ChemicalBook > CAS DataBase List > 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester

2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester

Product Name
2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester
CAS No.
710348-69-9
Chemical Name
2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester
Synonyms
2-Oxo-2,3-dihydro-1H-benzoiMidazole-5-boronic acid;2-Hydroxybenzimidazole-5-boronic acid, pinacol ester;2-Oxo-2,3-dihydrobenzimidazole-5-boronic Acid Pinacol Ester;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydrob...;2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzo[d]imidazol-2-ol;2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester;5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one;5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydrobenzimidazol-2-one;5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benziMidazol-2-one
CBNumber
CB91486464
Molecular Formula
C13H17BN2O3
Formula Weight
260.1
MOL File
710348-69-9.mol
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2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester Property

storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
form 
solid
color 
grey
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Safety

WGK Germany 
3
HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
BML00181
Product name
2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester
Purity
Aldrich
Packaging
1g
Price
$475
Updated
2025/07/31
TRC
Product number
H949558
Product name
2-Hydroxybenzimidazole-5-boronicacid,pinacolester
Packaging
25mg
Price
$45
Updated
2021/12/16
AK Scientific
Product number
X0959
Product name
2,3-Dihydro-2-oxo-1H-benzimidazole-5-boronicacid,pinacolester
Packaging
250mg
Price
$119
Updated
2021/12/16
SynQuest Laboratories
Product number
8H60-1-V2
Product name
2,3-Dihydro-2-oxo-1H-benzimidazole-5-boronic acid, pinacol ester
Packaging
250mg
Price
$180
Updated
2021/12/16
SynQuest Laboratories
Product number
8H60-1-V2
Product name
2,3-Dihydro-2-oxo-1H-benzimidazole-5-boronic acid, pinacol ester
Packaging
1g
Price
$360
Updated
2021/12/16
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2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester Chemical Properties,Usage,Production

Synthesis

39513-26-3

73183-34-3

710348-69-9

5-Bromo-1,3-dihydrobenzimidazol-2-one (20.0 g, 93.9 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF, 150 mL) purged with argon. To this solution was sequentially added bis(pinacolato)diboron (28.6 g, 113 mmol), potassium acetate (KOAc, 27.6 g, 282 mmol), and a 1:1 complex of dichlorobis(triphenylphosphine)palladium(II) (PdCl2(DPPF), 7.67 g, 9.40 mmol) with dichloromethane (CH2Cl2). The reaction mixture was heated to 95 °C and kept overnight under mechanical stirring. After completion of the reaction, it was cooled to room temperature and diluted with brine (500 mL) and ethyl acetate (EtOAc, 750 mL). The mixture was filtered to remove the dark brown solid and the solid portion was washed well with ethyl acetate. The organic layer was separated, washed with water (3 x 500 mL), subsequently dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The crude product was washed with dichloromethane/hexane (1:1) to afford the target product 2-oxo-2,3-dihydro-1H-benzimidazole-5-boronic acid pinacol ester (10.9 g, 44% yield). Thin layer chromatography (TLC) Rf = 0.52 (silica gel plate, unfolding reagent: dichloromethane/methanol = 85:15); melting point 313-315 °C (decomposition); 1H NMR (300 MHz, DMSO-d6) δ 1.27 (s, 12H), 6.92 (d, J = 7.7 Hz, 1H), 7.17 (s, 1H), 7.28 (d, J = 7.7 Hz, 1H), 10.62 (s, 1H), 10.74 (s, 1H); APCI MS m/z 261 [C13H17BN2O3 + H]+; HPLC purity 98.3%, retention time (tR) = 18.3 min; Calculated values for elemental analysis (C13H17BN2O3): C, 57.07; H, 6.82; N. Measured values: C, 56.69; H, 6.44; N, 10.21. HPLC conditions: Waters Symmetry C18 column (4.6 mm × 250 mm); mobile phase: water/acetonitrile (95:5 to 0:100 gradient elution); flow rate 1.0 mL/min (25 min); detection wavelength 254 nm.

References

[1] Patent: WO2004/52847, 2004, A2. Location in patent: Page 298
[2] Patent: WO2016/176449, 2016, A1. Location in patent: Page/Page column 94; 95; 97
[3] Patent: WO2007/80382, 2007, A1. Location in patent: Page/Page column 133

2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester Preparation Products And Raw materials

Raw materials

Preparation Products

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2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester Suppliers

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View Lastest Price from 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester manufacturers

Career Henan Chemical Co
Product
2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester 710348-69-9
Price
US $3.00/KG
Min. Order
1KG
Purity
96%-99%
Supply Ability
500kg
Release date
2020-03-06

710348-69-9, 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol esterRelated Search:

1-(4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL)UREA 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid, pinacol ester 3,4-DIAMINOPHENYLBORONIC ACID, PINACOL ESTER N-[3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]FORMAMIDE

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  • 710348-69-9