Name: 89691-67-8|2'-Bromo-4'-methoxyacetophenone|98%
Brand: Ambeed
SKU: A826460
Price: 12.0 USD
Availability: InStock
Rating: 97 (29 reviews)

1
[ 89691-67-8 ]
[ 852946-96-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 1-(2-bromo-4-methoxyphenyl)ethanone With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: With water In dichloromethane	10.1.2 Reduction of the Carbonyl FunctionUnder inert atmosphere, to a solution of the ketone previously prepared (1eq) in dichloromethane cooled at 0° C. were added boron trifluoride diethyletherate (2eq) then triethylsilane (3eq) drop by drop. The recation mixture was stirred at room temperature for 24 hours then water was added. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel.10.1.2 3-Bromo-4-ethylanisole Prepared following the reduction method previously described (Method 10A) using (1-(2-bromo-4-methoxyphenyl)ethanone) (example 10.1.1). The product was chromatographed over silica gel (eluent petroleum ether/ethyl acetate 98/2). The product was obtained as a colorless oil. Yield: 93% Rf (petroleum ether/ethyl acetate 95/5): 0.5 NMR 1H (DMSO): 1.10 (t, 3H, J=7.5 Hz); 2.67 (q, 2H); 3.71 (s, 3H); 6.80 (dd, 1H, J=8.3 Hz and J=2.8 Hz); 6.93 (d, 1H, J=2.8 Hz); 7.05 (d, 1H, J=8.3 Hz).
	With hydrogenchloride; amalgamated zinc

Reference： [1]Current Patent Assignee: SA GENFIT - US2010/4159, 2010, A1 Location in patent: Page/Page column 59-60
[2]Baddeley; Plant [Journal of the Chemical Society, 1943, p. 525]

2
[ 2398-37-0 ]
[ 75-36-5 ]
[ 89691-67-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With aluminum (III) chloride In dichloromethane at 0 - 20℃; Inert atmosphere;	24.a Acetyl chloride (3.56 mL, 0.06 mol) is added dropwise to a stirred suspension of 3-bromoanisole (9.35 g, 0.05 mol) and AlCl3 (8.00 g, 0.06 mol) in dichloromethane (50 mL) at 0 °C under argon. The resulting mixture is stirred at 0 0C for 40 min and then at room temperature for 1 h, and diluted with H2O (100 mL) and 2 N HCl (35 mL), and extracted with ethyl acetate (2 x 100 mL and 50 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (12.5% to 14.3% ethyl acetate/hexane) to give 9.55 g (83%) of 2 as a colorless liquid. IR 2964, 1688, 1596, 1252 cm"1; 1H NMR (CDCI3) δ 2.66 (s, 3H, CH3CO), 3.88 (s, 3H, CH3O), 6.91 (dd, J= 8.4 Hz, 2.4 Hz, IH, 5-PhH), 7.19 (d, J= 2.4 Hz, IH, 3- PhH), 7.63 ppm (d, J= 8.4 Hz, IH, 6-PhH).
75%	With aluminum (III) chloride In dichloromethane at -20℃; for 3h;	eq. 1 1-Bromo-3-methoxybenzene (20 mmol), CH2Cl2 (50 mL) and CH3COCl (1.5 eq., 30 mmol) were added to a 250 mL round-bottom flask. After cooled to -20 oC, AlCl3 (3 eq., 8.0 g) was added to the mixture slowly. The reaction was stirred vigorously for 3 h at -20 oC. Ice water ( 80 mL ) was added to the flask and the mixture was extracted with CH2Cl2 (30 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided 1-(2-bromo-4-methoxyphenyl)ethanone, yield 75%.
70%	With aluminum (III) chloride In dichloromethane at 0 - 20℃;

65%	With aluminum (III) chloride In dichloromethane at 20℃; for 16h; Inert atmosphere;
59%	With aluminium trichloride In dichloromethane at 20℃;
59%	With aluminium trichloride
59%	With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 2h;
57%	With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 1.66667h; Inert atmosphere;
55%	With zirconium(IV) chloride In dichloromethane at -10 - 20℃; for 1h; Inert atmosphere;
51%	With aluminum (III) chloride In carbon disulfide for 16h;	129.1 A round-bottomed flask was charged acetyl chloride (4.20g, 53.56mmol, leq), AICI3 (7.13g, 53.56mmol, leq), and carbon disulfide (80mL). To the mixture was added dropwise a solution of 3-bromoanisole (9.75g, 52.13mmol) in carbon disulfide (20mL) and stirred for 16 h. The resulting solution was diluted with ice water (l OOmL) and extracted with CH2G12 (50mLx3). The extracts were washed with H20, brine, and IN NaOH (30mL). The organic layer was dried over MgS04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes = 1 :10) to afford the title compound (6.2g, 51%).1H NMR (300MHz, CDC13) δ 7.48(dd, J = 8.4Hz, 1,2Hz, 1H), 7.04(brs. 1H), 6.76(dd, 1H), 3.74(s, 3H), 2.52(s, 3H)
51%	With aluminum (III) chloride In carbon disulfide for 16h;	129.1 Step 1. 1-(2-Bromo-4-methoxyphenyl)ethanone A round-bottomed flask was charged acetyl chloride (4.20 g, 53.56 mmol, 1 eq), AlCl3 (7.13 g, 53.56 mmol, 1 eq), and carbon disulfide (80 mL). To the mixture was added dropwise a solution of 3-bromoanisole (9.75 g, 52.13 mmol) in carbon disulfide (20 mL) and stirred for 16 h. The resulting solution was diluted with ice water (100 mL) and extracted with CH2Cl2 (50 mLx3). The extracts were washed with H2O, brine, and 1N NaOH (30 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes=1:10) to afford the title compound (6.2 g, 51%). 1H NMR (300 MHz, CDCl3) δ 7.48 (dd, J=8.4 Hz, 1.2 Hz, 1H), 7.04 (brs. 1H), 6.76 (dd, 1H), 3.74 (s, 3H), 2.52 (s, 3H)
30%	With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique;
	With carbon disulfide; aluminium trichloride
	With aluminum (III) chloride

Reference： [1]Current Patent Assignee: SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE - WO2010/33643, 2010, A2 Location in patent: Page/Page column 79; 80
[2]Lou, Zhen-Bang; Pang, Xin-Long; Chen, Chao; Wen, Li-Rong; Li, Ming [Chinese Chemical Letters, 2015, vol. 26, # 10, p. 1231 - 1235]
[3]Chen, Qiang; Huo, Xing; Zheng, Huaiji; She, Xuegong [Synlett, 2012, vol. 23, # 9, p. 1349 - 1352]
[4]Akgun, Burcin; Li, Caishun; Hao, Yubin; Lambkin, Gareth; Derda, Ratmir; Hall, Dennis G. [Journal of the American Chemical Society, 2017, vol. 139, # 40, p. 14285 - 14291]
[5]Wang, Feijun; Zhang, Yong Jian; Wei, Hao; Zhang, Jiaming; Zhang, Wanbin [Tetrahedron Letters, 2007, vol. 48, # 23, p. 4083 - 4086]
[6]Wang, Feijun; Zhang, Yong Jian; Yang, Guoqiang; Zhang, Wanbin [Tetrahedron Letters, 2007, vol. 48, # 24, p. 4179 - 4182]
[7]Pump, Eva; Poater, Albert; Zirngast, Michaela; Torvisco, Ana; Fischer, Roland; Cavallo, Luigi; Slugovc, Christian [Organometallics, 2014, vol. 33, # 11, p. 2806 - 2813]
[8]Zhang, Wen; Chen, Pinhong; Liu, Guosheng [Angewandte Chemie - International Edition, 2017, vol. 56, # 19, p. 5336 - 5340][Angew. Chem., 2017, vol. 129, # 19, p. 5420 - 5424]
[9]Moreno-Sanz, Guillermo; Duranti, Andrea; Melzig, Laurin; Fiorelli, Claudio; Ruda, Gian Filippo; Colombano, Giampiero; Mestichelli, Paola; Sanchini, Silvano; Tontini, Andrea; Mor, Marco; Bandiera, Tiziano; Scarpelli, Rita; Tarzia, Giorgio; Piomelli, Daniele [Journal of Medicinal Chemistry, 2013, vol. 56, # 14, p. 5917 - 5930]
[10]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - WO2011/30955, 2011, A1 Location in patent: Page/Page column 111-112
[11]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2012/214991, 2012, A1 Location in patent: Page/Page column 45-46
[12]Casnati, Alessandra; Fontana, Marco; Motti, Elena; Della Ca, Nicola [Organic and Biomolecular Chemistry, 2019, vol. 17, # 25, p. 6165 - 6173]
[13]Oki [Bulletin of the Chemical Society of Japan, 1953, vol. 26, p. 331,334]
[14]Liu, Yi; Marszalek, Tomasz; Müllen, Klaus; Pisula, Wojciech; Feng, Xinliang [Chemistry - An Asian Journal, 2016, vol. 11, # 15, p. 2107 - 2112]

3
[ 56222-08-3 ]
[ 89691-67-8 ]
[ 128739-13-9 ]

Reference： [1]Acta Chimica Hungarica,1989,vol. 126,p. 441 - 454

4
[ 89691-67-8 ]
[ 74317-85-4 ]

Yield	Reaction Conditions	Operation in experiment
68%		Br2 (8.5 mL, 165.89 mmol) is added dropwise to 20% NaOH (97 mL) at 0-10 0C in a 15-min period. The resulting solution is warmed to room temperature before l-(2-bromo-4-methoxyphenyl)ethanone (2) (9.50 g, 41.47 mmol) is added. The mixture is stirred at 36 C for 29 h and at room temperature for 17 h, diluted with 0.5 M NaHSO3 (25 mL), and extracted with ether (100 mL and 70 mL). The aqueous layer is acidified with cone. HCl (30 mL) to give 6.56 g (68%) of 3 as a white solid, mp 195-197 C. IR 2997, 1686, 1596, 1290 cm"1; 1R NMR (CDCl3) delta 3.80 (s, 3H, CH3O), 6.83 (dd, J= 7.2, 2.0 Hz, IH, 5-PhH), 7.15 (d, J= 2.0 Hz, IH, 3PhrH), 7.90 ppm (d, J= 7.2 Hz, IH, 6-PhH).

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4083 - 4086
[2]Tetrahedron Asymmetry,2008,vol. 19,p. 482 - 488
[3]Organometallics,2014,vol. 33,p. 2806 - 2813
[4]Patent: WO2010/33643,2010,A2 .Location in patent: Page/Page column 79; 80
[5]Archiv der Pharmazie,1990,vol. 323,p. 73 - 78
[6]Tetrahedron Letters,2007,vol. 48,p. 4179 - 4182
[7]Journal of Medicinal Chemistry,2013,vol. 56,p. 5917 - 5930

5
[ 89691-67-8 ]
[ 89691-60-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With lithium aluminium tetrahydride In diethyl ether 1.) RT, 3 h, 2.) reflux, 1 h;
	With sodium tetrahydroborate In methanol at 0℃;

Reference： [1]Hartmann; Heindl; Schwarz; Schonenberger [Journal of Medicinal Chemistry, 1984, vol. 27, # 7, p. 819 - 824]
[2]Casnati, Alessandra; Fontana, Marco; Motti, Elena; Della Ca, Nicola [Organic and Biomolecular Chemistry, 2019, vol. 17, # 25, p. 6165 - 6173]

6
[ 100-06-1 ]
[ 89691-67-8 ]

Yield	Reaction Conditions	Operation in experiment
45.4%	With bromine In chloroform at 0 - 5℃; for 1h;

Reference： [1]Zara-Kaczian, Erzsebet; Deak, Gyula; Gyoergy, Lajos [Acta Chimica Hungarica, 1989, vol. 126, # 4, p. 441 - 454]

7
[ 89691-67-8 ]
[ 123-11-5 ]
E-1-(2-bromo-4-methoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydroxide In ethanol; water for 12h; Ambient temperature;

Reference： [1]Kammermeier; Wiegrebe [Archiv der Pharmazie, 1994, vol. 327, # 9, p. 547 - 561]

8
[ 89691-67-8 ]
[ 3319-15-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Heating;

Reference： [1]Takano, Daisuke; Fukunaga, Yuki; Doe, Matsumi; Yoshihara, Kazuo; Kinoshita, Takamasa [Journal of Heterocyclic Chemistry, 1997, vol. 34, # 4, p. 1111 - 1114]

9
[ 2398-37-0 ]
[ 75-36-5 ]
[ 30186-18-6 ]
[ 89691-67-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 25%	With aluminium trichloride In carbon disulfide for 12h; Ambient temperature;

Reference： [1]Takano, Daisuke; Fukunaga, Yuki; Doe, Matsumi; Yoshihara, Kazuo; Kinoshita, Takamasa [Journal of Heterocyclic Chemistry, 1997, vol. 34, # 4, p. 1111 - 1114]

10
[ 2398-37-0 ]
[ 108-24-7 ]
[ 89691-67-8 ]
[ 89368-12-7 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 6331 - 6333

11
[ 89691-67-8 ]
1,3,5-tris-(2’-bromo-4’-methoxylphenyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrachlorosilane In ethanol at 20℃; for 15h;
	With tetrachlorosilane In ethanol

Reference： [1]Luo, Jia; Zhou, Yan; Niu, Zhi-Qiang; Zhou, Qi-Feng; Ma, Yuguo; Pei, Jian [Journal of the American Chemical Society, 2007, vol. 129, # 37, p. 11314 - 11315]
[2]Liu, Yi; Marszalek, Tomasz; Müllen, Klaus; Pisula, Wojciech; Feng, Xinliang [Chemistry - An Asian Journal, 2016, vol. 11, # 15, p. 2107 - 2112]

12
[ 89691-67-8 ]
[ 17100-65-1 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4179 - 4182
[2]Tetrahedron Letters,2007,vol. 48,p. 4083 - 4086

13
[ 89691-67-8 ]
[ 89691-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85 percent / LiAlH₄ / diethyl ether / 1.) RT, 3 h, 2.) reflux, 1 h 2: 14 percent / TiCl₃, LiAlH₄ / 1,2-dimethoxy-ethane / 16 h / Heating 3: 81 percent / BBr₃ / CH₂Cl₂ / 4.5 h / -60 - 20 °C

Reference： [1]Hartmann; Heindl; Schwarz; Schonenberger [Journal of Medicinal Chemistry, 1984, vol. 27, # 7, p. 819 - 824]

14
[ 89691-67-8 ]
[ 89691-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / LiAlH₄ / diethyl ether / 1.) RT, 3 h, 2.) reflux, 1 h 2: 14 percent / TiCl₃, LiAlH₄ / 1,2-dimethoxy-ethane / 16 h / Heating

Reference： [1]Hartmann; Heindl; Schwarz; Schonenberger [Journal of Medicinal Chemistry, 1984, vol. 27, # 7, p. 819 - 824]

15
[ 89691-67-8 ]
[ 89691-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / LiAlH₄ / diethyl ether / 1.) RT, 3 h, 2.) reflux, 1 h 2: TiCl₃, LiAlH₄ / 1,2-dimethoxy-ethane / 16 h / Heating

Reference： [1]Hartmann; Heindl; Schwarz; Schonenberger [Journal of Medicinal Chemistry, 1984, vol. 27, # 7, p. 819 - 824]

16
[ 89691-67-8 ]
[ 128739-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 87.5 percent / triethylamine / diethyl ether / 6 h / Ambient temperature 2: 80.6 percent / NaBH₄ / H₂O; methanol / 4 h / Ambient temperature 3: 84 percent / H₂ / Raney Ni / ethanol / 760 Torr / Ambient temperature

Reference： [1]Zara-Kaczian, Erzsebet; Deak, Gyula; Gyoergy, Lajos [Acta Chimica Hungarica, 1989, vol. 126, # 4, p. 441 - 454]

17
[ 472967-24-1 ]
[ 89691-67-8 ]
[ 472967-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃;	32 Example 32; 1-(2-(4-Methoxyphenyl)-2-oxoethyl)-5,5-dimethyl-3-naphthylcarbonylimidaz olidine-2,4-dione (Compound 32) Example 32 1-(2-(4-Methoxyphenyl)-2-oxoethyl)-5,5-dimethyl-3-naphthylcarbonylimidaz olidine-2,4-dione (Compound 32) 5,5-Diemthyl-3-naphthylcarbonylimidazolidine-2,4-dione (35 mg) was dissolved in DMF (0.4 ML), and sodium hydride (60%, in oil) (5 mg) was added.. Then, 30 mg of 2-bromo4-methoxyacetophenone was added, and the mixture was stirred at room temperature overnight.. ethyl acetate was (9.5 ML) was added to the reaction solution, separated out white precipitates were filtered, and the filtrate was concentrated and purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 11 mg of white crystals.1H-NMR (CDCl3) δ2.04 (6H, s), 3.85 (3H, s), 4.79 (2H, s), 6.90 (2H, dt, J=8.9, 2.0 Hz), 7.46-7.58 (4H, m), 7.80-7.95 (5H, m).13C-NMR (CDCl3) δ22.8, 44.5, 55.5, 64.7, 114.1, 123.8, 124.7, 124.7, 126.3, 127.0, 127.4, 128.6, 129.7, 130.3, 130.6, 133.2, 133.7, 152.3, 164.3, 168.4, 175.3, 188.0.

Reference： [1]Current Patent Assignee: SENJU PHARMACEUTICAL CO.,LTD. - EP1384715, 2004, A1 Location in patent: Page 15

18
[ 472967-24-1 ]
[ 89691-67-8 ]
[ 472967-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃;	31 Example 31; 5,5-Dimethyl-3-naphthylcarbonyl-1-(2-oxo-2-p-tolylethyl)imi dazolidine -2,4-dione (Compound 31) 5,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione (35 mg) was dissolved in DMF (0.4 mL), and sodium hydride (60%, in oil) (5 mg) was added. Then, 2-brondo-4-methylacetophenone (27 mg) was added, and the mixture was stirred at room temperature overnight. Ethyl acetate (9.5 mL) was added to the reaction solution, separated out white precipitates were filtered, and the filtrate was concentrated and purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 12 mg of white crystals.1H-NMR (CDCl3) δ2.04 (6H, s), 2.39 (3H, s), 4.81 (2H, s), 7.23 (2H, dd, J=8.6, 0.7 Hz), 7.46-7.55 (3H, m), 7.56 (1H, dd, J=7.8, 1.5 Hz), 7.74 (2H, dt, J=8.2, 1.8 Hz), 7.84-7.95 (3H, m).13C-NMR (CDCl3) δ21.8, 22.8, 44.7, 64.7, 123.8, 124.7, 124.7, 126.4, 127.4, 128.1, 128.6, 129.6, 129.6, 130.6, 131.5, 133.2, 133.7, 145.3, 152.2, 168.4, 175.2, 189.2.

Reference： [1]Current Patent Assignee: SENJU PHARMACEUTICAL CO.,LTD. - EP1384715, 2004, A1 Location in patent: Page 15

19
[ 89691-67-8 ]
[ 55-21-0 ]
[ 855239-80-4 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 2h; Inert atmosphere;

Reference： [1]Huang, Jinkun; Chen, Ying; King, Anthony O.; Dilmeghani, Mina; Larsen, Robert D.; Faul, Margaret M. [Organic Letters, 2008, vol. 10, # 12, p. 2609 - 2612]

20
[ 89691-67-8 ]
[ 77287-34-4 ]
[ 42465-53-2 ]
[ 3219-34-9 ]
[ 190516-85-9 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2609 - 2612

21
[ 89691-67-8 ]
[ 60100-09-6 ]
[ 3219-34-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;

Reference： [1]Huang, Jinkun; Chen, Ying; King, Anthony O.; Dilmeghani, Mina; Larsen, Robert D.; Faul, Margaret M. [Organic Letters, 2008, vol. 10, # 12, p. 2609 - 2612]

22
[ 89691-67-8 ]
[ 60100-09-6 ]
[ 3219-34-9 ]
[ 82121-05-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 61 %Chromat. 2: 29 %Chromat.	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;

Reference： [1]Huang, Jinkun; Chen, Ying; King, Anthony O.; Dilmeghani, Mina; Larsen, Robert D.; Faul, Margaret M. [Organic Letters, 2008, vol. 10, # 12, p. 2609 - 2612]

23
4-chloro-2-aldehyde phenylboronic acid [ No CAS ]
[ 89691-67-8 ]
[ 1149344-95-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium fluoride; palladium diacetate; di‐tert‐butyl‐(1‐phenylindol‐2‐yl)phosphane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

Reference： [1]Young, Lok Choi; Yu, Chan-Mo; Bum, Tae Kim; Heo, Jung-Nyoung [Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 3948 - 3951]

24
[ 1005346-96-2 ]
[ 89691-67-8 ]
[ 1149344-85-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium fluoride; palladium diacetate; di‐tert‐butyl‐(1‐phenylindol‐2‐yl)phosphane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

Reference： [1]Young, Lok Choi; Yu, Chan-Mo; Bum, Tae Kim; Heo, Jung-Nyoung [Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 3948 - 3951]

25
[ 40138-16-7 ]
[ 89691-67-8 ]
[ 1149344-94-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium fluoride; palladium diacetate; di‐tert‐butyl‐(1‐phenylindol‐2‐yl)phosphane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

Reference： [1]Young, Lok Choi; Yu, Chan-Mo; Bum, Tae Kim; Heo, Jung-Nyoung [Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 3948 - 3951]

26
[ 2398-37-0 ]
[ 108-24-7 ]
[ 89691-67-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With [t-BuCpZr(OH₂)₃]₂(μ²-OH)₂(OSO₂C₈F₁₇)₄2(C₃H₆O)8H₂O In neat (no solvent) at 20℃; Inert atmosphere; Sealed tube;	Typical procedure for Friedel-Crafts acylation of anisole withacetic anhydride catalyzed by 1a: General procedure: To a 10 mL sealed tubewas added anisole (108 mg, 1.0 mmol), aceticanhydride (204 mg, 2.0 mmol) and catalyst (2.5 mol%). Then the mixture wasstirred at room temperature until complete consumption of starting material asmonitored by TLC or GC-MS analysis. Then the reaction mixture was evaporated invacuum, and CH2Cl2 (3×10 ml) was added to the reactionmixture. The catalyst was then filtered out for the next cycle of reaction. Thecombined CH2Cl2 solution was removed by evaporation invacuum and was then subject to silica gel column chromatograph.
61%	With [{CH₃CpZr(OH₂)₃}₂(μ²-OH)₂][OSO₂C₈F₁₇]₄ In neat (no solvent) at 50℃; Sealed tube; Inert atmosphere;	3.3 Typical procedure for Friedel-Crafts acylation of anisole (2a) with acetic anhydride catalyzed by 1a General procedure: To a 10mL sealed tube was added anisole (2a) (108mg, 1.0mmol), acetic anhydride (204mg, 2.0mmol) and catalyst 1a (67.6mg, 2.5mol%). Then the mixture was stirred at room temperature until complete consumption of starting material as monitored by TLC or GC-MS analysis. Then the reaction mixture was evaporated in vacuum, CH2Cl2 (3×10mL was added to the reaction mixture and the catalyst was filtered for the next cycle of reaction. The combined CH2Cl2 solution was removed by evaporation in vacuum and was then subject to silica gel column chromatograph. the Friedel-Crafts acylation product (3a) was obtained: 124mg, isolated yield 83%.
40%	With lithium perchlorate at 100℃; for 5h;

Reference： [1]Zhang, Xiaohong; Xu, Xinhua; Li, Ningbo; Liang, Zhiwu; Tang, Zilong [Tetrahedron, 2018, vol. 74, # 15, p. 1926 - 1932]
[2]Zhang, Xiaohong; Lou, Cong; Li, Ningbo; Xu, Xinhua; Qiu, Renhua; Yin, Shuangfeng [Journal of Organometallic Chemistry, 2014, vol. 749, p. 241 - 245]
[3]Tan, Lay Pheng; Wu, Hao; Yang, Peng-Yu; Kalesh, Karunakaran A.; Zhang, Xiaohua; Hu, Mingyu; Srinivasan, Rajavel; Yao, Shao Q. [Organic Letters, 2009, vol. 11, # 22, p. 5102 - 5105]

27
[ 89691-67-8 ]
[ 7565-57-3 ]
[ 1196517-15-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide In tetrahydrofuran; N,N-dimethyl acetamide at 100℃; for 0.666667h; Microwave irradiation;

Reference： [1]Tan, Lay Pheng; Wu, Hao; Yang, Peng-Yu; Kalesh, Karunakaran A.; Zhang, Xiaohua; Hu, Mingyu; Srinivasan, Rajavel; Yao, Shao Q. [Organic Letters, 2009, vol. 11, # 22, p. 5102 - 5105]

28
[ 2398-37-0 ]
[ 75-36-5 ]
[ 89691-67-8 ]
[ 89368-12-7 ]

Yield	Reaction Conditions	Operation in experiment
55%; 18%		Friedel-Craft's Reaction Under inert atmosphere, to a solution of aluminium trichloride (1.25eq) in dichloromethane cooled at 0 C. was added the appropriate bromobenzene (1eq) drop by drop during 10 minutes. The reaction mixture was stirred at 0 C. for 1 hour then was added acyl chloride (1.05eq) in dichloromethane drop by drop. The reaction mixture was stirred for 2 hours then poured into ice. The phases were separated. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel. Example 10.1.3-Bromo-4-ethylanisole and 3-Bromo-6-ethylanisole10.1.11-(2-Bromo-4-methoxyphenyl)ethanone and 1-(4-Bromo-2-methoxyphenyl)ethanone Prepared following the Friede-Craft's method previously described (Method 10A) using 3-bromoanisole and acetyl chloride. The products were chromatographed over silica gel (elution gradient petroleum ether/ethyl acetate 98/2 to 90/10). 1-(2-bromo-4-methoxyphenyl)ethanone was obtained as a colorless oil and 1-(4-bromo-2-methoxyphenyl)ethanone was obtained as a white solid.Yield: 55% (1-(2-bromo-4-methoxyphenyl)ethanone) and 18% (1-(4-bromo-2-methoxyphenyl)ethanone)Rf (petroleum ether/ethyl acetate 95/5): 0.33 (1-(2-bromo-4-methoxyphenyl)ethanone) and 0.5 (1-(4-bromo-2-methoxyphenyl)ethanone)NMR 1H (CDCl3) (1-(2-bromo-4-methoxyphenyl)ethanone): 2.60 (s, 3H); 3.82 (s, 3H); 6.85 (d, 1H, J=1.9 Hz); 7.13 (s, 1H); 7.58 (d, 1H, J=5.0 Hz).NMR 1H (CDCl3) (1-(4-bromo-2-methoxyphenyl)ethanone): 2.61 (s, 3H); 3.94 (s, 3H); 7.15 (m, 2H); 7.64 (d, 1H, J=8.3 Hz).

Reference： [1]Patent: US2010/4159,2010,A1 .Location in patent: Page/Page column 59-60

29
[ 89691-67-8 ]
[ 104-94-9 ]
[ 91444-13-2 ]

Yield	Reaction Conditions	Operation in experiment
15%	In ethyl acetate; <i>N</i>,<i>N</i>-dimethyl-aniline at 180℃;	21 To a boiling mixture of p-anisidine (2.46 g, 20 mmol, 6.66 eq) and N,N-dimethylaniline (3.5 ml) is slowly added dropwise 2-bromo-4-methoxyacetophenone (0.7 g, 3 mmol, 1 eq) dissolved in ethyl acetate (12 ml). After the addition is complete, the reaction mixture is stirred at 180° C. for 2 h. To the cooled mixture are added ethyl acetate and 2 M HCl. The aqueous phase is extracted with ethyl acetate several times, and the combined organic phases are washed with a saturated NaCl solution, dried over MgSO4, filtered and evaporated to dryness on a rotary evaporator. Purification by column chromatography (eluent dichloromethane/hexane 7/3) yields the desired product in a yield of 15% (760 mg). C16H15NO2; MW 253; 1H-NMR (CDCl3): δ 8.22 (bs, 1H), 7.33 (t, J=7.9 Hz, 1H), 7.25 (d, J=8.8 Hz, 1H), 7.21 (d, J=7.6 Hz, 1H), 7.16 (t, J=2.5 Hz, 1H), 7.07 (d, J=2.2 Hz, 1H), 6.84 (dt, J=2.5 Hz, J=8.8 Hz, 2H), 6.74 (d, J=2.2 Hz, 1H), 3.86 (s, 3H), 3.85 (s, 3H); 13C-NMR (CDCl3): δ 160.1, 154.5, 138.5, 133.9, 132.0, 130.1, 129.6, 117.6, 113.0, 112.7, 110.9, 102.3, 100.1, 55.9, 55.4; IR: 3364 (NH), 2998, 2835, 1610, 1581, 1483 1/cm; MS (ESI): 254 (M+H)+

Reference： [1]Current Patent Assignee: UNIVERSITY OF SAARLAND - US2010/204234, 2010, A1 Location in patent: Page/Page column 17

30
[ 89691-67-8 ]
[ 149-73-5 ]
C₁₁H₁₅BrO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In methanol at 23℃; Inert atmosphere;

Reference： [1]Teng, Tse-Min; Liu, Rai-Shung [Journal of the American Chemical Society, 2010, vol. 132, # 27, p. 9298 - 9300]

31
[ 89691-67-8 ]
[ 100-52-7 ]
[ 1274882-05-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 1-(2-bromo-4-methoxyphenyl)ethanone; benzaldehyde With sodium hydroxide In ethanol; water at 0 - 20℃; for 4h; Stage #2: With hydrogenchloride In ethanol; water	129.2 To a solution of l-(2-bromo-4-methoxyphenyl)ethanone (6.2g, 27.06mmol) obtained in Step 1 in EtOH (50mL) at 0°C was added sequentially aq. NaOH solution (8.12mL, 81.19mmol, 3eq) and benzaldehyde (3.3mL, 32.48mmol, 1.2eq). After being stirred for additional 4 h at room temperature, the mixture was diluted with H20 and neutralized with 3N HC1. The resulting mixture was extracted with EtOAc (20mLx3). The extracts were washed with brine, dried over MgS04j and concentrated in vacuo to obtain the desired product (6g, 70%). NMR (300MHz, CDC13) δ 7.54-7.59(m, 2H), 7.46-7.49(m, 2H), 7.39-7.42(m, 3H), 7.15-7.21(m, 2H), 6.93(dd, 1H), 3.85(s, 3H)
70%	With sodium hydroxide In ethanol; water at 0 - 20℃; for 4h;	129.2 Step 2. (E)-1-(2-Bromo-4-methoxyphenyl)-3-phenyl-2-propen-1-one To a solution of 1-(2-bromo-4-methoxyphenyl)ethanone (6.2 g, 27.06 mmol) obtained in Step 1 in EtOH (50 mL) at 0° C. was added sequentially aq. NaOH solution (8.12 mL, 81.19 mmol, 3 eq) and benzaldehyde (3.3 mL, 32.48 mmol, 1.2 eq). After being stirred for additional 4 h at room temperature, the mixture was diluted with H2O and neutralized with 3N HCl. The resulting mixture was extracted with EtOAc (20 mLx3). The extracts were washed with brine, dried over MgSO4, and concentrated in vacuo to obtain the desired product (6 g, 70%). 1H NMR (300 MHz, CDCl3) δ 7.54-7.59 (m, 2H), 7.46-7.49 (m, 2H), 7.39-7.42 (m, 3H), 7.15-7.21 (m, 2H), 6.93 (dd, 1H), 3.85 (s, 3H)

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - WO2011/30955, 2011, A1 Location in patent: Page/Page column 112
[2]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2012/214991, 2012, A1 Location in patent: Page/Page column 46

32
[ 89691-67-8 ]
[ 1274882-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 4 h / 0 - 20 °C 2: potassium carbonate / triphenylphosphine; palladium dichloride / N,N-dimethyl-formamide / 3 h / 110 °C / Sealed tube
	Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 4 h / 0 - 20 °C 2: potassium carbonate / triphenylphosphine; palladium dichloride / N,N-dimethyl-formamide / 3 h / 110 °C

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - WO2011/30955, 2011, A1
[2]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2012/214991, 2012, A1

33
[ 89691-67-8 ]
[ 154276-92-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 4 h / 0 - 20 °C 2: potassium carbonate / triphenylphosphine; palladium dichloride / N,N-dimethyl-formamide / 3 h / 110 °C / Sealed tube 3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 2 h / Reflux
	Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 4 h / 0 - 20 °C 2: potassium carbonate / triphenylphosphine; palladium dichloride / N,N-dimethyl-formamide / 3 h / 110 °C 3: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 2 h / Reflux

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - WO2011/30955, 2011, A1
[2]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2012/214991, 2012, A1

34
[ 89691-67-8 ]
[ 552-41-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 1-(2-bromo-4-methoxyphenyl)ethanone With copper(l) iodide; tetra(n-butyl)ammonium hydroxide In water at 60℃; for 24h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; for 2h; Inert atmosphere; chemoselective reaction;

Reference： [1]Xu, Hua-Jian; Liang, Yu-Feng; Cai, Zhen-Ya; Qi, Hong-Xia; Yang, Chun-Yan; Feng, Yi-Si [Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2296 - 2300]

35
[ 89691-67-8 ]
[ 103-81-1 ]
[ 1315568-06-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With copper(l) iodide; caesium carbonate; ethylenediamine In toluene at 110℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Location in patent: experimental part Fu, Liangbing; Huang, Xiaoli; Wang, Deping; Zhao, Pinghua; Ding, Ke [Synthesis, 2011, # 10, p. 1547 - 1554]

36
[ 2999-46-4 ]
[ 89691-67-8 ]
[ 2400-35-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(l) iodide In dimethyl sulfoxide at 50℃; for 0.166667h; Ionic liquid; Inert atmosphere; Microwave irradiation; Sealed tube;

Reference： [1]Location in patent: experimental part Gu, Lijun; Li, Xiangguang [Journal of the Brazilian Chemical Society, 2011, vol. 22, # 11, p. 2036 - 2039]

37
[ 89691-67-8 ]
2-bromo-1-(2-bromo-4-methoxyphenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With bromine In tetrahydrofuran at 20℃; for 2h;	6.a Step a: Preparation of 2-bromo-l-(2-bromo-4-methoxyphenyl)ethan-l-one Bromine (0.25 mL, 4.36 mmol) was added dropwise to a solution containing l-(2-bromo-4- methoxyphenyl)ethan-l-one (1.00 g, 4.36 mmol) dissolved in THF (20 mL). The mixture was stirred at r.t. for 2 h. The mixture was diluted with sat. sodium thiosulfate (20 mL) and extracted with EtOAc (20 mL). The organic layer was separated, dried over MgSCL, and concentrated in vacuo. The crude compound was then purified by silica column chromatography (0-100% EtOAc in hexanes) to give the desired compound mixed with the starting material as a colorless oil (0.42 g, 31%). The mixture was taken into the next step without further purification. LC-MS calcd for CgFLB^Ch 308.98 [M+H]+, found 308.9 [M+H]+ .
	With bromine In diethyl ether at 20℃;

Reference： [1]Current Patent Assignee: ONCOVALENT THERAPEUTICS - WO2021/150918, 2021, A1 Location in patent: Paragraph 0186
[2]Chen, Qiang; Huo, Xing; Zheng, Huaiji; She, Xuegong [Synlett, 2012, vol. 23, # 9, p. 1349 - 1352]

38
[ 89691-67-8 ]
ethyltriphenylphosphonium bromide [ No CAS ]
[ 1404083-22-2 ]
[ 1404083-21-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 2.16667h; Inert atmosphere; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Overall yield = 89 %;

Reference： [1]Yang, Guoqiang; Shen, Chaoren; Zhang, Wanbin [Angewandte Chemie - International Edition, 2012, vol. 51, # 36, p. 9141 - 9145][Angewandte Chemie, 2012, vol. 124, # 36, p. 9275 - 9279]

39
[ 89691-67-8 ]
[ 28547-28-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5917 - 5930

40
[ 89691-67-8 ]
[ 95-92-1 ]
[ 1208075-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;

Reference： [1]Moreno-Sanz, Guillermo; Duranti, Andrea; Melzig, Laurin; Fiorelli, Claudio; Ruda, Gian Filippo; Colombano, Giampiero; Mestichelli, Paola; Sanchini, Silvano; Tontini, Andrea; Mor, Marco; Bandiera, Tiziano; Scarpelli, Rita; Tarzia, Giorgio; Piomelli, Daniele [Journal of Medicinal Chemistry, 2013, vol. 56, # 14, p. 5917 - 5930]

41
[ 89691-67-8 ]
[ 131923-69-8 ]
(Z)-1-(2-bromo-4-methoxyphenyl)-3-(2,7-dichloro-8-methylquinolin-3-yl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium hydroxide In methanol at 20℃; for 2h;	5 General method for the synthesis of quinolinyl chalcones (A1-A14) General procedure: A mixture of formylquinoline (1 mmol) and an aromatic ketone(1 mmol) in methanol (50 mL) was stirred at room temperature,followed by dropwise addition of aq. NaOH (4 mL, 10%). The stirringwas continued for 2 h and the reaction mixture was then keptat 0 C for 24 h. Subsequently, it was poured onto ice-cold water(200 mL). The precipitates were collected by filtration, washedwith cold water followed by cold MeOH. The resulting chalconeswere recrystallized from CHCl3 and dried in vacuo.

Reference： [1]Abdullah, Muhammad Imran; Mahmood, Asif; Madni, Murtaza; Masood, Sara; Kashif, Muhammad [Bioorganic Chemistry, 2014, vol. 54, p. 31 - 37]

42
[ 89691-67-8 ]
[ 1779-49-3 ]
2-bromo-4-methoxy-1-(prop-1-en-2-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.1%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; Inert atmosphere;
86%	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;
85%	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 2h; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In tetrahydrofuran at 20℃; for 17h;

85%	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone at 20℃; Inert atmosphere;
85%	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In tetrahydrofuran Inert atmosphere;	2 Example 2:(1S, 3S, 3'S)-6,6'-dimethoxy-3,3'-dimethyl-2,2', 3,3'-tetrahydro-1,1'-spirobi[benzo [b]thiole] (Ib)Synthesis In a nitrogen atmosphere, dissolve methyltriphenylphosphine bromide (7.1g, 20mmol), potassium tert-butoxide (2.8g, 25mmol), 30mL tetrahydrofuran and 100mL dry Schlenk tube, and stir at room temperature for 0.5h, then dissolve A solution of 1-(2-bromo-4-methoxyphenyl)ethanone (2.3g, 10.0mmol) in tetrahydrofuran (5mL) was added dropwise to the previous system,The reaction was detected by TLC. The reaction was quenched by adding saturated aqueous ammonium chloride dropwise.Extracted with ethyl acetate three times, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, left to stand, and filtered to remove the desiccant,The filtrate was removed with a rotary evaporator and purified by column chromatography to obtain 2-bromo-4-methoxy-1-(prop-1-en-2-yl)benzene(1.94g, yield: 85%).
56%	Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
	With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 20h; Inert atmosphere;
	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In tetrahydrofuran at 20℃; for 36h; Inert atmosphere;

Reference： [1]Zhao, Nan; Xie, Shengling; Chen, Gui; Xu, Jing [Chemistry - A European Journal, 2016, vol. 22, # 36, p. 12634 - 12636]
[2]Zhang, Wen; Chen, Pinhong; Liu, Guosheng [Angewandte Chemie - International Edition, 2017, vol. 56, # 19, p. 5336 - 5340][Angew. Chem., 2017, vol. 129, # 19, p. 5420 - 5424]
[3]Yada, Akira; Okajima, Satoshi; Murakami, Masahiro [Journal of the American Chemical Society, 2015, vol. 137, # 27, p. 8708 - 8711]
[4]Chang, Xin; Chen, Hong-Chao; Li, Chuan-Ying; Ma, Pei-Long; Wang, Peng [Angewandte Chemie - International Edition, 2020, vol. 59, # 23, p. 8937 - 8940][Angew. Chem., 2020, vol. 132, # 23, p. 9022 - 9025,4]
[5]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111171068, 2020, A Location in patent: Paragraph 0210-0212
[6]Boureghda, Chaima; Macé, Aurélie; Berrée, Fabienne; Roisnel, Thierry; Debache, Abdelmadjid; Carboni, Bertrand [Organic and Biomolecular Chemistry, 2019, vol. 17, # 23, p. 5789 - 5800]
[7]Mizoguchi, Haruki; Micalizio, Glenn C. [Journal of the American Chemical Society, 2015, vol. 137, # 20, p. 6624 - 6628]
[8]Ye, Chenghao; Kou, Xuezhen; Xia, Jingzhao; Yang, Guoqiang; Kong, Li; Wei, Quhao; Zhang, Wanbin [Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901]

43
[ 89691-67-8 ]
5-methoxy-2-(prop-1-en-2-yl) benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 20 °C 1.2: 17 h / 20 °C 2.1: n-butyllithium / hexane; diethyl ether / 0.17 h / 0 °C 2.2: 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 10 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / 0.5 h / 0 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 36 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C

Reference： [1]Yada, Akira; Okajima, Satoshi; Murakami, Masahiro [Journal of the American Chemical Society, 2015, vol. 137, # 27, p. 8708 - 8711]
[2]Zhang, Wen; Chen, Pinhong; Liu, Guosheng [Angewandte Chemie - International Edition, 2017, vol. 56, # 19, p. 5336 - 5340][Angew. Chem., 2017, vol. 129, # 19, p. 5420 - 5424]
[3]Ye, Chenghao; Kou, Xuezhen; Xia, Jingzhao; Yang, Guoqiang; Kong, Li; Wei, Quhao; Zhang, Wanbin [Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901]

44
[ 89691-67-8 ]
3-(2-bromo-4-methoxyphenyl)-6-methoxynaphthalen-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With copper(l) iodide; 1,10-Phenanthroline; sodium t-butanolate In toluene at 120℃; for 4h; Inert atmosphere; Sealed tube;	General procedure for the preparation of desired compound General procedure: A sealed tube was charged with the mixture of CuI (0.1 mmol, 19.0 mg), 1,10-phenanthroline (0.2 mmol, 36.0 mg), NaOtBu (6 mmol, 0.576 g) and bromine acetophenone derivative 1 (1.0 mmol). The tube was evacuated and recharged with N2 for 3 times. Before toluene (2.0 mL) were added, the tube was sealed and the mixture was allowed to stir at 120 °C for 4 hours. After completion, the mixture was cooled to room temperature, then 2N HCl aq. (1-2 mL) was added and the mixture was extracted with Et2O (5 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel (petroleum ether/diethyl ether: 25/1 to 10/1) provided the corresponding product 3a-l as a solid or yellow oil.

Reference： [1]Lou, Zhen-Bang; Pang, Xin-Long; Chen, Chao; Wen, Li-Rong; Li, Ming [Chinese Chemical Letters, 2015, vol. 26, # 10, p. 1231 - 1235]

45
[ 120-75-2 ]
[ 89691-67-8 ]
[ 100-52-7 ]
C₂₄H₂₀BrNO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tin(II) chloride dihdyrate In neat (no solvent) at 120℃; for 24h;

Reference： [1]Chavan, Santosh S.; Pathan, Mohsinkhan Y.; Mulla, Shafeek A. R. [RSC Advances, 2015, vol. 5, # 125, p. 103091 - 103094]

46
[ 89691-67-8 ]
1,1'-(5'-(2-(dibenzo[b,d]thiophen-1-yl)-4-methoxyphenyl)-4,4''-dimethoxy-[1,1':3',1''-terphenyl]-2,2''-diyl)didibenzo[b,d]thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrachlorosilane / ethanol 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; toluene; water / Schlenk technique; Reflux

Reference： [1]Liu, Yi; Marszalek, Tomasz; Müllen, Klaus; Pisula, Wojciech; Feng, Xinliang [Chemistry - An Asian Journal, 2016, vol. 11, # 15, p. 2107 - 2112]

47
[ 89691-67-8 ]
2,2''-bis(dibenzo[b,d]thiophen-4-yl)-5'-(2-(dibenzo[b,d]thiophen-4-yl)-4-hydroxyphenyl)-[1,1':3',1''-terphenyl]-4,4''-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrachlorosilane / ethanol 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; toluene; water / Schlenk technique; Reflux 3: boron tribromide / dichloromethane; acetone / 20 °C / Inert atmosphere

Reference： [1]Liu, Yi; Marszalek, Tomasz; Müllen, Klaus; Pisula, Wojciech; Feng, Xinliang [Chemistry - An Asian Journal, 2016, vol. 11, # 15, p. 2107 - 2112]

48
[ 89691-67-8 ]
potassium isopropenyltrifluoroborane [ No CAS ]
C₁₂H₁₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In propan-1-ol at 100℃; for 5h; Inert atmosphere;

Reference： [1]Hugelshofer, Cedric L.; Magauer, Thomas [Chemistry - A European Journal, 2016, vol. 22, # 42, p. 15125 - 15136]

49
[ 89691-67-8 ]
2-(5-methoxy-2-(prop-1-en-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C / Inert atmosphere 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / isopropyl alcohol / 4 h / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / toluene / 15 h / 80 °C

Reference： [1]Zhao, Nan; Xie, Shengling; Chen, Gui; Xu, Jing [Chemistry - A European Journal, 2016, vol. 22, # 36, p. 12634 - 12636]
[2]Boureghda, Chaima; Macé, Aurélie; Berrée, Fabienne; Roisnel, Thierry; Debache, Abdelmadjid; Carboni, Bertrand [Organic and Biomolecular Chemistry, 2019, vol. 17, # 23, p. 5789 - 5800]

50
[ 89691-67-8 ]
[ 1449-46-3 ]
2-bromo-4-methoxy-1-(1-phenylprop-1-en-2-yl)benzene [ No CAS ]
C₁₆H₁₅BrO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.333 % de	Stage #1: benzyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In toluene at 0℃; for 0.5h; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In toluene at 20℃; Overall yield = 82 %;

Reference： [1]Yang, Junfeng; Rérat, Alice; Lim, Yang Jie; Gosmini, Corinne; Yoshikai, Naohiko [Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2449 - 2453][Angew. Chem., 2017, vol. 129, # 9, p. 2489 - 2493,5]

51
[ 89691-67-8 ]
[ 544-97-8 ]
[ 14034-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: dimethyl zinc(II) With titanium tetrachloride In hexane; dichloromethane at -40℃; for 0.25h; Inert atmosphere; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In hexane; dichloromethane at 0℃; Inert atmosphere;

Reference： [1]Wu, Zhuo; Ma, Ding; Zhou, Bo; Ji, Xiaoming; Ma, Xiaotian; Wang, Xiaoling; Zhang, Yanghui [Angewandte Chemie - International Edition, 2017, vol. 56, # 40, p. 12288 - 12291][Angew. Chem., 2017, vol. 129, p. 12456 - 12459,4]

52
[ 89691-67-8 ]
[ 73183-34-3 ]
1-(4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 90℃; for 16h; Inert atmosphere;

Reference： [1]Akgun, Burcin; Li, Caishun; Hao, Yubin; Lambkin, Gareth; Derda, Ratmir; Hall, Dennis G. [Journal of the American Chemical Society, 2017, vol. 139, # 40, p. 14285 - 14291]

53
[ 67-56-1 ]
[ 1006-39-9 ]
[ 89691-67-8 ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium hydroxide; In dimethyl sulfoxide; at 20℃; for 16h;	General procedure: A mixture of 2-fluorobenzamide (1a, 69.5 mg, 0.5 mmol), MeOH (ca. 32.0 mg, 1.0 mmol), KOH (56.0 mg, 1.0 mmol) and DMSO (2.0 mL) in a 25 mL screw-capped thick-walled Pyrex tube was stirred at room temperature for 16 h, and then water (10 mL) was added to the reaction mixture with stirring, and the mixture was extracted with ethyl acetate three times (3 * 10 mL). The combined organic phases were dried over Na2SO4 overnight. The filtered solution was concentrated under reduced pressure, and the crude residue was purified by column chromatography on silica gel with the use of petroleum ether/ethyl acetate/trimethylamine (gradient mixture ratio from 6:1:0.05 to 2:1:0.05 in volume) to afford 2aa as a white solid in 80% yield (60.7 mg).

Reference： [1]Tetrahedron,2018,vol. 74,p. 303 - 307

54
[ 4165-81-5 ]
[ 89691-67-8 ]
C₂₅H₂₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 1,1-diphenyl-1,3-butadiene With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran at 25℃; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide In tetrahydrofuran at 40℃;

Reference： [1]Zhang, Xiao-Ming; Yang, Jie; Zhuang, Qing-Bo; Tu, Yong-Qiang; Chen, Zongyuan; Shao, Hui; Wang, Shao-Hua; Zhang, Fu-Min [ACS Catalysis, 2018, vol. 8, # 7, p. 6094 - 6099]

55
[ 89691-67-8 ]
ethyl 10-hydroxy-3,6,7-trimethoxyphenanthrene-9-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol / 110 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 80 °C 3: tert.-butylhydroperoxide; sodium dihydrogenphosphate dihydrate; N-Bromosuccinimide / tetrahydrofuran; water / 15 h / Reflux

Reference： [1]Jiang, Ya-Ting; Yu, Zhen-Zhen; Zhang, Ya-Kai; Wang, Bin [Organic Letters, 2018, vol. 20, # 13, p. 3728 - 3731]

56
[ 89691-67-8 ]
ethyl 3-oxo-3-(3',4',5-trimethoxy-[1,1'-biphenyl]-2-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol / 110 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 80 °C

Reference： [1]Jiang, Ya-Ting; Yu, Zhen-Zhen; Zhang, Ya-Kai; Wang, Bin [Organic Letters, 2018, vol. 20, # 13, p. 3728 - 3731]

57
[ 89691-67-8 ]
[ 122775-35-3 ]
C₁₇H₁₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene at 110℃; Inert atmosphere;

Reference： [1]Jiang, Ya-Ting; Yu, Zhen-Zhen; Zhang, Ya-Kai; Wang, Bin [Organic Letters, 2018, vol. 20, # 13, p. 3728 - 3731]

58
[ 89691-67-8 ]
N-(allyloxy)-5-methoxy-2-(prop-1-en-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 36 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C 3.1: triethylamine / dichloromethane / 0.17 h 3.2: 48 h / 20 °C

Reference： [1]Ye, Chenghao; Kou, Xuezhen; Xia, Jingzhao; Yang, Guoqiang; Kong, Li; Wei, Quhao; Zhang, Wanbin [Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901]

59
[ 89691-67-8 ]
7-methoxy-4a-methyl-3-methylene-2,3,4,4a-tetrahydro-9H-[1,2]oxazino[3,2-a]isoindol-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 36 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C 2.2: -78 - 20 °C 3.1: triethylamine / dichloromethane / 0.17 h 3.2: 48 h / 20 °C 4.1: Pentafluorobenzoic acid; palladium diacetate; p-benzoquinone; 3-Methylpyridine / 1,4-dioxane / 24 h / 60 °C / Schlenk technique

Reference： [1]Ye, Chenghao; Kou, Xuezhen; Xia, Jingzhao; Yang, Guoqiang; Kong, Li; Wei, Quhao; Zhang, Wanbin [Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901]

60
[ 89691-60-1 ]
[ 89691-67-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With silica gel; pyridinium chlorochromate In dichloromethane at 20℃;
	With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;
	With pyridinium chlorochromate In dichloromethane at 20℃;

	With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 2h;
	With pyridinium chlorochromate In dichloromethane at 20℃; for 3h; Schlenk technique;

Reference： [1]Chang, Xin; Chen, Hong-Chao; Li, Chuan-Ying; Ma, Pei-Long; Wang, Peng [Angewandte Chemie - International Edition, 2020, vol. 59, # 23, p. 8937 - 8940][Angew. Chem., 2020, vol. 132, # 23, p. 9022 - 9025,4]
[2]Ye, Chenghao; Kou, Xuezhen; Xia, Jingzhao; Yang, Guoqiang; Kong, Li; Wei, Quhao; Zhang, Wanbin [Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901]
[3]Wang, Zhixin; Li, Yang; Chen, Fan; Qian, Peng-Cheng; Cheng, Jiang [Chemical Communications, 2021, vol. 57, # 14, p. 1810 - 1813]
[4]Zhou, Liwei; Qiao, Shujia; Zhou, Fengru; Xuchen, Xinyu; Deng, Guobo; Yang, Yuan; Liang, Yun [Organic Letters, 2021, vol. 23, # 8, p. 2878 - 2883] Zhou, Liwei; Sun, Mingjie; Zhou, Fengru; Deng, Guobo; Yang, Yuan; Liang, Yun [Organic Letters, 2021, vol. 23, # 18, p. 7150 - 7155]
[5]Yoon, Wan Seok; Han, Jung Tae; Yun, Jaesook [Advanced Synthesis and Catalysis, 2021, vol. 363, # 21, p. 4953 - 4959]

61
[ 43192-31-0 ]
[ 89691-67-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 3 h / 0 °C / Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 °C / Inert atmosphere 2: pyridinium chlorochromate; silica gel / dichloromethane / 20 °C
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 °C / Schlenk technique; Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 20 °C

	Multi-step reaction with 2 steps 1: magnesium; iodine / diethyl ether / 3 h / -10 - 0 °C 2: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / -78 - 20 °C / Schlenk technique 2: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Schlenk technique
	Multi-step reaction with 2 steps 1.1: magnesium; iodine / diethyl ether 1.2: 3 h / -10 - 0 °C 2.1: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C

Reference： [1]Ye, Chenghao; Kou, Xuezhen; Xia, Jingzhao; Yang, Guoqiang; Kong, Li; Wei, Quhao; Zhang, Wanbin [Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901]
[2]Chang, Xin; Chen, Hong-Chao; Li, Chuan-Ying; Ma, Pei-Long; Wang, Peng [Angewandte Chemie - International Edition, 2020, vol. 59, # 23, p. 8937 - 8940][Angew. Chem., 2020, vol. 132, # 23, p. 9022 - 9025,4]
[3]Wang, Zhixin; Li, Yang; Chen, Fan; Qian, Peng-Cheng; Cheng, Jiang [Chemical Communications, 2021, vol. 57, # 14, p. 1810 - 1813]
[4]Zhou, Liwei; Qiao, Shujia; Zhou, Fengru; Xuchen, Xinyu; Deng, Guobo; Yang, Yuan; Liang, Yun [Organic Letters, 2021, vol. 23, # 8, p. 2878 - 2883]
[5]Yoon, Wan Seok; Han, Jung Tae; Yun, Jaesook [Advanced Synthesis and Catalysis, 2021, vol. 363, # 21, p. 4953 - 4959]
[6]Zhou, Liwei; Sun, Mingjie; Zhou, Fengru; Deng, Guobo; Yang, Yuan; Liang, Yun [Organic Letters, 2021, vol. 23, # 18, p. 7150 - 7155]

62
[ 89691-67-8 ]
1-(2-deuterium-4-methoxyphenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With 5%-palladium/activated carbon; water-d2; deuterium In N,N-dimethyl-formamide	27 Step A: To a mixture of 1-(2-bromo-4-methoxyphenyl)ethanone (1.28 g, 5.59 mmol) and deuteroxide (0.5 mL)in DMF (10 mL) was added palladium on activated carbon (5%, 100 mg). After exchanged with deuterium gas, thereaction mixture was stirred under deuterium gas from a deuterium gas balloon overnight and filtered through a celitepad. To the filtrate was added water (40 mL), and the mixture extracted with ethyl acetate (30 mL32). The combinedorganic layer was washed with water (10 mL34), dried over anhydrous sodium sulfate, concentrated under vacuum togive 1-(2-deuterium-4-methoxyphenyl)ethanone (59)(910 mg) with 100% yield.

Reference： [1]Current Patent Assignee: JIANGSU ATOM BIOSCIENCE AND PHARMACEUTICAL - EP3348557, 2018, A1 Location in patent: Paragraph 0124; 0125

63
[ 89691-67-8 ]
[ 104-88-1 ]
C₁₆H₁₂BrClO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 1-(2-bromo-4-methoxyphenyl)ethanone With sodium hydroxide In ethanol; water at 0℃; for 0.0833333h; Stage #2: 4-chlorobenzaldehyde In ethanol; water at 20℃; for 1h;	13 Example 13: Synthesis of 3-hydroxyphenanthrene-9,10-dione (Compound 1.013) A mixture of compound 13.1 (10 g, 50.25 mmol, 1.0 eq) in EtOH/ H20 (100 mL / 20 mL) was stirred at 0 °C for 5 mm. Then compound 13.2 (7 g, 100.5 mmol, 2.0 eq) was added. The mixture was allowed to warm to room temperature and stirred at room temperature for 1 h. TLC analysis of the reaction mixture showed full conversion to the desired product. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give compound 13.3 (11.7 g, 76%). TLC: PE: EA=15:1, 254 nm; Rf (13.1) =0.6; Rf(13.3) =0.5.

Reference： [1]Current Patent Assignee: TRANSFUSION HEALTH LLC - WO2018/217567, 2018, A1 Location in patent: Paragraph 0333

64
[ 89691-67-8 ]
6-methoxy-1,9-dimethyl-9H-fluoren-9-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0 °C 2: caesium carbonate; triphenylphosphine; potassium iodide; norbornene; palladium(II) iodide / toluene / 24 h / 20 - 90 °C / Schlenk technique; Inert atmosphere

Reference： [1]Casnati, Alessandra; Fontana, Marco; Motti, Elena; Della Ca, Nicola [Organic and Biomolecular Chemistry, 2019, vol. 17, # 25, p. 6165 - 6173]

65
[ 89691-67-8 ]
ethyl 2-hydroxy-4-(2-hydroxy-4-methoxyphenyl)pent-4-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / toluene / 15 h / 80 °C 3.1: scandium tris(trifluoromethanesulfonate) / dichloromethane; toluene / 0 - 20 °C 4.1: sodium perborate tetrahydrate / tetrahydrofuran; water / 20 °C

Reference： [1]Boureghda, Chaima; Macé, Aurélie; Berrée, Fabienne; Roisnel, Thierry; Debache, Abdelmadjid; Carboni, Bertrand [Organic and Biomolecular Chemistry, 2019, vol. 17, # 23, p. 5789 - 5800]

66
[ 89691-67-8 ]
[ 33513-42-7 ]
[ 536-74-3 ]
6-methoxy-N,N-dimethyl-3-phenylnaphthalen-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With copper(l) iodide; sodium hydroxide In water at 120℃; for 24h; Inert atmosphere;	12 Synthesis of 6-methoxy-N,N-dimethyl-3-phenylnaphthalen-1-amine The reactor was charged with 0.20 mmol of phenylacetylene, 0.40 mmol of 1-(2-bromo-4-methoxyphenyl)ethanone, 0.30 mmol of N,N-dimethylformamide,0.02 mmol of cuprous iodide, 0.40 mmol of sodium hydroxide, 1.0 mL of water. Heated to 120 ° C under nitrogen atmosphere, stirring was continued for 24 h, the reaction was stopped, cooled to room temperature, washed with saturated ammonium chloride solution, extracted with ethyl acetate, dried, and the solvent was evaporated under reduced pressure. Separation to obtain the target product, yield 89%.

Reference： [1]Current Patent Assignee: HUNAN UNIVERSITY - CN110092724, 2019, A Location in patent: Paragraph 0054-0056

67
[ 89691-67-8 ]
[ 135-02-4 ]
(R)-5-methoxy-3-(2-methoxyphenyl)-1-indanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethanol / 12 h / 0 - 20 °C 2: water; C₃₆H₄₉N₃O₂; nickel(II) bromide dimethoxyethane; manganese; lithium carbonate / N,N-dimethyl-formamide; tetrahydrofuran / 24 h / 80 °C / Inert atmosphere; Glovebox; Schlenk technique

Reference： [1]Qin, Xurong; Yao Lee, Marcus Wen; Zhou, Jianrong Steve [Organic Letters, 2019, vol. 21, # 15, p. 5990 - 5994]

68
[ 89691-67-8 ]
[ 135-02-4 ]
(E)-2'-bromo-4'-methoxy-2-methoxychalcone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water at 0 - 20℃; for 12h;

Reference： [1]Qin, Xurong; Yao Lee, Marcus Wen; Zhou, Jianrong Steve [Organic Letters, 2019, vol. 21, # 15, p. 5990 - 5994]

69
[ 89691-67-8 ]
1-(4-methoxy-2-(7-methyl-4-phenylcinnolin-3-yl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.08 h / Inert atmosphere 1.2: Inert atmosphere; Heating 2.1: methanol / 60 °C / Inert atmosphere 3.1: copper diacetate; potassium carbonate / 1,2-dichloro-ethane; methanol / 0.08 h / Inert atmosphere 3.2: 5 h / 40 °C / Inert atmosphere

Reference： [1]Yao, Biao; Miao, Tao; Wei, Wei; Li, Pinhua; Wang, Lei [Organic Letters, 2019, vol. 21, # 23, p. 9291 - 9295]

70
[ 89691-67-8 ]
C₂₄H₂₂N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.08 h / Inert atmosphere 1.2: Inert atmosphere; Heating 2.1: methanol / 60 °C / Inert atmosphere

Reference： [1]Yao, Biao; Miao, Tao; Wei, Wei; Li, Pinhua; Wang, Lei [Organic Letters, 2019, vol. 21, # 23, p. 9291 - 9295]

71
[ 89691-67-8 ]
[ 100-52-7 ]
6-methoxy-3-(5-phenyl-1H-1,2,3-triazol-4-yl)benzo[c]isoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium azide; potassium carbonate; copper(II) oxide In dimethyl sulfoxide at 120℃; for 48h;

Reference： [1]Wang, Yuwei; Yu, Pei; Ren, Qingyun; Jia, Fengcheng; Chen, Yunfeng; Wu, Anxin [Journal of Organic Chemistry, 2020, vol. 85, # 4, p. 2688 - 2696]

72
[ 89691-67-8 ]
bis(5-methoxy-2-(prop-1-en-2-yl)phenyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C 2.2: -78 - 20 °C 2.3: 0 - 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere 2.3: 0 - 20 °C / Schlenk technique

Reference： [1]Chang, Xin; Chen, Hong-Chao; Li, Chuan-Ying; Ma, Pei-Long; Wang, Peng [Angewandte Chemie - International Edition, 2020, vol. 59, # 23, p. 8937 - 8940][Angew. Chem., 2020, vol. 132, # 23, p. 9022 - 9025,4]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111171068, 2020, A

73
[ 89691-67-8 ]
(1S,3S,3'S)-6,6'-dimethoxy-3,3'-dimethyl-2,2',3,3'-tetrahydro-1,1'-spirobi[benzo[b]silole] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C 2.2: -78 - 20 °C 2.3: 0 - 20 °C / Inert atmosphere 3.1: 1,5-hexadienerhodium(I)-chloride dimer; EtDUPHOS / dichloromethane / 12 h / 20 °C / Inert atmosphere; Sealed tube
	Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere 2.3: 0 - 20 °C / Schlenk technique 3.1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,2-bis((2R,5R)-2,5-diethylphosphoranylidene)benzene / dichloromethane / 12 h / 20 °C / Inert atmosphere

Reference： [1]Chang, Xin; Chen, Hong-Chao; Li, Chuan-Ying; Ma, Pei-Long; Wang, Peng [Angewandte Chemie - International Edition, 2020, vol. 59, # 23, p. 8937 - 8940][Angew. Chem., 2020, vol. 132, # 23, p. 9022 - 9025,4]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111171068, 2020, A

74
[ 89691-67-8 ]
[ 33901-36-9 ]
5-(2-bromo-4-methoxyphenyl)-2-(4-methoxyphenyl)thiazolo[3,2-b][1,2,4]triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With sulfuric acid; acetic acid In ethanol Reflux;	4.1.1. Synthesis of 2,5-di (substituted phenyl) thiazolo[3,2-b][1,2,4]triazole (3a-n) General procedure: 4.1.1.1. General method. The mercaptotriazole 1a-c (10 mmol) andsubstituted acetophenones 2a-e (15 mmol) was refluxed for 2-3 h inacetic acid containing 2 drops of conc. H2SO4. Using NH4OH solution,the reaction mix was neutralized. The resulting precipitate was filtered,washed with water, dried well and the resulting 3a-n were crystallizedin ethanol.

Reference： [1]Gomaa, Hesham A.M.; El-Sherief, Hany A.M.; Hussein, Shaimaa; Gouda, Ahmed M.; Salem, Ola I.A.; Alharbi, Khalid Saad; Hayallah, Alaa M.; Youssif, Bahaa G.M. [Bioorganic Chemistry, 2020, vol. 105]

75
[ 89691-67-8 ]
[ 14803-86-2 ]
5-(2-bromo-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sulfuric acid; acetic acid In ethanol Reflux;	4.1.1. Synthesis of 2,5-di (substituted phenyl) thiazolo[3,2-b][1,2,4]triazole (3a-n) General procedure: 4.1.1.1. General method. The mercaptotriazole 1a-c (10 mmol) andsubstituted acetophenones 2a-e (15 mmol) was refluxed for 2-3 h inacetic acid containing 2 drops of conc. H2SO4. Using NH4OH solution,the reaction mix was neutralized. The resulting precipitate was filtered,washed with water, dried well and the resulting 3a-n were crystallizedin ethanol.

Reference： [1]Gomaa, Hesham A.M.; El-Sherief, Hany A.M.; Hussein, Shaimaa; Gouda, Ahmed M.; Salem, Ola I.A.; Alharbi, Khalid Saad; Hayallah, Alaa M.; Youssif, Bahaa G.M. [Bioorganic Chemistry, 2020, vol. 105]

76
[ 89691-67-8 ]
[ 3414-94-6 ]
5-(2-bromo-4-methoxyphenyl)-2-phenylthiazolo[3,2-b][1,2,4]triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With sulfuric acid; acetic acid In ethanol Reflux;	4.1.1. Synthesis of 2,5-di (substituted phenyl) thiazolo[3,2-b][1,2,4]triazole (3a-n) General procedure: 4.1.1.1. General method. The mercaptotriazole 1a-c (10 mmol) andsubstituted acetophenones 2a-e (15 mmol) was refluxed for 2-3 h inacetic acid containing 2 drops of conc. H2SO4. Using NH4OH solution,the reaction mix was neutralized. The resulting precipitate was filtered,washed with water, dried well and the resulting 3a-n were crystallizedin ethanol.

Reference： [1]Gomaa, Hesham A.M.; El-Sherief, Hany A.M.; Hussein, Shaimaa; Gouda, Ahmed M.; Salem, Ola I.A.; Alharbi, Khalid Saad; Hayallah, Alaa M.; Youssif, Bahaa G.M. [Bioorganic Chemistry, 2020, vol. 105]

77
[ 89691-67-8 ]
[ 100-53-8 ]
1-[2-(benzylthio)-4-methoxyphenyl]-1-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: phenylmethanethiol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 1-(2-bromo-4-methoxyphenyl)ethanone In N,N-dimethyl-formamide at 75℃; for 12h;

Reference： [1]Alemán, José; Berton, Mateo; Cabrera-Afonso, María Jesús; Cembellín, Sara; Halima-Salem, Adnane; Maestro, M. Carmen; Marzo, Leyre; Miloudi, Abdellah [Green Chemistry, 2020, vol. 22, # 20, p. 6792 - 6797]

78
[ 89691-67-8 ]
2-(((1-(2-(benzylthio)-4-methoxyphenyl)ethylidene)amino)oxy)-2-methylpropanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 12 h / 75 °C 2.1: sodium acetate / ethanol / Reflux

Reference： [1]Alemán, José; Berton, Mateo; Cabrera-Afonso, María Jesús; Cembellín, Sara; Halima-Salem, Adnane; Maestro, M. Carmen; Marzo, Leyre; Miloudi, Abdellah [Green Chemistry, 2020, vol. 22, # 20, p. 6792 - 6797]

79
[ 89691-67-8 ]
6-methoxy-3-methylbenzo[d]isothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C 1.2: 12 h / 75 °C 2.1: sodium acetate / ethanol / Reflux 3.1: sodium acetate; 9-(2-mesityl)-10-methylacridinium perchlorate; oxygen / acetone / 16 h / 20 °C / Irradiation; Green chemistry

Reference： [1]Alemán, José; Berton, Mateo; Cabrera-Afonso, María Jesús; Cembellín, Sara; Halima-Salem, Adnane; Maestro, M. Carmen; Marzo, Leyre; Miloudi, Abdellah [Green Chemistry, 2020, vol. 22, # 20, p. 6792 - 6797]

80
[ 89691-67-8 ]
[ 98-80-6 ]
[ 717917-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene at 110℃; for 24h; Inert atmosphere;
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene at 110℃; for 24h; Inert atmosphere;

Reference： [1]Guo, Jia-Dong; Yang, Xiu-Long; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu [Organic Letters, 2020, vol. 22, # 24, p. 9627 - 9632]
[2]Guo, Jia-Dong; Yang, Xiu-Long; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu [Green Chemistry, 2021, vol. 23, # 18, p. 7193 - 7198]

81
[ 14900-39-1 ]
[ 89691-67-8 ]
C₁₇H₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene at 110℃; for 18h; Schlenk technique; Inert atmosphere;

Reference： [1]Wang, Zhixin; Li, Yang; Chen, Fan; Qian, Peng-Cheng; Cheng, Jiang [Chemical Communications, 2021, vol. 57, # 14, p. 1810 - 1813]

82
2-bromo-1-ethynyl-4-methoxybenzene [ No CAS ]
[ 89691-67-8 ]

Yield	Reaction Conditions	Operation in experiment
69%	With ethyl 2-hydroxypropionate; water at 110℃; Green chemistry;	3.3. General process for alkyne hydration to form compounds 2 General procedure: Alkynes (2mmol) were added to a stirred 35mL solution of EL:H2O(1:3). The reaction mixture was stirred at 110 °C for a suitable time.After successful conversion, the resultant solution was cooled to roomtemperature and extracted with ethyl acetate (4-6 mL). The combinedorganic phaseswere dehydrated over anhydrous sodium sulfate and filtered.The filtered solution was concentrated under reduced pressureand purified by column chromatography on silica gel (hexane:EtOAcas the eluent) to provide the pure desired product

Reference： [1]Dandia, Anshu; Saini, Pratibha; Chithra; Vennapusa, Sivaranjana Reddy; Parewa, Vijay [Journal of Molecular Liquids, 2021, vol. 331]

83
dienyl pinacol boronic ester [ No CAS ]
[ 89691-67-8 ]
C₁₃H₁₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; palladium dichloride; XPhos In tetrahydrofuran; water at 80℃; Schlenk technique;

Reference： [1]Yoon, Wan Seok; Han, Jung Tae; Yun, Jaesook [Advanced Synthesis and Catalysis, 2021, vol. 363, # 21, p. 4953 - 4959]

84
[ 89691-67-8 ]
[ 552-89-6 ]
C₁₆H₁₂BrNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium hydroxide In ethanol at 25℃; for 6h;

Reference： [1]Cui, Bing-Hui; Huang, Wen-Yu; Jia, Yi-Xia; Liang, Ren-Xiao; Liu, Hang; Liu, Jia-Liang; Wang, Qiang; Yang, Peng; Zhang, Xiao-Dong; Zhang, Yue-Yuan [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1087 - 1093]

85
[ 89691-67-8 ]
(S)-5-methoxy-2,3-dimethyl-1'H-spiro[indene-1,2'-quinoline] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium hydroxide; potassium carbonate / ethanol / 6 h / 25 °C 2: iron; ammonium chloride / ethanol; water / 12 h / 90 °C 3: cobalt(II) iodide; (R,R)-chiraphos; indium; isopropyl alcohol / acetonitrile / 36 h / 60 °C / Inert atmosphere

Reference： [1]Cui, Bing-Hui; Huang, Wen-Yu; Jia, Yi-Xia; Liang, Ren-Xiao; Liu, Hang; Liu, Jia-Liang; Wang, Qiang; Yang, Peng; Zhang, Xiao-Dong; Zhang, Yue-Yuan [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1087 - 1093]

86
[ 89691-67-8 ]
2-(2-bromo-4-methoxyphenyl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide; potassium carbonate / ethanol / 6 h / 25 °C 2: iron; ammonium chloride / ethanol; water / 12 h / 90 °C

Reference： [1]Cui, Bing-Hui; Huang, Wen-Yu; Jia, Yi-Xia; Liang, Ren-Xiao; Liu, Hang; Liu, Jia-Liang; Wang, Qiang; Yang, Peng; Zhang, Xiao-Dong; Zhang, Yue-Yuan [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1087 - 1093]

87
3-(4-(benzyloxy) phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde [ No CAS ]
[ 89691-67-8 ]
(E)-3-(3-(4-(benzyloxy)phenyl)-1-phenyl-1H-pyrazol-4-yl)-1-(2-bromo-4-methoxyphenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium hydroxide In ethanol at 20℃; for 24h;

Reference： [1]Alam, Md. Jahangir; Alam, Ozair; Alshehri, Sultan; Ghoneim, Mohammed M.; Imran, Mohd; Naidu, Vegi G. M.; Naim, Mohd Javed; Perwez, Ahmad; Rizvi, Moshahid Alam; Shakeel, Faiyaz [Pharmaceuticals, 2022, vol. 15, # 3]

88
[ 89691-67-8 ]
[ 124-40-3 ]
[ 536-74-3 ]
6-methoxy-N,N-dimethyl-3-phenylnaphthalen-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper (I) iodide; sodium iodide; sodium hydroxide In water monomer at 120℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Ma, Peng; Wang, Jianhui; Liu, Guiyan [Applied Organometallic Chemistry, 2022, vol. 36, # 6]

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CAS No. :	89691-67-8	MDL No. :	MFCD00465443
Formula :	C₉H₉BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YCISNMVJZZPXBG-UHFFFAOYSA-N
M.W :	229.07	Pubchem ID :	10657006
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-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.
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. 89691-67-8 ] {[proInfo.proName]}

Quality Control of [ 89691-67-8 ]

Related Doc. of [ 89691-67-8 ]

Product Details of [ 89691-67-8 ]

Safety of [ 89691-67-8 ]

Application In Synthesis of [ 89691-67-8 ]

[ 89691-67-8 ] Synthesis Path-Upstream 1~6

[ 89691-67-8 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 89691-67-8 ]

Aryls

Bromides

Ethers

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 89691-67-8 ] {[proInfo.proName]}

Quality Control of [ 89691-67-8 ]

Related Doc. of [ 89691-67-8 ]

Product Details of [ 89691-67-8 ]

Safety of [ 89691-67-8 ]

Application In Synthesis of [ 89691-67-8 ]

[ 89691-67-8 ] Synthesis Path-Upstream 1~6

[ 89691-67-8 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 89691-67-8 ]

Aryls

Bromides

Ethers

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 89691-67-8 ]