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CAS No.: | 162011-90-7 |
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Name: | Rofecoxib |
Article Data: | 38 |
Molecular Structure: | |
Formula: | C17H14O4S |
Molecular Weight: | 314.362 |
Synonyms: | 3-(4-Methanesulfonylphenyl)-2-phenyl-2-buten-4-olide;3-Phenyl-4-[4-(Methylsulfonyl)phenyl]-2(5H)-furanone;4-(4-(Methanesulfonyl)phenyl)-3-phenyl-5H-furan-2-one;4-[(4-Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone;Ceeoxx;Ceoxx;MK 0966;MK 966;Rhuma-cure;2(5H)-Furanone,4-[4-(methylsulfonyl)phenyl]-3-phenyl-;Vioxx; |
EINECS: | 803-260-0 |
Density: | 1.333 g/cm3 |
Melting Point: | 207 °C |
Boiling Point: | 577.6 °C at 760 mmHg |
Flash Point: | 303.1 °C |
Solubility: | 9mg/L(25 oC) |
Appearance: | off-white (pale yellow) crystalline powder |
Hazard Symbols: | Xn |
Risk Codes: | 22 |
PSA: | 68.82000 |
LogP: | 3.63850 |
4-(4-(methylthio)phenyl)-3-phenylfuran-2(5H)-one
rofecoxib
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid at 0 - 21℃; Oxidation; | 99% |
With Oxone In water; acetone at 0 - 25℃; for 24h; Product distribution / selectivity; | 95% |
With oxone In water; acetone at 0 - 25℃; for 24h; | 91% |
rofecoxib
Conditions | Yield |
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With triethylamine In N,N-dimethyl-formamide at 0 - 30℃; for 2h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; | 95% |
Conditions | Yield |
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With triethylamine In tetrahydrofuran; water; ethyl acetate | 94% |
2-bromo-1-(4-methanesulfonylphenyl)ethanone
2-(diethoxyphosphino)-2-phenylacetic acid
rofecoxib
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 0 - 30℃; for 2h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
Stage #1: phenylacetic acid With sodium hydroxide In DMF (N,N-dimethyl-formamide); water at 4℃; for 1h; Stage #2: 2-bromo-1-(4-methanesulfonylphenyl)ethanone With diisopropylamine at 45℃; for 3.5h; | 78% |
Stage #1: phenylacetic acid With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-bromo-1-(4-methanesulfonylphenyl)ethanone In N,N-dimethyl-formamide for 1h; Stage #3: With diisopropylamine In N,N-dimethyl-formamide at 60℃; for 4h; | 76% |
Stage #1: phenylacetic acid; 2-bromo-1-(4-methanesulfonylphenyl)ethanone With triethylamine In acetonitrile at 20 - 25℃; for 0.333333h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃; for 0.333333h; | 58% |
3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one
phenylboronic acid
rofecoxib
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride; bis-triphenylphosphine-palladium(II) chloride In water; toluene for 7h; Suzuki cross-coupling; Heating; | 74% |
With cesium fluoride; bis-triphenylphosphine-palladium(II) chloride; N-benzyl-N,N,N-triethylammonium chloride In water; toluene for 7h; Product distribution / selectivity; Suzuki Coupling; Heating / reflux; | 74% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium metabisulfite; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tin; potassium hydrogenphosphate trihydrate; tetrabutylammomium bromide In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere; Schlenk technique; | 59% |
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium metabisulfite; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tin; potassium hydrogenphosphate trihydrate; tetrabutylammomium bromide In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere; | 59% |
Conditions | Yield |
---|---|
With palladium(0)bis(tricyclohexylphosphine) In water; toluene at 100℃; for 24h; Inert atmosphere; Glovebox; | 45% |
4-(methylsulfonyl)benzoylmethyl phenylacetate
rofecoxib
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃; for 0.5h; | |
With diisopropylamine In DMF (N,N-dimethyl-formamide) at 45℃; for 4.25h; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Horner-Wadsworth-Emmons Olefination; |
phenylacetic acid
rofecoxib
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / acetonitrile / 0.5 h / 25 °C 2: DBU / acetonitrile / 0.5 h / 0 °C View Scheme |
Structure of Rofecoxib (CAS NO.162011-90-7):
IUPAC Name: 3-(4-Methylsulfonylphenyl)-4-phenyl-2H-furan-5-one
Molecular Formula: C17H14O4S
Molar mass: 314.3557g/mol
Density: 1.333 g/cm3
Melting Point: 207 °C
Flash Point: 303.1 °C
Boiling Point: 577.6 °C at 760 mmHg
Index of Refraction: 1.619
Vapour Pressure:2.42E-13 mmHg at 25 °C
XLogP3-AA: 2.3
H-Bond Acceptor: 4
Rotatable Bond Count: 3
Exact Mass: 314.06128
MonoIsotopic Mass: 314.06128
Topological Polar Surface Area: 60.4
Heavy Atom Count: 22
Canonical SMILES: CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
InChI: InChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,
1H3
InChIKey: RZJQGNCSTQAWON-UHFFFAOYSA-N
Product Categories: Active Pharmaceutical Ingredients; Osteoarthritis and Rheumatoid Arthritis; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals
Rofecoxib was approved by the Food and Drug Administration (FDA) on May 20, 1999, and was subsequently marketed under the brand names Vioxx, Ceoxx, and Ceeoxx.
Rofecoxib (CAS NO.162011-90-7) is a nonsteroidal anti-inflammatory drug (NSAID) that has now been withdrawn over safety concerns. It was used to treat osteoarthritis, acute pain conditions, and dysmenorrhoea.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | oral | 20mg/kg/4W-I (20mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Annals of Internal Medicine. Vol. 133, Pg. 394, 2000. |
Rofecoxib (CAS NO.162011-90-7) is also named as 3-Phenyl-4-(4-(methylsulfonyl)phenyl))-2(5H)-furanone ; 4-(4-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone ; 4-(p-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone ; CCRIS 8967 ; Ceoxx ; HSDB 7262 ; MK 0966 ; MK 966 ; MK0966 ; UNII-0QTW8Z7MCR ; Vioxx . Rofecoxib (CAS NO.162011-90-7) is off-white to pale yellow crystalline powder.