[ CAS No. 324-93-6 ]

Name: 324-93-6|4'-Fluoro-[1,1'-biphenyl]-4-amine|98%
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Quality Control of [ 324-93-6 ]

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Product Details of [ 324-93-6 ]

CAS No. :	324-93-6	MDL No. :	MFCD00025338
Formula :	C₁₂H₁₀FN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HTRVALPKPVGOSZ-UHFFFAOYSA-N
M.W :	187.21	Pubchem ID :	9462
Synonyms :

Safety of [ 324-93-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 324-93-6 ]

* 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 [ 324-93-6 ]

[ 324-93-6 ] Synthesis Path-Downstream 1~58

1
[ 398-24-3 ]
[ 324-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; for 1h;	General procedure: Pd cNPs/CFe3O4(0.73 mol% of Pd, 20 mg), aryl halide(0.5 mmol), phenylboronic acid (0.6 mmol), K2CO3(1.5 mmol), andEtOH (3 mL) were taken in a schlenk tube with a teflon stopcock,sealed and heated at 70C for a given time with constant stir-ring. For chloro derivatives, the reaction was performed using TBABas additive (0.5 mmol), DMF (3 mL), at 110C and catalyst 40 mg(1.5 mol%). After optimized time, 3 equvalents of N2H4·H2O wereadded to the reaction mixture and allowed to stir further 1 h. Aftercompletion of the reaction, the catalyst was separated by an exter-nal magnet and reaction mixture was washed with water to removeexcess of boronic acids and the mixture was further separated byethyl acetate. The solvent was evaporated and the residue was sub-jected to GC analysis (retention time of haloaminobenzene wasused as internal standard) followed by column chromatography forfurther purification. The purified compounds were further charac-terized by1H and13C NMR spectroscopies with CDCl3as solventand TMS as internal standard. The spectral details and spectra aregiven in supporting information section (Fig. S9, S25-S27).

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2412 - 2418
[2]Journal of the Chemical Society,1931,p. 1359,1362
[3]Journal of the American Chemical Society,1966,vol. 88,p. 3318 - 3327
[4]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401
[5]Journal of Molecular Catalysis A: Chemical,2016,vol. 423,p. 511 - 519
[6]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 12039 - 12047

2
[ 398-32-3 ]
[ 324-93-6 ]

Reference： [1]Journal of Organic Chemistry,1954,vol. 19,p. 1594,1597
[2]Journal of the American Chemical Society,1966,vol. 88,p. 3318 - 3327

3
[ 324-93-6 ]
[ 398-22-1 ]

Reference： [1]Journal of the Chemical Society,1931,p. 1359,1362

4
[ 16130-58-8 ]
[ 324-93-6 ]
2-Cyano-N-(4'-fluoro-biphenyl-4-yl)-acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4608 - 4621

5
[ 324-93-6 ]
[ 207287-82-9 ]

Reference： [1]Canadian Journal of Chemistry,1998,vol. 76,p. 78 - 84

6
[ 1765-93-1 ]
[ 106-40-1 ]
[ 324-93-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃; for 12h;Inert atmosphere;	General procedure: To a solution of 4-bromoaniline (7, 2.00 g, 11.60 mmol) and phenylboronicacid (1.56 g, 12.78 mmol) in a mixed solution of water,ethanol and toluene (30 mL, H2O:EtOH:toluene = 3:3:10, v/v) wereadded Pd(PPh3)4 (0.13 g, 0.12 mmol) and K2CO3 (16.00 g,116.00 mmol) neatly. The reaction mixture was purged with Ar gas.The reaction mixture was stirred at 100 C for 12 h in Ar atmosphereand concentrated under reduced pressure to give the crude product. The crude product was extracted with dichloromethane (50 mL) and water(40 mL), dried (MgSO4) and concentrated in vacuo. The residue waspurified by flash column chromatography (CH2Cl2:hexane = 2:5) toprovide desired product 8.

Reference： [1]ARKIVOC,2012,vol. 2012,p. 62 - 75,14
[2]Bioorganic and medicinal chemistry,2020
[3]Canadian Journal of Chemistry,1998,vol. 76,p. 78 - 84
[4]Chemical Communications,2014,vol. 50,p. 5733 - 5736
[5]Organic Letters,2022,vol. 24,p. 349 - 353

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; for 16h;Reflux; Inert atmosphere;	General procedure: To a stirred solution of the arylhalide (1 equiv.), boronic acid (1.1 equiv.) and sodium carbonate (2 equiv.) in dioxane (0.02 M) and water (0.05 M) was degassed for 10 min with nitrogen. Bis(cyclopentyldiphenylphosphane) dichloromethane palladium chloride iron (0.1 equiv.) was added to the reaction mixture and it was heated to reflux for 16 h. The reaction mixture was allowed to cool and filtered over Celite. It was diluted with water and extracted with ethyl acetate. The combined organic layers were dried with magnesium sulphate and concentrated under vacuum. The crude compound was purified by column chromatography to afford the desired product.

8
4'-fluoro-4-nitro-diphenyl [ No CAS ]
[ 324-93-6 ]

Reference： [1]Bulletin de la Classe des Sciences, Academie Royale de Belgique,1922,vol. <5> 8,p. 507,527
Chemisches Zentralblatt,1923,vol. 94,p. 313

9
[ 17763-80-3 ]
[ 324-93-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401

10
[ 1765-93-1 ]
[ 324-93-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401
[2]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 12039 - 12047

11
[ 324-93-6 ]
[ 1359844-10-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401

12
[ 324-93-6 ]
[ 10540-37-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401

13
[ 1765-93-1 ]
[ 540-37-4 ]
[ 324-93-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 1.66667h;	General procedure: A mixture of halobenzene (1 mmol), K2CO3(2 mmol), phenylboronic acid(1 mmol), and Pd-Schiff-Base(at)Fe3O4 MNPs (5 mg) as catalyst was taken in a 5-mLround-bottomed flask in dimethylformamide (DMF) and heated at 90 C. After reaction completion (monitored by TLC), the mixture was cooled to room temperatureand the catalyst was separated from the reaction mixture using an external magnet and washed with diethyl ether. The reaction mixture was extracted with water and diethyl ether. The organic layer was dried over Na2SO4.Then, the solvent was evaporated under reduced pressure, and pure biphenyl derivatives were obtained in high yields. Further purification was achieved by column chromatography usingn-hexane:EtOAc (8:2).
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux;	General procedure: To 0.329 g (1.5 mmol) 4-iodoaniline, 1.8 mmol ArB(OH)2, 0.318 g (3 mmol) Na2CO3 and 75 mg (0.075 mmol) PdCl2(PPh3)2, 15 mL of a blended solution of dioxane and water (v/v = 3/1) was added under N2 atmosphere. Then the reaction was heated to reflux and monitored by TLC. Upon cooling, the reaction mixture was dilute with sat. NH4Cl solution, then extracted with EA (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography to afford different 4-aminobiphenyl derivatives. According to the reductive amination procedure, the 4-aminobiphenyl derivative was further treated with salicylaldehyde and to afford the corresponding compound 5&6.

Reference： [1]Research on Chemical Intermediates,2019,vol. 45,p. 2605 - 2639
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 3923 - 3933
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3057 - 3061

14
[ 398-24-3 ]
1,2-bis(4'-fluoro-[1,1'-biphenyl]-4-yl)diazene [ No CAS ]
[ 324-93-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2412 - 2418

15
[ 398-24-3 ]
1,2-bis(4'-fluoro-[1,1'-biphenyl]-4-yl)diazene oxide [ No CAS ]
[ 324-93-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2412 - 2418

16
[ 371-40-4 ]
[ 321-63-1 ]
[ 324-93-6 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11555 - 11559,5

17
[ 1416964-69-6 ]
[ 62-53-3 ]
[ 321-63-1 ]
[ 324-93-6 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11555 - 11559,5

18
[ 1415130-93-6 ]
[ 324-93-6 ]
[ 1415130-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 50℃; for 16h;	Solid NaBH(OAc)3 (106 mg, 0.50 mmol) was added to a DCE solution (10 mL) of ethyl 3-(5-(3-chloro-5-formylphenyl)picolinamido)propanoate (90 mg, 0.25 mmol), <strong>[324-93-6]4'-fluoro-[1,1'-biphenyl]-4-amine</strong> (47 g, 0.25 mmol), and AcOH (0.06 mL, 1.00 mmol) and the resulting mixture was heated to 50 C. After 16 h the mixture was concentrated and purified via column chromatography to yield the title compound

Reference： [1]Patent: US2012/302610,2012,A1 .Location in patent: Page/Page column 103

19
[ 1086601-87-7 ]
[ 324-93-6 ]
[ 1415130-73-2 ]

Yield	Reaction Conditions	Operation in experiment
		Neat methanesulfonyl chloride (0.18 mL, 2.4 mmol) was added to a 0 C., DCM solution (20 mL) of 1-(2-bromo-4-chlorophenyl)ethanol (558 mg, 2.4 mmol) and Et3N (0.36 mL, 2.6 mmol) and the resulting mixture was allowed to warm to room temperature gradually. After 30 min Et3N (0.36 mL, 2.6 mmol) and <strong>[324-93-6]4'-fluoro-[1,1'-biphenyl]-4-amine</strong> (444 g, 2.4 mmol) were added sequentially and stirred at room temperature. After 16 h the resulting mixture was concentrated and purified via column chromatography to yield the title compound.

Reference： [1]Patent: US2012/302610,2012,A1 .Location in patent: Page/Page column 88

20
[ 1415130-76-5 ]
[ 324-93-6 ]
[ 1415130-77-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 16h;	Solid NaBH(OAc)3 (114 mg, 0.54 mmol) was added to a DCE solution (8 mL) of ethyl 3-(5-(2-(((4'-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(prop-1-en-2-yl)phenyl)picolinamido)propanoate (99 mg, 0.27 mmol), <strong>[324-93-6]4'-fluoro-[1,1'-biphenyl]-4-amine</strong> (50 mg, 0.27 mmol) and HOAc (0.02 mL, 0.27 mmol) the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with DCM and washed with saturated aqueous NaHCO3 and water. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Reference： [1]Patent: US2012/302610,2012,A1 .Location in patent: Page/Page column 89; 90

21
2-(4-fluorophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione [ No CAS ]
[ 106-40-1 ]
[ 324-93-6 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 17707 - 17710

22
[ 324-93-6 ]
[ 1582285-74-2 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 3865 - 3867
[2]Organic Letters,2022,vol. 24,p. 349 - 353

23
[ 324-93-6 ]
[ 920-46-7 ]
C₁₆H₁₄FNO [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 3865 - 3867
[2]Organic Letters,2022,vol. 24,p. 349 - 353

24
[ 324-93-6 ]
[ 160732-56-9 ]
[ 1609111-29-6 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 5733 - 5736

25
[ 324-93-6 ]
[ 90-02-8 ]
2-(((4'-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Under an atmosphere of N2, 0.175 g (1 mmol) compd. 2 was dissolved in methanol, 0.11 mL (1.05 mmol) salicylaldehyde was added and stirred overnight at room temperature. When compd. 2 disappeared, NaBH4 (61 mg, 1.6 mmol) was added. After stirring for 10 min, the reaction was quenched by sat. NH4Cl solution, then extracted with CH2Cl2 (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE:EtOAc = 15:1) to afford 0.230 g (82%) E6 as white solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3057 - 3061

26
[ 324-93-6 ]
[ 67-68-5 ]
4-fluoro-4’-(methylsulfinyl)biphenyl [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 8557 - 8560

27
[ 324-93-6 ]
C₃₀H₄₀FN₃O₈S [ No CAS ]
C₃₇H₄₀F₂N₄O₅S [ No CAS ]

Reference： [1]Asian Journal of Chemistry,2017,vol. 29,p. 1018 - 1022

28
(4-aminophenyl)boronic acid hydrochloride [ No CAS ]
[ 460-00-4 ]
[ 324-93-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 75℃; for 12h;Reflux; Inert atmosphere;	In a three-necked flask,8.75 g (50 mmol) of 4-bromofluorobenzene was added,9.4 g (55 mmol) of p-aminobenzeneboronic acid hydrochloride,2mol / LPotassium carbonate solution75ml,Phase transfer catalyst with several drops and250mlTetrahydrofuran,Magnetic stirring and argon,The oil bath was heated to 75 C,0.02 g of tetraphenylphenylphosphine palladium was added,After refluxing for 12 h, the mixture was partitioned and removed to remove the aqueous layer. After mixing the silica gel, the column was collected and collected Point of the solution spin to dry white solid,Dry in a vacuum at 60 C for 12 h to give a white intermediate4'-fluoro- [1,1'-biphenyl] -4-amine 8.61g,The yield was 92%.The intermediate structure is as follows

Reference： [1]Patent: CN104016870,2017,B .Location in patent: Paragraph 0049; 0050

29
[ 324-93-6 ]
5'-(4-fluorophenyl)-3,3"-dinitro-1,1':3',1"-terphenyl [ No CAS ]

Reference： [1]Patent: CN104016870,2017,B

30
[ 324-93-6 ]
5'-(4-fluorophenyl)-[1,1':3',1"-terphenyl]-3,3"-diamine [ No CAS ]

Reference： [1]Patent: CN104016870,2017,B

31
[ 324-93-6 ]
3,5-dibromo-4'-fluoro-[1,1'-biphenyl]-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 2h;	A solution of 4'-fluoro- [1,1'-biphenyl] -4-amine 5.62 g (30 mmol) and 30 ml of DMF were dissolved in a three-necked flask and cooled to 0 C. N-bromosuccinimide NBS) 11.2 g (63 mmol) was dissolved in 30 ml of DMF and slowly added dropwise to the above reaction system.After dripping for 0 h, the reaction was continued for 1 h, then poured into 1 L of cold water, allowed to stand for 12 h and then filtered. After drying at 70 C for 12 h, the mixture was dissolved in methylene chloride and spin-dried. The column was collected. The white solid was dried in vacuo at 60 C for 12 h to give a white intermediate 3,5-dibromo-4'-fluoro- [1,1'-biphenyl] -4-amine, 8.79 g in 85% yield.The intermediate structure is as follows.

Reference： [1]Patent: CN104016870,2017,B .Location in patent: Paragraph 0051; 0052

32
[ 324-93-6 ]
3,5-dibromo-4'-fluoro-1,1'-biphenyl [ No CAS ]

Reference： [1]Patent: CN104016870,2017,B

33
phenyl 4'-fluoro-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
[ 324-93-6 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4282 - 4285
Angew. Chem.,2017,vol. 129,p. 4346 - 4349

34
C₂₅H₁₈FN [ No CAS ]
[ 324-93-6 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4282 - 4285
Angew. Chem.,2017,vol. 129,p. 4346 - 4349

35
[ 324-93-6 ]
C₃₀H₂₃N₃O₅ [ No CAS ]
6-([1,1'-biphenyl]-4-ylamino)-3-(benzyloxy)-N-(4'-fluoro-[1,1'-biphenyl]-4-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5045 - 5056

36
[ 1103929-71-0 ]
[ 324-93-6 ]
[ 1190220-66-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 809 - 813

37
[ 1103929-71-0 ]
[ 324-93-6 ]
[ 1190221-90-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide; at 20℃;	General procedure: A mixture of the carboxylic acid 6a (0.5 g, 1.66 mmol), amine (8a) (0.193 g, 1.74 mmol), WSC HCl(0.382 g, 1.99 mmol), HOBt (0.269 g, 1.99 mmol) in DMA (5 mL) was stirred at room temperature. Aftercompletion of the reaction, the reaction mixture was poured into an aqueous NaHCO3 solution. The solidwas separated by filtration, and washed with water to afford the corresponding amide (12a) as a solid(0.281g, 82%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 809 - 813

38
[ 324-93-6 ]
[ 24271-82-7 ]
6-((4’-fluoro-[1,1‘-biphenyl]-4-yl)amino)quinazoline-5,8-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 1576 - 1594

39
[ 135-88-6 ]
[ 324-93-6 ]
C₂₈H₂₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With caesium carbonate; In N,N-dimethyl-formamide; at 170℃; for 15h;	In a dry 2 L three-necked flask was added 21.9 g (100 mmol, 1.0 eq.) of N-phenyl-2-naphthylamine and 18.7 g.(100 mmol, 1.0 eq.) 4-fluoro-4-aminobiphenyl, followed by addition of dry and degassed 800 ml of DMF as a solvent, and mechanically stirring, and then slowly adding 65.2 g (200 mmol, 2.0 eq.) of cesium carbonate. The temperature was raised to 170 C and the reaction was allowed to continue for 15 hours. After the reaction was completed, it was cooled to room temperature, stirred with water for 1 hour, solid formed, suction filtered, washed with a small amount of ethanol, beaten with ethanol at room temperature 3 times, suction filtered, dried to give 38.5 g of intermediate-4, yield 82 %.

Reference： [1]Patent: CN108178765,2018,A .Location in patent: Paragraph 0054; 0071; 0073; 0074

40
[ 324-93-6 ]
C₅₃H₃₃BrN₂O₂ [ No CAS ]

Reference： [1]Patent: CN108178765,2018,A

41
[ 324-93-6 ]
C₅₃H₃₂BrIN₂O₂ [ No CAS ]

Reference： [1]Patent: CN108178765,2018,A

42
[ 324-93-6 ]
C₅₉H₃₇N₃O₂ [ No CAS ]

Reference： [1]Patent: CN108178765,2018,A

43
[ 324-93-6 ]
[ 25015-63-8 ]
4-amino-4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)biphenyl [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7249 - 7252

44
[ 106-40-1 ]
[ 225916-39-2 ]
[ 324-93-6 ]