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| | 4-PHENOXYPHENYLBORONIC ACID Basic information |
| | 4-PHENOXYPHENYLBORONIC ACID Chemical Properties |
| Melting point | 141-145 °C(lit.) | | Boiling point | 377.0±44.0 °C(Predicted) | | density | 1.23±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 8.76±0.10(Predicted) | | form | Crystalline Powder | | color | White to beige | | InChI | InChI=1S/C12H11BO3/c14-13(15)10-6-8-12(9-7-10)16-11-4-2-1-3-5-11/h1-9,14-15H | | InChIKey | KFXUHRXGLWUOJT-UHFFFAOYSA-N | | SMILES | B(C1=CC=C(OC2=CC=CC=C2)C=C1)(O)O | | CAS DataBase Reference | 51067-38-0(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29319090 | | Storage Class | 11 - Combustible Solids |
| | 4-PHENOXYPHENYLBORONIC ACID Usage And Synthesis |
| Chemical Properties | white to off-white powder and chunk | | Uses | suzuki reaction | | Uses | 4-Phenoxybenzeneboronic Acid is an intermediate used to prepare biphenyl derivatives of nitotrifluoromethoxybenzyloxydihydroimidazooxazines with antitubercular activity. It is also used in the synthesis of pyrrolo pyrimidines as potent inhibitors of Lck kinase. | | Uses | 4-Phenoxyphenylboronic acid can be used as a reactant:
- In the Suzuki-Miyaura coupling reaction to synthesize aryl derivatives via C-C bond formation by reacting with different aryl halides over a palladium catalyst.
- To prepare 1-phenoxy-4-(trifluoromethyl)benzene via oxidative trifluoromethylation using Chan-Lam-type reaction conditions.
- To synthesize evobrutinib, a potent Bruton′s tyrosine kinase (BTK) inhibitor.
| | Synthesis | 4-Bromodiphenyl ether (100 g, 0.402 mol)Was dissolved in anhydrous THF (800 mL)Under nitrogen protection,Cooled to -78 ° C,N-butyllithium (n-BuLi) (177 mL, 0.442 mol)The temperature is kept below -65 ° C,After stirring for 1 h,Continue to maintain the temperature -60 ,Triisopropyl borate (90 g, 0.482 mol) was added dropwise,Slowly rose to 0 ° C, stir for 3 h.Water (300 mL) was added under ice bath overnight. The reaction solution was concentrated to remove the organic phase,With 12N concentrated hydrochloric acid pH adjusted to 1 ~ 2,Precipitation of solids,Filtration and drying gave 4-phenoxyphenylboronic acid (77 g, yield 90%). | | References | [1] Patent: CN106146511, 2016, A. Location in patent: Paragraph 0147; 0148; 0149
[2] Organic Process Research and Development, 2018, vol. 22, # 6, p. 741 - 746
[3] Patent: US2002/156081, 2002, A1
[4] Patent: US6921763, 2005, B2 |
| | 4-PHENOXYPHENYLBORONIC ACID Preparation Products And Raw materials |
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