2-Methoxy-5-methylphenylboronic acid Chemical Properties

Melting point:

92-97 °C (lit.)

Boiling point:

342.0±52.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in methanol.

form 

powder to crystal

pka

8.65±0.58(Predicted)

color 

White to Almost white

CAS DataBase Reference

127972-00-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-60-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

2-Methoxy-5-methylphenylboronic acid Usage And Synthesis

Chemical Properties

White solid

Uses

Reactant for:

• Coupling reactions
• Preparation of selective quinazolinyl-phenol inhibitors of CHK1 as potential antitumors and radioprotectants
• Rh-catalyzed asymmetric arylation of aldehydes
• Stereoselective hydroarylation reactions
• Suzuki-Miyaura cross-coupling

Uses

suzuki reaction

Synthesis

To a solution of 2-bromo-1-methoxy-4-methylbenzene (1.39 g, 15 mmol) in tetrahydrofuran (THF) was slowly added n-butyllithium (15 mmol) dropwise under nitrogen protection and -78 °C. The solution was stirred for 1 h. The solution was then mixed with tetramethyl borate (100 mL). After maintaining -78 °C and stirring for 1 h, the solution was transferred to a solution of THF (100 mL) containing trimethyl borate (15 mmol). The reaction mixture was gradually warmed to room temperature and stirred continuously for 4 hours. Subsequently, the reaction mixture was poured into 3N hydrochloric acid (125 mL) and extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give the yellowish white solid product 2-methoxy-5-methylphenylboronic acid (2.2 g, 89% yield). The product was characterized by 1H NMR (300 MHz, d6-DMSO): δ 7.6 (s, 1H), 7.38 (d, J = 2.3 Hz, 1H), 7.19 (dd, J = 8.4 Hz, 2.3 Hz, 1H), 6.87 (d, J = 8.4 Hz, 1H), 3.78 (s, 3H), 2.2 (s, 3H).

References

[1] Patent: US2004/19190, 2004, A1. Location in patent: Page 24
[2] Patent: US5688808, 1997, A
[3] Patent: US5693646, 1997, A
[4] Patent: US5688810, 1997, A
[5] Patent: US5693647, 1997, A

2-Methoxy-5-methylphenylboronic acid(127972-00-3)Related Product Information

• 3-(METHOXYMETHOXY)BENZALDEHYDE
• 4-Tolylboronic acid
• 4-Methoxyphenylboronic acid
• Anisole
• p-Anisaldehyde
• 4-Methoxybenzoic acid
• (4-METHOXYPHENYL)-BORANE
• Phenylboronic acid
• 3-Methoxyacetophenone
• (Trifluoromethoxy)benzene
• 4'-Methoxyacetophenone
• Ascoric Acid
• 3-BROMO-2-BUTOXY-5-METHYLPHENYLBORONIC &
• 3-BROMO-5-METHYL-2-PROPOXYPHENYLBORONIC&
• 2-ISOPROPOXY-5-METHYLPHENYLBORONIC ACID
• 5-METHYL-2-PROPOXYPHENYLBORONIC ACID
• 3-BROMO-2-ETHOXY-5-METHYLPHENYLBORONIC &
• 2-METHOXY-5-TRIFLUOROMETHYLPHENYLBORONIC ACID