| Identification | More | [Name]
4-Nitrophenylboronic acid pinacol ester | [CAS]
171364-83-3 | [Synonyms]
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)NITROBENZENE
4-NITROPHENYLBORONIC ACID PINACOL ESTER
4-Nitrobenzeneboronic acid, pinacol ester | [Molecular Formula]
C12H18BNO5 | [MDL Number]
MFCD02179437 | [Molecular Weight]
267.09 | [MOL File]
171364-83-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
112-116 °C (lit.) | [Boiling point ]
357.5±25.0 °C(Predicted) | [density ]
1.14±0.1 g/cm3(Predicted) | [storage temp. ]
Store Cold | [form ]
powder or crystals | [color ]
White to Orange to Green | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C12H16BNO4/c1-11(2)12(3,4)18-13(17-11)9-5-7-10(8-6-9)14(15)16/h5-8H,1-4H3 | [InChIKey]
LUWACRUAJXZANC-UHFFFAOYSA-N | [SMILES]
O1C(C)(C)C(C)(C)OB1C1=CC=C([N+]([O-])=O)C=C1 | [CAS DataBase Reference]
171364-83-3(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 . | [WGK Germany ]
2
| [Hazard Note ]
Harmful/Store Cold | [HazardClass ]
IRRITANT | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
Reactant involved in: • ;Synthesis of aryl azides 1• ;Arylation of allylic chlorides2• ;Syntehsis of RNA conjugates3• ;Alkoxycarbonylation4• ;Synthesis of mTOR and PI3K inhibitors as antitumor agents5• ;Electrooxidative synthesis of biaryls6 | [Uses]
suzuki reaction | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 60, p. 7508, 1995 DOI: 10.1021/jo00128a024 | [Synthesis]
GENERAL PROCEDURE: 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 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 reaction mixture was stirred at 0-5 °C for 30 min, followed by the addition of a methanol (1.0 mL) solution of pinacol ester of bisboronic acid (2,381 mg, 1.5 mmol, 3.0 equiv). Stirring was continued for 60 minutes. Upon completion of the reaction, water (10 mL) was added to the mixture, which was then extracted with dichloromethane (50 mL, 3 times). The organic layers were combined and washed with saturated sodium bicarbonate solution followed by drying with anhydrous sodium sulfate. After drying, the solvent was evaporated and the crude product was purified by fast chromatography. | [References]
[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[4] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1551 - 1554
[5] Synlett, 2012, vol. 23, # 9, p. 1394 - 1396 |
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