4-METHOXY-2-METHYLPHENYLBORONIC ACID

4-METHOXY-2-METHYLPHENYLBORONIC ACID Property

Melting point:

169-174 °C (lit.)

Boiling point:

327.1±52.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

9.03±0.58(Predicted)

form 

Crystalline Solid

color 

White

Water Solubility 

Insoluble in water.

BRN 

8111222

InChI

InChI=1S/C8H11BO3/c1-6-5-7(12-2)3-4-8(6)9(10)11/h3-5,10-11H,1-2H3

InChIKey

AMSQNQJCBXQYEX-UHFFFAOYSA-N

SMILES

B(C1=CC=C(OC)C=C1C)(O)O

CAS DataBase Reference

208399-66-0(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

4-METHOXY-2-METHYLPHENYLBORONIC ACID Chemical Properties,Usage,Production

Uses

4-Methoxy-2-Methylphenylboronic Acid is a useful research chemical.

Chemical Properties

White solid

Uses

Reactant for preparation of biologically active molecule preparation of hydroxyphenylnaphthols as 17?-hydroxysteroid dehydrogenase Type 2 inhibitors

Uses

suzuki reaction

Synthesis

4-Methoxy-2-methylphenylboronic acid was synthesized as follows: 4-bromo-3-methylanisole (10 g, 0.050 mol) was used as starting material, and reacted with n-butyllithium (24 mL of 2.5 M hexane solution, 0.055 mol) under anhydrous and anaerobic conditions at a low temperature (-78°C) to generate the corresponding aryl lithium intermediate. Subsequently, triisopropyl borate (57.7 mL, 47.02 g, 0.25 mol) was added to the reaction system, slowly warmed to room temperature and stirred overnight. Upon completion of the reaction, the crude product was obtained by acidic hydrolysis treatment and purified to give 5.7 g of 4-methoxy-2-methylphenylboronic acid white solid in 69% yield. The product was characterized by mass spectrometry (ESI), m/z 313 (2M-H2O-H)-.

References

[1] Organic Letters, 2001, vol. 3, # 26, p. 4263 - 4265
[2] Patent: US2003/181519, 2003, A1