| Identification | More | [Name]
3-(Hydroxymethyl)phenylboronic acid | [CAS]
87199-15-3 | [Synonyms]
3-(HYDROXYMETHYL)BENZENEBORONIC ACID
3-(HYDROXYMETHYL)PHENYLBORONIC ACID
RARECHEM AH PB 0189
(3-Boronophenyl)methanol
3-Boronobenzyl alcohol
3-(Hydroxymethyl)phenylboronic Acid (contains varying amounts of Anhydride)
3-hydroxymethylboronic acid
3-(Hydroxymethyl)phenylboronic acid ,98% | [Molecular Formula]
C7H9BO3 | [MDL Number]
MFCD01317846 | [Molecular Weight]
151.96 | [MOL File]
87199-15-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
95-99 °C (lit.) | [Boiling point ]
380.5±44.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [form ]
powder to crystal | [pka]
8.31±0.10(Predicted) | [color ]
White to Almost white | [Water Solubility ]
Soluble in water. | [Detection Methods]
HPLC | [BRN ]
8832019 | [InChI]
InChI=1S/C7H9BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,9-11H,5H2 | [InChIKey]
HGTDLKXUWVKLQX-UHFFFAOYSA-N | [SMILES]
B(C1=CC=CC(CO)=C1)(O)O | [CAS DataBase Reference]
87199-15-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29319099 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
Reactant used for copper-mediated trifluoromethylation, copper-catalyzed transformations from arylboronic acids in water, Mitsunobu, Suzuki, and amidation reactions with hydroxyphenylamino bromopyrazinecarboxylate. Reactant involved in the synthesis of biologically active molecules including Mycobacterium tuberculosis H37Rv chorismate mutase inhibitors via Suzuki coupling reactions, HIV protease inhibitors with antiviral activity against drug-resistant viruses, Pyrrole derivatives for use as PDE4B inhibitors. | [Uses]
suzuki reaction | [Synthesis]
The general procedure for the synthesis of 3-hydroxymethylphenylboronic acid from triisopropyl borate and ((3-bromobenzyl)oxy)(tert-butyl)dimethylsilane is as follows:
Example 3B: Synthesis of 3-(hydroxymethyl)phenylboronic acid
Example 3A (150 mg, 0.498 mmol) was dissolved in THF (2.49 mL) and the solution was cooled to -78 °C. Under stirring, n-butyllithium (431.1 μL, 0.647 mmol) was slowly added and stirred continuously for 30 hours at this temperature. Subsequently, triisopropyl borate (231 μL, 0.996 mmol) was added and stirring was continued for 20 minutes. After that, the reaction mixture was slowly warmed up to room temperature and stirring was continued for 2.5 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed sequentially with water and brine, then dried with anhydrous sodium sulfate, filtered, and concentrated under vacuum. The resulting crude product was dissolved in HPLC solvent B (90:10:0.1 MeCN:H2O:TFA) and stirred at room temperature for 1 hour. Afterwards, the solution was concentrated in vacuum and purified by preparative liquid chromatography (using an Axia Luna 5μ C18 30×100 mm column with a 10-minute gradient, 20 to 100% B, A = 10:90:0.1 MeCN:H2O:TFA, B = 90:10:0.1 MeCN:H2O:TFA) to give Example 3B (57 mg, yield 75%).
1H NMR (400 MHz, ACETONITRILE-d3) δ ppm: 7.75 (1H, s), 7.67 (1H, d, J = 7.28 Hz), 7.40-7.48 (1H, m), 7.30-7.40 (1H, m), 4.60 (2H, s). | [References]
[1] Patent: WO2014/201073, 2014, A1. Location in patent: Paragraph 00214
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 1, p. 67 - 72 |
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