4-(Methylthio)phenylboronic acid Chemical Properties

Melting point:

210-214 °C (lit.)

Boiling point:

333.5±44.0 °C(Predicted)

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

8.56±0.10(Predicted)

form 

Crystalline Powder

color 

Off-white

BRN 

3247219

CAS DataBase Reference

98546-51-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36-7/9

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:4-Thioanisoleboronic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-(Methylthio)phenylboronic acid Usage And Synthesis

Chemical Properties

Off-white crystalline powder

Uses

Reactant involved in:

• Suzuki-Miyaura cross coupling reactions with 2-aryl-1-bromo-1-nitroethenes or alkynyl bromides
• Addition reactions with naphthyridine N-oxides
• Oxyarylation of Heck reaction intermediates for synthesis of THF derivatives
• Sulfoxidation reactions
• Copper-catalyzed halogenation

Synthesis

Step 1: Preparation of 4-methylthiophenylboronic acid To a tetrahydrofuran (THF) (15 mL) solution of 4-bromoanisothioether (10) (3 g, 14.8 mmol) cooled to -78 °C and stirred under nitrogen protection, n-butyllithium (n-BuLi) (10 mL) was slowly added. The mixture was warmed to room temperature and stirring was continued for 20 minutes. Subsequently, the mixture was cooled again to -78 °C and a solution of triisopropyl borate (10 mL, 17.7 mmol) in THF (10 mL) was slowly added. After stirring at -78 °C for 1 hour, the mixture was warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, it was acidified with cold 5% hydrochloric acid (HCl), diluted with water (25 mL) and extracted with ethyl acetate. The organic layers were combined, washed sequentially with brine solution (20 mL) and water (20 mL), dried over anhydrous sodium sulfate (Na2SO4) and concentrated. The resulting residue was purified by column chromatography (eluent: ethyl acetate-hexane) to afford the target product 4-methylthiophenylboronic acid (11) (170 mg, 10% yield). 1H NMR (200 MHz, CDCl3): δ 8.10 (d, J=7.9 Hz, 2H), 7.33 (d, J=7.9 Hz, 2H), 2.55 (s, 3H, SCH3), 1.56 (bs, D2O exchangeable, OH), 1.25 (s, exchangeable, OH). IR: vmax (KBr, cm-1): 3406,1594.

References

[1] Journal of Organic Chemistry, 2001, vol. 66, # 6, p. 2104 - 2117
[2] Tetrahedron Letters, 2010, vol. 51, # 52, p. 6839 - 6842
[3] Patent: US2006/128729, 2006, A1. Location in patent: Page/Page column 94
[4] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 305 - 311

4-(Methylthio)phenylboronic acid(98546-51-1)Related Product Information

• 4-Tolylboronic acid
• Thioanisole
• 4-Methoxyphenylboronic acid
• Phenylboronic acid
• Phenethylboronic acid
• 4-Aminophenylboronic acid
• 4-Hydroxyphenylboronic acid
• PHENYLMERCURIC BORATE
• 4-Formylphenylboronic acid
• 4-ISOPROPYLTHIOPHENYLBORONIC ACID
• 4-ETHYLSULFINYLPHENYLBORONIC ACID
• 4-(ISOPROPYLSULFONYLPHENYL)BORONIC ACID
• 4-(METHANESULFINYL)BENZENEBORONIC ACID
• 4-(ETHYLTHIO)BENZENEBORONIC ACID
• 4-(ETHYLSULFONYL)PHENYLBORONIC ACID
• 4-(METHYLSULFONYL)PHENYLBORONIC ACID
• 4-(Methanesulfonyl)phenylboronic acid pinacol ester
• 3-(Methylthio)phenylboronic acid