| Identification | More | [Name]
4-Nitrophenylboronic acid | [CAS]
24067-17-2 | [Synonyms]
4-NITROBENZENEBORONIC ACID
4-NITROPHENYLBORONIC ACID
P-NITROPHENYLBORONIC ACID
RARECHEM AH PB 0141
4-Nitrophenylboronic Acid (contains varying amounts of Anhydride) | [EINECS(EC#)]
627-647-7 | [Molecular Formula]
C6H6BNO4 | [MDL Number]
MFCD00161360 | [Molecular Weight]
166.93 | [MOL File]
24067-17-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
285-290°C (dec.) | [Boiling point ]
373.7±44.0 °C(Predicted) | [density ]
1.40±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMF: 15 mg/ml; DMSO: 15 mg/ml; Ethanol: 15 mg/ml; Ethanol:PBS (pH 7.2) (1:5): 0.16 mg/ml | [form ]
Crystalline Powder | [pka]
7.04±0.10(Predicted) | [color ]
White to yellow | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C6H6BNO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,9-10H | [InChIKey]
NSFJAFZHYOAMHL-UHFFFAOYSA-N | [SMILES]
B(C1=CC=C([N+]([O-])=O)C=C1)(O)O | [CAS DataBase Reference]
24067-17-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Harmful | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Description]
4-Nitrobenzeneboronic acid is an arylboronic acid building block that has been used in the synthesis of phenols.1,2 | [Chemical Properties]
White to brown powder or crystal | [Uses]
4-Nitrophenylboronic Acid is a useful synthetic intermediate. It is a reagent used for ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines and Diels-Alder or C-H activation reactions. | [Uses]
suzuki reaction | [Synthesis]
GENERAL METHOD: To a solution of 4-nitroaniline (0.5 mmol, 1.0 eq.) in methanol (1.0 mL) was added hydrochloric acid (0.5 mL, 1.5 mmol, 3.0 eq.) followed by water (0.5 mL). The reaction mixture was stirred for 2 minutes and then sodium nitrite solution (0.25 mL) was added. Sodium nitrite solution was prepared by dissolving 35 mg of sodium nitrite in water (0.25 mL). The mixture was stirred at 0-5 °C for 30 min, followed by the addition of hydrochloric acid (135 mg, 1.5 mmol, 3.0 equiv) in methanol (1.0 mL). Stirring of the reaction mixture was continued for 60 min. Upon completion of the reaction, it was diluted with the addition of water (10 mL) and extracted with dichloromethane (50 mL, 3 times). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4-nitrophenylboronic acid. | [References]
[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
[2] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612 |
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