4-(Methylsulfonyl)phenol Chemical Properties

Melting point:

90-95 °C

Boiling point:

272.52°C (rough estimate)

Density 

1.3692 (rough estimate)

refractive index 

1.5151 (estimate)

RTECS 

SM1530000

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO, Methanol

form 

Powder

pka

pK1:7.83 (25°C)

color 

Tan to pink-brown

Water Solubility 

slight

BRN 

1866322

LogP

0.886 (est)

CAS DataBase Reference

14763-60-1(CAS DataBase Reference)

NIST Chemistry Reference

4-(Methylsulfonyl)phenol(14763-60-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

24/25-26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29309090

MSDS

• Language:English Provider:4-Methylsulfonylphenol
• Language:English Provider:ACROS

4-(Methylsulfonyl)phenol Usage And Synthesis

Chemical Properties

Tan to pink-brown powder

Uses

4-(Methylsulfonyl)phenol is a reagent in the synthesis of pyrazolo[3,4-d]pyrimidine derivatives as GPR119 agonists. Also a reagent in the synthesis of novel 2-(pyridine-2-yl)-1H-benzimidazole derivatives as potent glucokinase activators.

Reactions

The reaction of 4-(methylsulfonyl)phenol (17.2 g, 100.0 mmol) with p-Toluenesulfonic anhydride as outlined in the general procedure provided 4-(methylsulfonyl)phenyl 4-methylbenzenesulfonate (26.1 g, 81%).

Synthesis

Step 2. Synthesis of 4-(methylsulfonyl)phenol Oxone (0.99 g, 6.5 mmol) was added batchwise to a solution of 4-(methylthio)phenol (0.50 g, 3.2 mmol) in ethanol (10.0 mL). Subsequently, water (10.0 mL) was added at room temperature. The reaction mixture was stirred for 18 h, after which it was partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under vacuum to afford 4-(methylsulfonyl)phenol as a semi-solid (0.60 g, 96% yield). LCMS calculated value C7H9O3S ([M + H]+): m/z = 173.0; measured value: 173.0.

References

[1] Patent: WO2015/164480, 2015, A1. Location in patent: Page/Page column 106; 107
[2] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5388 - 5391
[3] Green Chemistry, 2014, vol. 16, # 4, p. 2190 - 2196
[4] Journal of the Indian Chemical Society, 1982, vol. 59, # 1, p. 52 - 54
[5] Patent: EP1598349, 2005, A1. Location in patent: Page/Page column 127

4-(Methylsulfonyl)phenol(14763-60-1)Related Product Information

• Bis(4-hydroxyphenyl) Sulfone
• 4,4'-BIS(3-AMINOPHENOXY)DIPHENYL SULFONE
• BIS(4-HYDROXY-3,5-DIMETHYLPHENYL) SULFONE
• 4,4'-Sulphonylbis(2,6-dibromophenol)
• Bis[4-(4-aminophenoxy)phenyl]sulfone
• 4-METHOXYPHENYLMETHYLSULFONE
• 4-(Methylsulfonyl)phenol
• REACTIVE VIOLET 5
• 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone
• 4-(methylsulphonyl)-2-nitrophenol
• 3-AMINO-4-METHOXYPHENYL ETHYL SULFONE
• 2-AMINO-4-(ETHYLSULFONYL)PHENOL
• 2-PROPANONE, 1-[(4-METHOXYPHENYL)SULFONYL]-
• P-FLUOROPHENYL-P-METHOXYPHENYL SULFONE
• ETHYL 2-[(4-METHOXYPHENYL)SULFONYL]ACETATE
• 4-((4-[(3-CHLORO-2,2-DIMETHYLPROPANOYL)OXY]-3,5-DIMETHYLPHENYL)SULFONYL)-2,6-DIMETHYLPHENYL 3-CHLORO-2,2-DIMETHYLPROPANOATE
• AKOS BBS-00002840