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4-(Methylsulfonyl)phenol

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4-(Methylsulfonyl)phenol Basic information
Product Name:4-(Methylsulfonyl)phenol
Synonyms:4-METHANESULFONYL-PHENOL;4-(methylsulfonyl)-pheno;4-Hydroxyphenyl methyl sulfone;4-hydroxyphenylmethylsulfone;p-(methylsulfonyl)-pheno;p-(Methylsulfonyl)phenol;Phenol, 4-(methylsulfonyl)-;Phenol, p-(methylsulfonyl)-
CAS:14763-60-1
MF:C7H8O3S
MW:172.2
EINECS:632-596-9
Product Categories:
Mol File:14763-60-1.mol
4-(Methylsulfonyl)phenol Structure
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
pkapK1:7.83 (25°C)
color Tan to pink-brown
Water Solubility slight
BRN 1866322
LogP0.886 (est)
CAS DataBase Reference14763-60-1(CAS DataBase Reference)
NIST Chemistry Reference4-(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 Information
ProviderLanguage
4-Methylsulfonylphenol English
ACROS English
4-(Methylsulfonyl)phenol Usage And Synthesis
Chemical PropertiesTan to pink-brown powder
Uses4-(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.
ReactionsThe 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
4-(Methylthio)phenol

1073-72-9

4-(Methylsulfonyl)phenol

14763-60-1

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
Tag: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

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