4-(tert-Butyldimethylsilyloxy)phenylboronic acid

Base Information

• Chemical Name: 4-(tert-Butyldimethylsilyloxy)phenylboronic acid
• CAS No.: 159191-56-7
• Molecular Formula: C12H21BO3Si
• Molecular Weight: 252.193
• Hs Code.: 2931900090
• European Community (EC) Number: 691-472-2
• DSSTox Substance ID: DTXSID90455505
• Nikkaji Number: J997.964F
• Wikidata: Q82277554
• Mol file: 159191-56-7.mol

Synonyms:159191-56-7;4-(tert-Butyldimethylsilyloxy)phenylboronic acid;4-(tert-Butyldimethylsiloxy)phenyl boronic acid;4-(tert-Butyl dimethylsiloxy)phenyl boronic acid;4-(tert-Butyldimethylsilyloxy)benzeneboronic Acid;4-(tert-butyldimethylsiloxy)phenylboronic acid;[4-[tert-butyl(dimethyl)silyl]oxyphenyl]boronic acid;MFCD03093888;Boronic acid, [4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-;(4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid;{4-[(tert-butyldimethylsilyl)oxy]phenyl}boronic acid;4-(tert-Butyldimethylsiloxy)phenylboronicacid;AKOS BRN-0412;SCHEMBL282583;DTXSID90455505;NVHHEADQQACSCJ-UHFFFAOYSA-N;AMY29925;AKOS004119209;AB13279;CS-W000878;AS-18694;SY023718;4(t-Butyldimethylsilyloxy)phenylboronic acid;B3739;FT-0757570;4-(t-butyldimethylsilyloxy)benzeneboronic acid;4-tert-butyl-dimethylsilyoxyphenylboronic acid;4-tert-butyldimethylsilyloxyphenylboronic acid;4-(tert-butyl dimethylsiloxy)phenylboronic acid;4-(TERT-BUTYLDIMETHYLSILYOXY)PHENYLBORON;4-(tertbutyldimethylsilyloxy)phenylboronic acid;4-tert-butyl-dimethylsilyoxyphenyl-boronic acid;4-tert-butyldimethylsilyloxyphenyl boronic acid;EN300-343309;(4-((t-butyldimethylsilyl)oxy)phenyl)boronic acid;A810006;4-(T-BUTYL DIMETHYLSILOXY) PHENYL BORONIC ACID;4-(TERT-BUTYLDIMETHYLSILYOXY)PHENYLBORONIC ACID;4-[[tert-butyl(dimethyl)silyl]oxy]-phenylboronic acid;4-[[tert-butyl(dimethyl)silyl]oxy]phenylboronic acid;(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)boronic acid;4-(tert-Butyldimethylsilyloxy)phenylboronic acid, >=95%;4-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)

Chemical Property of 4-(tert-Butyldimethylsilyloxy)phenylboronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 194-198 °C(lit.)
• Refractive Index: 1.49
• Boiling Point: 321.358 °C at 760 mmHg
• PKA: 8.68±0.16(Predicted)
• Flash Point: 148.152 °C
• PSA: 49.69000
• Density: 1.019g/cm³
• LogP: 1.75040
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 252.1353012
• Heavy Atom Count: 17
• Complexity: 243

Purity/Quality:

98% ^*data from raw suppliers

4-(tert-Butyldimethylsilyloxy)phenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)O[Si](C)(C)C(C)(C)C)(O)O
• Uses: Reactant involved in:? ;Asymmetric addition reactions with β-substituted cyclic enones1? ;Hydroarylation and heterocyclization with phenylpropiolates2? ;Double Suzuki-Miyaura coupling reactions3Starting material for the synthesis of red electroluminescent polyfluorenes4Reactant involved in the synthesis of biologically active molecules including:? ;Phenylpyridone derivatives as MCH1R antagonists5? ;Atromentin and its O-alkylated derivatives3? ;Gelatinases and MT1-MMP inhibitors6 Reactant involved in:Asymmetric addition reactions with β-substituted cyclic enonesHydroarylation and heterocyclization with phenylpropiolatesDouble Suzuki-Miyaura coupling reactionsStarting material for the synthesis of red electroluminescent polyfluorenesReactant involved in the synthesis of biologically active molecules including:Phenylpyridone derivatives as MCH1R antagonistsAtromentin and its O-alkylated derivativesGelatinases and MT1-MMP inhibitors

Technology Process of 4-(tert-Butyldimethylsilyloxy)phenylboronic acid

There total 11 articles about 4-(tert-Butyldimethylsilyloxy)phenylboronic 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: 97.0%

t-butyldimethylsilyl-4-bromophenol (67963-68-2) → (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (159191-56-7)

Guidance literature:

t-butyldimethylsilyl-4-bromophenol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 0 ℃;

With hydrogenchloride; In tetrahydrofuran; hexane; water;

DOI:10.1021/ja9702778

Reference yield: 92.0%

Triisopropyl borate (5419-55-6) + t-butyldimethylsilyl-4-bromophenol (67963-68-2) → (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (159191-56-7)

Guidance literature:

t-butyldimethylsilyl-4-bromophenol; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ol016092u

Reference yield: 90.0%

(p-hydroxyphenyl)boronic acid (71597-85-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (159191-56-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1071/CH18251

upstream raw materials:

t-butyldimethylsilyl-4-bromophenol

Triisopropyl borate

4-bromo-phenol

tert-butyldimethylsilyl chloride

Downstream raw materials:

2,5-dimethoxy-4-(3-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)-biphenyl-3,4'-diol

4-(benzyloxy)-3',6'-dimethoxy-[1,1':4',1'']terphenyl-3,2',4''-triol

tert-butyl 4-[4-(tert-butyl-dimethyl-silanoxy)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylate

3-benzyl-5-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-3-phenyl-2-pyrazinamine

Refernces

• 1、 Walter, Isabell,Adam, Sebastian,Gentilini, Maria Virginia,Kany, Andreas M.,Brengel, Christian,Thomann, Andreas,Sparwasser, Tim,K?hnke, Jesko,Hartmann, Rolf W.. "Structure-Activity Relationship and Mode-Of-Action Studies Highlight 1-(4-Biphenylylmethyl)-1H-imidazole-Derived Small Molecules as Potent CYP121 Inhibitors". . p. 2786 - 2801. Retrieved 2021/06/27.
• 2、 -. "CHEMILUMINESCENT IMIDAZOPYRAZINONE-BASED PHOTOSENSITIZERS WITH AVAILABLE SINGLET AND TRIPLET EXCITED STATES". Page/Page column 29. . Retrieved 2019/11/19.