3,4-Dimethoxyphenylboronic acid Chemical Properties

Melting point:

245-250 °C (lit.)

Boiling point:

336.7±52.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Powder and Granules

pka

8.48±0.10(Predicted)

color 

White to light beige

Water Solubility 

25 g/L

BRN 

5334877

InChI

InChI=1S/C8H11BO4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5,10-11H,1-2H3

InChIKey

RCVDPBFUMYUKPB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

122775-35-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36/37

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

3,4-Dimethoxyphenylboronic acid Usage And Synthesis

Chemical Properties

white to light beige powder and granules

Uses

suzuki reaction

Uses

3,4-Dimethoxyphenylboronic acid can be used:

• As a substrate in the cross-coupling reaction with 5,7-dichloropyrido[4,3-d]pyrimidine catalyzed by palladium.
• As a starting material for the synthesis of buflavine 1, a natural alkaloid.
• In one of the key synthetic steps for the preparation of lipidated malarial glycosylphosphatidylinositols (GPI) disaccharide.
• To prepare 3,3″,4,4″-tetramethoxy-1,1′:4′,1″-terphenyl by reacting with 1,4-dibromobenzene using Pd catalyst.

Synthesis

GENERAL PROCEDURE: 3,4-Dimethoxyaniline (0.5 mmol, 1.0 eq.) was dissolved in methanol (1.0 mL), hydrochloric acid (0.5 mL, 1.5 mmol, 3.0 eq.) was slowly added, followed by water (0.5 mL). The reaction mixture was stirred for 2 min, then sodium nitrite solution (0.25 mL, prepared by dissolving 35 mg NaNO2 in 0.25 mL of water) was added. The reaction mixture was stirred at 0-5 °C for 30 min, followed by the addition of methanol (1.0 mL) and hydrochloric acid (135 mg, 1.5 mmol, 3.0 equiv). Stirring was continued for 60 min. Upon completion of the reaction, it was diluted with water (10 mL) and extracted with dichloromethane (50 mL, 3 times). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3,4-dimethoxyphenylboronic acid.

References

[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584

3,4-Dimethoxyphenylboronic acid(122775-35-3)Related Product Information

• 2,6-Dimethoxybenzaldehyde
• 3,5-Dimethylphenylboronic acid
• 4-Methoxyphenylboronic acid
• (4-METHOXYPHENYL)-BORANE
• Phenylboronic acid
• Dimethyldimethoxysilane
• 1,1-Dimethoxyethane
• Diphenyldimethoxysilane
• Dimethoxymethane
• 3,4,5-Trimethoxyphenylboronic acid
• 3,4-DIHYDRO-2H-1,5-BENZODIOXEPIN-7-YLBORONIC ACID
• 3,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER
• 3-CYCLOPENTYLOXY-4-METHOXYBENZENEBORONIC ACID
• 1,4-Benzodioxane-6-boronic acid
• 4-Benzyloxy-3-methoxybenzeneboronic acid
• 4-CHLORO-2,6-DIMETHOXY PHENYLBORONIC ACID
• 3,5-Dimethoxyphenylboronic acid
• 2,3,4-Trimethoxyphenylboronic acid