4-Phenoxyphenylboronic acid

Base Information

• Chemical Name: 4-Phenoxyphenylboronic acid
• CAS No.: 51067-38-0
• Molecular Formula: C12H11BO3
• Molecular Weight: 214.029
• Hs Code.: 29319090
• European Community (EC) Number: 687-755-5
• DSSTox Substance ID: DTXSID70370267
• Nikkaji Number: J1.694.614A
• Wikidata: Q72501058
• ChEMBL ID: CHEMBL459151
• Mol file: 51067-38-0.mol

Synonyms:4-Phenoxyphenylboronic acid;51067-38-0;(4-phenoxyphenyl)boronic acid;4-Phenoxybenzeneboronic acid;Boronic acid, (4-phenoxyphenyl)-;MFCD00093312;CHEMBL459151;(4-Phenoxyphenyl)boronic acid;4-phenoxyphenyl boronic acid;D0D2JA;4-phenyoxyphenylboronic acid;SCHEMBL9285;4-phenoxy-phenylboronic acid;4-Phenoxyphenyl-boronic acid;4- phenoxybenzeneboronic acid;4-phenoxy-phenyl boronic acid;(4-phenoxyphenyl) boronic acid;AMY479;DTXSID70370267;KFXUHRXGLWUOJT-UHFFFAOYSA-N;BCP27808;CS-M1047;BDBM50275011;STK503707;AKOS000264865;AB03336;GS-6829;4-Phenoxyphenylboronic acid, >=95.0%;NCGC00249484-01;AC-27607;BP-11448;PD182301;SY014269;FT-0619375;P1974;EN300-1262826;A828424;J-515926;F2135-0364;Z381541034;4-phenoxyphenylboronic acid (contains varying amounts of anhydride)

Chemical Property of 4-Phenoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: white to off-white powder and chunk
• Vapor Pressure: 2.36E-06mmHg at 25°C
• Melting Point: 141-145 °C(lit.)
• Refractive Index: 1.605
• Boiling Point: 377 °C at 760 mmHg
• PKA: 8.76±0.10(Predicted)
• Flash Point: 181.8 °C
• PSA: 49.69000
• Density: 1.23 g/cm³
• LogP: 1.15870
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.0801244
• Heavy Atom Count: 16
• Complexity: 196

Purity/Quality:

98% ^*data from raw suppliers

4-Phenoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)OC2=CC=CC=C2)(O)O
• Uses: suzuki reaction 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. 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.

Technology Process of 4-Phenoxyphenylboronic acid

There total 13 articles about 4-Phenoxyphenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.3%

4-Bromodiphenyl ether (101-55-3) → 4-phenoxyphenylboronic acid (51067-38-0)

Guidance literature:

4-Bromodiphenyl ether; With Trimethyl borate; In tetrahydrofuran; at -20 - 0 ℃; Inert atmosphere;

With sulfuric acid; In tetrahydrofuran; at 0 - 10 ℃; for 10h; Inert atmosphere;

DOI:10.1039/c2ob25926e

Reference yield: 91.0%

Triisopropyl borate (5419-55-6) + 4,4'-dibromodiphenyl ether (2050-47-7) + water (7732-18-5) → 4-phenoxyphenylboronic acid (51067-38-0)

Guidance literature:

Triisopropyl borate; 4,4'-dibromodiphenyl ether; With n-butyllithium; In tetrahydrofuran; hexane; at -70 - 20 ℃; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; hexane; at 0 ℃; Solvent; Inert atmosphere;

Reference yield: 90.0%

4-Bromodiphenyl ether (101-55-3) + Triisopropyl borate (5419-55-6) → 4-phenoxyphenylboronic acid (51067-38-0)

Guidance literature:

4-Bromodiphenyl ether; With n-butyllithium; In tetrahydrofuran; at -78 - -65 ℃; for 1h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; at -60 - 0 ℃; for 3h;

upstream raw materials:

boric acid tributyl ester

4-Bromodiphenyl ether

Triisopropyl borate

triethyl borate

Downstream raw materials:

2-(4-phenoxy-phenyl)-[1,3,6,2]dioxazaborocane

4-chloro-5-(4-phenoxyphenyl)-7-(1,4-dioxaspiro[4.5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidine

1-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1-phenoxy-4-methylphenylsulfanyl-benzene

Refernces

• 1、 Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup. "Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source". . p. 10966 - 10972. Retrieved 2020/09/23.
• 2、 Usutani, Hirotsugu,Cork, David G.. "Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis". . p. 741 - 746. Retrieved 2018/06/11.