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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

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%).

4-PHENOXYPHENYLBORONIC ACID(51067-38-0)Related Product Information

• 4-PHENOXYBENZOIC ACID
• (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)propan-1-one
• 4''-PROPYL-3-FLUOROBIPHENYL-4-BORONIC ACID
• 3,4,5-Trifluorophenylboronic acid
• 4-Chloro-2-fluoro-3-methoxyphenylboronic acid
• 4-(Hydroxymethyl)phenylboronic acid
• 3-Carboxyphenylboronic acid
• 3-Tolylboronic acid
• 1-Methyl-4-pyrazole boronic acid pinacol ester
• Ibrutinib Impurity 24
• Ibrutinib
• (S)-Ibrutinib
• (S)-3-Hydroxypiperidine
• Ibrutinib Dimer Impurity
• Ibrutinib Impurity 28
• Ibrutinib Impurity 25
• Acrylic anhydride
• 3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine