobenzamide (2.32 g, 9.06 mmol), Pd2 dba3 (0.08 g, 0.091 mmol), (+)-BINAP (0.17 g, 0.272 mmol) and sodium t-butoxide (1.22 g, 12.7 mmol) in 18 mL of dry toluene was heated at 120° C. under Argon in a pressure vessel for 48 h. The mixture was cooled, and dichloromethane (75 mL) and water (75 mL) were added to the reaction flask. The layers were separated, and the aqueous layer was extracted twice with dichloromethane (75 mL). The organic layers were combined and washed with brine (75 mL) and dried (Na2SO4). Evaporation of the solvent afforded a dark brown semi-solid. This material was purified on a flash silica gel column (5% methanol-chloroform) to provide 2.79 g of impure product. This material was repurified on a flash silica gel column (5% methanol-chloroform) to give 1.11 g of N,N-diethyl-4-[phenyl(1-(tert-butoxycarbonyl)piperidin-4-yl)amino]benzamide as a golden-brown semisolid. MS (ES), m/z 466 (MH+). 300 MHz 1H NMR (CDCl3) δ1.02-1.33 (br m, 6H), 1.17 (t, J=7.0 Hz, 3H), 1.45 (s, 9H), 11.50-1.69 (br q, 2H), 1.85 (br d, J=12.1 Hz, 2H), 2.81 (br t, J=12.3 Hz, 2H), 3.16-3.34 (br m, 2H), 3.32-3.48 (br q, 2H), 3.47-3.62 (br m, 2H), 3.88-4.02 (br m, 1H), 4.02-4.38 (br m, 2H), 4.48 (br s, 2H), 6.67 (d, J=8.8 Hz, 2H), 7.14-7.29 (m, 4H), 7.32-7.40 (m, 3H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2004/82612, 2004, A1

39
(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-(3-methoxy-phenyl)-methanone [ No CAS ]
[ 5892-99-9 ]
4-[(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-hydroxy-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-N,N-diethylbenzamide With n-butyllithium In tetrahydrofuran; hexanes at -100 - -90℃; for 0.25h; Stage #2: (8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-(3-methoxy-phenyl)-methanone In tetrahydrofuran; hexanes at -78 - 20℃; for 4h;	3 EXAMPLE 3 4-R (8-BENZVL-8-AZA-BICVCLOF3. 2. 1 (3-METHOXV-PHENYL)-METHVLL-N, N- DIETHVL-BENZAMIDE. To a solution of 4-bromo-N, N-diethyl-benzamide (3.16g) in THF (20 mL) at-100 C was added n-BuLi (2.5M in hexanes, 4.9 mL) slowly so the internal temperature would not rise above-90 C. The mixture was stirred at-100 C for 15 minutes. To the reaction was added a solution of ketone 3 (2.75 g) in THF (10 mL) in one portion. The reaction mixture was stirred at-78 C for 1 hour and then was warmed to room temperature over the course of 3 hours. The mixture was poured into a saturated aqueous solution of sodium bicarbonate (30 mL). The aqueous layer was washed with EtOAc (3x 30 mL) and the combined organic extracts were dried over magnesium sulfate and concentrated under vacuum. Purification by flash chromatography with methanol/EtOAc (1: 10) afforded alcohol 12 (2.1 g).'HNMR (400 MHz, CDCI3) 8 6.65 (d, 1 H), 3.21 (s, 2H), 2.94-2. 81 (m, 1 H); MS (M+1) = 513

Reference： [1]Current Patent Assignee: PFIZER INC - WO2004/92165, 2004, A1 Location in patent: Page 27-28

40
[ 202859-14-1 ]
[ 5892-99-9 ]
[ 346664-66-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 110℃;

Reference： [1]Location in patent: scheme or table Jones, Paul; Griffin, Andrew M.; Gawell, Lars; Lavoie, Rico; Delorme, Daniel; Roberts, Edward; Brown, William; Walpole, Christopher; Xiao, Wenhau; Boulet, Jamie; Labarre, Maryse; Coupal, Martin; Butterworth, Joanne; St-Onge, Stephane; Hodzic, Lejla; Salois, Dominic [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 5994 - 5998]

41
[ 477179-13-8 ]
[ 5892-99-9 ]
[ 437986-94-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate In toluene at 110℃;

Reference： [1]Location in patent: scheme or table Griffin, Andrew M.; Brown, William; Walpole, Christopher; Coupal, Martin; Adam, Lynda; Gosselin, Mylene; Salois, Dominic; Morin, Pierre-Emmanuel; Roumi, Marie [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 5999 - 6003]

42
[ 477178-66-8 ]
[ 5892-99-9 ]
[ 477178-67-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 110℃;

Reference： [1]Location in patent: scheme or table Griffin, Andrew M.; Brown, William; Walpole, Christopher; Coupal, Martin; Adam, Lynda; Gosselin, Mylene; Salois, Dominic; Morin, Pierre-Emmanuel; Roumi, Marie [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 5999 - 6003]

43
[ 50541-93-0 ]
[ 5892-99-9 ]
[ 209902-02-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃;

Reference： [1]Location in patent: scheme or table Griffin, Andrew M.; Brown, William; Walpole, Christopher; Coupal, Martin; Adam, Lynda; Gosselin, Mylene; Salois, Dominic; Morin, Pierre-Emmanuel; Roumi, Marie [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 5999 - 6003]

44
[ 5892-99-9 ]
[ 1122-91-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.0333333h;	1a Synthesis of 4-Bromobenzaldehyde Using the In Situ Schwartz Reagent Method To a solution of N,N-diethyl-4-bromo-benzamide (128 mg, 0.5 mmol) (see structural formula at entry 3 of Table 1) and Cp2ZrCl2(207 mg, 0.7 mmol, 1.4 eq.) in THF (3 mL) at RT was rapidly added a 1 M tetrahydrofuran (THF) solution of LiAlH(Ot-Bu)3 (0.7 mL, 0.7 mmol, 1.4 eq.). After addition, thin layer chromatography (TLC) using EtOAc/Hexanes showed the substrate had been consumed completely. The reaction was quenched by distilled H2O immediately. Dilute acid (0.5 N HCl in distilled water) was added until the pH was less than 5. Then EtOAc was added (3×10 mL) and the mixture was extracted. Combined organic layers were washed with brine, dried over MgSO4 and concentrated via evaporation under reduced pressure. Initial purification of the crude product was performed by passing the solution through a filter of silica gel (silica gel 60, 230-400 mesh). Purity was then checked by TLC. If further purification was needed, it was performed by flash column chromatography (silica gel 60, 230-400 mesh) using EtOAc/hexanes as eluent. 4-Bromobenzaldehyde (89 mg, 96% yield) was obtained as a colorless solid. Its melting point was determined to be 55-56° C. (hexanes).1H NMR (400 MHz, CDCl3) δ ppm: 9.98 (s, 1H), 7.75 (d, J=8.31 Hz, 2H), 7.69 (d, J=8.37 Hz, 2H).13C NMR (101 MHz, CDCl3) δ ppm: 191.02, 135.05, 132.42, 130.94, 129.76.The physical and spectral data were consistent with those reported by Lee et al. (see Lee, K.; Maleczka, R. E., Org. Lett. 2006, 8, 1887-1888), who reported a melting point of 54-56° C.
96%	With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere;

Reference： [1]Current Patent Assignee: QUEEN'S UNIVERSITY AT KINGSTON - US2010/145060, 2010, A1 Location in patent: Page/Page column 7
[2]Zhao, Yigang; Snieckus, Victor [Organic Letters, 2014, vol. 16, # 2, p. 390 - 393]

45
[ 5892-99-9 ]
[ 4294-57-9 ]
N,N-diethyl-4′-methylbiphenyl-4-carboxamide [ No CAS ]
[ 613-33-2 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 10332 - 10336

46
[ 5892-99-9 ]
[ 33513-42-7 ]
[ 918811-37-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Stage #2: 4-bromo-N,N-diethylbenzamide In tetrahydrofuran; hexane at -78℃; for 1h; Stage #3: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 0.833333h;	134.134B An oven dried round bottom flask was charged with anhydrous THF (20 mL) and 2,2,6,6-tetramethyl piperidine (0.68 mL, 4.0 mmol). The mixture was cooled in an ice bath and 1.46 M n-butyl lithium in hexane (2.8 mL, 4.09 mmol) was added dropwise over 5 min. After 10 min, the solution was cooled to -78° C. and a solution of 134A (512 mg, 2.0 mmol) in anhydrous THF (2 mL) was added quickly down the side of flask to precool the solution. After 1 h at -78° C. dimethyl formamide (0.5 mL, 6.38 mmol) was added dropwise and the mixture was stirred at -78° C. for 20 min and at RT for 30 min. Water was added dropwise followed by ethyl acetate. The mixture was extracted twice with ethyl acetate. The organic layer was washed with water, saturated sodium chloride solution, dried (MgSO4) and concentrated in vacuo to give 134B (0.256 g, 45%) as yellow oil. LC-MS m/z: 286.16 (M+H)+.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/3539, 2007, A1 Location in patent: Page/Page column 105

47
[ 99-61-6 ]
[ 5892-99-9 ]
[ 691877-61-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane at -10 - -5℃; for 1.5h; Inert atmosphere; Stage #2: 3-nitro-benzaldehyde; 4-bromo-N,N-diethylbenzamide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane at -40 - -20℃; Stage #3: With hydrogenchloride; sodium hydroxide In tetrahydrofuran; hexane; water	n-BuLi (234 mL, 2.5 M solution in hexanes, 585 mmol) was added to a solution of THF (300 mL) and n-BuMgCl (146 mL, 292 mmol, 2M in THF) at -10 to -5 °C over a period of 60 min and the resulting solution was stirred for a further 30 min. The resulting solution was cooled to -40 °C. A solution of N,N-diethyl-4-bromobenzamide (150 g, 586 mmol) in THF (150 mL) was then added over 90 min, and following complete addition the reaction mixture was held for 30 min before being warmed to -25 to -20 °C. l,3-dimethyl-3,4,5,6-tetrahydro- 2(lH)-pyrimidinone (150 mL) was added, followed the addition of a solution of 3- nitrobenzaldehyde (79.7 g, 527 mmol) in THF (150 mL) over at least 60 min. The reaction was held for 60 min before concentrated HC1 (103 g of 36-38% w/w) in water (131 mL) was added and the reaction was allowed to warm to room temperature. The lower aqueous phase was discarded and the organic layer was washed with aqueous NaHC03 (7.1 g in 150 mL), followed by water (150 mL). The residue was purified by flash chromatography on silica gel eluting with toluene and then butyl acetate to provide Compound 2 (129.5 g, 67%).Analysis: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06 (m, 6 H) 3.16 (m, 2 H) 3.39 (m, 2 H) 5.91 (d, J=4.2 Hz, 1 H) 6.30 (d, J=4.2 Hz, 1 H) 7.29 (d, J=8.2 Hz, 2 H) 7.45 (d, J=8.2 Hz, 2 H) 7.61 (t, J=8.1 Hz, 1 H) 7.82 (m, 1 H) 8.09 (ddd, J=8.1, 2.4, 1.1 Hz, 1 H) 8.26 (m, 1 H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1 Location in patent: Page/Page column 59-60

48
[ 5892-99-9 ]
AZD₂₃₂₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C
	Multi-step reaction with 5 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak_.(R). AD 20 micron / isopropyl alcohol; ethanol

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1

49
[ 5892-99-9 ]
[ 875647-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1

50
[ 5892-99-9 ]
[ 1309859-17-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C 7.1: hydrogenchloride / isopropyl alcohol; ethanol / 1 h / 55 °C
	Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak_.(R). AD 20 micron / isopropyl alcohol; ethanol 6.1: hydrogenchloride / isopropyl alcohol; ethanol / 1 h / 55 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1

51
[ 5892-99-9 ]
4-{(R)-(3-aminophenyl)[4-(4-fluorobenzyl)piperazin-1-yl]methyl}-N,N-diethylbenzamide trihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C 7.1: hydrogenchloride / isopropyl alcohol; tert-butyl methyl ether
	Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak_.(R). AD 20 micron / isopropyl alcohol; ethanol 6.1: hydrogenchloride / isopropyl alcohol; tert-butyl methyl ether

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1

52
[ 5892-99-9 ]
C₂₉H₃₅FN₄O*(x)H₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C 7.1: sulfuric acid / ethyl acetate; isopropyl alcohol / 20 - 80 °C
	Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak_.(R). AD 20 micron / isopropyl alcohol; ethanol 6.1: sulfuric acid / ethyl acetate; isopropyl alcohol / 20 - 80 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1

53
[ 5892-99-9 ]
4-{(R)-(3-aminophenyl)[4-(4-fluorobenzyl)piperazin-1-yl]methyl}-N,N-diethylbenzamide phosphate acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C 7.1: phosphoric acid / ethanol; cyclopentylmethyl ether / 20 - 80 °C
	Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak_.(R). AD 20 micron / isopropyl alcohol; ethanol 6.1: phosphoric acid / ethanol; cyclopentylmethyl ether / 20 - 80 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2011/65905, 2011, A1

54
[ 55441-26-4 ]
[ 374564-35-9 ]
[ 5892-99-9 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 6587 - 6589

55
[ 64-10-8 ]
[ 5892-99-9 ]
[ 940532-00-3 ]

Yield	Reaction Conditions	Operation in experiment
291 mg	With t-BuBrettPhos; palladium diacetate; caesium carbonate In tetrahydrofuran; water at 85℃; for 7h; Inert atmosphere;

Reference： [1]Breitler, Simon; Oldenhuis, Nathan J.; Fors, Brett P.; Buchwald, Stephen L. [Organic Letters, 2011, vol. 13, # 12, p. 3262 - 3265]

56
[ 5892-99-9 ]
[ 123-11-5 ]
[ 1321617-00-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In tetrahydrofuran at 110℃; for 20h; Inert atmosphere; regioselective reaction;

Reference： [1]Park, Jihye; Park, Eonjeong; Kim, Aejin; Lee, Youngil; Chi, Ki-Whan; Kwak, Jong Hwan; Jung, Young Hoon; Kim, In Su [Organic Letters, 2011, vol. 13, # 16, p. 4390 - 4393]

57
[ 617-84-5 ]
[ 873-75-6 ]
[ 5892-99-9 ]

Yield	Reaction Conditions	Operation in experiment
54%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In 1,1,2-trichloroethane; water; at 90℃; for 12h;	General procedure: To a solution of alcohols 1 (0.1 mmol) in TCE (1.0 mL) was added n-Bu4NI (20 mol%) and N, N-disubstituted formamides 2 (0.5 mmol), followed by adding a solution of TBHP (6.0 equiv., 70% aqueous solution). The resulting mixture was stirred at 90 oC until it completed. When the reaction was finished, the reaction mixture was cooled to room temperature and poured into saturated Na2S2O3 solution (3.0 mL), extracted with EtOAc (3×8.0 mL), then washed with saturated brine. The combined organic layers were dried over anhydrous Na2SO4. After removing the solvents in vacuo, the residue was purified by flash column chromatography on silica gel or preparative TLC on GF 254 to afford the desired products 3.
65%Chromat.		General procedure: Various N,N-dimethyl benzamides were obtained followinga simple procedure which involves charging the reactionmixture containing benzyl alcohols (1mmol), catalyst(20wt%) and DMF (5mL) into a two necked 50mL roundbottom flask (RBF) and stirred for 10min at RT and then70% aqueous TBHP (5mmol) was introduced dropwiseto the mixture under continuous stirring at RT. The RBFwas fitted with a water condenser and heated for 24h at100C. After 24h, the reaction mixture was cooled to RTand catalyst was then separated by filtration. The reactionmixture was diluted with 100mL of DW and extractedusing ethyl acetate (2 × 60mL). The combined organiclayer was dried using Na2SO4and concentrated underrotatory evaporator. The crude products were purified bychromatography using silica gel, hexane and ethyl acetate.Similarly a range of N,N-substituted benzamides werealso obtained by taking the stoichiometric amount of variousN-substituted formamides in 5mL of toluene keepingother parameters constant.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6479 - 6482,4
[2]Catalysis Letters,2018,vol. 148,p. 3102 - 3111

58
[ 5892-99-9 ]
[ 185990-03-8 ]
N,N-diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 0.166667h; Inert atmosphere; Stage #2: N,N-diethyl-4-bromobenzamide In 1,2-dimethoxyethane at 30℃; for 1.25h;
51%	Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 0.166667h; Inert atmosphere; Stage #2: N,N-diethyl-4-bromobenzamide In 1,2-dimethoxyethane at 30℃; for 1h;

Reference： [1]Ito, Hajime; Shishido, Ryosuke [Organic Syntheses, 2022, vol. 99, # 1, p. 39 - 52]
[2]Yamamoto, Eiji; Izumi, Kiyotaka; Horita, Yuko; Ito, Hajime [Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 19997 - 20000]

59
[ 5892-99-9 ]
[ 762-04-9 ]
[ 1450829-69-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dipotassium peroxodisulfate; silver sulfate In water; acetonitrile at 90℃; regioselective reaction;

Reference： [1]Mao, Xuerong; Ma, Xiao; Zhang, Shuwei; Hu, Hongwen; Zhu, Chengjian; Cheng, Yixiang [European Journal of Organic Chemistry, 2013, # 20, p. 4245 - 4248]

60
[ 617-84-5 ]
[ 16532-79-9 ]
[ 5892-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(I) oxide; 1,10-Phenanthroline; oxygen; toluene-4-sulfonic acid at 140℃; for 24h; Sealed tube;

Reference： [1]Hu, Chenxu; Yan, Xufei; Zhou, Xiangge; Li, Zhengkai [Organic and Biomolecular Chemistry, 2013, vol. 11, # 47, p. 8179 - 8182]

61
C₈H₁₅BrZn*LiCl [ No CAS ]
[ 5892-99-9 ]
(E)-N,N-diethyl-4-(3,4,4-trimethylpent-2-en-1-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With 2′-(dicyclohexylphophanyl)-N₂,N₂,N₆,N₆-tetramethyl[1,1′-biphenyl]-2,6-diamine; [(2-dicyclohexylphosphino-2’,6’-bis(N,N-dimethylamino)-1,1‘-biphenyl)-2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;

Reference： [1]Yang, Yang; Mustard, Thomas J. L.; Cheong, Paul Ha-Yeon; Buchwald, Stephen L. [Angewandte Chemie - International Edition, 2013, vol. 52, # 52, p. 14098 - 14102][Angew. Chem., 2013, vol. 125, # 52, p. 14348 - 14352,5]

62
[ 586-76-5 ]
[ 5892-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / toluene / 20 °C 2: triethylamine / dichloromethane / 0 - 20 °C
	Multi-step reaction with 2 steps 1: thionyl chloride / Reflux; Inert atmosphere 2: triethylamine / Inert atmosphere

Reference： [1]Zhao, Yigang; Snieckus, Victor [Organic Letters, 2014, vol. 16, # 2, p. 390 - 393]
[2]Zhuang, Zhe; Hu, Zhi-Peng; Liao, Wei-Wei [Organic Letters, 2014, vol. 16, # 12, p. 3380 - 3383]

63
[ 5892-99-9 ]
[ 79119-31-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With cesiumhydroxide monohydrate; t-BuBrettPhos; C₄₄H₆₂NO₅PPdS; water In 1,4-dioxane at 20℃; for 18h; Inert atmosphere;

Reference： [1]Cheung, Chi Wai; Buchwald, Stephen L. [Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 5351 - 5358]

64
[ 100-42-5 ]
[ 5892-99-9 ]
[ 1620210-46-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; 1,4-bis[bis(pentafluorophenyl)phosphino]butane In 1,4-dioxane at 100℃; for 48h; Sealed tube; Inert atmosphere;

Reference： [1]Crisenza, Giacomo E. M.; McCreanor, Niall G.; Bower, John F. [Journal of the American Chemical Society, 2014, vol. 136, # 29, p. 10258 - 10261]

65
[ 1569-69-3 ]
[ 5892-99-9 ]
C₁₇H₂₅NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98 %Spectr.	With [(C₆H₃(OP(i-Pr)2)2)RhHCl]; sodium t-butanolate In toluene at 110℃; for 3h; Sealed tube; Inert atmosphere;

Reference： [1]Timpa, Samuel D.; Pell, Christopher J.; Ozerov, Oleg V. [Journal of the American Chemical Society, 2014, vol. 136, # 42, p. 14772 - 14779]

66
[ 5892-99-9 ]
[ 22483-09-6 ]
C₁₅H₂₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; sodium t-butanolate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Schlenk technique;

Reference： [1]Shi, Shi-Liang; Buchwald, Stephen L. [Angewandte Chemie - International Edition, 2015, vol. 54, # 5, p. 1646 - 1650][Angew. Chem., 2015, vol. 127, # 5, p. 1666 - 1670]

67
[ 618859-85-1 ]
[ 5892-99-9 ]
5'-(tert-butyl)-N,N-diethyl-2'-(imidazo[1,5-a]pyridin-3-yl)[1,1'-biphenyl]-4-carboxamide [ No CAS ]
5'-(tert-butyl)-N₄,N₄,N₄'',N₄''-tetraethyl-2'-(imidazo[1,5-a]pyridin-3-yl)-[1,1':3',1''-terphenyl]-4,4''-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 69% 2: 9%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; mesitylenecarboxylic acid; potassium carbonate In toluene at 130℃; for 15h; Inert atmosphere; Microwave irradiation; Glovebox; regioselective reaction;

Reference： [1]Roman, Daniela Sustac; Poiret, Valentin; Pelletier, Guillaume; Charette, Andr B. [European Journal of Organic Chemistry, 2015, vol. 2015, # 1, p. 67 - 71]

68
[ 201230-82-2 ]
[ 5467-74-3 ]
[ 109-89-7 ]
[ 5892-99-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With N-chloro-succinimide; palladium 10% on activated carbon; sodium hydrogencarbonate In tert-butyl methyl ether at 45℃; for 18h; Inert atmosphere; Autoclave;

Reference： [1]Li, Wanfang; Wu, Xiao-Feng [Chemistry - A European Journal, 2015, vol. 21, # 20, p. 7374 - 7378]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	5892-99-9	MDL No. :	MFCD00463697
Formula :	C₁₁H₁₄BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LDUPVXSXLZOQAF-UHFFFAOYSA-N
M.W :	256.14	Pubchem ID :	4498254
Synonyms :

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	4
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.65
TPSA :	20.31 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.49 cm/s

Log Po/w (iLOGP) :	2.7
Log Po/w (XLOGP3) :	1.94
Log Po/w (WLOGP) :	2.93
Log Po/w (MLOGP) :	3.12
Log Po/w (SILICOS-IT) :	2.67
Consensus Log Po/w :	2.67

[ CAS No. 5892-99-9 ]

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[ 5892-99-9 ] Synthesis Path-Downstream 1~68

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[ 5892-99-9 ]

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

Log S (ESOL) :	-2.7
Solubility :	0.507 mg/ml ; 0.00198 mol/l
Class :	Soluble
Log S (Ali) :	-1.99
Solubility :	2.62 mg/ml ; 0.0102 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-4.12
Solubility :	0.0193 mg/ml ; 0.0000753 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.24

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	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.
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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.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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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
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P332	IF SKIN irritation occurs:
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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
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P413
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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. 5892-99-9 ]

Quality Control of [ 5892-99-9 ]

Related Doc. of [ 5892-99-9 ]

Product Details of [ 5892-99-9 ]

Calculated chemistry of [ 5892-99-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5892-99-9 ]

Application In Synthesis of [ 5892-99-9 ]

[ 5892-99-9 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 5892-99-9 ]

Aryls

Bromides

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5892-99-9 ]