4-Ethoxyphenylboronic acid Chemical Properties

Melting point:

121-128 °C(lit.)

Boiling point:

317.6±44.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

8.98±0.10(Predicted)

form 

solid

color 

White to Light yellow

BRN 

3530408

InChI

InChI=1S/C8H11BO3/c1-2-12-8-5-3-7(4-6-8)9(10)11/h3-6,10-11H,2H2,1H3

InChIKey

WRQNDLDUNQMTCL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

22237-13-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

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

4-Ethoxyphenylboronic acid Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

4-Methoxybenzeneboronic acid is used for suzuki reaction.

Application

Reactant involved in Suzuki cross coupling reactions
Reactant involved in the synthesis of biologically active molecules including:
Novel modulators of survival motor neuron protein for treatment of spinal muscular atrophy
Amino-trimethoxyphenyl-aryl thiazoles for use as microtubule inhibitors and antitumor agents
Bicyclic hydroxyphenyl methanone derivatives for use as hydroxysteroid dehydrogenase inhibitors
Dual immunosuppressive and anti-inflammatory agents
Antiproliferatives via Suzuki cross-coupling / amination reactions

Synthesis

A hexane solution of butyllithium (30 mL, 1.58 M, 47 mmol) was added dropwise to a THF solution (50 mL) of 2-bromo-??,??-trifluorotoluene (9.79 g, 43.5 mmol) at -78?? C. The aryllithium was then transferred to a THF solution of B(OEt)3 (30 mL, 176 mmol) by cannulae. After stirring at this temperature for 3 hours, the resulting aryl lithium was transferred via cannula to a THF solution (100 mL) of triethyl borate (B(OEt)3, 30 mL, 176 mmol) (aryl lithium may be unstable at higher temperatures. We recommend making the transfer as soon as possible). Warm the reaction mixture to room temperature and stir overnight. Hydrochloric acid (2M, 80 mL) was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried with anhydrous sodium sulfate and then evaporated under vacuum. The desired boric acid was dissolved in hot toluene and separated from the toluene-insoluble residue. The combined toluene solutions were evaporated and the remaining solid was recrystallized from toluene to give 4-ethoxyphenylboronic acid in 6.02 g, 73% yield. Yield 16%.

4-Ethoxyphenylboronic acid(22237-13-4)Related Product Information

• 2-CHLORO-4-ETHOXYPHENYLBORONIC ACID
• (4-CHLORO-2-ETHOXYPHENYL)BORONIC ACID
• 5-CHLORO-2-ETHOXYPHENYLBORONIC ACID
• 3,5-DIMETHYL-4-ETHOXYPHENYLBORONIC ACID
• 3-CHLORO-4-ETHOXYPHENYLBORONIC ACID
• 2,3-Difluoro-4-ethoxyphenylboronic acid
• 6-Bromo-2-chloro-3-ethoxyphenylboronic acid
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• 2,5-Dimethyl-4-ethoxyphenylboronic acid
• 2-Bromo-6-ethoxyphenylboronic acid
• 3-Ethoxyphenylboronic Acid (contains varying amounts of Anhydride),3-Ethoxyphenylboronic acid ,98%,3-ETHOXYPHENYLBORONIC ACID,M-ETHOXYPHENYLBORONIC ACID
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• 2,3-Difluoro-6-ethoxyphenylboronic acid
• 5-Fluoro-2-(trifluoroethoxy)phenylboronicacid
• Phenylboronic acid
• 3-BROMO-2-ETHOXYPHENYLBORONIC ACID
• 2,6-DIFLUORO-3-ETHOXYPHENYLBORONIC ACID
• 5-FORMYL-2-ETHOXYPHENYLBORONIC ACID