642622
3-Pyridineboronic acid neopentylglycol ester
97%
Synonym(s):
5,5-Dimethyl-2-(3-pyridyl)-1,3,2-dioxaborinane, Pyridine-3-boronic acid neopentylglycol ester
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About This Item
Empirical Formula (Hill Notation):
C10H14BNO2
CAS Number:
Molecular Weight:
191.03
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
solid
mp
92-96 °C (lit.)
SMILES string
CC1(C)COB(OC1)c2cccnc2
InChI
1S/C10H14BNO2/c1-10(2)7-13-11(14-8-10)9-4-3-5-12-6-9/h3-6H,7-8H2,1-2H3
InChI key
QMEKTOQBDDVVBE-UHFFFAOYSA-N
Application
3-Pyridineboronic acid neopentylglycol ester can be used as a reactant:
- To synthesize N-alkyl-3-boronopyridinium salts by reacting with corresponding alkyl halides.
- In the ruthenium-catalyzed diastereoselective C-H bond α-arylation of cyclic amines.
- To prepare 2-(3-pyridyl)benzoxazole by reacting with benzoxazole via copper-catalyzed oxidative arylation reaction.
- In the Suzuki-Miyaura cross-coupling reaction.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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sp3 C- H bond arylation directed by amidine protecting group: α-arylation of pyrrolidines and piperidines
Pastine SJ, et al.
Journal of the American Chemical Society, 128(44), 14220-14221 (2006)
Preparation of a series of N-alkyl-3-boronopyridinium halides and study of their stability in the presence of hydrogen peroxide
Karpichev Y, et al.
Central European Journal of Chemistry, 10(4), 1059-1065 (2012)
Nickel/N-Heterocyclic carbene-catalyzed Suzuki-Miyaura type cross-coupling of aryl carbamates
Ohtsuki A, et al.
The Journal of Organic Chemistry, 81(19), 9409-9414 (2016)
Copper-Catalyzed Oxidative Arylation of Heteroarenes under Mild Conditions Using Dioxygen as the Sole Oxidant
Yang F, et al.
Chemistry?A European Journal , 17(23), 6321-6325 (2011)
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