| Identification | More | [Name]
4-Aminophenylboronic acid pinacol ester | [CAS]
214360-73-3 | [Synonyms]
2-(4-AMINOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-Y)ANILINE
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ANILINE
4-AMINOBENZENEBORONIC ACID PINACOL ESTER
4-AMINOPHENYLBORONIC ACID PINACOLATE
4-AMINOPHENYLBORONIC ACID PINACOL CYCLIC ESTER
4-AMINOPHENYLBORONIC ACID PINACOL ESTER
(4-AMINOPHENYL)BORONIC ACID, PINACOL ESTER, HCL
(4-AMINOPHENYL)BORONIC ACID PINACOL ESTER HYDROCHLORIDE
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENAMINE
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline,min.97%
4-METHYLPHENYLBORONIC ACID PINACOLATE
4-AMINOBENZENEBORONIC ACID PINACOL ESTE
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ANILINE, MIN. 97%
4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)aniline
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 4-Aminophenylboronic acid, pinacol cyclic ester | [EINECS(EC#)]
629-061-7 | [Molecular Formula]
C12H20BNO3 | [MDL Number]
MFCD02258965 | [Molecular Weight]
237.1 | [MOL File]
214360-73-3.mol |
| Questions And Answer | Back Directory | [Synthesis]
Potassium acetate (1.71 g, 17.4 mmol) was added to a solution of 4-bromoaniline (1.0 g, 5.8 mmol) and bis(pinacol)diboron (1.78 g, 7.0 mmol) in dioxane (15.0 mL). The reaction mixture was degassed with nitrogen for 30.0 min, and PdCl2(dppf) (0.21 g, 0.3 mmol) was added. The reaction was stirred at 100 °C for 6 h. The reaction progress was monitored by TLC. After the reaction was complete, dioxane was removed from the reaction mixture by evaporation, the residue was quenched with water, and the compound was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to obtain a crude compound, which was then purified by Combi-flash™ column chromatography (4.0 g column) eluting with 20% ethyl acetate in hexane to give 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.65 g, 50.78%) as a pale yellow solid. MS: 220.20 [M+1]. |
| Chemical Properties | Back Directory | [Appearance]
almost white to light beige crystalline powder | [Melting point ]
165-169 °C (lit.) | [Boiling point ]
340.0±25.0 °C(Predicted) | [density ]
1.05±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [solubility ]
Chloroform | [form ]
Crystalline Powder | [pka]
4.24±0.10(Predicted) | [color ]
Almost white to light beige | [Water Solubility ]
Insoluble | [InChI]
InChI=1S/C12H18BNO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,14H2,1-4H3 | [InChIKey]
ZANPJXNYBVVNSD-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1 | [CAS DataBase Reference]
214360-73-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
No | [HazardClass ]
IRRITANT | [HS Code ]
29349900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Triethylamine-->1,4-Dioxane-->Palladium (II) Acetate-->4-Bromoaniline-->(Oxydi-2,1-phenylene)bis(diphenylphosphine)-->Pinacolborane | [Preparation Products]
4-Aminophenylboronic acid-->4-(N-Methylamino)phenylboronic acid, pinacol ester-->4'-(4-Aminophenyl)-2,2':6',2''-terpyridine-->4-Trifluoromethylphenylboronic acid, pinacol ester-->4-(Methylsulfonylamino)phenylboronic acid-->4,4''-Diamino-p-terphenyl-->3,3-difluoro-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one-->2,3,6,7,10,11-hexa(4'-aminophenyl) trimethylene-->4-(Phenoxycarbonylamino)benzeneboronic acid pinacol ester, 95%-->1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-2-one |
| Hazard Information | Back Directory | [Description]
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline is an important organic reagent with an appearance ranging from white to yellow to orange powder to crystal. This compound can be used as a chemical reaction reagent or for preparing fluorescent probes. | [Chemical Properties]
almost white to light beige crystalline powder | [Uses]
4-Aminophenylboronic acid pinacol ester can be used as a reagent for:
- The preparation of substituted 3-phenyl-4H-1-benzopyran-4-ones by reacting with iodochromones via Pd catalyzed Suzuki-Miyaura cross-coupling reaction.
- Mercury(II) detection by fluorometry with new fluorogenic indicators based on through-bond energy transfer from pentaquinone to rhodamine.
- Rhodium-catalyzed amination reactions.
- Palladium-catalyzed Suzuki cross-coupling to synthesize potential antitubercular and antimicrobial compounds.
It can also be used to prepare:
- Hexaphenylbenzene derivatives as a potential bioprobe and multichannel keypad system.
- Pyromellitic diimide-based polymer as matrix for solution-processable n-channel field-effect transistors.
- Alternating copolymers of oligoarylenes and naphthalene bisimides as low band-gap semiconductors with electrochemical and spectroelectrochemical behavior.
- γ-secretase modulators in the treatment of amyloid β formation.
| [Uses]
suzuki reaction |
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 97%(214360-73-3) | [Sigma Aldrich]
214360-73-3(sigmaaldrich) | [TCI AMERICA]
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline,>98.0%(GC)(214360-73-3) |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Jia Xing Isenchem Co.,Ltd
|
| Telephone: |
0573-85285100 18627885956 |
| Website: |
https://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm |
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