3,5-Dimethylphenylboronic acid Chemical Properties

Melting point:

261-265 °C (lit.)

Boiling point:

312.7±52.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Slightly soluble in water

form 

solid

pka

8.72±0.10(Predicted)

color 

White to Orange to Green

BRN 

7368658

InChI

InChI=1S/C8H11BO2/c1-6-3-7(2)5-8(4-6)9(10)11/h3-5,10-11H,1-2H3

InChIKey

DJGHSJBYKIQHIK-UHFFFAOYSA-N

SMILES

B(C1=CC(C)=CC(C)=C1)(O)O

CAS DataBase Reference

172975-69-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

37/39-26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

3,5-Dimethylphenylboronic acid Usage And Synthesis

Chemical Properties

off-white to light yellow crystalline powder

Uses

suzuki reaction

Uses

3,5-Dimethylphenylboronic Acid is a useful research intermediate for organic synthesis

Uses

3,5-Dimethylphenylboronic acid (DMPBA) can be used as:

• A reactant in the palladium-catalyzed Suzuki coupling reactions.
• A co-extractant in the combination with modified Aliquat 336 for the extraction of xylose, glucose, and fructose from aqueous solutions.
• A reactant to prepare penultimate methyl ester.

Synthesis

GENERAL PROCEDURE: A 1 M THF solution (375 μL, 375 μmol) of phenylmagnesium bromide (PhMgBr) was added dropwise to a tetrahydrofuran (THF, 4 mL) solution of diisopropylaminoborane (DIPAB, 863 mg, 7.5 mmol) and magnesium scrapings (Mg, 182 mg, 7.5 mmol) at room temperature. After 10 min of reaction, 30 mL of anhydrous THF was added, followed by 3,5-dimethylbromobenzene (5 mmol). The reaction mixture was cooled to 0 °C and quenched by slow addition of methanol (MeOH, 7 mL). After 1 h of reaction, the volatiles were removed under reduced pressure and the resulting solid was dissolved in a 1N hydrochloric acid/methanol (7:3, v/v) mixture. The reaction was continued for 1 h at room temperature, followed by the addition of ethyl acetate (AcOEt, 100 mL) for extraction. The organic phase was washed sequentially with 1N hydrochloric acid (30 mL) and saturated saline (3 x 30 mL). The organic phase was concentrated under reduced pressure to give the crude product, which was finally purified by recrystallization from water (H2O) to give 3,5-dimethylphenylboronic acid.

References

[1] Tetrahedron, 2019, vol. 75, # 2, p. 164 - 171

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