ChemicalBook > CAS DataBase List > 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline

Product Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline
CAS No.: 1167418-13-4
Chemical Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline
Synonyms: 2-dioxaborolan-2-yl)quinoxaline;Quinoxaline-6-boronic acid picol ester;6-(tetraMethyl-1,3,2-dioxaborolan-2-yl)quinoxaline;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline;Quinoxaline, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline 97%;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline - [T4861]
CBNumber: CB42499493
Molecular Formula: C14H17BN2O2
Formula Weight: 256.11
MOL File: 1167418-13-4.mol

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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline Property

Boiling point:: 387.8±22.0 °C(Predicted)
Density: 1.123 g/mL at 25℃
refractive index: n20/D1.560
Flash point:: >110℃
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
form: liquid
pka: 0.93±0.30(Predicted)
Appearance: Light yellow to yellow Viscous Liquid
InChIKey: ZYWICCYXTGRUNM-UHFFFAOYSA-N

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Safety

Risk Statements: 36/37/38
Safety Statements: 26
WGK Germany: 3
HS Code: 2933998090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 708631
Product name: Quinoxaline-6-boronic acid pinacol ester
Purity: 97%
Packaging: 1g
Price: $137.9
Updated: 2025/07/31

Sigma-Aldrich

Product number: 708631
Product name: Quinoxaline-6-boronic acid pinacol ester
Purity: 97%
Packaging: 250mg
Price: $68
Updated: 2023/06/20

TRC

Product number: T890008
Product name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline
Packaging: 50mg
Price: $65
Updated: 2021/12/16

Apolloscientific

Product number: OR18030
Product name: Quinoxaline-6-boronic acid, pinacol ester
Packaging: 1g
Price: $144
Updated: 2021/12/16

SynQuest Laboratories

Product number: 8H60-1-3X
Product name: Quinoxaline-6-boronic acid, pinacol ester
Purity: 95.0%
Packaging: 1g
Price: $170
Updated: 2021/12/16

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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline Chemical Properties,Usage,Production

Uses

Quinoxaline-6-boronic acid pinacol ester is a common reactant of a Suzuki coupling reaction that can be used:

To prepare quinoxalin based PI3Kδ inhibitors.
As a substrate in the Cu(II) catalyzed [¹¹C]-radiocyanation of arylboronic acids.
To prepare 6-quinoxaline boronic acid, which is used as a substrate in the silver-mediated fluorination of boronic acids.

Synthesis

50998-17-9

73183-34-3

1167418-13-4

To a solution of 6-bromoquinoxaline (418 mg, 2.00 mmol, 1.00 eq.) in dioxane (10 mL) at 23 °C was sequentially added PdCl2(dppf)-CH2Cl2 (163 mg, 0.200 mmol, 0.100 eq.), bis(pinacolide)diboron (610 mg, 2.40 mmol, 1.20 eq.) and KOAc (392 mg, 4.00 mmol, 2.00 equiv). The reaction mixture was stirred at 90 °C for 1.5 h, subsequently cooled to 23 °C and concentrated in vacuum. The residue was dissolved with CH2Cl2 and filtered through a diatomaceous earth plug. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography with hexane/EtOAc (4:1, v/v) as eluent to give 500 mg of quinoxaline-6-boronic acid pinacol ester as a colorless solid (98% yield). Thin layer chromatography Rf = 0.45 (unfolding agent: hexane/EtOAc, 1:1, v/v). Nuclear magnetic resonance hydrogen spectrum (1H NMR, 500 MHz, CDCl3, 23°C) δ: 8.86-8.82 (m, 2H), 8.59 (s, 1H), 8.12 (dd, J = 8.0 Hz, 2.0 Hz, 1H), 8.06 (d, J = 8.0 Hz, 1H), 1.37 (s, 12H). Nuclear magnetic resonance carbon spectrum (13C NMR, 125 MHz, CDCl3, 23°C) δ: 145.53, 145.03, 144.37, 142.41, 137.31, 134.75, 131.90 (br), 128.44, 84.36, 24.86. high-resolution mass spectra (HRMS-FIA) m/z: [M + H]+ Calculated value 257.14558, measured value 257.14440.

References

[1] Organic Letters, 2009, vol. 11, # 13, p. 2860 - 2863
[2] Patent: WO2010/59943, 2010, A2. Location in patent: Page/Page column 86
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4735 - 4751
[4] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[5] Organic Letters, 2018, vol. 20, # 6, p. 1530 - 1533

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline Preparation Products And Raw materials

Raw materials

Preparation Products

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1167418-13-4, 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxalineRelated Search:

Quinoxaline-6-sulfonyl chloride QUINOXALINE-6-CARBALDEHYDE (6-HYDROXYMETHYL)QUINOXALINE QUINOXALINE-5-CARBOXYLIC ACID (5-METHOXY-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL)-ACETIC ACID 1-Boc-4-bromopyrazole tert-Butyl 1H-pyrazole-1-carboxylate t-Butyl 4-bromo-1-naphthalenecarboxylate 2-Quinoxalinecarboxylic acid methyl ester Quinazoline tert-Butyl Quinazoline-4-acetate Ethyl Quinazoline-4-acetate 5-Hydroxyquinoxaline QUINOXALIN-2-YLMETHANOL Boronic acid, 6-quinoxalinyl- (9CI) Quinoxaline-6-carboxylic acid methoxy-methyl-amide Quinoxalin-5-ylboronic acid pinacol ester 6-Quinazolinecarboxylic acid (9CI)

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline 97%

6-(tetraMethyl-1,3,2-dioxaborolan-2-yl)quinoxaline

2-dioxaborolan-2-yl)quinoxaline

Quinoxaline-6-boronic acid picol ester

Quinoxaline, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline - [T4861]

1167418-13-4