| Identification | More | [Name]
4-Carboxylphenylboronic acid pinacol ester | [CAS]
180516-87-4 | [Synonyms]
[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORINAN-2-YL) BENZOIC ACID]
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID
4-CARBOXYBENZENEBORONIC ACID PINACOL CYCLIC ESTER
4-CARBOXYPHENYLBORONIC ACID PINACOLATE
4-CARBOXYPHENYLBORONIC ACID, PINACOL CYCLIC ESTER
4-CARBOXYPHENYLBORONIC ACID, PINACOL ESTER
4-CARBOXYPHENYLBORONIC ACID PINACOL ESRER
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoicacid,min.97%
4-carboxylphenylboronic acid pinacol ester
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID, MIN. 97%
4-Carboxybenzeneboronic acid pinacol ester, 97%
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid ,97% | [Molecular Formula]
C13H19BO5 | [MDL Number]
MFCD01863710 | [Molecular Weight]
266.1 | [MOL File]
180516-87-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
228-231 °C(lit.)
| [Boiling point ]
379.7±25.0 °C(Predicted) | [density ]
1.15±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [form ]
Crystalline Powder | [pka]
4.09±0.10(Predicted) | [color ]
White | [Water Solubility ]
Insoluble | [Detection Methods]
HPLC | [InChI]
InChI=1S/C13H17BO4/c1-12(2)13(3,4)18-14(17-12)10-7-5-9(6-8-10)11(15)16/h5-8H,1-4H3,(H,15,16) | [InChIKey]
IYDKBQIEOBXLTP-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1 | [CAS DataBase Reference]
180516-87-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29163990 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
n-Butyllithium-->Triisopropyl borate-->Pinacol-->4-Bromobenzoic acid-->4-Iodobenzeneboronic acid pinacol ester, 97%-->2-(4-BROMO-PHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE-->4-Iodobenzoic acid-->4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)CHLOROBENZENE-->4-Formylphenylboronic acid pinacol cyclic ester-->Carbon dioxide-->Hydrochloric acid-->4-Carboxyphenylboronic acid-->4-Aminobenzoic acid | [Preparation Products]
4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER |
| Hazard Information | Back Directory | [Chemical Properties]
white crystalline powder | [Uses]
4-Carboxybenzeneboronic acid pinacol ester is used to improvement of transition metal-mediated carbon-carbon as well as carbon-heteroatom cross-coupling reactions as a labeling feature with the focus on the preparation of radio labeled compounds for molecular imaging. | [Synthesis]
GENERAL METHODS: Tert-butyl nitrite (155 mg, 1.1 mmol) was added dropwise to a mixture containing bis(pinacolato)diboron (127 mg, 0.5 mmol), p-aminobenzoic acid (61 mg, 0.5 mmol) and eosin Y (0.01 mmol). The reaction mixture was stirred in acetonitrile (3 mL) under blue LED irradiation for 2 h at room temperature (the progress of the reaction was monitored by TLC). Upon completion of the reaction, the mixture was diluted with ethyl acetate (5 mL) and then filtered through diatomaceous earth. The filtrate was extracted with ethyl acetate (3 x 10 mL) and the combined organic phases were washed with saturated saline and dried over anhydrous Na2SO4. Concentration under reduced pressure afforded the crude product, which was purified by silica gel column chromatography using hexane-ethyl acetate (98:2) as eluent to afford pure 4-carboxyphenylboronic acid pinacol ester as a pale yellow viscous liquid (208 mg, 88% yield).IR (pure samples)2978, 2933, 2839, 2526, 2050, 1950, 1911, 1724, 1605, 1570 cm-1; 1H NMR (500 MHz, CDCl3) δ 1.33 (s, 12H), 7.82 (s, 3H), 6.89 (d, J = 8.0 Hz, 2H), 7.75 (d, J = 8.0 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 24.9 (4C), 55.2, 83.6 (2C), 113.4 (2C), 136.6 (2C), 162.3.The spectral data of the obtained compounds are in agreement with the 4-carboxyphenylboronic acid pinacol ester reported in the literature. | [References]
[1] Synlett, 2012, vol. 23, # 9, p. 1394 - 1396
[2] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1551 - 1554
[3] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933 |
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