2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL Chemical Properties

Boiling point:

282 °C(lit.)

Density 

1.05 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.506(lit.)

Flash point:

230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Insoluble in water

form 

liquid

pka

10.17±0.35(Predicted)

color 

pale yellow

CAS DataBase Reference

269409-97-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

No

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL Usage And Synthesis

Chemical Properties

pale yellow to brown liquid

Uses

Reactant involved in:

• Synthesis of indolo-fused heterocyclic inhibitors of polymerase enzyme of hepatitis C
• Studies of pi-interactions, electronic structure and transient UV absorption of subphthalocyanine-borate-bridged ferrocene-fullerene conjugates
• Synthesis of subphthalocyanine and fused-ring nicotine derivatives
• Suzuki-Miyaura coupling-triflation sequence, reduction and salt formation for synthesis of hydroxylated oligoarene phosphines

Uses

2-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)phenol can be widely used in Suzuki coupling chemistry.

Synthesis

GENERAL PROCEDURE: To a solution of o-aminophenol (0.5 mmol, 1.0 eq.) in methanol (1.0 mL) was added hydrochloric acid (0.5 mL, 1.5 mmol, 3.0 eq.) followed by water (0.5 mL). The mixture was stirred for 2 minutes and then sodium nitrite solution (0.25 mL) was added. Sodium nitrite solution was prepared by dissolving 35 mg of sodium nitrite in water (0.25 mL). The mixture was stirred at 0-5°C for 30 minutes, followed by the addition of a methanol (1.0 mL) solution of pinacol ester of bisboronic acid (2,381 mg, 1.5 mmol, 3.0 equiv). The reaction mixture was stirred for 60 minutes. Upon completion of the reaction, it was diluted with water (10 mL) and then extracted with dichloromethane (50 mL, 3 times). The organic layers were combined, washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, concentrated and the crude product was purified by fast chromatography to give 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol.

References

[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
[2] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933

2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL(269409-97-4)Related Product Information

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• 2-(5-[1,3]DIOXOLAN-2-YL-2,4-DIMETHOXY-PHENYL)-BORONIC ACID PINACOL ESTER
• 2-(TRIFLUOROMETHOXY)PHENYLBORONIC ACID, PINACOL ESTER
• 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER
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