ChemicalBook--->CAS DataBase List--->659742-21-9

659742-21-9

659742-21-9 Structure

659742-21-9 Structure
IdentificationMore
[Name]

2-Picoline-5-boronic acid
[CAS]

659742-21-9
[Synonyms]

2-METHYL-5-PYRIDINYLBORONIC ACID
2-METHYLPYRIDINE-5-BORONIC ACID
(6-METHYLPYRIDIN-3-YL)BORONIC ACID
6-METHYLPYRIDINE-3-BORONIC ACID
Boronicacid,(6-methyl-3-pyridinyl)
Boronic acid, (6-methyl-3-pyridinyl)-(9CI)
6-Methylpyridine-3-Boronic
2-Methylpyridin-5-ylboronic acid
2-Picoline-5-boronic acid
2-METHYL-5-PYRIDINEBORONIC ACID
Boronic acid, B-(6-methyl-3-pyridinyl)-
2-Methylpyridine-5-boronic acid ,98%
2-Methyl-5-boronic acid
[EINECS(EC#)]

689-887-9
[Molecular Formula]

C6H8BNO2
[MDL Number]

MFCD06801736
[Molecular Weight]

136.94
[MOL File]

659742-21-9.mol
Chemical PropertiesBack Directory
[Melting point ]

128-130°C
[Boiling point ]

294.7±42.0 °C(Predicted)
[density ]

1.18±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Powder
[pka]

4.27±0.10(Predicted)
[color ]

White to pale brown
[Detection Methods]

HPLC
[Stability:]

Hygroscopic
[InChI]

1S/C6H8BNO2/c1-5-2-3-6(4-8-5)7(9)10/h2-4,9-10H,1H3
[InChIKey]

MZUSCPDSQJSBSY-UHFFFAOYSA-N
[SMILES]

Cc1ccc(cn1)B(O)O
[CAS DataBase Reference]

659742-21-9(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36/37/39
[WGK Germany ]

3
[HS Code ]

29333990
[Storage Class]

11 - Combustible Solids
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Diethyl ether-->n-Butyllithium-->Nitrogen-->Triisopropyl borate-->5-Bromo-2-methylpyridine-->2-Methyl-5-pyridinetrifluoromethanesulf&-->3-Hydroxy-6-methylpyridine-->Bis(pinacolato)diboron-->Potassium Acetate-->Acetonitrile
[Preparation Products]

2-Picoline-->BenzaMide, N-[4-Methyl-3-[[4-(6-Methyl-3-pyridinyl)-2-pyriMidinyl]aMino]phenyl]-4-[(4-Methyl-1-piperazinyl)Methyl]--->6'-Methyl-[2,3']bipyridinyl
Hazard InformationBack Directory
[Chemical Properties]

White to off-white solid
[Uses]

6-Methylpyridine-3-boronic Acid is used in the preparation of various biologically active compound such as phosphoinositide-3-kinases (PI3K) and c-jun N-terminal kinase (JNK) inhibitors.
[Uses]

suzuki reaction
[Synthesis]

2-METHYL-5-PYRIDINETRIFLUOROMETHANESULF&

111770-91-3

Bis(pinacolato)diboron

73183-34-3

6-Methylpyridine-3-boronic Acid

659742-21-9

General procedure for the synthesis of 6-methyl-3-pyridineboronic acid from 6-methyl-3-pyridinol trifluoromethanesulfonate and bis(pinacolato)diboronate: 6-methyl-3-pyridinol trifluoromethanesulfonate (4.6 mmol) was dissolved in acetonitrile (30 mL) and transferred to a 5 mL microwave reaction tube. To this solution was added 1.5 equivalents of bis(pinacolato)diboron (6.9 mmol; 1.71 g). The mixture was stirred on a magnetic stirrer until complete dissolution. Subsequently, potassium acetate (13.8 mmol; 1.35 g) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (98 mg, 0.03 mol%) were added to the mixture. The reaction mixture was placed in a microwave reactor and heated at 160°C for 2 x 600 seconds. Upon completion of the reaction (monitored by LC-MS), the acetonitrile was removed by evaporation to give a black solid. The solid was dissolved in DMSO and purified by HPLC to give the final target product 6-methyl-3-pyridineboronic acid (580 mg, 92% yield; 4.2 mmol). Mass spectral data: MH+ = 138.

[References]

[1] Patent: WO2005/32493, 2005, A2. Location in patent: Page/Page column 40-41
[2] Patent: WO2005/32493, 2005, A2. Location in patent: Page/Page column 40-41
Spectrum DetailBack Directory
[Spectrum Detail]

6-Methylpyridine-3-boronic Acid(659742-21-9)1HNMR
6-Methylpyridine-3-boronic Acid(659742-21-9)FT-IR
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