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

Boiling point:

73 °C15 mm Hg(lit.)

Density 

0.912 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.409(lit.)

Flash point:

109 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

Specific Gravity

0.912

color 

Colorless

Water Solubility 

Soluble in water.

Sensitive 

Moisture Sensitive

BRN 

1906370

InChI

InChI=1S/C9H19BO3/c1-7(2)11-10-12-8(3,4)9(5,6)13-10/h7H,1-6H3

InChIKey

MRWWWZLJWNIEEJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

61676-62-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29209090

MSDS

• Language:English Provider:Isopropyl pinacolyl borate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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

Chemical Properties

Colorless liquid

Uses

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be used as a reagent to borylate arenes and to prepare fluorenylborolane.

It can also be used in the synthesis of following intermediates for generating conjugated copolymers:

• 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl1,3,2-dioxaborolane-2-yl)dibenzosilole.
• 3,9-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-di(1-decylundecyl)indolo[3,2-b]carbazole.
• 2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene.
• 2,7-Bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9′′-heptadecanylcarbazole.

Uses

suzuki reaction

Synthesis

Step c) Preparation of isopropyl pinacol borate: triisopropyl borate (261.0 g, 1.388 mol) and pinacol (142.5 g, 1.207 mol) were added to a 20 L four-necked flask, and the mixture was heated to about 90 °C and maintained for 12 to 16 hours. The progress of the reaction was monitored by gas chromatography (GC), and the completion of the reaction was measured by a pinacol content of less than 4.0%. Upon completion of the reaction, a distillation operation was performed to collect fractions with boiling points between 174 and 178 °C to obtain the target product isopropanol pinacol borate as a colorless oil. Yields ranged from 80-90% in six 20 L batches of the operation.GC analysis showed a product purity of 87-96%, while 1H NMR analysis indicated an extremely high product purity. [The difference between GC purity and 1H NMR purity is attributed to the instability of the product under GC conditions].

References

[1] Journal of the American Chemical Society, 2001, vol. 123, # 19, p. 4617 - 4618
[2] Organic Letters, 2012, vol. 14, # 22, p. 5644 - 5647
[3] Patent: US2013/40984, 2013, A1. Location in patent: Paragraph 0482-0483
[4] Chemische Berichte, 1989, vol. 122, p. 1777 - 1782
[5] Organic Letters, 2013, vol. 15, # 18, p. 4666 - 4669

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(61676-62-8)Related Product Information

• Methyltrimethoxysilane
• Ethyl 2-(Chlorosulfonyl)acetate
• Pinacol
• ISOPROPYL LAURATE
• Diethoxydimethylsilane
• Isopropyl alcohol
• Methyl acrylate
• BUTYL OLEATE
• 1,4-Dioxane
• Bis(pinacolato)diboron
• Tris(trimethylsilyl)phosphate
• Dimethyldimethoxysilane
• Pentaerythritol triacrylate
• Methyltriethoxysilane
• Rosin pentaerythrityl ester
• Titanium tetraisopropanolate
• Pinacolborane
• Potassium chloride