| Identification | More | [Name]
4-Methylsulfonylphenol | [CAS]
14763-60-1 | [Synonyms]
4-METHANESULFONYL-PHENOL
4-(METHYLSULFONYL)PHENOL
4-METHYLSULPHONYLPHENOL
4-(methylsulfonyl)-pheno
4-Hydroxyphenyl methyl sulfone
4-hydroxyphenylmethylsulfone
p-(methylsulfonyl)-pheno
p-(Methylsulfonyl)phenol
Phenol, 4-(methylsulfonyl)-
Phenol, p-(methylsulfonyl)-
p-Hydroxyphenyl methyl sulfone
p-hydroxyphenylmethylsulfone
4-METHANESULPHONYLPHENOL
4-METHYLSULPHONYLPHENOL 95%
4-Methylsulphonylphenol,95%
4-Mesylphenol | [EINECS(EC#)]
217-420-7 | [Molecular Formula]
C7H8O3S | [MDL Number]
MFCD00047806 | [Molecular Weight]
172.2 | [MOL File]
14763-60-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Tan to pink-brown powder | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36 | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [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 |
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