143418-49-9

Basic information

• Product Name: 3,4,5-Trifluorophenylboronic acid
• Synonyms: AKOS BRN-0138;3,4,5-TRIFLUOROPHENYLBORONIC ACID;3,4,5-TRIFLUOROBENZENEBORONIC ACID;3,4,5-Trifluophenylboronic acid ;3,4,5-Trifluorobenzeneboronic acid 97%;3,4,5-Trifluorobenzeneboronicacid97%;3,4,5-TRIFLUOROPHENYLBORONIC ACID MIN 96% HPLC;3,4,5-TRIFLUOROPHENYLBORONIC ACID, 95+%
• CAS NO: 143418-49-9
• Molecular Formula: C₆H₄BF₃O₂
• Molecular Weight: 175.9
• EINECS: -0
• Product Categories: Fluorin-contained phenyl boronic acid series;blocks;BoronicAcids;Boronic Acid series;Fluoro-Aromatics;Substituted Boronic Acids;Boronic Acid;Aryl;Fluorinated;Organoborons;Boronic Acids;Boronic Acids and Derivatives;Boronic Acids;Piperidines
• Mol File: 143418-49-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 290-295 °C(lit.)
• Boiling Point: 263.6 °C at 760 mmHg
• Flash Point: 113.2 °C
• Appearance: Tan/Powder
• Density: 1,087g/cm
• Vapor Pressure: 0.00513mmHg at 25°C
• Refractive Index: 1,423-1,425
• Storage Temp.: Store below +30°C.
• Solubility: 18.43g/l
• PKA: 6.54±0.11(Predicted)
• BRN: 7371914
• CAS DataBase Reference: 3,4,5-Trifluorophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-Trifluorophenylboronic acid(143418-49-9)
• EPA Substance Registry System: 3,4,5-Trifluorophenylboronic acid(143418-49-9)

Safety Data

• Hazard Codes: N-Xn,Xi
• Statements: 51/53-36-22-36/37/38
• Safety Statements: 61-26-37/39-36
• RIDADR: 3077
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 143418-49-9(Hazardous Substances Data)

Usage

Description

3,4,5-Trifluorophenylboronic acid is an organic compound with the molecular formula C6H4BF3O2. It is a tan powder and is commonly used as a reactant in various chemical reactions due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
3,4,5-Trifluorophenylboronic acid is used as a reactant for the preparation of phenylboronic catechol esters and determination of Lewis acidity. This application is crucial in the development of new pharmaceutical compounds and understanding the reactivity of different molecules.
Used in Chemical Synthesis:
3,4,5-Trifluorophenylboronic acid is used as a reactant in the synthesis of benzopyranone derivatives, which act as GABAA receptor modulators. These modulators have potential applications in the treatment of various neurological disorders.
Used in Organic Chemistry:
3,4,5-Trifluorophenylboronic acid is used as a reactant in the synthesis of multisubstituted olefins and conjugate dienes. These compounds are essential building blocks in organic chemistry and can be used to create a wide range of molecules with diverse applications.
Used in Suzuki Cross-Coupling Reactions:
3,4,5-Trifluorophenylboronic acid is used as a reactant in Suzuki cross-coupling reactions, which are widely employed in the formation of carbon-carbon bonds in organic synthesis. This reaction is crucial for the development of new compounds and materials.
Used in Polymer Industry:
3,4,5-Trifluorophenylboronic acid is used as a reactant in the preparation of fluorinated aromatic poly(ether-amide)s. These polymers have unique properties, such as high thermal stability and excellent mechanical properties, making them suitable for various applications in the polymer industry.
Used in Liquid Crystal Industry:
3,4,5-Trifluorophenylboronic acid is used as an intermediate in the production of liquid crystals. Liquid crystals are widely used in display technologies, such as LCD screens, due to their unique optical properties.

InChI:InChI=1/C6H4BF3O2/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,11-12H

Synthetic route

Trimethyl borate (121-43-7) + 3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Conditions	Yield
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 5 - 20℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -30 - -27℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 4h; Temperature;	82%
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran; ethylene dibromide at 5 - 25℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; ethylene dibromide at -30 - -27℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethylene dibromide at 20℃; for 4h; Temperature; Inert atmosphere;	81%
With magnesium In diethyl ether Grignard-comp. prepd. from Br-compd. and Mg in ether at 0 °C was added dropwise to 1.5 equiv. of pre-cooled (0 °C) soln. of B(OMe)3 in ether, mixt. was maintained at 0-10 °C for 1 h and allowed to warm up to 20 °C; pouring into 10 % HCl, org. layer was sepd., aq. layer was twice extd. with ether, extracts were combined, dried with MgSO4, evapd. under vac., end-product was contaminated with dehydration product;
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran at 25 - 35℃; for 7h; Grignard Reaction; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -5 - 25℃; for 4.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 25 - 50℃; for 1h;
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In 2-methyltetrahydrofuran at 20 - 80℃; for 4h; Inert atmosphere; Stage #2: Trimethyl borate In 2-methyltetrahydrofuran at -5 - 20℃; for 2.5h; Stage #3: With hydrogenchloride In 2-methyltetrahydrofuran; water at 20 - 50℃; for 1h;

Trimethyl borate (121-43-7) + 3,4,5-trifluorophenylmagnesium bromide (156006-28-9) + 3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Conditions	Yield
Stage #1: 3,4,5-trifluorophenylmagnesium bromide; 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran at 5 - 15℃; for 3h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -20℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran at -20 - 25℃; for 15h; Temperature; Inert atmosphere;	82%

Trimethyl borate (121-43-7) + water (7732-18-5) + 3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Conditions	Yield
Stage #1: 3,4,5-trifluoro-1-bromobenzene With iodine; magnesium In 2-methyltetrahydrofuran at 40 - 50℃; Stage #2: Trimethyl borate In 2-methyltetrahydrofuran at 10 - 20℃; for 8h; Stage #3: water With hydrogenchloride In 2-methyltetrahydrofuran Temperature;	78%

Triisopropyl borate (5419-55-6) + 3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9) + 3,4,5-C6H2F3B(O-i-Pr)2

Conditions	Yield
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In diethyl ether Grignard reaction; Stage #2: Triisopropyl borate In diethyl ether at -30 - 10℃; for 0.5h; boronation; Stage #3: With hydrogenchloride In diethyl ether at 20℃; for 1h; Hydrolysis; Title compound not separated from byproducts;

3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Conditions	Yield
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium Stage #2: With Trimethyl borate Stage #3: With hydrogenchloride In water

tris(3,4,5-trifluorophenyl)boroxine (223440-94-6) + water (7732-18-5) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Conditions	Yield
In acetonitrile
In diethyl ether

Trimethyl borate (121-43-7) + 3,4,5-trifluorophenylmagnesium bromide (156006-28-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;

C34H20B2F12O3 → tris(3,4,5-trifluorophenyl)boroxine (223440-94-6) + 3,4,5-trifluorophenylboronic acid (143418-49-9)

Conditions	Yield
at 20℃; for 144h;

C31H14B2F12O3 → tris(3,4,5-trifluorophenyl)boroxine (223440-94-6) + 3,4,5-trifluorophenylboronic acid (143418-49-9)

Conditions	Yield
at 20℃; for 144h;

(S)-3,3'-dibromo-6,6'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl + 3,4,5-trifluorophenylboronic acid (143418-49-9) → (S)-2,2'-dimethoxy-6,6'-dimethyl-5,5'-bis(3,4,5-trifluorophenyl)biphenyl

Conditions	Yield
With potassium phosphate; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide Suzuki-Miyaura coupling; Heating;	100%
With tripotassium phosphate "n" hydrate; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide Suzuki-Miyaura coupling; Reflux; Inert atmosphere;	100%
With tripotassium phosphate "n" hydrate; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;	100%

para-bromoacetophenone (99-90-1) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 1-(3',4',5'-trifluoro-[1,1'-biphenyl]-4-yl)ethan-1-one

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran for 2h; Suzuki Coupling; Inert atmosphere; Reflux;	100%
With 4-methoxy-6-(((methyl-2-pyridinylmethyl)imino)methyl)phenol; palladium diacetate; potassium hydroxide In ethanol; water for 1h; Suzuki-Miyaura Coupling; Reflux;	99%
With C34H54N2O2; palladium diacetate; potassium carbonate In water; acetone for 1h; Suzuki Coupling; Reflux; Green chemistry;	98%

para-iodoanisole (696-62-8) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 4-methoxy-3',4',5'-trifluorobiphenyl

Conditions	Yield
With sodium carbonate In ethanol; water at 80℃; for 0.25h; Catalytic behavior; Suzuki-Miyaura Coupling;	100%

2-bromo-9H-fluorene (1133-80-8) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2-(3,4,5-trifluorophenyl)-9H-fluorene

Conditions	Yield
With C35H40N4O9(2+)*2Cl(1-); palladium diacetate; potassium hydroxide In ethanol at 100℃; for 1.5h; Suzuki Coupling; Green chemistry;	99%
With potassium tert-butylate In ethanol; water Reflux;	98%
With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Suzuki Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	97%
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere;	97%

1,2,4,5-tetrafluoro-3-iodobenzene (5243-24-3) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2,3,3′,4′,5,5′,6-heptafluoro-1,1′-biphenyl

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; XPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	99%

1,3,5-trifluoro-2-iodobenzene (41860-63-3) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2,3′,4,4′,5′,6-hexafluoro-1,1′-biphenyl

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	99%

2-Chloroaniline (95-51-2) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 3’,4’,5’-trifluoro-[1,1’-biphenyl]-2-amine (915416-45-4)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate; palladium dichloride In water; isopropyl alcohol at 25 - 85℃; for 5.25h; Reagent/catalyst; Temperature; Inert atmosphere;	99%

2-Chloronitrobenzene (88-73-3) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2-nitro-3',4',5'-trifluoro-1,1'-biphenyl (1056196-56-5)

Conditions	Yield
With potassium tert-butylate; C33H46Cl2N4Pd In 2-methyltetrahydrofuran at 100℃; for 3h; Solvent; Reagent/catalyst; Temperature;	98%
With potassium phosphate tribasic trihydrate; (2-(anthracen-9-yl)-1H-inden-3-yl)dicyclohexylphosphine; palladium diacetate In water; isopropyl alcohol; toluene at 90℃; for 16h; Catalytic behavior; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	96%
With diamminedichloropalladium(II); triphenylphosphine; sodium hydroxide In tetrahydrofuran; water for 10h; Reagent/catalyst; Suzuki Coupling; Reflux; Inert atmosphere;	95%

4-bromo-benzaldehyde (1122-91-4) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 4-(3,4,5-trifluorophenyl)benzaldehyde (954369-65-4)

Conditions	Yield
With potassium carbonate In ethanol at 75℃; for 3h; Suzuki-Miyaura Coupling;	98%
With sodium hydrogencarbonate In water at 90℃; for 0.166667h; Suzuki Coupling; Green chemistry;	93%
With sodium hydrogencarbonate In ethanol; water at 70℃; for 4h; Catalytic behavior; Suzuki Coupling;	93%

2,7-dibromo-9H-fluorene (16433-88-8) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2,7-bis(3,4,5-trifluorophenyl)-9H-fluorene

Conditions	Yield
With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Suzuki Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	98%
With potassium tert-butylate In ethanol; water Reflux;	96%
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere;	96%

2,3,5,6-tetrafluoropyridin-4-yliodine (16297-19-1) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2,3,5,6-tetrafluoro-4-(3,4,5-trifluorophenyl)pyridine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	98%

9,9-bis-(n-butyl)-2,7-dibromofluorene (188200-91-1) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 9,9-dibutyl-2,7-bis(3,4,5-trifluorophenyl)-9H-fluorene

Conditions	Yield
With C35H40N4O9(2+)*2Cl(1-); palladium diacetate; potassium hydroxide In ethanol at 100℃; for 1.5h; Suzuki Coupling; Green chemistry;	98%
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere;	98%
With potassium tert-butylate In ethanol; water Reflux;	97%

2-Chlorobenzonitrile (873-32-5) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 3’,4’,5’-trifluoro-[1,1’-biphenyl]-2-carbonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; tricyclohexylphosphine tetrafluoroborate; sodium hydroxide In water; toluene at 85℃; for 12h; Catalytic behavior; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;	98%
With potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; tricyclohexylphosphine tetrafluoroborate In water; isopropyl alcohol; toluene at 100℃; for 12h; Temperature; Inert atmosphere;	92%

o-nitroiodobenzene (609-73-4) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2-nitro-3',4',5'-trifluoro-1,1'-biphenyl (1056196-56-5)

Conditions	Yield
With sodium hydrogencarbonate; palladium dichloride In methanol at 40℃;	98%

(R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol (765278-73-7) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → (R)-3,3'-bis-(3,4,5-trifluorophenyl)-5,5',6,6',7,7',8,8'-octahydro-[1,1'-binaphthalene]-2,2'-diol

Conditions	Yield
With palladium diacetate; potassium carbonate; catacxium A In 1,2-dimethoxyethane; water at 100℃; for 18h; Inert atmosphere; Sealed tube;	98%

iodobenzene (591-50-4) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 3,4,5-trifluoro-1-1’-biphenyl (178820-23-0)

Conditions	Yield
With sodium t-butanolate In water at 28℃; for 4h; Catalytic behavior; Suzuki-Miyaura Coupling; Irradiation;	97%

3,4,5-trifluorophenylboronic acid (143418-49-9) + 3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl (600172-56-3) → 5,5’-di-tert-butyl-4,4’-dimethoxy-2,2’-dimethyl-3,3’-(3,4,5-trifluorophenyl)biphenyl

Conditions	Yield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); water; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; Sealed tube;	97%

tert-butyl (5R,8S)-2-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate + 3,4,5-trifluorophenylboronic acid (143418-49-9) → tert-butyl (5R,8S)-2-methyl-3-(3,4,5-trifluorophenyl)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate

Conditions	Yield
With (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); sodium carbonate In 1,4-dioxane; water at 110℃; for 0.583333h; Inert atmosphere; Microwave irradiation;	97%

para-bromotoluene (106-38-7) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 3',4',5'-trifluoro-4-methyl-1,1'-biphenyl (524018-97-1)

Conditions	Yield
With potassium carbonate In ethanol; water at 80℃; for 0.75h; Suzuki Coupling;	96%
With Ph2P(CH2CH2O)22CH3; triethylamine; palladium dichloride In water at 80℃; for 4h; Suzuki coupling; Inert atmosphere;	68%

ethyl benzo[h]quinoline-10-carboxylate (1015758-32-3) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 10-(3,4,5-trifluorophenyl)benzo[h]quinoline (1415320-69-2)

Conditions	Yield
With tris(triphenylphosphine)rhodium(I) chloride; copper(l) chloride In toluene at 130℃; for 30h; Inert atmosphere;	96%

2,2',7,7'-tetrabromo-9,9'-spirobifluorene (128055-74-3) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2,2',7,7'-tetrakis(3,4,5-trifluorophenyl)spiro-9,9'-bifuorene (1425942-31-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;	96%

10,10'-dibromo-9,9'-bianthryl (121848-75-7) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 10,10'-bis(3,4,5-trifluorophenyl)-9,9'-bianthracene (1505455-99-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In tetrahydrofuran for 24h; Suzuki Coupling; Inert atmosphere; Reflux;	96%

4-methoxycarbonylphenyl bromide (619-42-1) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → C14H9F3O2

Conditions	Yield
With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 2h; Suzuki-Miyaura Coupling; Schlenk technique;	96%

p-nitrobenzene iodide (636-98-6) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → C12H6F3NO2

Conditions	Yield
With potassium carbonate In ethanol; water at 100℃; for 1h; Suzuki-Miyaura Coupling;	96%

C15H21Cl + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 4'-(trans-4-propylcyclohexyl)-3,4,5-trifluorobiphenyl

Conditions	Yield
With dichloro(cycloocta-1,5-diene)palladium (II); 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol); potassium carbonate In methanol Suzuki cross-coupling reaction; Microwave irradiation; Inert atmosphere;	95%

1-bromo-4-methoxy-benzene (104-92-7) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 4-methoxy-3',4',5'-trifluorobiphenyl

Conditions	Yield
With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 5h; Suzuki-Miyaura Coupling; Schlenk technique;	95%

C19H15FeIN2 + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 5-ferrocenyl-1-phenyl-4-(3,4,5-trifluorophenyl)-1H-pyrazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium hydrogencarbonate In water; N,N-dimethyl-formamide at 110℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;	95%

9-(5'-bromo-[2,2'-bipyridine]-5-yl)-9H-carbazole (1206209-16-6) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → C28H16F3N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 85℃; for 24h; Inert atmosphere; Reflux;	95%

C48H52BrIN2O4 + 3,4,5-trifluorophenylboronic acid (143418-49-9) → C60H56F6N2O4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 16h; Inert atmosphere; Reflux;	95%

3,4,5-trifluorophenylboronic acid (143418-49-9) + 1-bromo-2,3,4-trifluorobenzene (176317-02-5) → 2,3,3′,4,4′,5′-hexafluoro-1,1′-biphenyl

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	95%

Upstream product

• 7647-01-0 hydrogenchloride 
• 5419-55-6 Triisopropyl borate 
• 138526-69-9 3,4,5-trifluoro-1-bromobenzene 
• 121-43-7 Trimethyl borate 
• 7732-18-5 water 
• 156006-28-9 3,4,5-trifluorophenylmagnesium bromide 
• 223440-94-6 tris(3,4,5-trifluorophenyl)boroxine 

Downstream Products

• 165328-45-0 1-[2-(3,4,5-trifluorophenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene 
• 916235-55-7 3,4,5,3''',4''',5'''-hexafluoro-[1,3';1',1'';3'',1''']quaterphenyl-2',2''-dicarboxylic acid diisopropyl ester 
• 901528-88-9 C₁₂H₁₁F₃O 
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• 1489-53-8 1,2,3-trifluorobenzene 

Relevant articles and documents

Mechanistic insights into boron-catalysed direct amidation reactions

The generally accepted monoacyloxyboron mechanism of boron-catalysed direct amidation is brought into question in this study, and new alternatives are proposed. We have carried out a detailed investigation of boron-catalysed amidation reactions, through study of the interaction between amines/carboxylic acids and borinic acids, boronic acids and boric acid, and have isolated and characterised by NMR/X-ray crystallography many of the likely intermediates present in catalytic amidation reactions. Rapid reaction between amines and boron compounds was observed in all cases, and it is proposed that such boron-nitrogen interactions are highly likely to take place in catalytic amidation reactions. These studies also clearly show that borinic acids are not competent catalysts for amidation, as they either form unreactive amino-carboxylate complexes, or undergo protodeboronation to give boronic acids. It therefore seems that at least three free coordination sites on the boron atom are necessary for amidation catalysis to occur. However, these observations are not consistent with the currently accepted 'mechanism' for boron-mediated amidation reactions involving nucleophilic attack of an amine onto a monomeric acyloxyboron intermediate, and as a result of our observations and theoretical modelling, alternative proposed mechanisms are presented for boron-mediated amidation reactions. These are likely to proceed via the formation of a dimeric B-X-B motif (X = O, NR), which is uniquely able to provide activation of the carboxylic acid, whilst orchestrating the delivery of the amine nucleophile to the carbonyl group. Quantum mechanical calculations of catalytic cycles at the B3LYP+D3/Def2-TZVPP level (solvent = CH2Cl2) support the proposal of several closely related potential pathways for amidation, all of which are likely to be lower in energy than the currently accepted mechanism.

PROCESS FOR THE PREPARATION OF BIPHENYLAMINES

The invention relates to a method for the preparation of 2-aminobiphenyls, key intermediates in the preparation of compounds of interest in the agrochemical industry. The process comprises reacting an ortho-substituted aniline and a phenylboro derivative in the presence of a base and a palladium catalyst, said palladium catalyst comprising a palladium source and a biphenyl phosphine ligand of formula (III) or a salt thereof

Efficient and Practical Synthesis of 3′,4′,5′-Trifluoro-[1,1′-biphenyl]-2-amine: A Key Intermediate of Fluxapyroxad

An improved and practical method is reported here for accessing 3′,4′,5′-trifluoro-[1,1′-biphenyl]-2-amine (1), a key intermediate for Fluxapyroxad. The overall yield for the preparation of 1 was 73%, with a purity of 99.88%, after a three-step process. More importantly, this process was an improvement in the manufacture of biphenyl compounds by Suzuki-Miyaura coupling, which enabled catalyst loading as low as 0.04 mol %. This method could provide an economic and environment-friendly process leading to extensive prospects in industrial applications.