4-(Tert-Butyl Dimethylsiloxy)Phenyl Boronic Acid

• CAS: 159191-56-7
• Catalog Number: ACM159191567
• Category: Boronic Acids
• Molecular Weight: 252.19 g/mol
• Molecular Formula: C12H21BO3Si
• Synonyms: 4-(T-BUTYL DIMETHYLSILOXY) PHENYL BORONIC ACID;4-(TERT-BUTYL DIMETHYLSILOXY)PHENYL BORONIC ACID;4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENYLBORONIC ACID;4-(TERT-BUTYLDIMETHYLSILYOXY)PHENYLBORONIC ACID;AKOS BRN-0412;4-(TERT-BUTYLDIMETHYLSILYOXY)PHENYLBORON;4-(tert
• IUPAC Name: [4-[tert-butyl(dimethyl)silyl]oxyphenyl]boronic acid
• Canonical SMILES: B(C1=CC=C(C=C1)O[Si](C)(C)C(C)(C)C)(O)O
• InChI Key: NVHHEADQQACSCJ-UHFFFAOYSA-N
• Boiling Point: 321.4ºC at 760mmHg
• Melting Point: 194-198ºC(lit.)
• Flash Point: 148.2ºC
• Density: 1.01g/cm³
• Application: 4-(Tert-Butyl Dimethylsiloxy)Phenyl Boronic Acid serves as a versatile reactant extensively utilized in various chemical syntheses It plays a critical role in asymmetric addition reactions involving β-substituted cyclic enones and facilitates hydroarylation and heterocyclization with phenylpropiolates This compound is integral to double Suzuki-Miyaura coupling reactions providing valuable intermediates for a range of applications Additionally it acts as a starting material in the creation of red electroluminescent polyfluorenes Its utility extends to the synthesis of biologically active molecules including phenylpyridone derivatives functioning as MCH1R antagonists as well as atromentin and its O-alkylated derivatives Furthermore it contributes to the development of inhibitors targeting gelatinases and MT1-MMP underscoring its importance in medicinal chemistry
• Exact Mass: 252.13500
• Hazard Statements: Xi: Irritant
• H-Bond Acceptor: 3
• H-Bond Donor: 2

Synthetic Use

Upstream Synthesis Route 1

• 67963-68-2

• 159191-56-7

Reference: [1] Journal of the American Chemical Society, 1997, vol. 119, # 25, p. 5818 - 5827

Upstream Synthesis Route 2

• 71597-85-8
• 18162-48-6

• 159191-56-7

Reference: [1] Australian Journal of Chemistry, 2018, vol. 71, # 10, p. 789 - 797
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 22, p. 5852 - 5869
[3] Patent: EP2048153, 2009, A1, . Location in patent: Page/Page column 46
[4] Patent: US2011/275703, 2011, A1, . Location in patent: Page/Page column 35
[5] Organic Letters, 2011, vol. 13, # 19, p. 5314 - 5317

Upstream Synthesis Route 3

• 5419-55-6
• 67963-68-2

• 159191-56-7

Reference: [1] Organic letters, 2001, vol. 3, # 15, p. 2317 - 2320
[2] Patent: US6521643, 2003, B1,
[3] Patent: US2011/244481, 2011, A1,
[4] Patent: US2014/316137, 2014, A1, . Location in patent: Paragraph 0249; 0250

Upstream Synthesis Route 4

• 5419-55-6
• 67963-68-2

• 159191-56-7

Reference: [1]Organic letters,2001,vol. 3,p. 2317 - 2320
[2]Patent: US6521643,2003,B1
[3]Patent: US2011/244481,2011,A1
[4]Patent: US2014/316137,2014,A1 .Location in patent: Paragraph 0249; 0250