Product Name

  • Name

    Rofecoxib

  • EINECS 803-260-0
  • CAS No. 162011-90-7
  • Article Data38
  • CAS DataBase
  • Density 1.333 g/cm3
  • Solubility 9mg/L(25 oC)
  • Melting Point 207 °C
  • Formula C17H14O4S
  • Boiling Point 577.6 °C at 760 mmHg
  • Molecular Weight 314.362
  • Flash Point 303.1 °C
  • Transport Information
  • Appearance off-white (pale yellow) crystalline powder
  • Safety
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 162011-90-7 (Rofecoxib)
  • Hazard Symbols Xn
  • 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;
  • PSA 68.82000
  • LogP 3.63850

Synthetic route

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

4-(4-(methylthio)phenyl)-3-phenylfuran-2(5H)-one

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
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

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

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 30℃; for 2h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;95%
phenylacetic acid
103-82-2

phenylacetic acid

ethyl bromoacetate
105-36-2

ethyl bromoacetate

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water; ethyl acetate94%
2-bromo-1-(4-methanesulfonylphenyl)ethanone
50413-24-6

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

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

2-(diethoxyphosphino)-2-phenylacetic acid

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 30℃; for 2h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;92%
phenylacetic acid
103-82-2

phenylacetic acid

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

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

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
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
487047-31-4

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

phenylboronic acid
98-80-6

phenylboronic acid

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
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

C16H11IO2

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
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

C12H10O4

4-methanesulphonylphenylboronic acid
149104-88-1

4-methanesulphonylphenylboronic acid

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
With palladium(0)bis(tricyclohexylphosphine) In water; toluene at 100℃; for 24h; Inert atmosphere; Glovebox;45%
4-(methylsulfonyl)benzoylmethyl phenylacetate
201737-94-2

4-(methylsulfonyl)benzoylmethyl phenylacetate

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
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
103-82-2

phenylacetic acid

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

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

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / acetonitrile / 0.5 h / 25 °C
2: DBU / acetonitrile / 0.5 h / 0 °C
View Scheme
2-bromo-1-(4-methanesulfonylphenyl)ethanone
50413-24-6

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

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / acetonitrile / 0.5 h / 25 °C
2: DBU / acetonitrile / 0.5 h / 0 °C
View Scheme
(4-thiomethoxyphenyl)boronic acid
98546-51-1

(4-thiomethoxyphenyl)boronic acid

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: cesium fluoride; BnEt3NCl / PdCl2(PPh3)2 / toluene; H2O / 72 h / 20 - 25 °C
2: 85 percent / Oxone(R) / acetone; H2O / 0 - 25 °C
3: 74 percent / cesium fluoride; BnEt3NCl / PdCl2(PPh3)2 / toluene; H2O / 7 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: cesium fluoride; BnEt3NCl / PdCl2(PPh3)2 / toluene; H2O / 72 h / 20 - 25 °C
2: cesium fluoride; BnEt3NCl / PdCl2(PPh3)2 / toluene; H2O / 20 - 25 °C
3: 91 percent / Oxone(R) / acetone; H2O / 24 h / 0 - 25 °C
View Scheme
3-bromo-4-(4'-methylthiophenyl)-5H-furan-2-one
329328-49-6

3-bromo-4-(4'-methylthiophenyl)-5H-furan-2-one

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / cesium fluoride; BnEt3NCl / PdCl2(PPh3)2 / toluene; H2O / Heating
2: 91 percent / Oxone(R) / acetone; H2O / 24 h / 0 - 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 68 percent / AsPh3; CuI / Pd2(dba)3 / 1-methyl-pyrrolidin-2-one / 63 h / 80 °C
2: 80 percent / oxone; aq. Bu4NBr / CH2Cl2 / 46.5 h / 20 °C
View Scheme
3-chloro-4-(4'-methylthiophenyl)-5H-furan-2-one
487047-30-3

3-chloro-4-(4'-methylthiophenyl)-5H-furan-2-one

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / Oxone(R) / acetone; H2O / 0 - 25 °C
2: 74 percent / cesium fluoride; BnEt3NCl / PdCl2(PPh3)2 / toluene; H2O / 7 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: cesium fluoride; BnEt3NCl / PdCl2(PPh3)2 / toluene; H2O / 20 - 25 °C
2: 91 percent / Oxone(R) / acetone; H2O / 24 h / 0 - 25 °C
View Scheme
4-(Methylthio)acetophenone
1778-09-2

4-(Methylthio)acetophenone

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 100 percent / MMPP / methanol; CH2Cl2 / 3 h / 20 °C
2.1: 86 percent / Br2; AlCl3 / CHCl3 / -5 °C
3.1: Et3N / acetonitrile / 0.33 h / 25 °C
3.2: 54 percent / DBU / acetonitrile / 0.33 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid; dihydrogen peroxide; sulfuric acid / 2 h / 0 - 70 °C
2.1: acetic acid; hydrogen bromide / 0.08 h / 20 °C
2.2: 2.5 h / 25 - 58 °C
3.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 1 h
3.3: 4 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: tetra-N-butylammonium tribromide / methanol; dichloromethane
2: sodium hydroxide / water; dichloromethane
3: diisopropylamine / dimethyl sulfoxide
4: dihydrogen peroxide; sodium tungstate (VI) dihydrate / water; acetonitrile / 5.5 h / 65 - 70 °C
View Scheme
methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 82 percent / AlCl3 / CHCl3 / 1.5 h / 5 °C
2.1: 100 percent / MMPP / methanol; CH2Cl2 / 3 h / 20 °C
3.1: 86 percent / Br2; AlCl3 / CHCl3 / -5 °C
4.1: Et3N / acetonitrile / 0.33 h / 25 °C
4.2: 54 percent / DBU / acetonitrile / 0.33 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: aluminum (III) chloride / chloroform / 1.5 h / -5 - 5 °C / Cooling with ice
2.1: acetic acid; dihydrogen peroxide; sulfuric acid / 2 h / 0 - 70 °C
3.1: acetic acid; hydrogen bromide / 0.08 h / 20 °C
3.2: 2.5 h / 25 - 58 °C
4.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C
4.2: 1 h
4.3: 4 h / 60 °C
View Scheme
4-(methanesulfonyl)acetophenone
10297-73-1

4-(methanesulfonyl)acetophenone

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 86 percent / Br2; AlCl3 / CHCl3 / -5 °C
2.1: Et3N / acetonitrile / 0.33 h / 25 °C
2.2: 54 percent / DBU / acetonitrile / 0.33 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: acetic acid; hydrogen bromide / 0.08 h / 20 °C
1.2: 2.5 h / 25 - 58 °C
2.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C
2.2: 1 h
2.3: 4 h / 60 °C
View Scheme
tributylphenylstannane
960-16-7

tributylphenylstannane

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68 percent / AsPh3; CuI / Pd2(dba)3 / 1-methyl-pyrrolidin-2-one / 63 h / 80 °C
2: 80 percent / oxone; aq. Bu4NBr / CH2Cl2 / 46.5 h / 20 °C
View Scheme
3-Phenyl-2-propyn-1-ol
1504-58-1

3-Phenyl-2-propyn-1-ol

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran; cyclohexane / 19 h / 80 °C
3: 99 percent / m-CPBA / 0 - 21 °C
View Scheme
(4-methylsulfanylphenyl)magnesium chloride

(4-methylsulfanylphenyl)magnesium chloride

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran; cyclohexane / 19 h / 80 °C
3: 99 percent / m-CPBA / 0 - 21 °C
View Scheme
C16H14MgOS

C16H14MgOS

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 99 percent / m-CPBA / 0 - 21 °C
View Scheme
phenylacetic acid
103-82-2

phenylacetic acid

water
7732-18-5

water

triethylamine
121-44-8

triethylamine

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

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

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile
...Expand
phenylacetic acid
103-82-2

phenylacetic acid

triethylamine
121-44-8

triethylamine

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

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

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; acetonitrile
...Expand
2-bromo-1-(4-methylsulfanyl-phenyl)-ethanone
42445-46-5

2-bromo-1-(4-methylsulfanyl-phenyl)-ethanone

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C
2: sodium hydride / dimethyl sulfoxide / 1 h / 0 °C
3: uranyl(VI) acetate dihydrate; oxygen / water; acetonitrile; o-xylene / 20 °C / 760.05 Torr / Schlenk technique; Irradiation
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water; dichloromethane
2: diisopropylamine / dimethyl sulfoxide
3: dihydrogen peroxide; sodium tungstate (VI) dihydrate / water; acetonitrile / 5.5 h / 65 - 70 °C
View Scheme
phenylacetic acid
103-82-2

phenylacetic acid

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C
2: sodium hydride / dimethyl sulfoxide / 1 h / 0 °C
3: uranyl(VI) acetate dihydrate; oxygen / water; acetonitrile; o-xylene / 20 °C / 760.05 Torr / Schlenk technique; Irradiation
View Scheme
2-(4-(methylthio)phenyl)-2-oxoethyl 2-phenylacetate

2-(4-(methylthio)phenyl)-2-oxoethyl 2-phenylacetate

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / dimethyl sulfoxide / 1 h / 0 °C
2: uranyl(VI) acetate dihydrate; oxygen / water; acetonitrile; o-xylene / 20 °C / 760.05 Torr / Schlenk technique; Irradiation
View Scheme
Multi-step reaction with 2 steps
1: diisopropylamine / dimethyl sulfoxide
2: dihydrogen peroxide; sodium tungstate (VI) dihydrate / water; acetonitrile / 5.5 h / 65 - 70 °C
View Scheme
3-phenyltetronic acid
23782-85-6

3-phenyltetronic acid

rofecoxib
162011-90-7

rofecoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / toluene / 17 h
2: palladium(0)bis(tricyclohexylphosphine) / toluene; water / 24 h / 100 °C / Inert atmosphere; Glovebox
View Scheme
rofecoxib
162011-90-7

rofecoxib

(3S,4R)-4-(4-Methanesulfonyl-phenyl)-3-phenyl-dihydro-furan-2-one

(3S,4R)-4-(4-Methanesulfonyl-phenyl)-3-phenyl-dihydro-furan-2-one

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol; ethyl acetate under 2585.74 Torr;100%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-89-6

(5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;95%
rofecoxib
162011-90-7

rofecoxib

5-Hydroxyrofecoxib
185147-17-5

5-Hydroxyrofecoxib

Conditions
ConditionsYield
With oxygen; pyrographite In ethyl acetate92%
With hepatic enzymes; oxygen; NADPH
Multi-step reaction with 2 steps
1: NBS
2: aq. AcOH / tetrahydrofuran
View Scheme
With sodium sulfite In dimethyl sulfoxide at 60℃; for 6h; Temperature; Time;
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(2-methoxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-79-4

(5Z)-5-(2-methoxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;92%
piperonal
120-57-0

piperonal

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-((benzo[d][1,3]dioxol-5-yl)methylene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-91-0

(5Z)-5-((benzo[d][1,3]dioxol-5-yl)methylene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;91%
benzaldehyde
100-52-7

benzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-77-2

(5Z)-5-(benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;90%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(3-nitrobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-78-3

(5Z)-5-(3-nitrobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;90%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(3,4,5-trimethoxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-80-7

(5Z)-5-(3,4,5-trimethoxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;90%
vanillin
121-33-5

vanillin

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-82-9

(5Z)-5-(4-hydroxy-3-methoxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;90%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(4-methoxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-92-1

(5Z)-5-(4-methoxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;90%
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(4-cyanobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

(5Z)-5-(4-cyanobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With piperidine In methanol at 20℃; for 12h; Darkness;89%
furfural
98-01-1

furfural

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-((furan-2-yl)methylene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-81-8

(5Z)-5-((furan-2-yl)methylene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;88%
1-naphthaldehyde
66-77-3

1-naphthaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-4-(4-(methylsulfonyl)phenyl)-5-((naphthalen-1-yl)methylene)-3-phenylfuran-2(5H)-one
1448458-93-2

(5Z)-4-(4-(methylsulfonyl)phenyl)-5-((naphthalen-1-yl)methylene)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;88%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(4-fluorobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-84-1

(5Z)-5-(4-fluorobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;86%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(4-chlorobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-85-2

(5Z)-5-(4-chlorobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;85%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

rofecoxib
162011-90-7

rofecoxib

(5Z)-5-(4-hydroxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448458-83-0

(5Z)-5-(4-hydroxybenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;84%
rofecoxib
162011-90-7

rofecoxib

(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

(5Z)-5-((Z/E)-3,7-dimethylocta-2,6-dienylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
1448459-29-7

(5Z)-5-((Z/E)-3,7-dimethylocta-2,6-dienylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;80%
acetone
67-64-1

acetone

rofecoxib
162011-90-7

rofecoxib

4-(4-(methylsulfonyl)phenyl)-3-phenyl-5-(propan-2-ylidene)furan-2(5H)-one
1448458-94-3

4-(4-(methylsulfonyl)phenyl)-3-phenyl-5-(propan-2-ylidene)furan-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;70%
acetic acid methyl ester
79-20-9

acetic acid methyl ester

rofecoxib
162011-90-7

rofecoxib

5-methoxy-5-methyl-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
185147-25-5

5-methoxy-5-methyl-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With sodium carbonate In methanol at 65℃; stereoselective reaction;63%
rofecoxib
162011-90-7

rofecoxib

(2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol
179174-76-6

(2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol

Conditions
ConditionsYield
With diisobutylaluminium hydride In tetrahydrofuran at 0 - 25℃;
Stage #1: rofecoxib With diisobutylaluminium hydride In dichloromethane at -78 - 20℃;
Stage #2: With sodium hydroxide; water In dichloromethane at -78 - 20℃;
With sodium hydroxide; diisobutylaluminium hydride In dichloromethane
Stage #1: rofecoxib With diisobutylaluminium hydride In dichloromethane at -78 - 20℃;
Stage #2: With sodium hydroxide In dichloromethane; water at -78 - 20℃;
rofecoxib
162011-90-7

rofecoxib

(+/-)-5-bromo-4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one
691005-66-0

(+/-)-5-bromo-4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With N-Bromosuccinimide
With N-Bromosuccinimide; dibenzoyl peroxide In chloroform for 24h; Heating / reflux;

Rofecoxib Chemical Properties

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 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.

Rofecoxib 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.

Rofecoxib 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.

Rofecoxib 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.

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View