Pyridine, 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-


Chemical Name: Pyridine, 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-
CAS Number: 845885-86-1
Product Number: AG003I5J(AGN-PC-0KL724)
Synonyms:
MDL No:
Molecular Formula: C10H14BNO2
Molecular Weight: 191.0347

Identification/Properties


Properties
MP:
92-96 °C(lit.)
BP:
309.8±15.0 °C(Predicted)
Storage:
2-8℃;
Form:
Solid
Computed Properties
Molecular Weight:
191.037g/mol
Hydrogen Bond Donor Count:
0
Hydrogen Bond Acceptor Count:
3
Rotatable Bond Count:
1
Exact Mass:
191.112g/mol
Monoisotopic Mass:
191.112g/mol
Topological Polar Surface Area:
31.4A^2
Heavy Atom Count:
14
Formal Charge:
0
Complexity:
189
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

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NMR Spectrum


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Chemical Structure



3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine is a versatile and valuable reagent in chemical synthesis. With its unique structure containing a boronate ester and a pyridine ring, this compound is commonly used as a catalyst in various organic reactions. One of its primary applications is in Suzuki-Miyaura cross-coupling reactions, where it acts as a ligand in conjunction with palladium catalysts to facilitate the bond formation between aryl halides or pseudohalides and boronic acids. This reaction is widely employed in the synthesis of biaryl compounds, pharmaceuticals, agrochemicals, and materials science. Additionally, 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine has shown utility in other transition metal-catalyzed coupling reactions, such as Heck and Sonogashira reactions, further expanding its scope in organic synthesis. Its high reactivity, stability, and compatibility with various functional groups make it a valuable tool for chemists seeking to construct complex molecular structures efficiently and selectively.