CAS No.162011-90-7,Rofecoxib Suppliers

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Basic Information

Molecular Structure:
CAS No.:	162011-90-7
Name:	Rofecoxib
Article Data:	38

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

Synthetic route

: 162012-30-8
4-(4-(methylthio)phenyl)-3-phenylfuran-2(5H)-one

: 162011-90-7
rofecoxib

Conditions

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%

: 2-(4-methanesulfonylphenyl)-2-oxoethyl 2-(diethoxyphosphoryl)-2-phenylacetate

: 162011-90-7
rofecoxib

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 30℃; for 2h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;	95%

: 103-82-2
phenylacetic acid

: 105-36-2
ethyl bromoacetate

: 162011-90-7
rofecoxib

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; water; ethyl acetate	94%

: 50413-24-6
2-bromo-1-(4-methanesulfonylphenyl)ethanone

: 38654-91-0
2-(diethoxyphosphino)-2-phenylacetic acid

: 162011-90-7
rofecoxib

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 30℃; for 2h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;	92%

: 103-82-2
phenylacetic acid

: 50413-24-6
2-bromo-1-(4-methanesulfonylphenyl)ethanone

: 162011-90-7
rofecoxib

Conditions

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%

: 487047-31-4
3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one

: 98-80-6
phenylboronic acid

: 162011-90-7
rofecoxib

Conditions

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%

: C16H11IO2

: 80-48-8
methyl p-toluene sulfonate

: 162011-90-7
rofecoxib

Conditions

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%

: C12H10O4

: 149104-88-1
4-methanesulphonylphenylboronic acid

: 162011-90-7
rofecoxib

Conditions

Conditions	Yield
With palladium(0)bis(tricyclohexylphosphine) In water; toluene at 100℃; for 24h; Inert atmosphere; Glovebox;	45%

: 201737-94-2
4-(methylsulfonyl)benzoylmethyl phenylacetate

: 162011-90-7
rofecoxib

Conditions

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;

: 103-82-2
phenylacetic acid

Fmoc-L-Val-(p-methylbenzhydrylamine resin): Fmoc-L-Val-(p-methylbenzhydrylamine resin)

: 162011-90-7
rofecoxib

Conditions

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

Raw Materials

98-80-6

960-16-7

Downstream Products

Total:114 Page 1 of 3 1 2 3 Next>>

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Chemistry

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

History

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.

Uses

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.

Toxicity Data With Reference

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.

Specification

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.