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ChemicalBook--->CAS DataBase List--->839714-33-9

839714-33-9

839714-33-9 Structure

839714-33-9 Structure
IdentificationBack Directory
[Name]

1-Isopropylpyrazole-5-boronic Acid
[CAS]

839714-33-9
[Synonyms]

1-Isopropylpyrazole-5-boronic Acid
1-Isopropyl-1H-pyrazole-5-boronic acid
1-isopropyl-1H-pyrazol-5-ylboronic acid
(2-propan-2-ylpyrazol-3-yl)boronic acid
1-Isopropyl-1H-pyrazole-5-boronic acid 95+%
1-(1-methylethyl)-1H-pyrazol-5-yl]boronic acid
B-[1-(1-methylethyl)-1H-pyrazol-5-yl]-Boronic acid
Boronic acid, [1-(1-methylethyl)-1H-pyrazol-5-yl]-
Boronic acid, B-[1-(1-methylethyl)-1H-pyrazol-5-yl]-
[Molecular Formula]

C6H11BN2O2
[MDL Number]

MFCD11098002
[MOL File]

839714-33-9.mol
[Molecular Weight]

153.97
Chemical PropertiesBack Directory
[Boiling point ]

312.0±34.0 °C(Predicted)
[density ]

1.15±0.1 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Store in freezer, under -20°C
[form ]

solid
[pka]

8.02±0.58(Predicted)
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
[HS Code ]

2933199090
Spectrum DetailBack Directory
[Spectrum Detail]

1-Isopropylpyrazole-5-boronic Acid(839714-33-9)1HNMR
Hazard InformationBack Directory
[Synthesis]

1-Isopropylpyrazole

18952-87-9

1-Isopropylpyrazole-5-boronic Acid

839714-33-9

The general procedure for the synthesis of 1-isopropylpyrazole-5-boronic acid from 1-isopropylpyrazole was as follows: n-BuLi (17.46 g, 110 ml, 273 mM in hexane) was slowly added to a THF solution of 1-isopropyl-1H-pyrazole over a period of 30 min at -78 °C. The reaction mixture was stirred at -78 °C for 2 hours. Subsequently, a cooled solution of triisopropoxyborate (170.0 g, 909 mmol) was slowly added through a cannula over 45 minutes. The reaction mixture was slowly warmed from -50 °C to room temperature and stirred overnight. The pH of the reaction mixture was adjusted to 6-7 with 1 M HCl (170 mL). the solvent was evaporated to dryness and the resulting residue was ground with a 1:1 mixture of ethyl acetate:dichloromethane. The suspension was filtered and the solvent was evaporated in vacuo to give 1-isopropylpyrazole-5-boronic acid as a colorless solid (20.0 g, 58% yield).LCMS m/z (%) = 154 [M+H]+ (100).1H NMR (400 MHz, DMSO-d6) δ: 8.14 (s, 2H), 7.2 (s, 1H), 6.5 (s, 1H). 5.05 (m, 1H), 1.2 (d, J = 9.0Hz, 6H).

[References]

[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 1923 - 1936
[2] Patent: WO2005/12254, 2005, A1. Location in patent: Page/Page column 129
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