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(3,5-Bis(trifluoromethyl)phenyl)boronic acid

Catalog Number
ACM73852194-1
Product Name
(3,5-Bis(trifluoromethyl)phenyl)boronic acid
Structure
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CAS
73852-19-4
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Synonyms
CB-110; 3,5-Bis-trifluoromethylphenylboronic acid; (3,5-Bis(trifluoromethyl)phenyl)boronic acid; ST2414244; SCHEMBL126169; AKOS000285053; Boronic acid, [3,5-bis(trifluoromethyl)phenyl]-; 133412-EP2295406A1; ZINC169743211; 3,5-di(trifluoromethyl)-phenylboronic acid;
IUPAC Name
[3,5-bis(trifluoromethyl)phenyl]boronic acid;
Molecular Weight
257.926g/mol
Molecular Formula
C8H5BF6O2;
Canonical SMILES
B(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(O)O;
InChI
InChI=1S/C8H5BF6O2/c10-7(11,12)4-1-5(8(13,14)15)3-6(2-4)9(16)17/h1-3,16-17H;
InChI Key
BPTABBGLHGBJQR-UHFFFAOYSA-N;
Complexity
242
Covalently-Bonded Unit Count
1
Exact Mass
258.029g/mol
H-Bond Acceptor
8
H-Bond Donor
2
Heavy Atom Count
17
Monoisotopic Mass
258.029g/mol
Rotatable Bond Count
1
Topological Polar Surface Area
40.5A^2
Application
The purpose of (3,5-Bis(trifluoromethyl)phenyl)boronic acid is to serve as a versatile reactant in various chemical synthesis processes. It plays a crucial role in the Suzuki reaction, particularly in producing methylene-arylbutenones through carbonylative arylation of allenols. Additionally, it is involved in synthesizing 4-aminoquinoline analogs using methods such as Ullman, Suzuki, and Negishi coupling. This compound is also vital in creating primary amino acid derivatives with anticonvulsant properties, facilitating the formation of alkyl arylcarbamates via copper-catalyzed coupling with potassium cyanate, and assisting in the asymmetric conjugate addition to produce aryl-substituted succinimides and cyclic ketones. Moreover, (3,5-Bis(trifluoromethyl)phenyl)boronic acid is instrumental in synthesizing axially chiral dicarboxylic acids for asymmetric Mannich-type reactions, underscoring its importance in advanced chemical transformations.
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