4'-(Methylsulfonyl)acetophenone

Base Information

• Chemical Name: 4'-(Methylsulfonyl)acetophenone
• CAS No.: 10297-73-1
• Molecular Formula: C9H10O3S
• Molecular Weight: 198.243
• Hs Code.: 29144000
• European Community (EC) Number: 233-672-0
• NSC Number: 403928
• UNII: 9D65F147ZN
• DSSTox Substance ID: DTXSID70145593
• Nikkaji Number: J236.753J
• Wikidata: Q27272383
• ChEMBL ID: CHEMBL41043
• Mol file: 10297-73-1.mol

Synonyms:10297-73-1;4'-(Methylsulfonyl)acetophenone;1-(4-(Methylsulfonyl)phenyl)ethanone;4-METHYLSULFONYLACETOPHENONE;4-(Methylsulfonyl)acetophenone;1-(4-methylsulfonylphenyl)ethanone;4-methylsulphonylacetophenone;p-methylsulfonylacetophenone;4-acetylphenyl methyl sulphone;4-(methylsulphonyl)acetophenone;C9H10O3S;Ethanone, 1-[4-(methylsulfonyl)phenyl]-;1-(4-Methanesulfonyl-phenyl)-ethanone;1-(4-methanesulfonylphenyl)ethan-1-one;UNII-9D65F147ZN;1-(4-(Methylsulphonyl)phenyl)ethan-1-one;9D65F147ZN;EINECS 233-672-0;MFCD00025072;1-[4-(Methylsulfonyl)phenyl]ethanone;NSC-403928;1-[4-(methylsulfonyl)phenyl]-1-ethanone;1-[4-(methylsulfonyl)phenyl]ethan-1-one;1-[4-(methylsulphonyl)phenyl]ethan-1-one;Ethanone, 1-(4-(methylsulfonyl)phenyl)-;4'-methylsulfonylacetophenone;NSC403928;4-methanesulfonylacetophenone;4(methylsulfonyl)acetophenone;4-methylsulfonyl acetophenone;SCHEMBL28229;CHEMBL41043;4-(Methylsulfonyl) acetophenone;4`-(Methylsulfonyl)acetophenone;4\'-(Methylsulfonyl)acetophenone;DTXSID70145593;(4-methanesulphonylphenyl)-ethanone;CS-D1688;P-ACETYLPHENYL METHYL SULFONE;STL166134;AKOS001081732;4'-(Methylsulfonyl)acetophenone, 97%;AB01457;AC-6694;Ethanone, 1-(4-methylsulfonylphenyl)-;NSC 403928;1-[4-(Methylsulfonyl)phenyl]ethanone #;SY012991;AM20061182;FT-0616803;M1678;EN300-11476;1-(4-(METHYLSULFONYL)PHENYL)-ETHANONE;9W-0290;J-802121;W-108861;Q27272383;Z57046982;4 inverted exclamation mark -(Methylsulfonyl)acetophenone

Chemical Property of 4'-(Methylsulfonyl)acetophenone

Chemical Property:

• Appearance/Colour: White to slightly yellow cryst. powder or needles
• Melting Point: 126-129 °C(lit.)
• Refractive Index: 1.5250 (estimate)
• Boiling Point: 385.4 °C at 760 mmHg
• Flash Point: 242 °C
• PSA: 59.59000
• Density: 1.218 g/cm³
• LogP: 2.37350
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 198.03506535
• Heavy Atom Count: 13
• Complexity: 279

Purity/Quality:

98.00% ^*data from raw suppliers

4-(Methylsulfonyl)acetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(C=C1)S(=O)(=O)C
• Uses: 4-(Methylsulfonyl)acetophenone is an impurity of Etoricoxib (E934100), which is a specific inhibitor of COX-2. 4′-(Methylsulfonyl)acetophenone may be used in the synthesis of:3-(4-Methylsulfonylphenyl)-4-phenyl-2(5H)-furanone with potent apoptosis-inducing ability.Bromo-4-methylsulfonylacetophenone, an intermediate for preparing DL-threo-2-dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol.1-N-Substituted-3,5-diphenyl-2-pyrazoline derivatives, which show promising anti-inflammatory activity.

Technology Process of 4'-(Methylsulfonyl)acetophenone

There total 33 articles about 4'-(Methylsulfonyl)acetophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(4-methoxyphenyl)ethanone (100-06-1) → 4-(methanesulfonyl)acetophenone (10297-73-1)

Guidance literature:

1-(4-methoxyphenyl)ethanone; With sodium tungstate (VI) dihydrate; sodium peroxoborate tetrahydrate; In acetone; at 40 ℃;

With sulfuric acid; In water; Temperature; Solvent; Reflux;

Reference yield: 94.9%

4-Iodoacetophenone (13329-40-3) + sodium methansulfinate (20277-69-4) → 4-(methanesulfonyl)acetophenone (10297-73-1)

Guidance literature:

With copper(l) iodide; N,N-dimethyl-N-benzyl-N-(2-methacryloyloxyethyl)ammonium bromide; caesium carbonate; In chlorobenzene; at 110 ℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

Reference yield: 94.0%

4-(Methylthio)acetophenone (1778-09-2) → 1-(4-methansulfinylphenyl)ethanone (32361-73-2) + 4-(methanesulfonyl)acetophenone (10297-73-1)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; for 0.0833333h; cooling;

DOI:10.1016/j.tetlet.2005.04.058

upstream raw materials:

methyl magnesium iodide

4-(methylsulfonyl)benzonitrile

4-(Methylthio)acetophenone

4-methylsulfonylbenzoyl chloride

Downstream raw materials:

1,3,5-Tris<(4-methansulfonyl)phenyl>pentan-1,5-dion

2-bromo-1-(4-methanesulfonylphenyl)ethanone

Refernces

• 1、 Hu, Changwen,Li, Peihe,Li, Xuanyao,Lin, Zhengguo,Liu, Jinghai. "Copper(ii)-containing tungstotellurates(vi): Syntheses, structures and their catalytic performances in selective oxidation of thioethers". . p. 22515 - 22521. Retrieved 2020.
• 2、 Kamata, Keigo,Hirano, Tomohisa,Mizuno, Noritaka. "Highly efficient oxidation of sulfides with hydrogen peroxide catalyzed by [SeO4{WO(O2)2}2]2-". . p. 3958 - 3960. Retrieved 2009.
• 3、 Cheng, Zhen,Sun, Pengchao,Tang, Ailing,Jin, Weiwei,Liu, Chenjiang. "Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O2/Air". . p. 8925 - 8929. Retrieved 2019.
• 4、 Therien,Yves Gauthier,Leblanc,Leger,Perrier,Prasit,Wang. "Synthesis of Rofecoxib, (MK 0966, Vioxx 4-(4′-Methylsulfonylphenyl)-3-phenyl-2(5H)-furanone), a selective and orally active inhibitor of cyclooxygenase-2". . p. 1778 - 1779. Retrieved 2001.
• 5、 Chen, Yao-Jung,Shen, Jiun-Yi. "Activation of superoxide by boron trifluoride: Chemoselective and efficient oxidation of sulfides to sulfoxides via tetrafluorodiboronperoxide". . p. 4205 - 4208. Retrieved 2005.
• 6、 Takahashi, Eri,Kamata, Keigo,Kikukawa, Yuji,Sato, Sota,Suzuki, Kosuke,Yamaguchi, Kazuya,Mizuno, Noritaka. "Synthesis and oxidation catalysis of a Ti-substituted phosphotungstate, and identification of the active oxygen species". . p. 4778 - 4789. Retrieved 2015.
• 7、 Baskin, Jeremy M.,Wang, Zhaoyin. "An Efficient Copper Catalyst for the Formation of Sulfones from Sulfinic Acid Salts and Aryl Iodides". . p. 4423 - 4425. Retrieved 2002.
• 8、 -. "Synthetic method of etoricoxib intermediate 4 - methylsulfonyl acetophenone". Paragraph 0049-0051; 0052; 0059-0061. . Retrieved 2021/08/25.
• 9、 Li, Jin-Heng,Li, Yang,Sun, Qing,Xue, Qi,Zhang, Ting-Ting. "Electrochemical oxygenation of sulfides with molecular oxygen or water: Switchable preparation of sulfoxides and sulfones". supporting information. p. 10314 - 10318. Retrieved 2021/12/17.