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Product Details of [ 16605-99-5 ]

CAS No. :	16605-99-5	MDL No. :	MFCD00452250
Formula :	C₁₄H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WNAFVJVEADYQAI-UHFFFAOYSA-N
M.W :	212.24	Pubchem ID :	9920766
Synonyms :

Safety of [ 16605-99-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16605-99-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 16605-99-5 ]

[ 16605-99-5 ] Synthesis Path-Downstream 1~10

1
[ 67-56-1 ]
[ 947-84-2 ]
[ 16605-99-5 ]

Yield	Reaction Conditions	Operation in experiment
96.7%	With sulfuric acid for 6h; Reflux;	1 19.8 g (0.1 mol) of biphenyl-2-carboxylic acid, 200 ml of methanol and 2 g (0.02 mol) of concentrated sulfuric acid were charged into a three-necked flask equipped with a mechanical stirrer and a thermometer, and heated to reflux for 6 hours. Cooling, crystallization, mother liquor recovery 3/4 solvent, continue to cool, crystallization. The two crystals were combined and dried to obtain 20.5 g of the biphenyl-2-carboxylic acid methyl ester in 96.7% yield.
95%	With hydrogenchloride for 4h; Heating;
87%	With dmap; triethylamine In dichloromethane at 20℃; for 1h;

87%	With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)pyridinium trifluoromethanesulfonate; triethylamine In dichloromethane at 20℃; for 1h;
87%	With sulfuric acid at 0 - 100℃; for 12h;	Methyl [1,1'-biphenyl]-2-carboxylate (S5-2). To an oven-dried round bottom flask equipped with a stirring bar a solution of [1,1'-biphenyl]-2-carboxylic acid (S5-1) (1.000 g, 5.04 mmol) in methanol (40 ml) was added sulfuric acid (49 mg, 0.50 mmol) at 0 oC. This solution was stirred for 12 hours at 100 oC. To the reaction mixture was added saturated sodium bicarbonate solution in water and extracted with diethyl ether (100 ml). The organic layer was washed with water (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate : hexane = 1 : 10) as a clear oil (S5-2) (0.930 g, 87 %). 1H NMR (400 MHz, CDCl3) : δ = 3.61 (s, 3H), 7.32-7.28 (m, 2H), 7.37 (dt, J = 13.3, 6.8 Hz, 5H), 7.50 (td, J = 7.5, 1.2 Hz, 1H), 7.81 (dd, J = 7.7, 0.7 Hz, 1H). ; 13C NMR (100MHz, CDCl3) : 52.2, 127.4, 127.5, 128.3, 128.5, 130.0, 131.0, 131.1, 131.5, 141.5, 142.7, 169.4. ; MS (m/z) calcd for C14H13O2 213.1, found 213.1 (M + H)+.
80.2%	With sulfuric acid Reflux;	3.1 General procedure for the synthesis of compounds General procedure: A mixture of organic acid (0.5 g) and methanol (100 ml) was heated under reflux in presence of sulphuric acid (0.8 ml) until the completion of the reaction which was checked by single spot TLC. Then, methanol was removed under reduced pressure a half and the solution was diluted with 20 ml of water. The product was extracted with ethyl acetate (30 ml). The organic phase was neutralized successively with NaHCO3 5%and water, dried over anhydrous Na2SO4, and filtered. The ethyl acetate phase was separated, which on evaporation yielded the ester derivatives
77%	With Oxone In toluene at 60℃; for 48h; Green chemistry;
59%	With sulfuric acid for 20h; Heating;
	With hydrogenchloride
	With boron trifluoride diethyl etherate
	With hydrogenchloride
	With sulfuric acid
	With sulfuric acid Reflux;
	With sulfuric acid for 8h; Reflux;	4.2 General procedure for the synthesis of compounds 2a-2q General procedure: The substituted benzoic acid 11q (1 eq.) in methanol was refluxed for 8h. The reactions were completed monitored by TLC (PE/EA=3:1). Then cooling to rt, the solution was adjusted to pH=7 with NaOH. The mixture was extracted with ethyl acetate and washed with brine to give the crude product.
	With sulfuric acid for 12h; Reflux;

Reference： [1]Current Patent Assignee: CHANGZHOU BOSHI WEIYE BIOTECHNOLOGY - CN105330541, 2016, A Location in patent: Paragraph 0035; 0036
[2]Caliendo; Greco; Perissutti; Santagada; Silipo; Vittoria; Turbanti; Renzetti; Benedetti; Pedone; Santini [Il Farmaco, 1993, vol. 48, # 10, p. 1359 - 1378]
[3]Matsugi, Masato; Hasegawa, Masakazu; Sadachika, Daisuke; Okamoto, Sachina; Tomioka, Mami; Ikeya, Yoshimi; Masuyama, Araki; Mori, Yuji [Tetrahedron Letters, 2007, vol. 48, # 23, p. 4147 - 4150]
[4]Location in patent: scheme or table Sugiyama, Yuya; Kurata, Yuki; Kunda, Yoko; Miyazaki, Atsushi; Matsui, Junko; Nakamura, Shuichi; Hamamoto, Hiromi; Shioiri, Takayuki; Matsugi, Masato [Tetrahedron, 2012, vol. 68, # 20, p. 3885 - 3892]
[5]Lee, Kyu Hwan; Jillella, Raveendra; Kim, Jaewoong; Oh, Chang Ho [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 651 - 656]
[6]Lima, Tamires C.; Ferreira, Alana R.; Silva, Daniele F.; Lima, Edeltrudes O.; de Sousa, Damião P. [Natural Product Research, 2018, vol. 32, # 5, p. 572 - 575]
[7]Hou, Fei; Wang, Xi-Cun; Quan, Zheng-Jun [Organic and Biomolecular Chemistry, 2018, vol. 16, # 48, p. 9472 - 9476]
[8]Sung, Yong Cho; Grimsdale, Andrew C.; Jones, David J.; Watkins, Scott E.; Holmes, Andrew B. [Journal of the American Chemical Society, 2007, vol. 129, # 39, p. 11910 - 11911]
[9]Graebe; Rateanu [Justus Liebigs Annalen der Chemie, 1894, vol. 279, p. 266 Anm.]
[10]Davies,D.I. et al. [Journal of the Chemical Society C: Organic, 1970, p. 2653 - 2660]
[11]Abramovitch, Rudolph A.; Shi, Qing [Heterocycles, 1994, vol. 37, # 3, p. 1463 - 1466]
[12]Santini, Antonello; Benedetti, Ettore; Pedone, Carlo; Giordano, Marialuisa; Caliendo, Giuseppe; Santagada, Vincenzo; Grieco, Paolo; Greco, Giovanni [Tetrahedron, 1995, vol. 51, # 7, p. 1995 - 2008]
[13]Arabaci, Gulnur; Yi, Tian; Fu, Hua; Porter, Mary E.; Beebe, Kirk D.; Pei, Dehua [Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3047 - 3050]
[14]Wang, Congcong; Zhang, Yu-Fang; Guo, Shimeng; Zhao, Quan; Zeng, Yanping; Xie, Zhicheng; Xie, Xin; Lu, Boxun; Hu, Youhong [Journal of Medicinal Chemistry, 2021, vol. 64, # 2, p. 941 - 957]
[15]Zhou, Wenjuan; Xu, Chenhao; Dong, Guanjun; Qiao, Hui; Yang, Jing; Liu, Hongmin; Ding, Lina; Sun, Kai; Zhao, Wen [European Journal of Medicinal Chemistry, 2021, vol. 217]
[16]Bettoni, Léo; Joly, Nicolas; Lohier, Jean-François; Gaillard, Sylvain; Poater, Albert; Renaud, Jean-Luc [Advanced Synthesis and Catalysis, 2021, vol. 363, # 16, p. 4009 - 4017]

2
[ 16605-99-5 ]
[ 2928-43-0 ]

Reference： [1]Journal of the American Chemical Society,1992,vol. 114,p. 2826 - 2832

3
[ 610-96-8 ]
[ 98-80-6 ]
[ 16605-99-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine-2-oxide; potassium phosphate; chloro(1-naphthyl)bis(triphenylphosphine)nickel(II); In toluene; at 110℃; for 18h;Schlenk technique; Inert atmosphere;	General procedure: Aryl chloride (1.0 mmol),arylboronic acid (1.2 mmol), precatalyst (0.05 mmol), preligand (0.05 mmol),and base (3.0 mmol) were added to a Schlenk tube equipped with a magnetic stirring bar, a septum, and a reflux condenser. After the tube was evacuated and refilled with nitrogen gas three times, degassed solvent (3 mL) was added via a syringe. The reaction mixture was heated to the described temperature for the required time. After the reaction cooled to room temperature, water (10 mL) was added tothe reaction mixture. The resulting mixture was extracted with CH2Cl2(3 x 10 mL). The combined organic layers were dried over anhydrous Na2SO4,filtered and concentrated to dryness. The remaining residue was analyzed by GC(Table 1) or purified by flash chromatogram phy on silica gel with ethylacetate-hexanes (0-20% ethyl acetate in hexanes) of as eluents.
	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In water; acetonitrile; at 60℃; for 24h;Inert atmosphere; Sealed vessel;	Typical preparative procedures were performed on 10.0 mmol scale using a Mettler-Toledo FlexiWeigh 30 automated solid handling unit to pre-weigh the aryl halide (10.0 mmol, 1.0 equiv), aryl boronic acid (12.0 mmol, 1.2 equiv) and Pd-118 (65.2 mg, 0.1 mmol, 1.0 mol %). Acetonitrile (10.0 mL) was added, followed by K2CO3 added as a stock aqueous solution (10.0 mL water containing 2.07 g, 15.0 mmol, 1.5 equiv). NB. No internal standard was added for preparative reactions. Reaction mixtures were sealed under a N2 atmosphere and heated to 60 C with magnetic stirring. HPLC analysis showed that reactions using aryl bromides were complete within 1 h but that aryl chlorides typically required 24 h.After reaction mixtures had cooled to room temperature, stirring was stopped and the phases were allowed to separate. The lower aqueous phase was removed and discarded (cutting away any interfacial catalyst residues if present) and the acetonitrile phase concentrated to dryness to give typically a light to dark brown solid or dark-coloured gum. Solids were triturated with methanol (20 mL) for 1-2 h, then isolated by filtration, washed once or twice with methanol (4 mL each wash) and dried under vacuum. Oils were purified by flash silica gel chromatography as noted below. All isolated compounds gave 1H NMR data in agreement with published values. Literature data is given for mp values for comparison.

Reference： [1]Synlett,2008,p. 1809 - 1812
[2]Chemistry - A European Journal,2008,vol. 14,p. 5538 - 5554
[3]Tetrahedron Letters,1996,vol. 37,p. 2993 - 2996
[4]Tetrahedron Letters,2014,vol. 55,p. 7215 - 7218
[5]Tetrahedron Letters,1997,vol. 38,p. 5575 - 5578
[6]Applied Organometallic Chemistry,2013,vol. 27,p. 419 - 424
[7]Journal of Organic Chemistry,1997,vol. 62,p. 8024 - 8030
[8]Synlett,2005,p. 1671 - 1674
[9]Synthesis,2006,p. 692 - 698
[10]Tetrahedron,2012,vol. 68,p. 6010 - 6017
[11]Russian Chemical Bulletin,2013,vol. 62,p. 657 - 660
Izv. Akad. Nauk, Ser. Khim.,2013,vol. 3,p. 656 - 659,4

4
[ 106-37-6 ]
[ 16605-99-5 ]
[ 128406-10-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: biphenyl-2-carboxylic acid methyl ester In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;	9,9-Bis(4-bromophenyl)-9H-fluorene (S5). To an oven-dried round bottom flask equipped with a stirring bar a solution of 1,4-dibromobenzene (2.170 g, 9.20 mmol) in tetrahydrofuran (40 ml) was injected dropwise n-butyl lithium solution (4.6 ml, 2.0 M in hexane, 9.2 mmol) at -78 oC under argon gas. This solution was stirred for 1 hours at -78 oC. To the reaction mixture was added methyl [1,1'-biphenyl]-2-carboxylate (S5-2) (0.930 g, 4.38 mmol) solution in THF (20ml) by cannula at the same temperature. The mixture was stirred at -78 oC for 2hours and then warmed up to room temperature. To the reaction mixture was added 1M hydrochloric acid solution in water (10 mL) and extracted with diethyl ether (100 ml). The organic layer was washed with water (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was dissolved in acetic acid (30ml) and sulfuric acid (10ml) was added to this solution. The mixture was refluxed for 12 hours. To the reaction mixture was added saturated sodium bicarbonate solution in water slowly at 0oC and extracted with diethyl ether (100 ml). The organic layer was washed with water twice (100 ml x 2), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane) as a white solid (S5) (1.397 g, 67 %). 1H NMR (400 MHz, CDCl3) : δ = 7.06-7.03 (m, 4H), 7.28 (d, J = 7.6 Hz, 2H), 7.40-7.31 (m, 8H), 7.76 (d, J = 7.2 Hz, 2H). ; 13C NMR (100 MHz, CDCl3) : δ = 64.6, 120.4, 120.9, 127.9, 130.0, 131.4, 140.0, 144.5, 150.1. ; LDI-TOF (m/z, %): 474 (M+, 100).
	With tert.-butyl lithium 1.) THF, -78 deg C, 1 h, 2.) THF, room temperature, 12 h, 3.) 80 deg C, 10 min; Yield given; Multistep reaction;

Reference： [1]Lee, Kyu Hwan; Jillella, Raveendra; Kim, Jaewoong; Oh, Chang Ho [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 651 - 656]
[2]Shultz, David A.; Boal, Andrew K.; Lee, Hyoyoung; Farmer, Gary T. [Journal of Organic Chemistry, 1999, vol. 64, # 12, p. 4386 - 4396]

5
[ 16605-99-5 ]
[ 947-84-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With water; lithium hydroxide In tetrahydrofuran; methanol at 70℃; for 8h;
	With sodium hydroxide In ethanol for 5h; Heating;
	With sodium hydroxide In methanol; water at 50℃; for 12h; Inert atmosphere;	4.6.1. Preparation of (1,10-biphenyl)-2-carboxylic acid 8 8 was synthesized according to reported literature. Procedure: To a solution of phenylboronic acid (2.1 mmol) in dry THF (4.5 mL) was added a prepared suspension of PdCl2(PPh3)2 in dry THF(0.5 mL, 0.1 M). The suspension was stirred and a Na2CO3 aqueous solution (5 mL, 0.8 M) was added. The reaction mixture was stirred under Ar atmosphere for 2 min at room temperature. Finally, methyl 2-iodobenzoate (294 mL, 2 mmol) was added and the reaction mixture was heated at 80°C for 12 h under Ar atmosphere. The resultant mixture was extracted with EtOAc (3 10 mL). The combined layers were washed with brine (1 x 5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (hexane/EtOAc 95:5 (V/V) to provide the corresponding methyl esters as pale yellow oils. A NaOH aqueous solution (7 mL, 1 M) was added to a stirring mixture of the desired ester (1.8 mmol) in MeOH (7 mL) under Ar atmosphere. The reaction mixture was heated to 50° C for 12 h. Upon completion, the reaction mixture was concentrated under reduced pressure. The residue was quenched with 6 M HCl until pH < 3 and was extracted with EtOAc (3 10 mL). The combined layers were washed with brine (1 x 5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to afford the desired pure biaryl 2-carboxylic acids 8. 4.6.1.1. (1,10-Biphenyl)-2-carboxylic acid (8). Prepared from methylbiphenyl-2-carboxylate ; isolated as Pink solid; 1H NMR (500 MHz,CDCl3): d 11.39 (s, 1H), 7.97 (d, J 7.5 Hz, 1H), 7.61e7.57 (m, 2H),7.36e7.36 (m, 7H); 13C NMR (125 MHz, CDCl3): d 173.4, 143.4, 141.0,132.1, 131.2, 130.7, 129.3, 128.5, 128.1, 127.4, 127.2.

792 mg	With potassium hydroxide In methanol Inert atmosphere; Schlenk technique;
	With water; sodium hydroxide In tetrahydrofuran at 80℃;
	With sodium hydroxide In methanol; water at 50℃; for 6h;
	With sodium hydroxide In methanol; water at 50℃; for 6h; Sealed tube;
	With potassium hydroxide In methanol at 80℃;	2. Preparation of starting materials^[1][2] General procedure: To a 50 mL oven-dried Schlenk flask equipped with a magnetic stir bar, were added methyl 2-iodobenzoate (2.62 g, 10 mmol), arylboronic acid (15 mmol),Pd(OAc)2 (22 mg, 1 mol%), PPh3 (52 mg, 2 mol%) and K3PO4 (4.24 g, 20 mmol).The Schlenk flask was evacuated and backfilled with N2 for 3 times. Then toluene (20mL) was added. The reaction mixture was heated at 80 C. The reaction progress wasmonitored by thin-layer chromatography (TLC) analysis. After the reaction was completed, the mixture was cooled to room temperature. Then the reaction mixture was concentrated on a rotary evaporator, and purified by column chromatography(PE/EtOAc = 50/1) to give the desired ester.KOH (3.0 g, 75 mmol), MeOH (20 mL) and the desired ester were added to a50-mL of flask, and the mixture was heated at 80 oC for 2-12 h (TLC monitored). The reaction mixture was cooled to room temperature. Then the reaction mixture was acidified and extracted with DCM (3 x 30 mL). Combined organic extract was dried with Na2SO4, concentrated on a rotary evaporator and the residue was purified bycolumn chromatography on silica gel using PE/EtOAc = 5/1 as eluent to afford theproduct. To a 50 mL oven-dried Schlenk flask equipped with a magnetic stir bar, were added methyl 2-iodobenzoate (10 mmol), phenylboronic acid (15 mmol), Pd(OAc)2(112 mg, 5 mol%), DPPF (338 mg, 6 mol%) and K3PO4 (20 mmol). The Schlenk flask was evacuated and backfilled with N2 for 3 times. Then 1,2-dimethoxyethane (30 mL)was added. The reaction mixture was heated at 80 C. The reaction progress was monitored by thin-layer chromatography (TLC) analysis. After the reaction was completed, the mixture was cooled to room temperature. Then the reaction mixture was concentrated on a rotary evaporator, and purified by column chromatography(PE/EtOAc = 50/1) to give the desired ester.KOH (3.0 g, 75 mmol), MeOH (20 mL) and the desired ester were added to a 50-mL of flask, and the mixture was heated at 80 oC for 2-12 h (TLC monitored). The reaction mixture was cooled to room temperature. Then the reaction mixture was acidified and extracted with DCM (3 x 30 mL). Combined organic extract was dried with Na2SO4, concentrated on a rotary evaporator and the residue was purified by column chromatography on silica gel using PE/EtOAc = 5/1 as eluent to afford theproduct.Other reagents and solvents were purchased from commercial supplier and used without any further treatment.
	With potassium hydroxide In ethanol; water for 4h; Reflux;	To a solution of methyl [1,1′-biphenyl]-2-carboxylate in EtOH/H2O (12 mL/24 mL) was addedpotassium hydroxide (1.35 g, 24.1 mmol, 3.0 equiv.). The resulting mixture was heated under refluxfor 4 h. The solvent was removed under vacuum, and the resulting residue was dissolved in water (30mL). To the aqueous solution was added 2M HCl until no more precipitate was formed. The mixturewas extracted with EtOAc (50 mL × 3), and the combined organic layers were dried with Na2SO4. Thesolvent was removed under reduced pressure, and the resulting solid was dissolved in CH2Cl2 (20 mL).To the solution was added 4-dimethylaminopyridine (DMAP) (1.46 g, 12.0 mmol, 1.5 equiv.) and N,Odimethylhydroxylaminehydrochloride (0.782 g, 8.03 mmol, 1.0 equiv.) in one portion, followed byaddition of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) (1.87 g, 12.1 mmol, 1.5 equiv.).The reaction mixture was allowed to stir at rt for 18 h. Saturated aqueous NaHCO3 (40 mL) was addedto the reaction mixture. The mixture was then extracted with EtOAc (40 mL × 3), and the combinedorganic layers were dried using Na2SO4. The solvent was removed under vacuum, and the resultingresidue was purified by automated column chromatography (hexane/EtOAc 6/4) to afford 4l as a whitesolid (1.00 g, 4.17 mmol, 52%).

Reference： [1]Bera, Shyamal Kanti; Mal, Prasenjit [Journal of Organic Chemistry, 2021, vol. 86, # 20, p. 14144 - 14159]
[2]Ksander; DeJesus; Yuan; Fink; Moskal; Carlson; Kukkola; Bilci; Wallace; Neubert; Feldman; Mogelesky; Poirier; Jeune; Steele; Wasvery; Stephan; Cahill; Webb; Navarrete; Lee; Gibson; Alexander; Sharif; Hospattankar [Journal of Medicinal Chemistry, 2001, vol. 44, # 26, p. 4677 - 4687]
[3]Zhang, Jian; Shi, Dongdong; Zhang, Haifeng; Xu, Zheng; Bao, Hanyang; Jin, Hongwei; Liu, Yunkui [Tetrahedron, 2017, vol. 73, # 2, p. 154 - 163]
[4]Pi, Jing-Jing; Lu, Xiao-Yu; Liu, Jing-Hui; Lu, Xi; Xiao, Bin; Fu, Yao; Guimond, Nicolas [Journal of Organic Chemistry, 2018, vol. 83, # 10, p. 5791 - 5800]
[5]Yang, Dongyan; Zhao, Bin; Fan, Zhijin; Yu, Bin; Zhang, Nailou; Li, Zhengming; Zhu, Yilin; Zhou, Jinghui; Kalinina, Tatiana A.; Glukhareva, Tatiana V. [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 47, p. 13185 - 13194]
[6]Wei, Yi; Duan, Abing; Tang, Pan-Ting; Li, Jia-Wei; Peng, Rou-Ming; Zhou, Zheng-Xin; Luo, Xiao-Peng; Kurmoo, Mohamedally; Liu, Yue-Jin; Zeng, Ming-Hua [Organic Letters, 2020, vol. 22, # 11, p. 4129 - 4134]
[7]Ke, Zhuofeng; Li, Ming; Liu, Yue-Jin; Luo, Xiao-Peng; Shao, You-Xiang; Tang, Pan-Ting; Wang, Liang-Neng; Wei, Yi; Zeng, Ming-Hua; Zhang, Ni-Juan [Chemical Communications, 2020, vol. 56, # 49, p. 6680 - 6683]
[8]Chen, Bajin; Hu, Baoxiang; Hu, Xinquan; Jin, Liqun; Li, Meichao; Shen, Zhenlu; Sun, Nan; Wang, Shengpeng; Wang, Yiqing [Synlett, 2020, vol. 31, # 3, p. 261 - 266]
[9]Abe, Manabu; Akita, Munetaka; Chitose, Youhei; Hyodo, Yuki; Koike, Takashi; Takahashi, Keigo; Yoshizawa, Michito [Synlett, 2021]

6
[ 16605-99-5 ]
[ 4569-45-3 ]

Reference： [1]Journal of the American Chemical Society,1941,vol. 63,p. 1948,1952

7
[ 109674-45-5 ]
[ 610-94-6 ]
[ 16605-99-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium phosphate; [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)]; tetrabutylammomium bromide In water at 90℃; for 4h; Inert atmosphere; Schlenk technique; Green chemistry;

Reference： [1]Li, Yabo; Wang, Jingran; Wang, Zhiwei; Huang, Mengmeng; Yan, Beiqi; Cui, Xiuling; Wu, Yusheng; Wu, Yangjie [RSC Advances, 2014, vol. 4, # 68, p. 36262 - 36266]

8
[ 50-00-0 ]
[ 16605-99-5 ]
[ 114772-38-2 ]

Yield	Reaction Conditions	Operation in experiment
84.4%		In the four reaction flask was added biphenyl-2-carboxylate starting material 15g (70.7mmol), paraformaldehyde 2.4g (80mmol) and carbon tetrachloride 80g, controlling the temperature 25 ~ 30 8 g (36 mmol) of zinc bromide as a catalyst was added and the reaction was stirred for 20 min. Was slowly added dropwise PBr311.5g (43mmol), dropwise addition time of about 1h, the addition was complete, the reaction was complete feed the HPLC analysis of samples, about 3 ~ 4h. Cooling to 10 , washed with ice water reservoir three times, dried, recycled carbon tetrachloride in crude, after recrystallization crude 4'-bromomethyl-biphenyl-2-carboxylic acid alkyl ester pure 18.2g, a yield of 84.4%

Reference： [1]Patent: CN105330541,2016,A .Location in patent: Paragraph 0035; 0037

9
[ 127-63-9 ]
[ 16605-99-5 ]
C₂₅H₁₈O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diphenyl sulphone; biphenyl-2-carboxylic acid methyl ester With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 27h; Cooling with ice; Stage #2: With ammonium chloride In tetrahydrofuran; hexane	Synthesis of 2-bromospiro[fluorene-9,9′-thioxanthene]-10′,10′-dioxide (BrSFXSO) General procedure: Diphenyl sulfone (3.93 g, 18 mmol) was dissolved in anhydrous THF solution (50 mL) and stirred at dry ice-alcohol bath, and then 1.6 M n-BuLi/n-hexane solution (22.5 mL, 36 mmol) was added slowly. Methyl 4′-bromobiphenyl-2-carboxylate (5 g, 16.4 mmol) was added into reaction after 3 h. Removing cool bath and stirring at room temperature about 24 h, then saturated NH4Cl solution was added to hydrolyze, and extracted with dichloromethane. The combined organic abstract was dried over anhydrous MgSO4 and filtered. The solution was evaporated under vacuum condition and the crude product was not purified. To a 2-kneck round flask, the crude product was dissolved by ice acetic acid (100 mL), and then heated to reflux. Concentrated sulfuric acid (2.0 mL) was added into the solution and continued to react about 4h. After the reaction had finished, the reaction mixture was poured into water, and filtered off and washed with water. The solid was re-dissolved with dichloromethane, dried over anhydrous MgSO4 and filtered. The solution was evaporated under vacuum condition. The product was purified with silica gel column chromatography to afford a white solid (5.6 g, 74.6%).

Reference： [1]Ou, Chang-Jin; Ren, Bao-Yi; Li, Jie-Wei; Lin, Dong-Qing; Zhong, Chao; Xie, Ling-Hai; Zhao, Jian-Feng; Mi, Bao-Xiu; Cao, Hong-Tao; Huang, Wei [Organic electronics, 2017, vol. 43, p. 87 - 95]

10
[ 137654-46-7 ]
[ 98-80-6 ]
[ 16605-99-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium phosphate; palladium diacetate; ruphos In N,N-dimethyl-formamide at 120℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Ding, Chengrong; Guan, Chenfei; Miao, Huihui; Zhang, Guofu; Zhao, Yiyong [New Journal of Chemistry, 2022, vol. 46, # 8, p. 3560 - 3564]

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Ghs Precautionary Statements

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

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[ 16605-99-5 ] Synthesis Path-Downstream 1~10

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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