2,6-Dimethoxyphenylboronic acid Chemical Properties

Melting point:

110-112 °C (lit.)

Boiling point:

372.8±52.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.58±0.58(Predicted)

form 

Powder

color 

White to beige

BRN 

3032352

InChI

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

InChIKey

BKWVXPCYDRURMK-UHFFFAOYSA-N

SMILES

B(C1=C(OC)C=CC=C1OC)(O)O

CAS DataBase Reference

23112-96-1(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:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,6-Dimethoxyphenylboronic acid Usage And Synthesis

Chemical Properties

white to beige powder

Uses

2,6-Dimethoxyphenylboronic acid can be used as a reagent in:
The palladium-catalyzed Suzuki-Miyaura coupling reaction to construct carbon-carbon bond.
The synthesis of 2H-imidazo[1,5-a]pyridin-4-ium bromides, which are utilized as precursors for the preparation of N-heterocyclic carbene ligands.
The preparation of monosubstituted benzothiazoloquinazolinones as potential monoamine oxidases inhibitors.
Reactant for:
Suzuki-Miyaura reactions

Synthesis

The general procedure for the synthesis of 2,6-dimethoxyphenylboronic acid from trimethyl borate and m-phenylene dimethyl ether was as follows: 41.5 g (0.3 mol) of 1,3-dimethoxybenzene and 170 g of THF were added to a dry 1L three-neck flask. The reaction system was cooled to -30~-40°C under nitrogen protection and stirred. 240 ml (0.6 mol) of n-butyllithium in hexane solution was added slowly dropwise. After the dropwise addition, the reaction system was slowly warmed to 10~30°C and maintained at this temperature for 1 hour. Subsequently, the system was again cooled to -30~-40 °C and 62.4 g (0.6 mol) of trimethyl borate was slowly added dropwise. After the dropwise addition was completed, the reaction was maintained at this temperature for 1 hour. After the reaction was completed, 148 g of concentrated hydrochloric acid and 150 g of water were added to the system and stirred at 20-30 °C for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure until no solvent evaporated. The residue was dissolved in 200 g of water and stirred for 20 min, followed by filtration using a Brinell funnel to give 45 g of white solid product in 90.0% yield. The product was analyzed by gas chromatography and the purity was 99.0%.

References

[1] Patent: WO2004/24738, 2004, A1. Location in patent: Page/Page column 13-14
[2] Patent: CN105348240, 2016, A. Location in patent: Paragraph 0059; 0060
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4664 - 4668
[4] Organic Letters, 2012, vol. 14, # 16, p. 4250 - 4253
[5] Patent: KR2016/90242, 2016, A. Location in patent: Paragraph 0162; 0163; 0164; 0165; 0166; 0167; 0168

2,6-Dimethoxyphenylboronic acid(23112-96-1)Related Product Information

• (4-METHOXYPHENYL)-BORANE
• 1,1-Dimethoxyethane
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• Phenylboronic acid
• Dimethyldimethoxysilane
• Diphenyldimethoxysilane
• 3,5-Dimethylphenylboronic acid
• Dibutyl phthalate
• Dimethoxymethane
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• 2,4,6-TRIMETHOXYBENZENEBORONIC ACID
• 4-CHLORO-2,6-DIMETHOXY PHENYLBORONIC ACID
• (2,3,6-TRIMETHOXY)BENZENEBORONIC ACID
• 2-ISOPROPOXY-6-METHOXYPHENYLBORONIC ACID
• 3,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER
• 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER
• 2,5-Dimethoxyphenylboronic acid