[4-(Morpholinomethyl)phenyl]boronic acid supplier

Name
4-(Morpholinomethyl)phenylboronic acid
EINECS
CAS No. 279262-23-6
Article Data10
CAS DataBase
Density 1.208 g/cm³
Solubility
Melting Point 85 °C
Formula C₁₁H₁₆BNO₃
Boiling Point 382.268 °C at 760 mmHg
Molecular Weight 221.064
Flash Point 184.989 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Boronicacid, [4-(4-morpholinylmethyl)phenyl]- (9CI);[4-(Morpholinomethyl)phenyl]boronic acid;boronic acid, B-[4-(4-morpholinylmethyl)phenyl]-;
PSA 52.93000
LogP -0.86350

Synthetic route

: 110-91-8
morpholine

: 68162-47-0
4-bromomethylphenylboronic acid

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

Conditions

Conditions	Yield
Stage #1: 4-bromomethylphenylboronic acid With N,N-diethanolaminomethyl polystyrene In dichloromethane at 20℃; for 1.66667h; Stage #2: morpholine In 1-methyl-pyrrolidin-2-one at 20℃; for 5h; Stage #3: In tetrahydrofuran; water at 20℃; Further stages.;	88%
In tetrahydrofuran for 2h; Heating / reflux;
With potassium carbonate In acetonitrile at 10 - 35℃; for 60h;	449 mg

: C11H14BF3NO(1-)*K(1+)

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

Conditions

Conditions	Yield
With water; silica gel In ethyl acetate at 20℃; for 3h;	87%

: 1072960-75-8
(OC4H8NCH2C6H4)BN(CH3)(CH2CO2)2

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

Conditions

Conditions	Yield
With sodium hydroxide; water In tetrahydrofuran at 23℃; for 0.166667h; Inert atmosphere;	76%

: (2R)-4-(6-bromo-1-oxoisoquinolin2(1H)-yl)-2-methyl-2-(methylsulfonyl)-N-((tetrahydro-2H-pyran-2-yl)oxy)butanamide

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: (2R)-2-methyl-2-(methylsulfonyl)-4-(6-(4-(morpholinomethyl)phenyl)-1-oxoisoquinolin-2(1H)-yl)-N-((tetrahydro-2H-pyran-2-yl)oxy)butanamide

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Sealed tube; Microwave irradiation;	96%

: C25H30BrN3O4

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 6-(4-morpholin-4-ylmethylphenyl)-4-(tetrahydropyran-4-yl)-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolin-4-ylmethyl)amide

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	89%

: 6-bromo-3-iodo-2-(naphthalen-1-ylmethoxy)quinoline

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 6-bromo-3-(4-(morpholinomethyl)phenyl)-2-(naphthalen-1-ylmethoxy)quinoline

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; Suzuki-Miyaura Coupling;	86.8%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 10h;	76.15%

: (R)-ethyl 4-(7-bromo-4-oxoquinazolin-3(4H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: (R)-ethyl 2-methyl-2-(methylsulfonyl)-4-(7-(4-(morpholinomethyl)phenyl)-4-oxoquinazolin-3(4H)-yl)butanoate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate at 110℃; for 0.5h; Microwave irradiation;	86%

: 5-bromo-3-(ethyl (tetrahydro-2H-pyran-4-yl)amino)-2-methyl-N-((1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolin-4-yl)methyl)benzamide

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4-methyl-N-((1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolin-4-yl)methyl)-4'-(morpholinomethyl)-[1,1'-biphenyl]-3-carboxamide

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 4h; Suzuki Coupling; Inert atmosphere;	85%

: 889939-26-8
4-bromo-2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 942920-82-3
4-bromo-2-[4-(N-morpholinylmethyl)phenyl]-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 100℃; for 16h; Suzuki coupling; Inert atmosphere;	84%

: (R)-ethyl 4-(7-bromo-8-methyl-4-oxoquinazolin-3(4H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: (R)-ethyl 2-methyl-4-(8-methyl-7-(4-(morpholinomethyl)phenyl)-4-oxoquinazolin-3(4H)-yl)-2-(methylsulfonyl)butanoate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 110℃; for 0.5h; Inert atmosphere;	82%

: (R)-3-bromo-6-((4-hydroxy-1-(4,4,4-trifluoro-3-phenylbutanoyl)piperidin-4-yl)methyl)-2-methyl-2H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: (R)-6-((4-hydroxy-1-(4,4,4-trifluoro-3-phenylbutanoyl)piperidin-4-yl)methyl)-2-methyl-3-(4-(morpholinomethyl)phenyl)-2H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 130℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Sealed tube; Microwave irradiation;	82%

: 143468-13-7
6-Bromo-1H-pyrrolo<2,3-b>pyridine

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 1542067-50-4
4-[[4-(1H-pyrrolo[2,3-b]pyridin-6-yl)phenyl]methyl]morpholine

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 110℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere;	81%

: C17H24BrO4P

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: (Z)-2-(1-phenyl-1-(4-(1-morpholinomethyl)phenyl)hexen-2-yloxy)-5,5-dimethyldioxaphosphorane

Conditions

Conditions	Yield
With potassium phosphate; palladium diacetate; ruphos In water; toluene at 50℃; for 20h; Suzuki Coupling; Inert atmosphere;	81%

: 53939-30-3
5-bromo-2-chloropyridine

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 4-(4-(6-chloropyridin-3-yl)benzyl)morpholine

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 4h; Inert atmosphere;	80.22%

: C22H26BrN3O3

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 4-cyclopentyl-6-(4-morpholin-4-ylmethylphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-ylmethyl)amide

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	79%

: 87864-14-0
2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide)

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: N-[2-(diethylamino)ethyl]-2-{4-[(morpholin-4-yl)methyl]phenyl}quinoline-4-carboxamide

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 140℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation;	77%

: C23H28BrN3O4

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: C34H42N4O5

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	77%

: C24H24BrN3O3

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 4-benzyl-6-(4-morpholin-4-ylmethylphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-ylmethyl)amide

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	76%

: ethyl 4-iodo-5-(5-isopropyl-2,4-dimethoxyphenyl)isoxazole-3-carboxylate

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: ethyl 5-(5-isopropyl-2,4-dimethoxyphenyl)-4-(4-(morpholinomethyl)phenyl)isoxazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: ethyl 4-iodo-5-(5-isopropyl-2,4-dimethoxyphenyl)isoxazole-3-carboxylate; [4-(morpholin-4-ylmethyl)phenyl]boronic acid With sodium hydrogencarbonate In water; N,N-dimethyl-formamide for 0.166667h; Suzuki Coupling; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In water; N,N-dimethyl-formamide at 90℃; for 8h; Suzuki Coupling; Inert atmosphere;	76%

: C27H28BrN3O3

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 4-benzyl-6-(4-morpholin-4-ylmethylphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolin-4-ylmethyl)amide

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	75%

: C26H32BrN3O4

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: C37H46N4O5

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	74%

: 7-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxamide

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2,2-dimethyl-7-(4-(morpholinomethyl)phenyl)-2,3-dihydrobenzofuran-5-carboxamide

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere; Sealed tube;	73%

: C16H22F2NO(1+)*CF3O3S(1-)

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: C21H23F2NO2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); copper(I) bromide dimethylsulfide complex; caesium carbonate; tris(para-trifluoromethyl)phenyl phosphine In 1,4-dioxane at 80℃; Molecular sieve; regioselective reaction;	72%

: C25H30BrN3O3

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 4-cyclopentyl-6-(4-morpholin-4-ylmethylphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolin-4-ylmethyl)amide

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	70%

: 1403258-28-5
tert-butyl ((1R,4R)-4-((5-bromo-3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-2-methylphenyl)(ethyl)amino)cyclohexyl)carbamate

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 1403258-30-9
tert-butyl ((1R,4R)-4-((5-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)-methyl)-carbamoyl)-4-methyl-4'-(morpholinomethyl)-[1,1'-biphenyl]-3-yl)-(ethyl)-amino)-cyclohexyl)-carbamate

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 3.5h; Suzuki Coupling; Inert atmosphere;	67.48%

: C20H24BrN3O3

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 4-isopropyl-6-(4-morpholin-4-ylmethylphenyl)-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-ylmethyl)amide

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Suzuki Coupling; Inert atmosphere;	66%

: 1403258-61-6
5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl-d5 (tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 1403256-15-4
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-(ethyl-d5(tetrahydro-2H-pyran-4-yl)amino)-4'-formyl-4-methyl-[1,1'-biphenyl]-3-carboxamide

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; for 4h; Suzuki Coupling; Inert atmosphere;	61%

: methyl 2-(5-iodo-4-(5-isopropyl-2,4-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)acetate

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: methyl 2-(4-(2,4-dihydroxy-5-isopropylphenyl)-5-(4-(morpholinomethyl)phenyl)-1H-1,2,3-triazol-1-yl)acetate

Conditions

Conditions	Yield
Stage #1: methyl 2-(5-iodo-4-(5-isopropyl-2,4-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)acetate; [4-(morpholin-4-ylmethyl)phenyl]boronic acid With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation; Stage #2: With boron tribromide In dichloromethane; water; N,N-dimethyl-formamide at 40℃; for 2h; Inert atmosphere;	60%

Yield

Stage #1: methyl 2-(5-iodo-4-(5-isopropyl-2,4-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)acetate; [4-(morpholin-4-ylmethyl)phenyl]boronic acid With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;
Stage #2: With boron tribromide In dichloromethane; water; N,N-dimethyl-formamide at 40℃; for 2h; Inert atmosphere;

60%

: 29241-60-9
5-bromo-2-chloro-3-methylpyridine

: 279262-23-6
4-(4-morpholin-1-ylmethyl)phenylboronic acid

: 4-(4-(6-chloro-5-methylpyridin-3-yl)benzyl)morpholine

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 4h; Inert atmosphere;	47.73%

[4-(Morpholinomethyl)phenyl]boronic acid Specification

The IUPAC name of this chemical is [4-(Morpholinomethyl)phenyl]boronic acid. With the CAS registry number 279262-23-6, it is also named as Boronic acid,B-[4-(4-morpholinylmethyl)phenyl]-. In addition, the molecular formula is C₁₁H₁₆BNO₃ and the molecular weight is 221.06. It should be stored in a cool and dry place.

Physical properties about [4-(Morpholinomethyl)phenyl]boronic acid are: (1)ACD/LogP: 0.47; (2)ACD/LogD (pH 5.5): -1 ; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 2; (6)ACD/KOC (pH 7.4): 33; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 52.93 Å²; (11)Index of Refraction: 1.57; (12)Molar Refractivity: 60.019 cm³; (13)Molar Volume: 182.961 cm³; (14)Polarizability: 23.794 ×10^-24cm³; (15)Surface Tension: 50.393 dyne/cm; (16)Density: 1.208 g/cm³; (17)Flash Point: 184.989 °C; (18)Enthalpy of Vaporization: 66.523 kJ/mol; (19)Boiling Point: 382.268 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: OB(O)c1ccc(cc1)CN2CCOCC2
(2)InChI: InChI=1/C11H16BNO3/c14-12(15)11-3-1-10(2-4-11)9-13-5-7-16-8-6-13/h1-4,14-15H,5-9H2
(3)InChIKey: QPFDUULIDNELSE-UHFFFAOYAQ

Product Name

4-(Morpholinomethyl)phenylboronic acid

Synthetic route

[4-(Morpholinomethyl)phenyl]boronic acid Specification

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