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761446-44-0

761446-44-0 Structure

761446-44-0 Structure
IdentificationMore
[Name]

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
[CAS]

761446-44-0
[Synonyms]

1-METHYL-1H-PYRAZOLE-4-BORONIC ACID PINACOL ESTER
1-METHYL-4-1H-PYRAZOLEBORONIC ACID, PINACOL ESTER
1-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-1H-PYRAZOLE
1-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE
1-METHYLPYRAZOLE-4-BORONIC ACID PINACOL ESTER
1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 97+%
1-Methyl-4-(4,4,5,5-Tetramethy
1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-
1-METHYL-4-PYRAZOLEBORONIC ACID PINACOL ESTER
1-METHYL-4-(4,4,5,5-TERAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE
1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-
1-Methyl-4-pyrazoleboronic acid pinacol ester, 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
1-Methyl-4-(4,4,5-trimethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
[EINECS(EC#)]

616-293-9
[Molecular Formula]

C10H17BN2O2
[MDL Number]

MFCD03789259
[Molecular Weight]

208.07
[MOL File]

761446-44-0.mol
Chemical PropertiesBack Directory
[Appearance]

White to light yellow crystal powde
[Melting point ]

59-64 °C(lit.)
[Boiling point ]

308.3±15.0 °C(Predicted)
[density ]

1.05±0.1 g/cm3(Predicted)
[storage temp. ]

Refrigerator (+4°C)
[solubility ]

Chloroform (slightly), Methanol (Slightly)
[form ]

Crystals
[pka]

2.09±0.10(Predicted)
[color ]

Off-white to yellow
[Water Solubility ]

Slightly soluble in water.
[InChI]

InChI=1S/C10H17BN2O2/c1-9(2)10(3,4)15-11(14-9)8-6-12-13(5)7-8/h6-7H,1-5H3
[InChIKey]

UCNGGGYMLHAMJG-UHFFFAOYSA-N
[SMILES]

N1(C)C=C(B2OC(C)(C)C(C)(C)O2)C=N1
[CAS DataBase Reference]

761446-44-0(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338-P280a-P304+P340-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
[Hazard Codes ]

Xn,F,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[Hazard Note ]

Irritant/Flammable
[TSCA ]

No
[HazardClass ]

IRRITANT
[HS Code ]

29349900
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Tetrahydrofuran-->Potassium hydroxide-->n-Butyllithium-->Iodomethane-->Trimethyl borate-->Methyl bromide-->Pinacol-->5A molecular sieve-->4-Bromopyrazole-->4-Iodo-1-methyl-1H-pyrazole-->4-Bromo-1-methylpyrazole-->4-Chloro-1-methylpyrazole-->1-Methyl-1H-pyrazole-4-boronic acid-->2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-->4-Pyrazoleboronic acid pinacol ester
[Preparation Products]

1-Methyl-1H-pyrazole-5-boronic acid pinacol ester-->7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline-->1-(2,2-difluoroethyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Hazard InformationBack Directory
[Chemical Properties]

White to light yellow crystal powde
[Uses]

1-Methyl-4-pyrazole boronic acid pinacol ester is a reagent used for:Suzuki-Miyaura cross-coupling reactions1,2,3• ;Transesterification reactions4Reagent used for preparation of• ;Aminothiazoles as γ-secretase modulators5• ;Amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy6• ;Pyridine derivatives as TGF-β1 and activin A signalling inhibitors7• ;MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer8.
[Uses]

suzuki reaction
[Synthesis]

To the solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.40 g, 2.06 mmol) in THF (10 mL) was added NaH (0.1.00 g, 4.12 mmol) followed by methyl iodide (0.25 mL, 4.12 mmol) at 0° C and the reaction mixture was stirred at ambient temperature for 4 hr. The reaction was quenched with saturated NH4Cl solution (20 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate, and distilled under reduced pressure to obtain 1-Methyl-4-pyrazole boronic acid pinacol ester.
[References]

[1] Patent: WO2018/93569, 2018, A1. Location in patent: Page/Page column 189
[2] Patent: WO2009/155527, 2009, A2. Location in patent: Page/Page column 137-138
[3] Patent: WO2005/85227, 2005, A1. Location in patent: Page/Page column 90-91
Spectrum DetailBack Directory
[Spectrum Detail]

1-Methyl-4-pyrazole boronic acid pinacol ester(761446-44-0)1HNMR
1-Methyl-4-pyrazole boronic acid pinacol ester(761446-44-0)1HNMR
1-Methyl-4-pyrazole boronic acid pinacol ester(761446-44-0)FT-IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 97+%(761446-44-0)
[Sigma Aldrich]

761446-44-0(sigmaaldrich)
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