352303-67-4

Basic information

• Product Name: 2-FLUORO-3-METHOXYPHENYLBORONIC ACID
• Synonyms: 3-Borono-2-fluoroanisole;Fluoro-3-Methoxyphenylboronic;2-F,3-MeOC6H3B(OH)2;2-FLUORO-3-METHOXYPHENYLBORONIC ACID;2-FLUORO-3-METHOXYBENZENEBORONIC ACID;2-Fluoro-3-Methoxyphenylboroni;2-FLUORO-3-METHOXYBENZENEBORONIC ACID 97%;2-Fluoro-3-methoxyphenylboronic acid ,98%
• CAS NO: 352303-67-4
• Molecular Formula: C₇H₈BFO₃
• Molecular Weight: 169.95
• Product Categories: blocks;BoronicAcids;FluoroCompounds;Boronic Acid;Aryl;Organoborons;Benzene derivatives;Boronic Acids;Boronic Acids and Derivatives;Boronic Acids;Boronate Ester;Potassium Trifluoroborate
• Mol File: 352303-67-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 117-122 °C(lit.)
• Boiling Point: 326.8 ºC at 760 mmHg
• Flash Point: 151.4 ºC
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 8.56E-05mmHg at 25°C
• Refractive Index: 1.503
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• PKA: 7.90±0.58(Predicted)
• BRN: 9191510
• CAS DataBase Reference: 2-FLUORO-3-METHOXYPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUORO-3-METHOXYPHENYLBORONIC ACID(352303-67-4)
• EPA Substance Registry System: 2-FLUORO-3-METHOXYPHENYLBORONIC ACID(352303-67-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 352303-67-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 352303-67-4 differently. You can refer to the following data:
1. suzuki reaction
2. Reactant for:Regioselective Suzuki couplingPreparation of inhibitors of 17β-hydroxysteroid dehydrogenase type 1Preparation of boronic esters

InChI:InChI=1/C7H8BFO3/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4,10-11H,1H3

Synthetic route

n-butyllithium (109-72-8, 29786-93-4) + tetramethylpiperidine + Trimethyl borate (121-43-7) + 1-fluoro-2-methoxybenzene (321-28-8) → (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4)

Conditions	Yield
In tetrahydrofuran	26%

C9H12BFO3 → (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4)

Conditions	Yield
With hydrogenchloride

1-bromo-2-fluoro-3-methoxybenzene (295376-21-5) → (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4)

Conditions	Yield
Stage #1: 2-fluoro-3-methoxy-1-bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran for 0.5h;

tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (881678-18-8) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → tert-butyl {[5-(2-fluoro-3-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (928325-18-2)

Conditions	Yield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 100℃; for 2h;	100%

(2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → (2-fluoro-3-hydroxyphenyl)boronic acid (855230-60-3)

Conditions	Yield
Stage #1: (2-fluoro-3-methoxyphenyl)boronic acid With boron tribromide In dichloromethane at 5 - 20℃; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In ethanol; dichloromethane Cooling;	96%
With boron tribromide In dichloromethane at 5 - 20℃; for 1h; Inert atmosphere;	96%
Stage #1: (2-fluoro-3-methoxyphenyl)boronic acid With boron tribromide In dichloromethane at 0℃; for 1h; Stage #2: With methanol In dichloromethane at 0℃; for 1h;

(2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 2-fluoro-3-methoxyphenol (447462-87-5)

Conditions	Yield
With dihydrogen peroxide In 1,4-dioxane at 20℃; Cooling with ice;	96%
With dihydrogen peroxide; acetic acid In tetrahydrofuran; water at 0 - 20℃;	81%
With water; triethylamine In acetonitrile at 20℃; for 36h; Irradiation;	72%

2-bromothiophene (1003-09-4) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 2-(2-fluoro-3-methoxyphenyl)thiophene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water for 4h; Suzuki Coupling; Inert atmosphere; Reflux;	96%

(6-bromopyridin-2-yl)-(4-fluoro-3-methoxyphenyl)-methanone (1357564-27-2) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → (4-fluoro-3-methoxyphenyl)[6-(2-fluoro-3-methoxyphenyl)-pyridin-2-yl]methanone

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	95%

(6-bromopyridin-2-yl)(2,3,4-trimethoxyphenyl)methanone + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → [6-(2-fluoro-3-methoxyphenyl)pyridin-2-yl](2,3,4-trimethoxyphenyl)methanone

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	94%

potassium hydrogen difluoride + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → potassium 2-fluoro-3-methoxy-phenyl-1-trifluoroborate

Conditions	Yield
In methanol; water at 70℃; for 24h;	94%

(6-bromopyridin-2-yl)(2,3-dimethoxyphenyl)methanone + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → (2,3-dimethoxyphenyl)[6-(2-fluoro-3-methoxyphenyl)pyridin-2-yl]methanone

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	93%

3-bromo-2-chlorobenzenamine (56131-46-5) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 2-chloro-2'-fluoro-3'-methoxybiphenyl-3-amine

Conditions	Yield
With [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II); sodium carbonate In 1,4-dioxane; water at 90℃; for 2h; Inert atmosphere;	93%

(6-bromopyridin-2-yl)(2,3-dimethoxyphenyl)methanol + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → (2,3-dimethoxyphenyl)[6-(2-fluoro-3-methoxyphenyl)pyridin-2-yl]methanol

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	92%

(6-bromopyridin-2-yl)(2-methoxyphenyl)methanone (80100-50-1) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → [6-(2-fluoro-3-methoxyphenyl)pyridin-2-yl](2-methoxyphenyl)methanone

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	92%

6-bromo-N-(4-fluoro-3-methoxyphenyl)pyridine-2-carboxamide + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 6-(2-fluoro-3-methoxyphenyl)-N-(4-fluoro-3-methoxyphenyl)pyridine-2-carboxamide

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	92%

[14C]1-(2-fluoro-6-(trifluoromethyl)benzyl)-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → [14C]5-(2-fluoro-3-methoxyphenyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione

Conditions	Yield
Stage #1: [14C]1-(2-fluoro-6-(trifluoromethyl)benzyl)-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione; (2-fluoro-3-methoxyphenyl)boronic acid With potassium hydroxide; tri tert-butylphosphoniumtetrafluoroborate In acetone at 45℃; for 0.5h; Inert atmosphere; Stage #2: With palladium diacetate In acetone at 55℃; for 1.5h; Inert atmosphere;	92%

3-bromo-2-fluorobenzaldehyde (149947-15-9) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 2,2’-difluoro-3’-methoxy-[1,1’-biphenyl]-3-carbaldehyde

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water Suzuki Coupling; Reflux;	90.3%

methyl 2-bromo-5-nitrobenzoate (6942-36-5) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 2'-fluoro-3'-methoxy-4-nitro-biphenyl-2-carboxylic acid methyl ester

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 18h; Suzuki coupling; Heating;	90%

3-bromo-4-(2,6-difluoro-4-nitrophenoxy)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 4-(2,6-difluoro-4-nitrophenoxy)-3-(2-fluoro-3-methoxyphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	90%

{(R)-2-[5-bromo-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (830346-49-1) + Pamoic acid (130-85-8) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 3-[2(R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4(1H,3H)-dione pamoic acid salt

Conditions

Yield

Stage #1: {(R)-2-[5-bromo-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester; (2-fluoro-3-methoxyphenyl)boronic acid With sodium carbonate In 1,4-dioxane; water for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 95 - 100℃; Inert atmosphere; Stage #3: Pamoic acid Further stages;

90%

3-(R)-2-(amino-2-phenylethyl)-1-(2-fluoro-6-trifluoromethylbenzyl)-5-iodo-6-methyl-1H-pyrimidine-2,4-dione hydrochloride + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 3-[(2R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione trifluoroacetate (830346-50-4)

Conditions	Yield
With potassium phosphate tribasic trihydrate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate In water; acetone at 20 - 60℃; for 20h; Time; Inert atmosphere;	89.2%

(6-bromopyridin-2-yl)(2,4-difluoro-3-methoxyphenyl)methanone + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → (2,4-difluoro-3-methoxyphenyl)[6-(2-fluoro-3-methoxyphenyl)pyridin-2-yl]methanone

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 150℃; for 1h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	89%

(3-bromophenyl)(2,3-dimethoxyphenyl)methanone + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → (2,3-dimethoxyphenyl)(2'-fluoro-3'-methoxybiphenyl-3-yl)methanone

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	89%

1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione (1150560-54-5) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 5-(2-fluoro-3-methoxyphenyl)-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methylpyrimidine-2,4(1H,3H)-dione (1150560-59-0)

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium hydroxide In water; acetone at 40 - 45℃; for 2.5h;	88.4%
Stage #1: 1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione; (2-fluoro-3-methoxyphenyl)boronic acid With potassium hydroxide In water; acetone for 0.5 - 1h; Stage #2: 1,1-(bis-di-t-butylphosphino)ferrocene palladium dichloride In water; acetone at 40 - 45℃; for 2.5h; Product distribution / selectivity;	87%
Stage #1: 1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione; (2-fluoro-3-methoxyphenyl)boronic acid With potassium hydroxide; tri tert-butylphosphoniumtetrafluoroborate In water; acetone at 15 - 45℃; for 0.833333h; Stage #2: With palladium diacetate In water; acetone	85%

3-bromo-2-fluorobenzoic acid (161957-56-8) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 2,2’-difluoro-3’-methoxy-[1,1‘-biphenyl]-3-carboxylic acid

Conditions	Yield
With potassium phosphate; potassium dihydrogenphosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In 1,2-dimethoxyethane; ethanol; water at 60℃; for 5h; Suzuki Coupling;	88%

2-bromo-6-(4-fluoro-3-methoxyphenoxy)pyridine + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 2-(4-fluoro-3-methoxyphenoxy)-6-(2-fluoro-3-methoxyphenyl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	88%

1-(3-bromophenyl)-2-phenylethane-1,2-dione (40396-54-1) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 1-(2'-fluoro-3'-methoxy-[1,1'-biphenyl]-3-yl)-2-phenylethane-1,2-dione

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere;	88%

5-bromo-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide (1252464-84-8) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 5-(2-fluoro-3-methoxyphenyl)-N-methyl-N-(m-tolylthiophene)-2-carboxamide (1396243-08-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 14h; Inert atmosphere;	85%

(2R)-4-(4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1312478-57-1) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → (2R)-4-[4-(2-fluoro-3-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1358778-86-5)

Conditions	Yield
With potassium carbonate In ethanol; water at 70℃; Suzuki-Miyaura coupling;	84%

5-bromo-N-(3-methoxyphenyl)thiophene-2-carboxamide (885572-88-3) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 5-(2-fluoro-3-methoxyphenyl)-N-(3-methoxyphenyl)thiophene-2-carboxamide (1396243-33-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 14h; Inert atmosphere;	84%

2-chloro-3-cyanopyrazine (55557-52-3) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 3-(2'-fluoro-3'-methoxyphenyl)pyrazine-2-carbonitrile (1439364-58-5)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 0.25h; Suzuki Coupling; Inert atmosphere;	84%

2-bromo-6-(dimethoxymethyl)-3-iodopyridine + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → 2-bromo-6-(dimethoxymethyl)-3-(2-fluoro-3-methoxyphenyl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki Coupling; Inert atmosphere;	84%

{(R)-2-[5-bromo-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (830346-49-1) + (2-fluoro-3-methoxyphenyl)boronic acid (352303-67-4) → (R)-(2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)carbamic acid tert-butyl ester (830346-51-5)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; Suzuki Coupling;	83%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; Suzuki coupling; Inert atmosphere;	83%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; Suzuki Coupling;	83%

Upstream product

• 109-72-8 n-butyllithium 
• 121-43-7 Trimethyl borate 
• 321-28-8 1-fluoro-2-methoxybenzene 
• 295376-21-5 2-fluoro-3-methoxy-1-bromobenzene 

Downstream Products

• 496913-09-8 {2-[2-(2,6-difluoro-benzyl)-6-(2-fluoro-3-methoxy-phenyl)-3,5-dioxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 1013647-97-6 tert-Butyl 2-chloro-6-(2-fluoro-3-methoxyphenyl)nicotinate 
• 1013647-56-7 2-chloro-6-(2-fluoro-3-methoxyphenyl)nicotinaldehyde 
• 1255940-17-0 [5-(2-fluoro-3-methoxyphenyl)-2-thienyl](3-methoxyphenyl)methanone 

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