Methylboronic acid

Base Information

• Chemical Name: Methylboronic acid
• CAS No.: 13061-96-6
• Molecular Formula: CH5BO2
• Molecular Weight: 59.8605
• Hs Code.: 29319090
• Mol file: 13061-96-6.mol

Synonyms:Methaneboronicacid (6CI,7CI,8CI);Boronicacid, methyl- (9CI);Methaneboronic acid;

Chemical Property of Methylboronic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 2.35mmHg at 25°C
• Melting Point: 91-94 °C
• Refractive Index: 1.345
• Boiling Point: 141.745 °C at 760 mmHg
• PKA: 9.97±0.43(Predicted)
• Flash Point: 39.526 °C
• PSA: 40.46000
• Density: 0.965 g/cm³
• LogP: -0.91100
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Sensitive.: Hygroscopic
• Solubility.: DMSO, Water
• Water Solubility.: Soluble in water.

Purity/Quality:

98% ^*data from raw suppliers

Methylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: suzuki reaction Methylboronic Acid is a methylated derivative of boronic acid, a building block towards various intermediates in suzuki coupling. Methylboronic acid can be used as a reagent:In the palladium-catalyzed Stille and Suzuki-Miyaura cross-couplings.In the microwave-heated heterogeneous palladium (Pd)-catalytized reactions.In ruthenium (Ru)-catalyzed silylation reactionsTo prepare bis(aminotropone) titanium (Ti) catalysts for ethylene polymerizations.In the enantioselective asymmetric bromoaminocyclization and bromoaminocyclization using amino-thiocarbamate catalysts.To prepare common building blocks for pharmaceuticals and agrochemicals.To prepare chrysin analogs by Suzuki-Miyaura coupling reactions.To prepare casein kinase I inhibitors.In the divergent C-H functionalizations directed by sulfonamide pharmacophores in drug discovery.In the synthesis of unsymmetrical monosulfides from disulfides via copper-catalyzed coupling with boronic acids.In a palladium-catalyzed coupling with enol tosylates.For derivatizing many carbohydrates and biologically active compounds for GLC analysis.

Technology Process of Methylboronic acid

There total 47 articles about Methylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

dimethyl sulfide borane (13292-87-0) → dihydroxy-methyl-borane (13061-96-6)

Guidance literature:

With carbon monoxide; water; In tetrahydrofuran; byproducts: S(CH3)2; a soln. of BH3*S(CH3)2 flushed with CO; a soln. of catalyst added, stirred rapidly and maintained at 25°C for 12-16 h; water added; evapd.;

DOI:10.1021/om00124a002

Reference yield: 79.0%

Triisopropyl borate (5419-55-6) + methyllithium (917-54-4) → dihydroxy-methyl-borane (13061-96-6)

Guidance literature:

With hydrogenchloride; In diethyl ether; byproducts: LiCl, i-propanol; (N2); a soln. of B(O-i-Pr)3 cooled with a dry ice-acetone bath; CH3Li added slowly and stirred for 1 h; allowed to warm to room temp. with stirring for 3 h; cooled to 0°C; a soln. of HCl in ether added and stirred for 0.5 h; decanted; hydrolyzed with water; distd.; dried;

DOI:10.1021/om00124a002

Reference yield:

U(4+)*3BH4(1-)*H3BCH3(1-)=U{(BH4)3(H3BCH3)} + water (7732-18-5) → dihydroxy-methyl-borane (13061-96-6) + metaboric acid (13460-50-9)

Guidance literature:

byproducts: U(OH)4, H2;

DOI:10.1021/ja01097a059

upstream raw materials:

methyl magnesium iodide

Trimethyl borate

methylmagnesium bromide

dibromomethylborane

Downstream raw materials:

1-methyl-1-vinylcyclohexane

n-propylidenecyclohexane

2-methyl-3-pyridinamine

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Refernces

• 1、 Hamzehpoor, Ehsan,Jonderian, Antranik,McCalla, Eric,Perepichka, Dmitrii F.. "Synthesis of Boroxine and Dioxaborole Covalent Organic Frameworks via Transesterification and Metathesis of Pinacol Boronates". supporting information. p. 13274 - 13280. Retrieved 2021/09/07.
• 2、 Stoddard,Shea. "Isolation and characterization of borane complexes of dimethylsulfoxonium methylide". . p. 1124 - 1131. Retrieved 2008/10/08.