2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical Properties

Boiling point:

120°C 228mm

Density 

0.9642 g/mL at 25 °C

refractive index 

1.4096

Flash point:

108°F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

clear liquid

color 

Colorless to Almost colorless

Sensitive 

Moisture Sensitive

BRN 

2827758

InChI

InChI=1S/C7H15BO3/c1-6(2)7(3,4)11-8(9-5)10-6/h1-5H3

InChIKey

JZZJAWSMSXCSIB-UHFFFAOYSA-N

SMILES

O1C(C)(C)C(C)(C)OB1OC

CAS DataBase Reference

1195-66-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36

Safety Statements 

26

RIDADR 

1993

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

2931900090

MSDS

• Language:English Provider:2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Language:English Provider:ALFA

2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Usage And Synthesis

Uses

suzuki reaction

Uses

It is employed in the synthesis, optical, and electrochemical properties of novel copolymers on the basis of benzothiadiazole and electron-rich arene units.

Synthesis

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.

References

[1] Polyhedron, 2014, vol. 84, p. 37 - 43
[2] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8872 - 8873
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 45, p. 11343 - 11345
[4] Angew. Chem., 2012, vol. 05, # 741, p. 11505 - 11507
[5] Journal of the American Chemical Society, 2015, vol. 137, # 16, p. 5332 - 5335

2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1195-66-0)Related Product Information

• Pentaborane
• 2-CYCLOHEXYLOXY-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE
• 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane