ChemicalBook CAS DataBase List 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesis

8synthesis methods

Product Name:2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS Number:1195-66-0
Molecular formula:C7H15BO3
Molecular Weight:158

124-38-9

25015-63-8

10221-56-4

1195-66-0

The general procedure for the synthesis of 2,2'-oxybis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) and 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane from carbon dioxide and pinacolborane was as follows: a solution of (PhPSiP)Ni(η3-C8H13) (1.0 mg, 0.0014 mmol) and 1 ,3,5-trimethoxybenzene (11.5 mg, 0.068 mmol) were added to a J.YY NMR tube and the solution was frozen. After cooling, a layer of pinacolborane (9.9 μL, 0.068 mmol) was added. On a double Schlenk line, the headspace was evacuated and passed through 1 atm of CO2 at room temperature.After 15 min, almost complete depletion of pinacolborane was observed, along with the appearance of three major products. The products were identified by comparison with those reported by Sabo-Etienne.After 15 min, products a, b, and c were present in a 61:5:34 ratio with unreacted pinacolborane. However, the product c was gradually consumed over time, and after 12 h, all pinacolborane was consumed, leaving only traces of product c in the reaction mixture.The product integrals showed the presence of 13% 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborole pentacyclic, 85% 2,2'-oxybis(4,4,5,5-tetramethyl-1,3,2-dioxaborole heterocyclopentane) and a small amount of unidentified by-products. In addition, a peak corresponding to formaldehyde at 8.72 ppm was observed.

76-09-5 Synthesis

76-09-5
396 suppliers
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121-43-7
385 suppliers
$13.00/25mL

1195-66-0
189 suppliers
$5.00/1g

Yield:1195-66-0 90%

Reaction Conditions:

for 6 h;Inert atmosphere;Reflux;

Steps:

Synthesis of 2-methoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane
Synthesis of 2-methoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane A flask equipped with a reflux condenser, stirrer, an inert gas inlet and a thermocouple set in heating mantle was charged with trimethyl borate and pinacol under positive pressure of nitrogen. The resulting mixture was heated at reflux for 6 hours. The mixture was cooled to ambient temperatures and transferred to a flask with a Vigreux column. The mixture was distilled at atmospheric pressure to afford 2-methoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (bp 159° C.) in high yield (90%). ¹H NMR (400 MHz, CDCl₃): δ 3.41 (m, 3H), 1.11 (m, 12H). ¹¹B NMR (128.3 MHz, CDCl₃): δ 22.2. ¹³C NMR (100.6 MHz, CDCl₃): δ 82.7, 52.6, 24.6.

References:

Anderson Development Company US2012/289733, 2012, A1 Location in patent:Page/Page column 4

FullText

124-38-9
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25015-63-8
223 suppliers
$22.39/5G

10221-56-4 Synthesis

10221-56-4
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1195-66-0
189 suppliers
$5.00/1g

References

616-38-6 Synthesis