| Identification | Back Directory | [Name]
(1-Methyl-1H-pyrazol-5-yl)-boronic acid | [CAS]
720702-41-0 | [Synonyms]
-5-yL
(1-Methyl-1H-pyrazol-5-yl...
1-Methyl-pyrazole-5-boronic acid
(2-methyl-3-pyrazolyl)boronic acid
(2-methylpyrazol-3-yl)boronic acid
1-Methyl-1H-pyrazole-5-boronic acid
1-Methyl-1H-pyrazol-5-yl-5-boronic acid
(1-Methyl-1H-pyrazol-5-yl)-boronic acid
BORONIC ACID, (1-METHYL-1H-PYRAZOL-5-YL)-
Boronic acid, B-(1-methyl-1H-pyrazol-5-yl)-
(1-methyl-1H-pyrazol-5-yl)boronic acid(SALTDATA: FREE) | [Molecular Formula]
C4H7BN2O2 | [MDL Number]
MFCD11053031 | [MOL File]
720702-41-0.mol | [Molecular Weight]
125.922 |
| Chemical Properties | Back Directory | [Boiling point ]
323.0±34.0 °C(Predicted) | [density ]
1.23±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [pka]
8.00±0.58(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C4H7BN2O2/c1-7-4(5(8)9)2-3-6-7/h2-3,8-9H,1H3 | [InChIKey]
MGNBKNBEZGLHNF-UHFFFAOYSA-N | [SMILES]
B(C1N(C)N=CC=1)(O)O |
| Hazard Information | Back Directory | [Uses]
1-Methyl-1H-pyrazole-5-boronic Acid acts as a reagent for the design, synthesis and evaluation of novel porcupine inhibitors featuring a fused 3-ring system based on ‘reversed’ amide scaffold. | [Synthesis]
General procedure for the synthesis of 1-methyl-1H-pyrazole-5-boronic acid from 1-methylpyrazole: 1-methylpyrazole (25 mL, 0.3 mol) was dissolved in 500 mL of tetrahydrofuran (THF). The solution was then cooled to -78°C in a dry ice/isopropanol bath. After the solution temperature stabilized at -78 °C, n-butyllithium (n-BuLi, 140 mL, 0.40 mol) was slowly added dropwise through the cannula. After the dropwise addition, the reaction mixture was stirred continuously at -78 °C for 1.5 hours. Next, triisopropyl borate (280 mL, 1.2 mol) was added to the reaction system via cannula and the reaction mixture was allowed to slowly warm from -78 °C to 0 °C while stirring overnight. Upon completion of the reaction, the pH of the mixture was adjusted to 6 with 1 N hydrochloric acid (HCl).Subsequently, THF was evaporated under reduced pressure and the remaining aqueous phase was extracted with ethyl acetate (EtOAc, 2 × 100 mL). Finally, the solid was collected by filtration to afford 108 g (100% yield) of 1-methyl-1H-pyrazole-5-boronic acid as a yellow solid. | [References]
[1] Patent: WO2005/12254, 2005, A1. Location in patent: Page/Page column 101
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 1923 - 1936
[3] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 6, p. 931 - 939
[4] Patent: WO2004/58722, 2004, A1. Location in patent: Page 63; 62 |
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