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402503-13-3

402503-13-3 Structure

402503-13-3 Structure
IdentificationBack Directory
[Name]

2-(BENZOFURAN-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
[CAS]

402503-13-3
[Synonyms]

Benzo[b]furan-2-boronicacidpinacolester
Benzofuran-2-boronic acid,pinacol ester
BENZOFURAN-2-YLBORONIC ACID PINACOL ESTER
Benzo[b]furan-2-boronicacidpinacolester96%
Benzo[b]furan-2-boronic acid pinacol ester 96%
2-(BENZOFURAN-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
Benzofuran, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
[EINECS(EC#)]

941-104-4
[Molecular Formula]

C14H17BO3
[MDL Number]

MFCD11870258
[MOL File]

402503-13-3.mol
[Molecular Weight]

244.09
Chemical PropertiesBack Directory
[Boiling point ]

340.0±15.0 °C(Predicted)
[density ]

1.10±0.1 g/cm3(Predicted)
[storage temp. ]

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

solid
[color ]

Off-white to light yellow
[InChI]

InChI=1S/C14H17BO3/c1-13(2)14(3,4)18-15(17-13)12-9-10-7-5-6-8-11(10)16-12/h5-9H,1-4H3
[InChIKey]

GVWNFCUCNAWDNO-UHFFFAOYSA-N
[SMILES]

O1C2=CC=CC=C2C=C1B1OC(C)(C)C(C)(C)O1
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2932990090
Spectrum DetailBack Directory
[Spectrum Detail]

2-(BENZOFURAN-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(402503-13-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

Benzofuran

271-89-6

Pinacolborane

25015-63-8

2-(BENZOFURAN-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

402503-13-3

General procedure for the synthesis of benzofuran-2-boronic acid pinacol esters from 2,3-benzofuran and pinacolborane: According to the reaction scheme for the boronation of Example 9-aromatic five-membered heterocyclic rings (Fig. 2a), cobalt complex (0.01 mmol, selected from 1-4), 2-methylfuran (1 mmol), and pinacolborane (1 mmol) were added to a scintillation vial fitted with magnetic stirring bar. The reaction process was monitored by analyzing an aliquot of the mixture by GC-FID. The reaction mixture was stirred at room temperature until the reaction was complete and subsequently quenched by exposure to air. The resulting solid was dissolved in CDCl3 and filtered through a Pasteur pipette fitted with a silicone stopper, followed by 1H and 13C NMR spectroscopy without further purification. Depending on the experimental requirements, the above reaction can also be carried out in 2 ml of tetrahydrofuran (THF). Figure 2a illustrates the percentage conversion of cobalt complexes 1-4, with the values in parentheses being the isolated yields. In addition, Figure 2b describes in detail the results of other boronation products achieved using cobalt complexes 2 and 3 under the same reaction conditions.

[References]

[1] Chemical Communications, 2003, # 23, p. 2924 - 2925
[2] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4133 - 4136
[3] Patent: WO2015/89119, 2015, A1. Location in patent: Page/Page column 34
[4] Chemical Communications, 2003, # 23, p. 2924 - 2925
[5] ACS Catalysis, 2018, vol. 8, # 6, p. 5017 - 5022
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