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4-(tert-Butoxycarbonyl)phenylboronic acid

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Name

4-(tert-Butoxycarbonyl)phenylboronic acid

EINECS N/A
CAS No. 850568-54-6 Density 1.15 g/cm3
PSA 66.76000 LogP 0.32170
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 N/A Appearance N/A
Safety 26-36/37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 850568-54-6 (4-(TERT-BUTOXYCARBONYL)PHENYLBORONIC ACID) Hazard Symbols Xi
Synonyms

Benzoicacid, 4-borono-, 1-(1,1-dimethylethyl) ester (9CI);4-(tert-Butoxycarbonyl)benzeneboronic acid;

Article Data 2

4-(tert-Butoxycarbonyl)phenylboronic acid 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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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

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