762287-57-0

Basic information

• Product Name: 4-Chloro-2-methoxyphenylboronic acid
• Synonyms: 4-CHLORO-2-METHOXYBENZENEBORONIC ACID;4-CHLORO-2-METHOXYPHENYLBORONIC ACID;REF DUPL: 4-Chloro-2-methoxyphenylboronic acid;4-chloro-2-Methoxybenzaldehyde acid;2-Borono-5-chloroanisole;Boronic acid, B-(4-chloro-2-Methoxyphenyl)-;4-Chloro-2-methoxyphenylboronic Acid (contains varying amounts of Anhydride);4-Chloro-2-methoxyphenylboronic
• CAS NO: 762287-57-0
• Molecular Formula: C₇H₈BClO₃
• Molecular Weight: 186.4
• Product Categories: blocks;BoronicAcids;Boronic Acid
• Mol File: 762287-57-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 128-134°C
• Boiling Point: 345.436 °C at 760 mmHg
• Flash Point: 162.714 °C
• Appearance: /
• Density: 1.325 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 8.42±0.58(Predicted)
• CAS DataBase Reference: 4-Chloro-2-methoxyphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-methoxyphenylboronic acid(762287-57-0)
• EPA Substance Registry System: 4-Chloro-2-methoxyphenylboronic acid(762287-57-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 762287-57-0(Hazardous Substances Data)

Usage

Uses

suzuki reaction

Synthetic route

2-bromo-5-chloroanisole (174913-09-8) + Trimethyl borate (121-43-7) → (4-chloro-2-methoxyphenyl)boronic acid (762287-57-0)

Conditions	Yield
Stage #1: 2-bromo-5-chloroanisole With n-butyllithium In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor;	98%
Stage #1: 2-bromo-5-chloroanisole With n-butyllithium In tetrahydrofuran at -78℃; for 0.666667h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	73%
Stage #1: 2-bromo-5-chloroanisole With n-butyllithium In tetrahydrofuran at -80℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃;	70%
Stage #1: 2-bromo-5-chloroanisole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 24h;	50%

2-bromo-5-chloroanisole (174913-09-8) → (4-chloro-2-methoxyphenyl)boronic acid (762287-57-0)

Conditions	Yield
Stage #1: 2-bromo-5-chloroanisole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: With triisopropyl borate Stage #3: With hydrogenchloride In water; ethyl acetate

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + tert-butyl 2-(6-methylene-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-yl)acetate → tert-butyl 2-(6-(4-chloro-2-methoxybenzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-yl)acetate

Conditions	Yield
With [Rh(OH)(cod)]2 In 1,4-dioxane; water at 80℃; for 2h;	100%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 1-bromo-2,3-difluorobenzene (38573-88-5) → 4'-chloro-2,3-difluoro-2'-methoxy-1,1'-biphenyl

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃;	99%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 1,3-dibromo-2-fluorobenzene (1435-54-7) → 3-bromo-4'-chloro-2-fluoro-2'-methoxy-1,1'-biphenyl

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃;	98%
With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 78℃; for 8h; Inert atmosphere;	76%

2,3,5,6-tetrachloropyridine (2402-79-1) + (4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) → 3,5-dichloro-2,6-bis-(4-chloro-2-methoxyphenyl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane for 6h; Inert atmosphere; Reflux;	95%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 5-bromo-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine (1620515-75-4) → 5-(4-chloro-2-methoxyphenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine (1620516-01-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 18h; Inert atmosphere;	89%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) → (4-chloro-2-hydroxyphenyl)boronic acid (1238196-66-1)

Conditions	Yield
Stage #1: (4-chloro-2-methoxyphenyl)boronic acid With boron tribromide In dichloromethane at 20℃; for 1h; Stage #2: With water In dichloromethane	87%
Stage #1: (4-chloro-2-methoxyphenyl)boronic acid With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere; Stage #2: With methanol In dichloromethane at -78℃; Inert atmosphere;
With boron tribromide In dichloromethane at 0 - 20℃; for 19h;

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 2-[3-bromo-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-methyl-1-[(3-trifluoromethyl)phenyl]ethyl}-acetamide (959139-32-3) → 2-[3-(4-chloro-2-methoxyphenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[1-methyl-1-(3-trifluoromethyl-phenyl)ethyl]-acetamide (959132-85-5)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 90℃; for 5h; Inert atmosphere;	83%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 4-bromo-3-(4-hydroxyphenyl)thiophene-2-carbaldehyde (1312098-71-7) → 4-bromo-3-(4-hydroxyphenyl)thiophene-2-carbaldehyde (1353572-40-3)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃;	79%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + C19H15ClN2O2 (1565836-98-7) → 1-(2-(5-chloro-2-methoxyphenyl)-4-methyl-6-(3-phenoxyphenyl)pyrimidin-5-yl)ethanone

Conditions	Yield
Stage #1: (4-chloro-2-methoxyphenyl)boronic acid; C19H15ClN2O2 In 1,4-dioxane at 20℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Stage #2: With palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane at 20 - 110℃; for 3.5h; Suzuki-Miyaura Coupling; Inert atmosphere;	78%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + tert-butyl 2-(6-chloropyridazin-3-yl)-2,7-diazaspiro[4.5]decane-7-carboxylate → tert-butyl 2-(6-(4-chloro-2-methoxyphenyl)pyridazin-3-yl)-2,7-diazaspiro[4.5]decane-7-carboxlate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 1h; Suzuki Coupling; Microwave irradiation; Inert atmosphere;	78%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + (3aR,6aS)-tert-butyl 5-(6-chloropyridazin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (1173179-68-4) → tert-butyl 5-(6-(4-chloro-2-methoxyphenyl)pyridazin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 90℃; Suzuki Coupling; Inert atmosphere;	77%

4-chloropyridine N-oxide (1121-76-2) + (4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) → 4-(4-chloro-2-methoxyphenyl)pyridine 1-oxide (1173157-19-1)

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide at 120℃; for 3h;	74%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 2-bromo-1-chlorobenzene (694-80-4) → 6-chloro-2'-chlorobiphenyl-2-yl methyl ether (852118-14-0)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 82℃; Suzuki Coupling;	73%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 1-chloro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide 2,2,2-trifluoroacetate → 1-(4-chloro-2-methoxyphenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 0.5h; Inert atmosphere; Microwave irradiation;	71%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 1-iodo-4-bromo-naphthalene (63279-58-3) → C17H12BrClO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h;	70%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + C20H14Br2 → C27H20BrClO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 70℃; for 5h;	64%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 1,4-dibromonaphthalene (83-53-4) → C17H12BrClO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 70℃; for 5h;	64%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 5-bromo-2-iodo-benzoic acid methyl ester (181765-86-6) → C15H12BrClO3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 100℃; for 12h;	64%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (1265397-22-5) → methyl 2-(4-(4-chloro-2-methoxyphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (1265399-69-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 2.5h; Sealed tube;	60%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-4-(4-chloro-2-methoxyphenyl)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile (1373210-81-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; sodium hydrogencarbonate In ethanol; water at 80℃; for 18h; Inert atmosphere;	60%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 6-chloro-N-cyclopropyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine → 6-(4-chloro-2-methoxyphenyl)-N-cyclopropyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 105℃; for 8h; Inert atmosphere;	53%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 3,3,3-trifluoro-1-phenylpropan-1-one (709-21-7) → (Z)-3-(4-chloro-2-methoxyphenyl)-3-fluoro-1-phenylprop-2-en-1-one

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In toluene at 110℃; for 10h; Schlenk technique; Inert atmosphere;	49%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 3-bromo-7-methoxy-4-methylcoumarin (75908-67-7) → C18H15ClO4

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium carbonate In tetrahydrofuran; water at 95℃; Inert atmosphere;	48%
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium carbonate In tetrahydrofuran; water at 95℃; Inert atmosphere;	48%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 4-(Bromomethyl)-2,5-difluoro-N-(methylsulfonyl)benzamide (1355070-71-1) → 4-(4-Chloro-2-methoxybenzyl)-2,5-difluoro-N-(methylsulfonyl)benzamide (1354960-49-8)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 6h; Inert atmosphere; Reflux;	36%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + 5-bromo-N-(1,3,4-thiadiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (1454667-90-3) + (3,4-difluorophenyl)boronic acid (168267-41-2) → 5-(3',4'-difluoro-3-methoxy-[1,1'-biphenyl]-4-yl)-N-(1,3,4-thiadiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (1454666-86-4)

Conditions

Yield

Stage #1: (4-chloro-2-methoxyphenyl)boronic acid; 5-bromo-N-(1,3,4-thiadiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide With potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In 1,4-dioxane; water at 150℃; for 0.5h; Microwave irradiation; Stage #2: (3,4-difluorophenyl)boronic acid In 1,4-dioxane; water at 150℃; for 0.5h; Microwave irradiation; Stage #3: With hydrogenchloride In 1,4-dioxane for 0.166667h;

35%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + (1R,3S,5S)-tert-butyl 3-((6-chloropyridazin-3-yl)(methyl)amino)-8-azabicyclo[3.2.1]octane-8-carboxylate → tert-butyl (1R,3s,5S)-3-((6-(4-chloro-2-methoxyphenyl)pyridazin-3-yl)(methyl)amino)-8-azabicyclo[3.2.1]octane-8-carboxylate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 105℃; for 6h; Inert atmosphere;	34%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + C11H10BrN5S → N-[7-(4-chloro-2-methoxyphenyl)-6-methylthieno[3,2-d]pyrimidinyl-2-yl]-1-methyl-1H-pyrazol-4-amine

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 90℃; for 1h; Inert atmosphere; Microwave irradiation;	23%

(4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) + (P)-1-(4-bromo-5-fluoro-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide → (P)-1-(4'-chloro-2-fluoro-2',5-dimethoxy-4-biphenylyl)-N-3-isoxazolyl-2-oxo-1,2-dihydro-6-quinolinesulfonamide

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 50℃; for 4h; Inert atmosphere;	12.35%

(4-bromo-2-chlorophenyl)(pyrrolidin-1-yl)methanone (877383-54-5) + (4-chloro-2-methoxyphenyl)boronic acid (762287-57-0) → 1-[(3,5'-dichloro-2'-methoxy-[1,1'-biphenyl]-4-yl)carbonyl]-pyrrolidine (877383-55-6)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 16h; Heating / reflux;

Upstream product

• 174913-09-8 2-bromo-5-chloroanisole 
• 121-43-7 Trimethyl borate 

Downstream Products

• 1173157-19-1 4-(4-chloro-2-methoxyphenyl)pyridine 1-oxide 
• 1448857-84-8 5-(4-chloro-2-methoxyphenyl)-2-(hex-5-en-1-yloxy)-1-methyl-1H-imidazole 
• 1238196-66-1 (4-chloro-2-hydroxyphenyl)boronic acid 
• 959132-85-5 2-[3-(4-chloro-2-methoxyphenyl)-4-(2-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[1-methyl-1-(3-trifluoromethyl-phenyl)ethyl]-acetamide 
• 374593-17-6 1,2-bis(4-chloro-2-methoxyphenyl)disulfane 

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