[ CAS No. 5728-66-5 ] {[proInfo.proName]}

Name: 5728-66-5|3'-Fluoro-[1,1'-biphenyl]-4-amine|97%
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Quality Control of [ 5728-66-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 5728-66-5 ]

CAS No. :	5728-66-5	MDL No. :	MFCD03424688
Formula :	C₁₂H₁₀FN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DOUHEBIOTFMLAJ-UHFFFAOYSA-N
M.W :	187.21	Pubchem ID :	2782681
Synonyms :

Safety of [ 5728-66-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5728-66-5 ]

* 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 [ 5728-66-5 ]

[ 5728-66-5 ] Synthesis Path-Downstream 1~17

1
[ 5728-57-4 ]
[ 5728-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	(i) PCl₅, benzene, (ii) aq. HCl, EtOH; Multistep reaction;

Reference： [1]Byron,D.J. et al. [Journal of the Chemical Society C: Organic, 1966, p. 840 - 845]

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 Suzuki Procedure B 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.

3
[ 5728-66-5 ]
[ 56875-59-3 ]
[ 1360630-58-5 ]

Yield	Reaction Conditions	Operation in experiment
30%	With pyridine	5.1.35. Methyl 4'-(naphthalene-2-sulfonamido)biphenyl-3-carboxylate (11a) General procedure: To a solution of 32a (230 mg, 1 mmol) in 3 mL pyridine was added 38 (230 mg, 1 mmol) and the reaction mixture was stirred overnight. The mixture was acidified to pH 2 and then extracted with EtOAc (2 × 75 mL), washed with water and brine, dried (Na2SO4), filtered, and concentrated to afford brown solid which was washed with methanol to provide 220 mg of 11a. White powder, Yield 53%

Reference： [1]Location in patent: experimental part Venkatraj, Muthusamy; Messagie, Jonas; Joossens, Jurgen; Lambeir, Anne-Marie; Haemers, Achiel; Van Der Veken, Pieter; Augustyns, Koen [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 4, p. 1557 - 1568]

4
[ 768-35-4 ]
[ 106-40-1 ]
[ 5728-66-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene Inert atmosphere; Reflux;	Biphenyl-4-ylamine (35a) General procedure: To a stirred solution of 4-bromoaniline (0.69g, 4 mmol) in 40 mL of toluene was added Pd(Ph3P)4 (0.32 g, 0.28 mmol), a solution of sodium carbonate (2.54 g, 24 mmol) in water (20 mL) and a solution of phenylboronic acid (0.98 g, 8 mmol) in EtOH (20 mL) under nitrogen atmosphere. The reaction mixture was stirred vigorously under reflux overnight and cooled, water was added and the reaction mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were dried and concentrated to provide brown solid which was flash chromatographed on silica gel eluting with 30% EtOAc in hexanes to provide 0.18 g (27%) of 35a

Reference： [1]Venkatraj, Muthusamy; Messagie, Jonas; Joossens, Jurgen; Lambeir, Anne-Marie; Haemers, Achiel; Van Der Veken, Pieter; Augustyns, Koen [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 4, p. 1557 - 1568]

5
[ 768-35-4 ]
[ 540-37-4 ]
[ 5728-66-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In water; acetonitrile at 100℃; for 3h; Microwave irradiation;
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water Inert atmosphere; Reflux;	General coupling procedure for compounds 5&6 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]Birch, Alan M.; Groombridge, Sam; Law, Robert; Leach, Andrew G.; Mee, Christine D.; Schramm, Carolin [Journal of Medicinal Chemistry, 2012, vol. 55, # 8, p. 3923 - 3933]
[2]Mou, Jianfeng; Park, Ann; Cai, Yu; Yuan, Junying; Yuan, Chengye [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061]

6
[ 5728-66-5 ]
[ 90-02-8 ]
2-(((3'-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3′-fluoro‐[1,1′‐biphenyl]‐4‐amine; salicylaldehyde In methanol at 20℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.166667h; Inert atmosphere;	Reductive amination procedure 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]Mou, Jianfeng; Park, Ann; Cai, Yu; Yuan, Junying; Yuan, Chengye [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061]

7
[ 74124-79-1 ]
[ 5728-66-5 ]
N‐methyl‐1‐(methylsulphonyl)piperidin‐2,2,6,6‐[¹³C₂,²H₄]‐4‐amine [ No CAS ]
3‐(3′‐fluoro‐[1,1′‐biphenyl]‐4‐yl)‐1‐methyl‐1‐(1‐(methylsulphonyl)piperidin‐4‐yl)‐2,2,6,6‐[¹³C₂,²H₄]-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: di(succinimido) carbonate; 3′-fluoro‐[1,1′‐biphenyl]‐4‐amine With pyridine In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: N‐methyl‐1‐(methylsulphonyl)piperidin‐2,2,6,6‐[¹³C₂,²H₄]‐4‐amine In tetrahydrofuran for 0.5h; Inert atmosphere;

Reference： [1]Hesk; Koharski; McNamara; Royster; Saluja; Truong; Voronin [Journal of labelled compounds and radiopharmaceuticals, 2018, vol. 61, # 7, p. 533 - 539]

8
[ 51-90-1 ]
[ 5728-66-5 ]
C₁₂⁽¹⁴⁾CH₈FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: [14C]carbon dioxide; 3′-fluoro‐[1,1′‐biphenyl]‐4‐amine With triethylamine In dichloromethane at -20℃; for 0.5h; Inert atmosphere; Stage #2: With trichlorophosphate In dichloromethane at -78 - 20℃; for 1.5h; Inert atmosphere;

Reference： [1]Hesk; Koharski; McNamara; Royster; Saluja; Truong; Voronin [Journal of labelled compounds and radiopharmaceuticals, 2018, vol. 61, # 7, p. 533 - 539]

9
1-ethyl-4-(3-fluorophenyl)benzene [ No CAS ]
[ 5728-66-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium azide; oxygen; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 40℃; for 4h; Sealed tube;	The general procedure for the C-C amination of alkylarenes is as follows. General procedure: A 20 ml vial equipped with a magnetic stirring bar was charged with alkylarenes (0.3 mmol, 1 equiv.), NaN3 (0.75 mmol, 2.5 equiv.), DDQ (0.45 mmol, 1.5 equiv.) and trifluoroacetic acid (TFA) (1.0 ml, 0.3 M). The vial was sealed and stirred under air at 40 °C for 4 h. On completion, the reaction mixture was quenched by 2 M NaOH (5 ml), extracted by ethyl acetate (5 × 2 ml) and the combined organic phase was washed with brine and dried over Na2SO4. Then the mixture was concentrated and purified by flash chromatography on a short silica gel column.
66%	With sodium azide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 40℃; for 24h;	31 Take a reaction tube and add sodium azide 49mg, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone 100mg,60% of 3'-fluoro-[4-(1,1'-biphenylyl)]ethylbenzene and 1.0 ml of trifluoroacetic acid were stirred at 40 ° C for 24 hours.After the reaction was completed, 10 mL of a sodium hydroxide solution was added to quench the reaction, and the mixture was extracted three times with ethyl acetate.Separation by column chromatography3'-Fluoro-[4-(1,1'-biphenylyl)aniline 37.1 mg, 66% yield.

Reference： [1]Liu, Jianzhong; Qiu, Xu; Huang, Xiaoqiang; Luo, Xiao; Zhang, Cheng; Wei, Jialiang; Pan, Jun; Liang, Yujie; Zhu, Yuchao; Qin, Qixue; Song, Song; Jiao, Ning [Nature Chemistry, 2019, vol. 11, # 1, p. 71 - 77]
[2]Current Patent Assignee: PEKING UNIVERSITY - CN109134267, 2019, A Location in patent: Paragraph 0206-0208

10
[ 5728-66-5 ]
1-{3’-fluoro-[1,1′-biphenyl]-4-yl}-1H,4H,9H-naphtho[2,3-d][1,2,3]triazole-4,9-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.5 h / -15 °C 1.2: 1 h / -15 °C 1.3: 75 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 80 °C

Reference： [1]Zuo, Zeping; Liu, Xiaocong; Qian, Xinying; Zeng, Ting; Sang, Na; Liu, Huan; Zhou, Yue; Tao, Lei; Zhou, Xia; Su, Na; Yu, Yamei; Chen, Qiang; Luo, Youfu; Zhao, Yinglan [Journal of Medicinal Chemistry, 2020, vol. 63, # 14, p. 7633 - 7652]

11
[ 5728-66-5 ]
4-azido-3'- fluoro[1,1'-biphenyl] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: 3′-fluoro‐[1,1′‐biphenyl]‐4‐amine With boron trifluoride diethyl etherate In tetrahydrofuran at -15℃; for 0.5h; Stage #2: With tert.-butylnitrite In tetrahydrofuran at -15℃; for 1h; Stage #3: With sodium azide In water; acetonitrile at 75℃;

12
[ 106-40-1 ]
[ 5728-66-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere;

13
[ 5728-66-5 ]
[ 98-58-8 ]
C₁₈H₁₃BrFNO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In dichloromethane at 0 - 20℃;

Reference： [1]Chen, Tao; Li, Wen-Qin; Liu, Zheng; Jiang, Wen; Liu, Tian; Yang, Qing; Zhu, Xiao-Lei; Yang, Guang-Fu [Journal of Agricultural and Food Chemistry, 2021, vol. 69, # 40, p. 12039 - 12047]

14
[ 349-88-2 ]
[ 5728-66-5 ]
C₁₈H₁₃F₂NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In dichloromethane at 0 - 20℃;

15
3-Fluoro-4'-nitro-biphenyl [ No CAS ]
[ 5728-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	With iron; ammonium chloride In ethanol Reflux;

16
[ 636-98-6 ]
[ 5728-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene / 100 °C / Inert atmosphere 2: iron; ammonium chloride / ethanol / Reflux

17
[ 768-35-4 ]
[ 5728-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene / 100 °C / Inert atmosphere 2: iron; ammonium chloride / ethanol / Reflux

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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Alkyl Halide Occurrence • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • An Alkane are Prepared from an Haloalkane • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Deprotonation of Methylbenzene • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nitrosation of Amines • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Preparation of LDA • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Ugi Reaction • Vilsmeier-Haack Reaction

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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

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. 5728-66-5 ] {[proInfo.proName]}

Quality Control of [ 5728-66-5 ]

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[ 5728-66-5 ] Synthesis Path-Downstream 1~17

Technical Information

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Fluorinated Building Blocks

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Precautionary Statements-General

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[ 5728-66-5 ]

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