4-(tert-Butoxycarbonyl)phenylboronic acid supplier

Name
4-(TERT-BUTOXYCARBONYL)PHENYLBORONIC ACID
EINECS
CAS No. 850568-54-6
Article Data2
CAS DataBase
Density 1.15 g/cm³
Solubility Slightly soluble in water.
Melting Point 100-106 ºC
Formula C₁₁H₁₅BO₄
Boiling Point 364.3 ºC at 760 mmHg
Molecular Weight 222.049
Flash Point 174.1 ºC
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Benzoicacid, 4-borono-, 1-(1,1-dimethylethyl) ester (9CI);4-(tert-Butoxycarbonyl)benzeneboronic acid;
PSA 66.76000
LogP 0.32170

Synthetic route

: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl ester

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

Conditions

Conditions	Yield
With sodium periodate; ammonium acetate In water; acetone at 20℃; for 12h;	83%

: 14047-29-1
4-carboxyphenylboronic acid

: 115-11-7
isobutene

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

Conditions

Conditions	Yield
With sulfuric acid In dichloromethane at 20℃; for 24h;

: 586-75-4
4-chlorobenzoyl chloride

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether / 1 h / 0 °C 2: potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 36 h / 100 °C / Inert atmosphere 3: ammonium acetate; sodium periodate / acetone; water / 12 h / 20 °C View Scheme

: 59247-47-1
tert-butyl-4-bromobenzoate

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 36 h / 100 °C / Inert atmosphere 2: ammonium acetate; sodium periodate / acetone; water / 12 h / 20 °C View Scheme

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 882029-80-3
p-toluenesulfonic acid 3,5-dibromo(pyridin-2-yl) ester

: di-tert-butyl 4,4’-[2-(tosyloxy)pyridine-3,5-diyl]dibenzoate

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; di(1-adamantyl)benzylphosphine In toluene at 50℃; for 0.833333h; Suzuki-Miyaura Coupling; Inert atmosphere; chemoselective reaction;	99%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 4,6-dibromo-2-tosyloxypyridine

: di-tert-butyl 4,4’-[6-(tosyloxy)pyridine-2,4-diyl] dibenzoate

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; di(1-adamantyl)benzylphosphine In toluene at 50℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; chemoselective reaction;	99%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 5-bromo-2-(4-methylphenylsulfonyloxy)pyridine

: tert-butyl 4-[6-(tosyloxy)pyridin-3-yl]benzoate

Conditions

Conditions	Yield
With palladium diacetate; C27H37P*H3P; potassium carbonate In water; toluene at 25℃; for 1.5h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; chemoselective reaction;	99%
With palladium diacetate; potassium carbonate; di(1-adamantyl)benzylphosphine In water; toluene Suzuki-Miyaura Coupling; Inert atmosphere; regioselective reaction;	99%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 4-bromopyridin-2-yl 4-methylbenzenesulfonate

: tert-butyl 4-(2-(tosyloxy)pyridin-4-yl)benzoate

Conditions

Conditions	Yield
With palladium diacetate; C27H37P*H3P; potassium carbonate In water; toluene at 25℃; for 3.5h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; chemoselective reaction;	97%
With palladium diacetate; potassium carbonate In water; toluene for 3.5h; Suzuki-Miyaura Coupling; Inert atmosphere; regioselective reaction;	97%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 199850-56-1
methyl 2-amino-4-chloro-5-iodobenzoate

: C19H20ClNO4

Conditions

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In water; acetonitrile for 48h; Suzuki Coupling; Inert atmosphere; Reflux;	96%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 1180009-36-2
1-acetyl-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

: 1180009-48-6
tert-butyl 4-(1-acetyl-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)benzoate

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In ethanol; water; toluene at 120℃; for 0.166667h; Suzuki cross-coupling; Inert atmosphere; Microwave irradiation;	95%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 174680-55-8
2-amino-5-bromo-3-phenylmethylpyrazine

: tert-butyl 4-(5-amino-6-benzylpyrazin-2-yl)benzoate

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane at 75℃; for 0.5h;	92%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 104-92-7
1-bromo-4-methoxy-benzene

: 944385-73-3
4-tert-butoxycarbonyl-4'-methoxy-1,1'-biphenyl

Conditions

Conditions	Yield
With palladium diacetate In ethanol at 20℃; for 0.25h; Suzuki-Miyaura Coupling;	92%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 109-83-1
(2-hydroxyethyl)(methyl)amine

: 131543-46-9
Glyoxal

: tert-butyl 4-(2-hydroxy-4-methylmorpholin-3-yl)benzoate

Conditions

Conditions	Yield
Stage #1: (4-(tert-butoxycarbonyl)phenyl)boronic acid; (2-hydroxyethyl)(methyl)amine In ethanol; water at 60℃; for 0.25h; Petasis Reaction; Inert atmosphere; Stage #2: Glyoxal In ethanol; water at 60℃; for 24h; Petasis Reaction; Inert atmosphere;	92%

...Expand

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 5-phenylpyridin-2-yl 4-methylbenzenesulfonate

: tert-butyl 4-(5-phenylpyridin-2-yl)benzoate

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In water; toluene at 100℃; for 1h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; Schlenk technique;	92%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 3-bromopyridin-2-yl trifluoromethanesulfonate

: tert-butyl 4-[2-[[(trifluoromethyl)sulfonyl]oxy]pyridin-3-yl]-benzoate

Conditions

Conditions	Yield
With palladium diacetate; C27H37P*H3P; potassium carbonate In water; toluene at 25℃; for 4h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; chemoselective reaction;	90%
With palladium diacetate; potassium carbonate In water; toluene for 2h; Suzuki-Miyaura Coupling; Inert atmosphere; regioselective reaction;	90%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 1072-97-5
5-bromo-2-pyridylamine

: tert-butyl 4-(6-aminopyridin-3-yl)benzoate

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 80℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere;	89%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 6-((2-chloro-6-fluorophenoxy)methyl)-3-iodo-1-((3-(trifluoromethyl)phenyl)sulfonyl)-1H-indole

: tert-butyl 4-(6-((2-chloro-6-fluorophenoxy)methyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)-1H-indol-3-yl)benzoate

Conditions

Conditions	Yield
With triphenylphosphine; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) In 1,2-dimethoxyethane at 90℃; Inert atmosphere; Sealed tube;	89%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 1609694-04-3
12-chloro-6-phenyl-5,6,7,12-tetrahydrodibenzo[c,f ][1,5]azastibocine

: tert-butyl 4-(6-phenyl-6,7-dihydrodibenzo[c,f][1,5]azastibocin-12(5H)-yl)benzoate

Conditions

Conditions	Yield
With water; nickel diacetate; sodium carbonate In toluene at 100℃; for 20h; Inert atmosphere; Schlenk technique;	89%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 7752-82-1
5-bromo-2-aminopyrimidine

: 1029715-16-9
tert-butyl 4-(2-aminopyrimidin-5-yl)benzoate

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 120℃; for 3h;	86.6%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

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

: tert-butyl (R)-4-(6-((4-hydroxy-1-(3-phenylbutanoyl)piperidin-4-yl)methyl)-2-methyl-7-oxo-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-3-yl)benzoate

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 120℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation; Sealed tube;	85%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 636-98-6
p-nitrobenzene iodide

: 914659-71-5
4-(4-nitrophenyl)-benzoic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 12h; Suzuki coupling; Heating;	84%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 1350915-26-2
((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-9-(trifluoromethylsulfonyloxy)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-3a-yl)methyl benzoate

: 1392113-09-5
tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(benzoyloxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Conditions

Conditions	Yield
With sodium carbonate monohydrate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water; isopropyl alcohol for 3.5h; Suzuki Coupling; Inert atmosphere;	83%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 1414578-42-9
5-amino-4-methyl-1-phenyl-1H-pyrazol-3-yl trifluoromethane sulfonate

: C21H23N3O2

Conditions

Conditions	Yield
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In 1,4-dioxane at 90℃; for 6h;	83%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 62067-29-2
5-bromo-tetrandrine

: 5-(4-t-butyloxycarbonylphenyl)tetrandrine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In water; toluene for 24h; Suzuki-Miyaura Coupling; Reflux;	81%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 131543-46-9
Glyoxal

: 104-15-4
toluene-4-sulfonic acid

: 104-63-2
N-Benzylethanolamine

: tert-butyl 4-(4-benzyl-2-hydroxymorpholin-3-yl)benzoate 4-toluenesulfonate

Conditions

Conditions	Yield
Stage #1: (4-(tert-butoxycarbonyl)phenyl)boronic acid; N-Benzylethanolamine at 115℃; for 0.333333h; Petasis Reaction; Inert atmosphere; Stage #2: Glyoxal In water at 115℃; for 1h; Petasis Reaction; Inert atmosphere; Stage #3: toluene-4-sulfonic acid In ethyl acetate at 50℃; Inert atmosphere;	81%

...Expand

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 68847-94-9
3-bromo-4H-thiochromen-4-one

: 1338224-17-1
tert-butyl 4-(4-oxo-4H-thiochromen-3-yl)benzoate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 60℃; for 72h; Suzuki-Miyaura coupling; Inert atmosphere;	80%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: (((azidosulfonyl)(methyl)amino)methyl)benzene

: C19H24N2O4S

Conditions

Conditions	Yield
With copper(l) chloride In methanol at 20℃; for 3h; Chan-Lam Coupling;	80%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 25016-01-7
5-bromo-2-methoxybenzaldehyde

: 3'-formyl-4'-methoxybiphenyl-4-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water for 4h; Suzuki Coupling; Inert atmosphere; Sealed tube; Heating;	79%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 890842-91-8
1,1-dimethylethyl 3-bromo-5-{6-[(N-{[(1,1-dimethylethyl)oxy]carbonyl}-β-alanyl)amino]-3-pyridinyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

: 890842-92-9
1,1-dimethylethyl 3-bromo-5-{6-[(N-{[(1,1-dimethylethyl)oxy]carbonyl}-β-alanyl)amino]-3-pyridinyl}-3-(4-{[(1,1-dimethylethyl)oxy]carbonyl}phenyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Conditions

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 80℃; for 1.5h; Suzuki Coupling;	78%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 1428482-15-8
2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester

: 1428482-16-9
4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4'-dicarboxylic acid 4'-tert-butyl ester 2-methyl ester

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95 - 100℃; Inert atmosphere;	78%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: Fmoc-4-bromo-L-phenylalanine

: (2S)-3-(4-{4-[(tert-butoxy)carbonyl]phenyl}phenyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid

Conditions

Conditions	Yield
With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate In tetrahydrofuran at 50℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;	78%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: 191170-76-0
benzyl N-[2-(4-bromophenyl)ethyl]carbamate

: 1146546-95-3
C27H29NO4

Conditions

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; N,N-dimethyl-formamide at 85℃; for 18.1667h;	77%

: 850568-54-6
(4-(tert-butoxycarbonyl)phenyl)boronic acid

: sodium carbonate monohydrate

: 1350915-20-6
(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-benzyl 5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-9-(((trifluoromethyl)sulfonyl)oxy)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate

: 67-63-0
isopropyl alcohol

: 1621533-75-2
(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-benzyl 9-(4-(tert-butoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine)palladium (0) In 1,4-dioxane; water	77%

...Expand

4-(tert-Butoxycarbonyl)phenylboronic acid Specification

The 4-(tert-Butoxycarbonyl)phenylboronic acid, with the CAS registry number 850568-54-6, is also known as 4-(tert-Butoxycarbonyl)benzeneboronic acid. It belongs to the product categories of Blocks; BoronicAcids; Carboxes; Benzene Series. This chemical's molecular formula is C₁₁H₁₅BO₄ and molecular weight is 222.05. What's more, its IUPAC name is called [4-[(2-Methylpropan-2-yl)oxycarbonyl]phenyl]boronic acid.

Physical properties about 4-(tert-Butoxycarbonyl)phenylboronic acid are: (1)ACD/LogP: 2.80; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.79; (4)ACD/LogD (pH 7.4): 2.7; (5)ACD/BCF (pH 5.5): 78.17; (6)ACD/BCF (pH 7.4): 63.17; (7)ACD/KOC (pH 5.5): 787.53; (8)ACD/KOC (pH 7.4): 636.43; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 44.76 Å²; (13)Index of Refraction: 1.517; (14)Molar Refractivity: 58.29 cm³; (15)Molar Volume: 192.6 cm³; (16)Surface Tension: 42.5 dyne/cm; (17)Density: 1.15 g/cm³; (18)Flash Point: 174.1 °C; (19)Enthalpy of Vaporization: 64.4 kJ/mol; (20)Boiling Point: 364.3 °C at 760 mmHg; (21)Vapour Pressure: 6.04E-06 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OC(C)(C)C)c1ccc(B(O)O)cc1
(2) InChI: InChI=1S/C11H15BO4/c1-11(2,3)16-10(13)8-4-6-9(7-5-8)12(14)15/h4-7,14-15H,1-3H3
(3) InChIKey: QMVMDYSTJSUDKC-UHFFFAOYSA-N

Product Name

4-(TERT-BUTOXYCARBONYL)PHENYLBORONIC ACID

Synthetic route

4-(tert-Butoxycarbonyl)phenylboronic acid Specification

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