| Identification | More | [Name]
4-(Dimethylamino)phenylboronic acid | [CAS]
28611-39-4 | [Synonyms]
4-(DIMETHYLAMINO)PHENYLBORONIC ACID
4-DIMETHYLAMINOPHENYLBORONIC ACID HCL
4-(N,N-DIMETHYLAMINO)BENZENEBORONIC ACID
4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID
AKOS BRN-0094
RARECHEM AH PB 0156
4-DIMENTHYLAMINOPHENYLBORONIC ACID
4-Dimethylaminophenylboronicacidhydrochloride
4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID 97%
4-(Dimethylamino)benzeneboronic acid | [Molecular Formula]
C8H12BNO2 | [MDL Number]
MFCD04112547 | [Molecular Weight]
165 | [MOL File]
28611-39-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to green-grey or blue-grey crystalline | [Melting point ]
227 °C(lit.)
| [Boiling point ]
329.9±44.0 °C(Predicted) | [density ]
1.12±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [form ]
Crystalline Powder | [pka]
8.78±0.10(Predicted) | [color ]
White to green-gray or blue-gray | [Water Solubility ]
Sparingly soluble in water. (~2.5%) | [InChI]
InChI=1S/C8H12BNO2/c1-10(2)8-5-3-7(4-6-8)9(11)12/h3-6,11-12H,1-2H3 | [InChIKey]
RIIPFHVHLXPMHQ-UHFFFAOYSA-N | [SMILES]
B(C1=CC=C(N(C)C)C=C1)(O)O | [CAS DataBase Reference]
28611-39-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [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 | [HazardClass ]
IRRITANT, AIR SENSITIVE, KEEP COLD | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to green-grey or blue-grey crystalline | [Uses]
4-(Dimethylamino)phenylboronic Acid can be used as reactant/reagent in preparation of biaryls via palladium-catalyzed Suzuki-Miyaura coupling of nitroarenes with boronic acids. | [Uses]
suzuki reaction | [Synthesis]
Under argon protection, 20 g (100 mmol) of 4-bromo-N,N-dimethylaniline was dissolved in 400 mL of anhydrous tetrahydrofuran and the mixture was cooled to -40°C. The reaction was carried out with the aid of a liquid solution of 1.6 M n-butyllithium in hexane. Subsequently, 63 mL (100 mmol) of a hexane solution of 1.6 M n-butyllithium was slowly added dropwise, stirring was maintained and the reaction mixture was gradually warmed to 0 °C for 1 hour. The reaction mixture was again cooled to -78 °C and 50 mL of anhydrous tetrahydrofuran was added. A solution containing 26 g (250 mmol) of trimethyl borate was added dropwise, followed by raising the reaction mixture to room temperature and stirring for 5 hours. After completion of the reaction, 200 mL of 1 N hydrochloric acid solution was added and stirred for 1 h. The aqueous layer was separated and discarded. The organic layer was dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. The resulting solid was washed with toluene to afford 12.38 g (75 mmol) of the target product 4-(N,N-dimethylamino)phenylboronic acid in 75% yield. | [References]
[1] Patent: CN108276337, 2018, A. Location in patent: Paragraph 0057; 0058; 0059 |
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