| Identification | More | [Name]
4-Formylphenylboronic acid pinacol cyclic ester | [CAS]
128376-64-7 | [Synonyms]
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZALDEHYDE
4-FORMYLBENZENEBORONIC ACID, PINACOL CYCLIC ESTER
4-FORMYLPHENYLBORONIC ACID PINACOLATE
4-FORMYLPHENYLBORONIC ACID, PINACOL CYCLIC ESTER
4-FORMYLPHENYLBORONIC ACID, PINACOL ESTER
AKOS BRN-1133
4-Formylbenzeneboronic acid, pinacol ester
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)- | [Molecular Formula]
C13H17BO3 | [MDL Number]
MFCD04972375 | [Molecular Weight]
232.08 | [MOL File]
128376-64-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
55-58°C | [Boiling point ]
341.3±25.0 °C(Predicted) | [density ]
1.06±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Solid | [color ]
Off-white | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-9H,1-4H3 | [InChIKey]
DMBMXJJGPXADPO-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1 | [CAS DataBase Reference]
128376-64-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H317 | [Precautionary statements ]
P280 | [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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [TSCA ]
No | [HS Code ]
2931900090 | [Storage Class]
13 - Non Combustible Solids | [Hazard Classifications]
Skin Sens. 1 |
| Hazard Information | Back Directory | [Uses]
A boronic acid benzaldehyde compound for proteomics research. | [Synthesis]
General procedure for the synthesis of 4-formylphenylboronic acid pinacol ester from p-bromobenzaldehyde and pinacol ester of biboronic acid: to a stirred solution of p-bromobenzaldehyde (8 g, 0.15 mol), pinacol ester of biboronic acid (45.7 g, 0.18 mol), and Pd(dppf)Cl2 (5.26 g, 7.5 mmol) in 1,4-dioxane, under argon protection, was KOAc (22.0 g, 0.225 mol) was added. The reaction mixture was stirred at 80 °C for 15 min. After completion of the reaction, the solvent was removed under reduced pressure. The residue was diluted with petroleum ether (500 mL) and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by fast chromatography (silica gel, petroleum ether/ethyl acetate, 10:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxolan-2-yl)benzaldehyde (32.5 g, 95% yield) as a white solid. | [References]
[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 977 - 983
[2] Patent: WO2013/170165, 2013, A1. Location in patent: Page/Page column 93
[3] Applied Organometallic Chemistry, 2011, vol. 25, # 7, p. 537 - 541
[4] Organic Letters, 2016, vol. 18, # 20, p. 5248 - 5251
[5] Journal of the American Chemical Society, 2016, vol. 138, # 1, p. 84 - 87 |
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