[ CAS No. 178305-99-2 ] {[proInfo.proName]}

Name: 178305-99-2|2-Fluoro-4-biphenylylboronic acid|98%
Brand: Ambeed
SKU: A267411
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Quality Control of [ 178305-99-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 178305-99-2 ]

CAS No. :	178305-99-2	MDL No. :	MFCD01075707
Formula :	C₁₂H₁₀BFO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BWYWXDFYJSIUBE-UHFFFAOYSA-N
M.W :	216.02	Pubchem ID :	2774698
Synonyms :

Calculated chemistry of [ 178305-99-2 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	61.66
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.55
Log Po/w (WLOGP) :	1.59
Log Po/w (MLOGP) :	2.28
Log Po/w (SILICOS-IT) :	1.3
Consensus Log Po/w :	1.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.21
Solubility :	0.134 mg/ml ; 0.000618 mol/l
Class :	Soluble
Log S (Ali) :	-3.05
Solubility :	0.194 mg/ml ; 0.000897 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.09
Solubility :	0.0175 mg/ml ; 0.0000811 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.14

Safety of [ 178305-99-2 ]

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

Application In Synthesis of [ 178305-99-2 ]

* 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 [ 178305-99-2 ]

[ 178305-99-2 ] Synthesis Path-Downstream 1~36

1
[ 178305-99-2 ]
[ 708244-10-4 ]
[ 708244-72-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene at 100℃;

Reference： [1]Joo, Yung Hyup; Kim, Jin Kwan; Kang, Seon-Hwa; Noh, Min-Soo; Ha, Jun-Yong; Choi, Jin Kyu; Lim, Kyung Min; Chung, Shin [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 9, p. 2195 - 2198]

2
[ 873431-61-9 ]
[ 178305-99-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane for 0.0833333h; microwave irradiation;

Reference： [1]Antane, Schuyler; Caufield, Craig E.; Hu, William; Keeney, David; Labthavikul, Pornpen; Morris, Koi; Naughton, Shaughnessy M.; Petersen, Peter J.; Rasmussen, Beth A.; Singh, Guy; Yang, Youjun [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 1, p. 176 - 180]

3
[ 945374-76-5 ]
[ 178305-99-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane for 0.0833333h; microwave irradiation;

4
[ 945374-31-2 ]
[ 178305-99-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane for 0.0833333h; microwave irradiation;

5
[ 945374-32-3 ]
[ 178305-99-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane for 0.0833333h; microwave irradiation;

6
[ 288370-80-9 ]
[ 178305-99-2 ]
[ 288398-13-0 ]

Yield	Reaction Conditions	Operation in experiment
50.6 mg (41.6%)		217.a 4-[(3-Fluoro-4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxamidine a) Methyl 4-[(3-fluoro-4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxylate Using a procedure similar to Example 208, step (a), 74.4 mg (0.36 mmol) of methyl 4-amino-5-methylthiothiophene-2-carboxylate was allowed to react with 155.5 mg (2 equiv, 0.72 mmol) of 3-fluoro-4-phenylphenyl boronic acid to give 50.6 mg (41.6%) of methyl 4-[(3-fluoro-4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxylate. 1H NMR (CDCl3, 400 MHz) δ2.44 (s, 3 H), 3.91 (s, 3 H), 6.19 (s, 1 H), 6.78-6.86 (m, 2 H), 7.32-7.39 (m, 2 H), 7.73-7.47 (m, 2 H), 7.55 (d, 1 H, J=6.9 Hz), 7.82 (s, 1 H).
50.6 mg (41.6%)		217.a 4-[(3-Fluoro-4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxamidine a) Methyl 4-[(3-fluoro-4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxylate Using a procedure similar to Example 208, step (a), 74.4 mg (0.36 mmol) of methyl 4-amino-5-methylthiothiophene-2-carboxylate was allowed to react with 155.5 mg (2 equiv, 0.72 mmol) of 3-fluoro-4-phenylphenyl boronic acid to give 50.6 mg (41.6%) of methyl 4-[(3-fluoro-4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxylate. 1H NMR (CDCl3, 400 MHz) δ 2.44 (s, 3H), 3.91 (s, 3H), 6.19 (s, 1H), 6.78-6.86 (m, 2H), 7.32-7.39 (m, 2H), 7.73-7.47 (m, 2H), 7.55 (d, 1H, J=6.9 Hz), 7.82 (s, 1H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2002/37915, 2002, A1
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - US6291514, 2001, B1

7
[ 301698-97-5 ]
[ 178305-99-2 ]
[ 301690-35-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
		9 2,2-Dimethyl-4-{4-(3-fluorophenyl)phenyl}-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone EXAMPLE 9 2,2-Dimethyl-4-{4-(3-fluorophenyl)phenyl}-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone 200 mg of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone was coupled with 170 mg of {(3-fluoro-4-phenyl)benzene}boronic acid by a procedure similar to the synthetic procedure in Example 2 to yield 110 mg of 2,2-dimethyl-4-{(3-fluoro-4-phenyl)phenyl}-5-{4-(methylsulfonyl)-phenyl}-3(2H)-furanone as a solid. mp: 163-164° C. NMR: δ1.60 (s, 6H), 3.09 (s, 3H), 7.13 (m, 2H), 7.41 (m, 2H), 7.45 (m, 2H), 7.57 (m, 2H), 7.91 (d, J=8.7 Hz, 2H), 7.98 (d, J=8.7 Hz, 2H). IR (cm-1): 3020, 1698, 1621, 1402, 1319, 1258, 1148, 957, 770.

Reference： [1]Current Patent Assignee: AMOREPACIFIC GROUP - US6492416, 2002, B1

8
[ 1053223-46-3 ]
[ 178305-99-2 ]
[ 1053223-70-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; palladium diacetate In tetrahydrofuran at 80℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Dai, Wei-Min; Li, Yannian; Zhang, Ye; Yue, Congyong; Wu, Jinlong [Chemistry - A European Journal, 2008, vol. 14, # 18, p. 5538 - 5554]

9
[ 29681-42-3 ]
(2-fluoro-[1,1'-biphenyl]-4-yl)boronic acid [ No CAS ]
[ 1244021-20-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; acetonitrile; at 60℃; for 2h;Inert atmosphere;	Example 41; 4-(2-Fluorobiphenyl-4-yl)-N-hydroxypicolinamideA. Methyl 4-(2-fluorobiphenyl-4-yl)picolinate; 2-Fluorobiphenyl-4-ylboronic acid (0.400 g, 1.85 mmol), <strong>[29681-42-3]methyl 4-bromopicolinate</strong> (0.4 g, 1.85 mmol), Cs2CO3 (1.20 g, 3.70 mmol) and [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.134 g, 0.19 mmol) were combined in acetonitrile (6 mL)/water (3 mL) and heated to 60 0C under argon. The reaction was then stirred for 2 hours. After this time, the reaction was cooled to room temperature and was diluted with water. The reaction mixture was extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and evaporated to a brown solid. Isco column (Silica Gel, 0%-50% ethyl acetate/dichloromethane) afforded the desired compound as a light yellow oil (0.451, 79%). LC-MS: [M+H]+ 308 Mass: calculated for Ci9Hi4FNO2, 307.32

Reference： [1]Patent: WO2010/100475,2010,A1 .Location in patent: Page/Page column 111-112

10
[ 887144-97-0 ]
[ 178305-99-2 ]
[ 1214369-54-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In diethylene glycol dimethyl ether at 35℃; for 14h; Inert atmosphere;

Reference： [1]Liu, Tianfei; Shen, Qilong [Organic Letters, 2011, vol. 13, # 9, p. 2342 - 2345]

11
[ 9002-83-9 ]
[ 178305-99-2 ]
[ 1403353-84-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium phosphate; tri-tert-butylphosphonium tetrafluoroborate; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In water; N,N-dimethyl-formamide; toluene at 80℃; for 2h; Schlenk technique; Inert atmosphere;

Reference： [1]Xu, Chunfa; Chen, Sheng; Lu, Long; Shen, Qilong [Journal of Organic Chemistry, 2012, vol. 77, # 22, p. 10314 - 10320]

12
[ 253195-66-3 ]
[ 178305-99-2 ]
[ 1442664-03-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In tetrahydrofuran; water at 80℃; Inert atmosphere; Sealed tube;

Reference： [1]De, Subhasis; Chen, Lu; Zhang, Shuxing; Gilbertson, Scott R. [ACS Combinatorial Science, 2013, vol. 15, # 7, p. 340 - 343]

13
[ 147583-45-7 ]
[ 178305-99-2 ]
[ 477860-13-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane at 20℃;

Reference： [1]Gatenyo, Julia; Vints, Inna; Rozen, Shlomo [Chemical Communications, 2013, vol. 49, # 67, p. 7379 - 7381]

14
[ 87-42-3 ]
[ 178305-99-2 ]
[ 1569291-42-4 ]

Yield	Reaction Conditions	Operation in experiment
25%	With 1,10-Phenanthroline; copper diacetate In dichloromethane at 20℃; for 48h; Molecular sieve;	General procedure for the preparation of compounds 3 General procedure: Method A, according to reported procedures 9bMethod B: Amixture of 6-chloropurine (1),boronic acid (2) (2 or 3 equiv. as specified Table 1), anhydrouscopper(II) acetate (1 equiv.),anhydrous triethylamine (2 or 3 equiv.) in dry DMF (15 mL/mmol) in the presence of 4Åmolecular sieves (0.75 g/mmol of 1)was stirred vigorously at r.t. or 50°C in a flask connected to a condenser opento air. When the reaction was judged complete, methanol was added and theresulting mixture was filteredthrough a pad of celite, and the filtrate was concentrated under reduced pressure. The crude material was purified by flashchromatography on silica gel eluting with EtOAc/cyclohexane or CH2Cl2/CH3OH. Method C: Similarto B, except that pyridine (2 equiv.) in dichloromethanewas used. The purity was checkedby analytical HPLC on a C18 reverse phase column and was found up to 95%.

Reference： [1]Morellato, Laurence; Huteau, Valérie; Pochet, Sylvie [Tetrahedron Letters, 2014, vol. 55, # 9, p. 1625 - 1627]

15
[ 87-42-3 ]
[ 178305-99-2 ]
[ 1569291-77-5 ]
[ 1569292-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper diacetate; 1,10-Phenanthroline / dichloromethane / 48 h / 20 °C / Molecular sieve 2: ammonia / 60 °C

Reference： [1]Morellato, Laurence; Huteau, Valérie; Pochet, Sylvie [Tetrahedron Letters, 2014, vol. 55, # 9, p. 1625 - 1627]

16
[ 1801340-63-5 ]
[ 178305-99-2 ]
[ 1801340-70-4 ]

Yield	Reaction Conditions	Operation in experiment
33%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In 1,4-dioxane; water at 80 - 85℃; for 16.5h; Inert atmosphere;	37 Example 37: 4-(2-Fluoro-[l,l'-biphenyl]-4-yl)-l-isopropyl-7-methyl-N-((6-methyl-2-oxo-4-propyl- l,2-dihydropyridin-3-yl)methyl)-lH-indole-6-carboxamide To a solution of 4-bromo-l-isopropyl-7-methyl-N-((6-methyl-2-oxo-4-propyl-l,2-dihydro pyridin-3-yl)methyl)-lH-indole-6-carboxamide (Example 30, 300 mg, 0.654 mmol) and (2-fluoro-[l,l'-biphenyl]-4-yl)boronic acid (198 mg, 0.916 mmol) in 1,4-dioxane (5 mL) was added water (2.500 mL) and bubbled argon gas for 30 minutes. To the reaction mixture, PdCi2(dppf)-CH2Cl2 adduct (53.4 mg, 0.065 mmol) was added and stirred at 80- 85 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to RT, filtered through celite, added water, extracted with ethyl acetate, concentrated and purified by column chromatography (silica gel, 5 % MeOH in chloroform) to obtain the title compound. Yield: 182 mg (33 ); JH NMR (DMSO-d6, 300 MHz): δ 11.48 (s, 1H), 8.05 (s, 1H), 7.78 (d, J = 7.2 Hz, 2H), 7.66 (m, 4H), 7.49 (t, J = 7.5 Hz, 2H), 7.42 (d, J = 7.2 Hz, 1H), 7.93 (s, 1H), 6.31 (s, 1H), 5.87 (s, 1H), 5.22 (m, 1H), 4.30 (d, J = 6.9 Hz, 2H), 2.68 (s, 3H), 2.09 (s, 3H), 1.52 (m, 3H), 1.47 (d, J = 6.6 Hz, 5H), 0.91 (d, J = 7.2 Hz, 3H); MS (ESI+): 550.4 [M+H]+; HPLC purity: 92.67 %.

Reference： [1]Current Patent Assignee: PIRAMAL ENTERPRISES LIMITED - WO2015/104677, 2015, A1 Location in patent: Page/Page column 86

17
[ 373-52-4 ]
[ 178305-99-2 ]
[ 1818297-27-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; 1,10-Phenanthroline; (1,2-dimethoxyethane)dichloronickel(II); potassium carbonate In 1,4-dioxane; 1,2-dimethoxyethane at 70℃; for 24h; Schlenk technique; Inert atmosphere;
83%	With dmap; 1,10-Phenanthroline; (1,2-dimethoxyethane)dichloronickel(II); potassium carbonate In 1,4-dioxane; 1,2-dimethoxyethane at 70℃; for 24h;	2 Example 2 To a 25 mL reaction tube was added 195 mg (0.9 mmol)2-fluorobiphenyl-4-boronic acid, 6.6 mg (5 mol%, mol% refers to the percentage of NiCl2 · DME and the molar ratio of compound B) NiCl2 · DME (nickel dimethoxide nickel chloride)5.4 mg (5 mol%, mol% refers to the percentage of the molar ratio of DMAP to compound B) of phen (1,10'-phenanthroline), 5.4 mg (5 mol%, mol% is the percentage of phenols of compound B) phen (1,10'-phenanthroline) (4-dimethylaminopyridine), 166 mg (1.2 mmol) of K2CO3, 2 mL of ethylene glycol dimethyl ether, 1.7 mL of 1,4-dioxane, and a solution of 300 uL of CH2FBr in 1,4-dioxane Concentration: 2M, 0.6 mmol) and stirred at 70 ° C for 24 hours. The isolated yield was 83%. The purity was identified by hydrogen spectroscopy greater than 95%

Reference： [1]An, Lun; Xiao, Yu-Lan; Min, Qiao-Qiao; Zhang, Xingang [Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9079 - 9083][Angew. Chem., 2015, vol. 127, # 31, p. 9207 - 9211,5]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN106278847, 2017, A Location in patent: Paragraph 0057; 0058; 0059

18
[ 1570346-27-8 ]
[ 178305-99-2 ]
[ 1570301-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (3R,3aR,6R,6aR)-6-[6-chloro-5-iodo-1-(2-trimethylsilylethoxymethyl)imidazol[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol; (2-fluoro-[1,1'-biphenyl]-4-yl)boronic acid With potassium phosphate; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II) In 1,4-dioxane at 25℃; Inert atmosphere; Stage #2: With trifluoroacetic acid In dichloromethane for 2h;	153; 163; 164 (3R,3aR,6R,6aR)-6-((6-chloro-5-(2-fluoro-[1,1′-biphenyl]-4-yl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol A mixture of (3R,3aR,6R,6aR)-6-((6-chloro-5-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (40 mg, 0.072 mmol) and (2-fluoro-[1,1′-biphenyl]-4-yl)boronic acid (18.72 mg, 0.087 mmol) in anhydrous dioxane (0.4 ml) was purged with N2 and then chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II) (7.4 mg, 0.014 mmol) and tripotassium phosphate (0.217 ml, 0.217 mmol) were added under N2 flow. The mixture was stirred at 25° C. overnight. The crude mixture was extracted with DCM and the combined organic extracts were washed with water and evaporated under reduced pressure. 1 ml of 1:1 CH2Cl2 and TFA was added to the resulting residue and the reaction mixture was stirred for 2 hours. Then the solvent was evaporated under reduced pressure to give an amber residue. The residue was diluted with 1.5 ml DMSO, filtered and purified by mass directed reverse phase column chromatography eluting with acetonitrile/water+0.1% TFA to give the title product. LC-MS: calculated for C24H19ClFN3O4, 467.10, observed m/e: 468.11 (M+H)+ (RT 0.76/2.00 min).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2015/284411, 2015, A1 Location in patent: Paragraph 0778; 0779

19
[ 513-42-8 ]
[ 178305-99-2 ]
[ 1256469-76-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; for 1h; Microwave irradiation;	Synthesis of Methylallyl Alkenes General procedure: A solution of 2-methyl-2-propen-1-ol (5 mL), boronic acid (4.1 mmol, 1 equiv.), palladium(II) acetate (3.8 mg, 0.017 mmol, 0.0041 equiv.), Xantphos (38 mg, 0.068 mmol, 0.0167 equiv.) and cesium carbonate (2.3 g, 7 mmol, 1.7 equiv.) was stirred in a sealed vial for 1.5 h at 140 °C, under microwave irradiation (reaction conditions a) or for 1 h at 120 °C, under microwave irradiation (reaction conditions b) or for 12 h at 100 °C, under classical heating (reaction conditions c). Then the solid residue was fitered off. The filtrate was puried by fractional distillation under atmospheric pressure on a Vigreux column (rst fraction: 2-methyl-2-propen-1-ol, b.p. 115 °C, second fraction: alkene with reported b.p.) to obtain desired alkene.
	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120 - 140℃; Microwave irradiation;

Reference： [1]Tabélé, Clémence; Curti, Christophe; Kabri, Youssef; Primas, Nicolas; Vanelle, Patrice [Molecules, 2015, vol. 20, # 12, p. 22890 - 22899]
[2]Tabélé, Clémence; Faiões, Viviane dos S.; Grimaud, Fabien; Torres-Santos, Eduardo Caio; Khoumeri, Omar; Curti, Christophe; Vanelle, Patrice [European Journal of Medicinal Chemistry, 2018, vol. 148, p. 154 - 164]

20
[ 934-32-7 ]
[ 178305-99-2 ]
[ 1941275-94-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With [2,2]bipyridinyl; copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 60℃; for 12h;

Reference： [1]Rao, Desaboini Nageswar; Rasheed, Sk.; Kumar, Karampoori Anil; Reddy, Annem Siva; Das, Parthasarathi [Advanced Synthesis and Catalysis, 2016, vol. 358, # 13, p. 2126 - 2133]

21
[ 1803444-99-6 ]
[ 178305-99-2 ]
[ 2065132-64-9 ]

Yield	Reaction Conditions	Operation in experiment
65.8%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere;	(S)-Ethyl 2-(tert-butoxy)-2-(4-(4, 4-dimethylpiperidin-l-yl)-5-(2-fluoro-[ 1, 1 '-biphenylJ-4- yl)-2, 6-dimethylpyridin-3-yl)acetate (S)-Ethyl 2-(tert-butoxy)-2-(4-(4, 4-dimethylpiperidin-l-yl)-5-(2-fluoro-[ 1, 1 '-biphenylJ-4- yl)-2, 6-dimethylpyridin-3-yl)acetate: A mixture of (S)-ethyl 2-(5-bromo-4-(4,4- dimethylpiperidin-l-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.0399 g, 0.088 mmol), (2-fluoro-[l, l'-biphenyl]-4-yl)boronic acid (0.028 g, 0.131 mmol) and 2M Na2C03 (0.110 ml, 0.219 mmol) in DMF (2 mL) was degassed for 10 min. Then, Pd(Ph3P)4 (10.12 mg, 8.76 μιηο) was added, degassed for 5 min and placed in a preheated oil bath at 110 °C. After 2 h, cooled and purified by pre-HPLC to afford (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-l-yl)-5-(2-fluoro-[l, r-biphenyl]-4-yl)-2,6- dimethylpyridin-3-yl)acetate (0.0315 g, 0.058 mmol, 65.8 % yield) as white solid. 1H MR (500 MHz, CC13) δ 7.63-7.67 (m, 2H), 7.49-7.59 (m, 3H), 7.40-7.46 (m, 1H), 7.10- 7.18 (m, 1H), 7.00-7.07 (m, 1H), 6.04 (br. s., 1H), 4.25-4.32 (m, 1H), 4.16-4.24 (m, 1H), 3.18-3.32 (m, 1H), 2.86-2.99 (m, 1H), 2.66 (br. s., 3H), 2.34-2.42 (m, 1H), 2.32 (br. s., 3H), 2.00-2.24 (m, 1H), 1.49-1.58 (m, 1H), 1.31-1.44 (m, 1H), 1.28 (dt, J=0.6, 7.1 Hz, 3H), 1.22 (s, 9H), 1.04-1.17 (m, 2H), 0.90 (br.s, 3H), 0.70 (br. s., 3H). LCMS (M+H) = 547.4.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2017/6281, 2017, A1 Location in patent: Page/Page column 61

22
[ 2122313-28-2 ]
[ 178305-99-2 ]
[ 2122313-35-1 ]

Yield	Reaction Conditions	Operation in experiment
47.5%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In water at -78℃; for 5h; Inert atmosphere; Reflux;	General procedure for Suzuki coupling of aryl compoundswith aryl boronic acids (11d-11j) General procedure: To the stirredmixture of compound 11a and aryl boronic acid (Table-1, entry1-7) in 1,2-dimethoxyethane and water was added sodiumcarbonate and Pd(dppf)Cl2-DCM (1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethaneadduct) under nitrogen atmosphere (at -78 °C). After completeaddition, the reaction mixture was stirred for 5 h (reflux). Themixture was cooled, filtered over celite and evaporated underreduced pressure. The residue was purified by chromatographyon silica gel (10 % ethyl acetate in hexane). We obtainedvarious compounds (11d-11j).

Reference： [1]Yoon, Hyun-Ah; Nam, Hwa-Jung; Kim, Uk-Il; Kim, Kyungjin; Kim, Bong Jin [Asian Journal of Chemistry, 2017, vol. 29, # 6, p. 1199 - 1205]

23
[ 178305-99-2 ]
[ 2225886-65-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 120 - 140 °C / Microwave irradiation 2: manganese(III) triacetate dihydrate; copper diacetate; acetic acid / 80 °C / Microwave irradiation 3: hydroxylamine hydrochloride; potassium <i>tert</i>-butylate / dimethyl sulfoxide / Inert atmosphere

Reference： [1]Tabélé, Clémence; Faiões, Viviane dos S.; Grimaud, Fabien; Torres-Santos, Eduardo Caio; Khoumeri, Omar; Curti, Christophe; Vanelle, Patrice [European Journal of Medicinal Chemistry, 2018, vol. 148, p. 154 - 164]

24
[ 1511-62-2 ]
[ 178305-99-2 ]
[ 2173247-81-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dmap; dibromobis(triphenylphosphine)nickel(II); potassium carbonate In tetrahydrofuran at 80℃; for 17h; Schlenk technique; Inert atmosphere; Sealed tube;

Reference： [1]Fu, Xia-Ping; Xiao, Yu-Lan; Zhang, Xingang [Chinese Journal of Chemistry, 2018, vol. 36, # 2, p. 143 - 146]

25
[ 76-09-5 ]
[ 178305-99-2 ]
[ 269410-15-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	In tetrahydrofuran at 20℃; for 12h; Molecular sieve;

Reference： [1]Iwamoto, Takahiro; Okuzono, Chiemi; Adak, Laksmikanta; Jin, Masayoshi; Nakamura, Masaharu [Chemical Communications, 2019, vol. 55, # 8, p. 1128 - 1131]

26
[ 178305-99-2 ]
[ 1614228-42-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 12 h / 20 °C / Molecular sieve 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -40 - 0 °C 2.2: 16 h / 25 °C / Schlenk technique

Reference： [1]Iwamoto, Takahiro; Okuzono, Chiemi; Adak, Laksmikanta; Jin, Masayoshi; Nakamura, Masaharu [Chemical Communications, 2019, vol. 55, # 8, p. 1128 - 1131]

27
[ 2374143-46-9 ]
[ 178305-99-2 ]
[ CAS Unavailable ]
[ 2374144-00-8 ]

Yield	Reaction Conditions	Operation in experiment
89 % ee	With potassium fluoride; C₄₆H₅₉NO₂P₂; palladium diacetate In toluene at 60℃; for 48h; Schlenk technique; Inert atmosphere; Overall yield = 60 percent; enantioselective reaction;
	With palladium diacetate; (2S,3S)-3-tert-butyl-2-(bis(adamantan-1-yl)phosphoryl)-6-(diphenylamino)-4-isopropoxy-2,3-dihydrobenzo[d][1,3]oxaphosphole In toluene at 60℃; for 48h; Inert atmosphere; Overall yield = 60 percent; Optical yield = 89 percent ee;	24 General procedure: Take a 25mL Schlenk tube and dry, add α-bromoamide racemate C1 (0.25mmol, 1equiv), aryl boron reagent D1 (0.5mmol, 2equiv), potassium fluoride or potassium carbonate (0.5mmol, 2equiv) , Palladium acetate (1mol%) and the compound bis((3S)-1-adamantyl)((2S,3S)-3-tert-butyl-6-diphenylamino-4-isopropyl prepared in Example 1 Oxy-2,3-dihydrobenzo[d][1,3]oxy, phosphine-pentyl-2-)phosphine oxide (I-1) as a chiral ligand (1.2mol%), palladium/coordination The volume molar ratio is 1:1.2, and the nitrogen is pumped three times and sealed. Toluene (2 mL) was added. The reaction system was heated to 60°C and reacted for 48 hours, cooled to room temperature, water (10 mL) and dichloromethane (10 mL) were added, liquid separation, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to obtain a white solid For the product, the enantiomeric excess (ee) is determined by a chiral high pressure liquid phase.(R)-N-(bis(2-methoxyphenyl)methyl)-2-(4-methoxyphenyl)propionamide (E1): white solid, 77% yield, 91% ee.

Reference： [1]Li, Bowen; Li, Tiejun; Aliyu, Muinat A.; Li, Zhen Hua; Tang, Wenjun [Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11355 - 11359][Angew. Chem., 2019, vol. 131, p. 11477 - 11481,5]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111848680, 2020, A Location in patent: Paragraph 0274-0278; 0284-0288; 0324-0328

28
[ 2417376-97-5 ]
[ 178305-99-2 ]
[ 2417376-78-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydrogencarbonate; copper(II) sulfate In methanol at 10 - 30℃; for 12h; Inert atmosphere; Sealed tube;	19 Example 19 General procedure: Operation steps: Under the condition of argon protection, weigh 0.9mmol boric acid,0.5mmol reagent, 0.05mmol copper sulfate, 0.75mmol sodium bicarbonate,5 mL of methanol was placed in a 25 mL sealed tube and reacted at room temperature for 12 h.After the reaction was completed, 10 mL of water was added and the mixture was extracted with anhydrous ether.It was dried over anhydrous magnesium sulfate, filtered through diatomaceous earth, and concentrated. The residue was subjected to flash silica gel column chromatography.127 mg of a colorless oily liquid was obtained with a yield of 94%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN110698375, 2020, A Location in patent: Paragraph 0119-0120; 0201-0204

29
[ 2411979-57-0 ]
[ 178305-99-2 ]
[ 2411979-51-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In 1,4-dioxane at 110℃; for 2h; Inert atmosphere; Sealed tube; regioselective reaction;	General procedure for the preparation of 2-aryl-3-chloro-5,5-dimethyl-2-cyclohexenones (5a-i) and 3-aryl-2-chloro-5,5-dimethyl-2-cyclohexenones (6a-i) General procedure: A suspension of 2-bromo-3-chloro-5,5-dimethyl-2-cyclohexenone (3a, 0.5 g, 2.11 mmoles); or 3-bromo-2-chloro-5,5-dimethyl-2-cyclohexenone (3b, 0.5 g, 2.11 mmoles), aryl boronic acid (4a-i, 1.1 mmolar equivalent), K2CO3 (0.87 g, 6.32 mmoles), Pd(dppf)2Cl2 catalyst (5 mg, 0.0068 mmoles, 0.32 mol%) in 6 mL of 1,4-dioxane was taken in a 15 mL Sigma-Aldrich ace pressure tube along with a magnetic pellet. The suspension was purged over 5 minutes with nitrogen gas and sealed. The pressure tube was introduced into a pre-heated oil bath at 110 °C and magnetically stirred for a period of 4 hours. Aliquots indicated the reaction to be completed within the duration of time as indicated in Table 1. The reaction was allowed to attain ambient temperature, transferred to a beaker and diluted with ethyl acetate (20 mL). The extract was filtered over a bed of CeliteVR. The filtrate was concentrated on a rotary evaporator and the crude product was purified by column chromatography using silica gel (Merck, 60-120 mesh) as the stationary phase and ethyl acetate: petroleum benzine (60-74 °C) as mobile phase to isolate the compounds 2-aryl-3-chloro-5,5-dimethyl-2-cyclohexenones 5a-i and 3-aryl-2-chloro-5,5-dimethyl-2-cyclohexenones 6a-i in greater than 90% yields. The novel compounds were characterized by spectral analysis and the yields are reported in Table 1.

Reference： [1]HariPrasad, S.; Jeevan Chakravarthy, A. S.; Pavan, K. P.; Venkatesh, G. B. [Synthetic Communications, 2020]

30
[ 2411979-56-9 ]
[ 178305-99-2 ]
[ 2411979-42-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In 1,4-dioxane at 110℃; for 4h; Inert atmosphere; Sealed tube; regioselective reaction;	General procedure for the preparation of 2-aryl-3-chloro-5,5-dimethyl-2-cyclohexenones (5a-i) and 3-aryl-2-chloro-5,5-dimethyl-2-cyclohexenones (6a-i) General procedure: A suspension of 2-bromo-3-chloro-5,5-dimethyl-2-cyclohexenone (3a, 0.5 g, 2.11 mmoles); or 3-bromo-2-chloro-5,5-dimethyl-2-cyclohexenone (3b, 0.5 g, 2.11 mmoles), aryl boronic acid (4a-i, 1.1 mmolar equivalent), K2CO3 (0.87 g, 6.32 mmoles), Pd(dppf)2Cl2 catalyst (5 mg, 0.0068 mmoles, 0.32 mol%) in 6 mL of 1,4-dioxane was taken in a 15 mL Sigma-Aldrich ace pressure tube along with a magnetic pellet. The suspension was purged over 5 minutes with nitrogen gas and sealed. The pressure tube was introduced into a pre-heated oil bath at 110 °C and magnetically stirred for a period of 4 hours. Aliquots indicated the reaction to be completed within the duration of time as indicated in Table 1. The reaction was allowed to attain ambient temperature, transferred to a beaker and diluted with ethyl acetate (20 mL). The extract was filtered over a bed of CeliteVR. The filtrate was concentrated on a rotary evaporator and the crude product was purified by column chromatography using silica gel (Merck, 60-120 mesh) as the stationary phase and ethyl acetate: petroleum benzine (60-74 °C) as mobile phase to isolate the compounds 2-aryl-3-chloro-5,5-dimethyl-2-cyclohexenones 5a-i and 3-aryl-2-chloro-5,5-dimethyl-2-cyclohexenones 6a-i in greater than 90% yields. The novel compounds were characterized by spectral analysis and the yields are reported in Table 1.

Reference： [1]HariPrasad, S.; Jeevan Chakravarthy, A. S.; Pavan, K. P.; Venkatesh, G. B. [Synthetic Communications, 2020]

31
[ 2415981-25-6 ]
[ 178305-99-2 ]
[ 2669750-36-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate; silver(l) oxide In ethanol at 100℃; for 20h; Inert atmosphere; Schlenk technique;

Reference： [1]Das, Mowpriya; Glorius, Frank; Maisuls, Iván; Strassert, Cristian A.; Tan, Guangying [Angewandte Chemie - International Edition, 2021, vol. 60, # 28, p. 15650 - 15655][Angew. Chem., 2021, vol. 133, # 28, p. 15780 - 15785]

32
[ 104-92-7 ]
[ 178305-99-2 ]
[ 164917-96-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate In ethanol; lithium hydroxide monohydrate for 3.5h; Heating;	2.3 General Method forSynthesis ofBiarylCompounds bySuzuki-Miyaura Cross-CouplingReaction General procedure: To a solution of 4-bromoanisole (6, 250mg, 1.28mmol),boronic acids (2a-i, 1.40mmol. eq.), PS-PdCl2(ABIMZ)2(30mg, 0.3mmol %), K2CO3(3.82mmol. eq.) in 10mlC2H5OH:H2O (1:1) solvent mixture was added and the reactionmixture was heated at 80°C with stirring for 4-8h.Progress of the reaction was monitored by micro work-upof aliquots at regular interval of time. After the completionof the reaction as indicated by TLC and GC chromatograms,the reaction mixture was cooled, diluted with 30ml ethylacetate and organic layer was separated. The organic layerwas filtered through a bed of Celite, washed with water(30ml × 3) and brine (30ml × 3). The solvent was removedon a rotary evaporator and crude product was purified bycolumn chromatography using silica gel (Merck, 60-120mesh) as the stationary phase and ethyl acetate: n-hexane(60-74°C) as mobile phase. The pure compounds (3a-i)which appeared as single spot on TLC under UV lamp wereisolated and characterized.

Reference： [1]Gayathri, V.; Hariprasad, S.; Jeevan Chakravarthy, A. S.; Madhura, M. J. [Catalysis Letters, 2022]

33
[ 1514-82-5 ]
[ 178305-99-2 ]
[ 2369617-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Yue, Fuyang; Liu, Jianhua; Ma, Henan; Liu, Yuxiu; Dong, Jianyang; Wang, Qingmin [Organic Letters, 2022, vol. 24, # 22, p. 4019 - 4023]

34
[ 178305-99-2 ]
[ 2771406-63-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate / tetrahydrofuran / 12 h / 60 °C / Schlenk technique; Inert atmosphere 2: [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; Quinuclidine; pyridine / acetonitrile / 36 h / 30 °C / Inert atmosphere; Irradiation

Reference： [1]Yue, Fuyang; Liu, Jianhua; Ma, Henan; Liu, Yuxiu; Dong, Jianyang; Wang, Qingmin [Organic Letters, 2022, vol. 24, # 22, p. 4019 - 4023]

35
[ 623-12-1 ]
[ 178305-99-2 ]
[ 164917-96-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; C₂₆H₅₀P₂; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 60℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Wei, Xiao-Jing; Xue, Bingxiang; Handelmann, Jens; Hu, Zhiyong; Darmandeh, Heidar; Gessner, Viktoria H.; Gooßen, Lukas J. [Advanced Synthesis and Catalysis, 2022, vol. 364, # 19, p. 3336 - 3341]

36
[ CAS Unavailable ]
[ 178305-99-2 ]
[ 2768154-73-8 ]

Yield	Reaction Conditions	Operation in experiment
29.4%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous potassium acetate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 16h; Inert atmosphere;	5 Example 5: Preparation of Compound P-5 Compound Int-2 (50 mg, 0.12 mmol) was dissolved in 11 mL (10:1) of a mixed solvent of dioxane/water, and added respectively. (2-Fluoro-[1,1'-biphenyl]-4-yl)boronic acid(SM10) (37.6 mg, 0.17 mmole),Potassium acetate (28.46 mg, 0.29 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (14 mg, 0.017 mmol),The reaction solution was stirred at 80°C for 16 hours under nitrogen protection.After the reaction was completed, water (5 mL) was added to dilute, and the mixture was extracted with EA (3 x 10 mL). The organic phase was washed with saturated brine (30 mL) and dried over sodium sulfate. Concentration gave crude product. The crude product was obtained by preparative silica gel purification using a developing solvent (petroleum ether/ethyl acetate = 1:3), and purified by high performance preparative liquid chromatography (mobile phase: acetonitrile/water: ) to obtain the white solid target product P- 5 (17.8 mg, 0.034 mmol, 29.4% yield).

Reference： [1]Current Patent Assignee: JIANGSU CAREPHAR PHARMACEUTICAL - WO2022/89629, 2022, A1 Location in patent: Page/Page column 28

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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. 178305-99-2 ] {[proInfo.proName]}

Quality Control of [ 178305-99-2 ]

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[ 178305-99-2 ] Synthesis Path-Downstream 1~36

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Fluorinated Building Blocks

Organoboron

Aryls

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[ 178305-99-2 ]