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| | 4-(Bromomethyl)benzeneboronic acid pinacol ester Basic information |
| Product Name: | 4-(Bromomethyl)benzeneboronic acid pinacol ester | | Synonyms: | 4-Bromomethylphenylboronic acid pinacol ester 95%;4-(BROMOMETHYL)BENZENEBORONIC ACID PINACOL ESTER;4-BROMOMETHYLPHENYLBORONIC ACID, PINACOL ESTER;4-(Bromomethyl)benzeneboronic acid pinacol cyclic ester;4-(Bromomethyl)phenylboronic acid pinacol cyclic ester~2-[(4-Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(Bromomethyl)phenylboronicacidpinacolcyclicester~2-[(4-Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(4-bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(bromomethyl)phenylboronic acid pinacol cyclic ester | | CAS: | 138500-85-3 | | MF: | C13H18BBrO2 | | MW: | 297 | | EINECS: | 679-122-7 | | Product Categories: | Boronic acids;blocks;BoronicAcids;Bromides | | Mol File: | 138500-85-3.mol |  |
| | 4-(Bromomethyl)benzeneboronic acid pinacol ester Chemical Properties |
| Melting point | 85-89 °C | | Boiling point | 351.2±25.0 °C(Predicted) | | density | 1.26±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Toluene | | form | powder | | color | white to off-white | | BRN | 7921808 | | InChI | InChI=1S/C13H18BBrO2/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-8H,9H2,1-4H3 | | InChIKey | CBUOGMOTDGNEAW-UHFFFAOYSA-N | | SMILES | O1C(C)(C)C(C)(C)OB1C1=CC=C(CBr)C=C1 | | CAS DataBase Reference | 138500-85-3(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38-34 | | Safety Statements | 26-36/37/39-45 | | RIDADR | 3261 | | WGK Germany | 3 | | Hazard Note | Harmful/Irritant/Keep Cold | | TSCA | No | | HazardClass | IRRITANT | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids |
| Provider | Language |
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ALFA
| English |
| | 4-(Bromomethyl)benzeneboronic acid pinacol ester Usage And Synthesis |
| Description | 4-(Bromomethyl)benzeneboronic acid pinacol ester can be used as an active oxygen source in biological assays, such as functional assays, because it generates reactive oxygen species and can act as a fluorescence probe for detection of biological samples.
| | Chemical Properties | White powder | | Uses |
4-(Bromomethyl)benzeneboronic acid pinacol ester is used in the synthesis of metalloproteinase-13 inhibitors in the treatment of osteoarthritis.
| | Synthesis |
Pinacol p-tolueneborate (10.91g, 50.0mmol), bromosuccinimide (NBS, 9.91g, 55.0mmol), and azobisisobutyronitrile (AIBN, 0.44g, 2.0mmol) were dissolved in dry of carbon tetrachloride (CCl4, 200 mL), stirred at reflux for 14 hours. The mixture was filtered, the solvent was evaporated, and the mixture was dissolved in ethyl acetate (200 mL). Wash once with distilled water (100 mL) and saturated sodium chloride aqueous solution (100 mL), dry with anhydrous sodium sulfate, and rotary evaporate. Finally, use petroleum ether as the eluent for column chromatography separation to obtain 4-(Bromomethyl)benzeneboronic acid pinacol ester
(11.30g, yield 76.1%).
| | References | [1] Patent: WO2013/25885, 2013, A1. Location in patent: Paragraph 0086
[2] Synthetic Communications, 2002, vol. 32, # 17, p. 2669 - 2676
[3] Patent: EP2450354, 2012, A1 |
| | 4-(Bromomethyl)benzeneboronic acid pinacol ester Preparation Products And Raw materials |
| Raw materials | N-Bromosuccinimide-->(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol-->4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)TOLUENE-->Carbon tetrabromide-->Triphenylphosphine-->Tetrahydrofuran | | Preparation Products | Filgotinib-->4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL-->4-(Cyanomethyl)benzeneboronic acid pinacol ester-->3',6'-Bis{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy]-3H-[spiro(isobenzofuran-1,9,-xanthen]-3-one} FBBBE-->N-Ethyl-N-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzyl)ethanaMine |
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