Methylboronic acid

• CAS: 13061-96-6
• Catalog Number: ACM13061966
• Category: Boronic Acids
• Molecular Weight: 59.86g/mol
• Molecular Formula: CH5BO2
• Synonyms: METHYLBORON DIHYDROXIDE;METHYLBORONIC ACID;METHANEBORONIC ACID;CH5BO2;dihydroxy-methyl-borane;METHYLBORONIC ACIDFOR GC;METHANDROSTENOLONE;Methylboron dihydroxide, GLC Grade
• IUPAC Name: methylboronic acid
• Canonical SMILES: B(C)(O)O
• InChI: InChI=1S/CH5BO2/c1-2(3)4/h3-4H,1H3
• InChI Key: KTMKRRPZPWUYKK-UHFFFAOYSA-N
• Application: Methylboronic acid is a versatile white to light yellow crystalline powder primarily serving as a reagent in various chemical processes. It plays a crucial role in palladium-catalyzed reactions, such as Stille and Suzuki-Miyaura cross-couplings, and can enhance microwave-heated heterogeneous reactions. It finds applications in ruthenium-catalyzed silylation reactions and is integral in preparing bis(aminotropone) titanium catalysts for ethylene polymerization. Additionally, it supports enantioselective asymmetric bromoaminocyclization processes, and aids in the synthesis of essential building blocks for pharmaceuticals and agrochemicals. Methylboronic acid is utilized in creating chrysin analogs, casein kinase I inhibitors, and in divergent C-H functionalizations directed by sulfonamide pharmacophores for drug discovery. It also facilitates the synthesis of unsymmetrical monosulfides from disulfides through copper-catalyzed coupling, and is employed in palladium-catalyzed coupling with enol tosylates. Moreover, it is effective for derivatizing carbohydrates and biologically active compounds for gas-liquid chromatography (GLC) analysis.
• Complexity: 13.5
• Covalently-Bonded Unit Count: 1
• Exact Mass: 60.03826g/mol
• Formal Charge: 0
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Heavy Atom Count: 4
• Monoisotopic Mass: 60.03826g/mol
• Rotatable Bond Count: 0
• UNII: 8Z1ME41SCH

Synthetic Use

Downstream Synthesis Route 1

• 611-35-8
• 13061-96-6

• 4295-06-1

Reference: [1] Chemical Science, 2016, vol. 7, # 10, p. 6407 - 6412

Downstream Synthesis Route 2

• 6298-19-7
• 13061-96-6

• 3430-10-2

Reference: [1] Tetrahedron, 1998, vol. 54, # 23, p. 6311 - 6318

Downstream Synthesis Route 3

• 13061-96-6
• 149806-06-4

• 53014-84-9

Reference: [1] Patent: WO2008/16968, 2008, A2, . Location in patent: Page/Page column 70

Downstream Synthesis Route 4

• 22348-32-9
• 13061-96-6

• 112022-81-8

Reference: [1]Tetrahedron,1998,vol. 54,p. 6311 - 6318

Downstream Synthesis Route 5

• 13061-96-6
• 237435-16-4

• 179056-98-5

Reference: [1]Helvetica Chimica Acta,2001,vol. 84,p. 431 - 472

Downstream Synthesis Route 6

• 13061-96-6
• 77771-02-9

• 135427-08-6

Reference: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4288 - 4312

* For details of the synthesis route, please refer to the original source to ensure accuracy.