Phenol, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-


Chemical Name: Phenol, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
CAS Number: 214360-76-6
Product Number: AG003I2V(AGN-PC-0KK6NK)
Synonyms:
MDL No:
Molecular Formula: C12H17BO3
Molecular Weight: 220.0726

Identification/Properties


Properties
MP:
94-98 °C(lit.)
BP:
343.5°C at 760 mmHg
Storage:
Keep in dry area;2-8℃;
Form:
Solid
Computed Properties
Molecular Weight:
220.075g/mol
Hydrogen Bond Donor Count:
1
Hydrogen Bond Acceptor Count:
3
Rotatable Bond Count:
1
Exact Mass:
220.127g/mol
Monoisotopic Mass:
220.127g/mol
Topological Polar Surface Area:
38.7A^2
Heavy Atom Count:
16
Formal Charge:
0
Complexity:
249
Isotope Atom Count:
0
Defined Atom Stereocenter Count:
0
Undefined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Covalently-Bonded Unit Count:
1
Compound Is Canonicalized:
Yes

Safety Information


GHS Pictogram:
Signal Word:
Warning
UN#:
N/A
Hazard Statements:
H315-H319-H335
Precautionary Statements:
P261-P305+P351+P338
Class:
N/A
Packing Group:
N/A

NMR Spectrum


Other Analytical Data


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Chemical Structure



The 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol is a versatile compound widely utilized in chemical synthesis processes. This compound plays a crucial role as a key building block in the production of various organic molecules. Its unique structure containing a boron atom bonded to a phenolic group imparts valuable reactivity and selectivity in synthetic pathways.One significant application of this compound lies in its function as a boron source in the Suzuki-Miyaura cross-coupling reaction. In this widely employed synthetic tool, the 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol acts as a boronate ester, reacting with aryl halides or pseudohalides in the presence of a palladium catalyst to form biaryl compounds. This reaction enables the formation of complex and structurally diverse organic molecules with high efficiency and control over regioselectivity.Furthermore, the presence of the boron moiety in this compound also facilitates its use in transition metal-catalyzed C-H activation reactions. Through coordination with transition metal catalysts, the 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol can participate in selective C-H functionalization processes, enabling the direct modification of carbon-hydrogen bonds in organic molecules. This strategy offers a powerful tool for the streamlined synthesis of intricate organic frameworks with high atom economy and reduced waste generation.