Product Name

  • Name

    LUMIRACOXIB

  • EINECS 1308068-626-2
  • CAS No. 220991-20-8
  • Article Data8
  • CAS DataBase
  • Density 1.363 g/cm3
  • Solubility
  • Melting Point 139-141 °C
  • Formula C15H13ClFNO2
  • Boiling Point 395.7 °C at 760 mmHg
  • Molecular Weight 293.725
  • Flash Point 193.1 °C
  • Transport Information
  • Appearance Pale yellow solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 220991-20-8 (LUMIRACOXIB)
  • Hazard Symbols
  • Synonyms 2-[(2-Chloro-6-fluorophenyl)amino]-5-methylbenzeneaceticacid;2-[2-(2-Chloro-6-fluorophenylamino)-5-methylphenyl]acetic acid;CGS35189;COX 189;Prexige;
  • PSA 49.33000
  • LogP 4.23120

Synthetic route

1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one
332903-83-0

1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Heating;90%
With hydrogenchloride; sodium hydroxide In ethanol; water
potassium 2-iodo-5-methylphenylacetate
1234562-75-4

potassium 2-iodo-5-methylphenylacetate

2-chloro-6-fluoroaniline
363-51-9

2-chloro-6-fluoroaniline

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; copper(l) iodide; potassium carbonate at 100℃; Ullmann coupling;41%
2-chloro-6-fluoroaniline
363-51-9

2-chloro-6-fluoroaniline

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: NaH / dimethylformamide / 1 h / 0 - 4 °C
1.2: 91 percent / dimethylformamide / 20 h / 50 - 55 °C
2.1: HCl gas / ethyl acetate / 2.5 h / -5 - 0 °C
2.2: H2O / ethyl acetate / 36 h / 20 - 25 °C
3.1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C
4.1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
5.1: 82 percent / toluene / 80 - 90 °C
6.1: 80 percent / AlCl3 / 3 h / 170 °C
7.1: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
Multi-step reaction with 4 steps
1: 90 percent / t-BuONa; t-Bu3P / Pd(dba)2 / toluene / 14 h / 110 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
Multi-step reaction with 3 steps
1: 76 percent / pTsOH*H2O / toluene / 18 h / Heating
2: 76 percent / I2; DBU / xylene / 36 h / 155 °C
3: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
para-bromotoluene
106-38-7

para-bromotoluene

Mo(CO)6

Mo(CO)6

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / t-BuONa; t-Bu3P / Pd(dba)2 / toluene / 14 h / 110 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
p-toluidine
106-49-0

p-toluidine

4-hydroxybenzaldehyde-linked-Wang-resin

4-hydroxybenzaldehyde-linked-Wang-resin

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / t-BuONa; (+)-BINAP / Pd(dba)2 / toluene / 110 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-bromo-3-fluoro-chlorobenzene
309721-44-6

2-bromo-3-fluoro-chlorobenzene

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / t-BuONa; (+)-BINAP / Pd(dba)2 / toluene / 110 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: NaH / dimethylformamide / 1 h / 0 - 4 °C
1.2: 91 percent / dimethylformamide / 20 h / 50 - 55 °C
2.1: HCl gas / ethyl acetate / 2.5 h / -5 - 0 °C
2.2: H2O / ethyl acetate / 36 h / 20 - 25 °C
3.1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C
4.1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
5.1: 82 percent / toluene / 80 - 90 °C
6.1: 80 percent / AlCl3 / 3 h / 170 °C
7.1: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-chloro-6-fluorophenol
2040-90-6

2-chloro-6-fluorophenol

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: propan-2-ol / Heating
2: MeONa / methanol / 2 h / 85 °C
3: 82 percent / toluene / 80 - 90 °C
4: 80 percent / AlCl3 / 3 h / 170 °C
5: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
N-(p-tolyl)-2-chloroacetamide
16634-82-5

N-(p-tolyl)-2-chloroacetamide

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: propan-2-ol / Heating
2: MeONa / methanol / 2 h / 85 °C
3: 82 percent / toluene / 80 - 90 °C
4: 80 percent / AlCl3 / 3 h / 170 °C
5: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
N-(2-chloro-6-fluoro-phenyl)-4-methylaniline
332903-74-9

N-(2-chloro-6-fluoro-phenyl)-4-methylaniline

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 82 percent / toluene / 80 - 90 °C
2: 80 percent / AlCl3 / 3 h / 170 °C
3: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
4-(2-chloro-6-fluorophenylamino)benzonitrile
817621-48-0

4-(2-chloro-6-fluorophenylamino)benzonitrile

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: HCl gas / ethyl acetate / 2.5 h / -5 - 0 °C
1.2: H2O / ethyl acetate / 36 h / 20 - 25 °C
2.1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C
3.1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
4.1: 82 percent / toluene / 80 - 90 °C
5.1: 80 percent / AlCl3 / 3 h / 170 °C
6.1: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
4-(2-chloro-6-fluoro-phenylamino)benzoic acid ethyl ester
817621-52-6

4-(2-chloro-6-fluoro-phenylamino)benzoic acid ethyl ester

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
1-(2-chloro-6-fluoro-phenyl)-5-methyl-1,4,5,6-tetrahydro-indol-2-one
817621-77-5

1-(2-chloro-6-fluoro-phenyl)-5-methyl-1,4,5,6-tetrahydro-indol-2-one

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / I2; DBU / xylene / 36 h / 155 °C
2: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-chloro-N-(2-chloro-6-fluoro-phenyl)-N-p-tolylacetamide
332903-78-3

2-chloro-N-(2-chloro-6-fluoro-phenyl)-N-p-tolylacetamide

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / AlCl3 / 3 h / 170 °C
2: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-(2-chloro-6-fluoro-phenoxy)-N-p-tolyl-acetamide

2-(2-chloro-6-fluoro-phenoxy)-N-p-tolyl-acetamide

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: MeONa / methanol / 2 h / 85 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
4-(2-chloro-6-fluoro-phenylamino)benzimidic acid ethyl ester hydrochloride

4-(2-chloro-6-fluoro-phenylamino)benzimidic acid ethyl ester hydrochloride

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C
2: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
3: 82 percent / toluene / 80 - 90 °C
4: 80 percent / AlCl3 / 3 h / 170 °C
5: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-Amino-5-methylbenzoic acid
2941-78-8

2-Amino-5-methylbenzoic acid

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) acetate monohydrate / 1,4-dioxane / 25 °C
2: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux
3: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C
4: dimethyl sulfoxide / 1.5 h / Inert atmosphere
5: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
(2-chloro-6-fluorophenyl)boronic acid

(2-chloro-6-fluorophenyl)boronic acid

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) acetate monohydrate / 1,4-dioxane / 25 °C
2: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux
3: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C
4: dimethyl sulfoxide / 1.5 h / Inert atmosphere
5: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
C14H12Cl2FN

C14H12Cl2FN

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 1.5 h / Inert atmosphere
2: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
2-[(2-chloro-6-fluorophenyl)amino]-5-methyl-benzoic acid
619296-47-8

2-[(2-chloro-6-fluorophenyl)amino]-5-methyl-benzoic acid

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux
2: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C
3: dimethyl sulfoxide / 1.5 h / Inert atmosphere
4: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzenemethanol

2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzenemethanol

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C
2: dimethyl sulfoxide / 1.5 h / Inert atmosphere
3: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetonitrile
1403226-56-1

2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetonitrile

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
With water; barium(II) hydroxide In 1,4-dioxane for 30h; Reflux; Inert atmosphere;
1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one
332903-83-0

1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Heating;90%
With hydrogenchloride; sodium hydroxide In ethanol; water
potassium 2-iodo-5-methylphenylacetate
1234562-75-4

potassium 2-iodo-5-methylphenylacetate

2-chloro-6-fluoroaniline
363-51-9

2-chloro-6-fluoroaniline

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; copper(l) iodide; potassium carbonate at 100℃; Ullmann coupling;41%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: NaH / dimethylformamide / 1 h / 0 - 4 °C
1.2: 91 percent / dimethylformamide / 20 h / 50 - 55 °C
2.1: HCl gas / ethyl acetate / 2.5 h / -5 - 0 °C
2.2: H2O / ethyl acetate / 36 h / 20 - 25 °C
3.1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C
4.1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
5.1: 82 percent / toluene / 80 - 90 °C
6.1: 80 percent / AlCl3 / 3 h / 170 °C
7.1: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
para-bromotoluene
106-38-7

para-bromotoluene

Mo(CO)6

Mo(CO)6

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / t-BuONa; t-Bu3P / Pd(dba)2 / toluene / 14 h / 110 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-chloro-6-fluorophenol
2040-90-6

2-chloro-6-fluorophenol

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: propan-2-ol / Heating
2: MeONa / methanol / 2 h / 85 °C
3: 82 percent / toluene / 80 - 90 °C
4: 80 percent / AlCl3 / 3 h / 170 °C
5: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-chloro-6-fluoroaniline
363-51-9

2-chloro-6-fluoroaniline

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: NaH / dimethylformamide / 1 h / 0 - 4 °C
1.2: 91 percent / dimethylformamide / 20 h / 50 - 55 °C
2.1: HCl gas / ethyl acetate / 2.5 h / -5 - 0 °C
2.2: H2O / ethyl acetate / 36 h / 20 - 25 °C
3.1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C
4.1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
5.1: 82 percent / toluene / 80 - 90 °C
6.1: 80 percent / AlCl3 / 3 h / 170 °C
7.1: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
Multi-step reaction with 4 steps
1: 90 percent / t-BuONa; t-Bu3P / Pd(dba)2 / toluene / 14 h / 110 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
Multi-step reaction with 3 steps
1: 76 percent / pTsOH*H2O / toluene / 18 h / Heating
2: 76 percent / I2; DBU / xylene / 36 h / 155 °C
3: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
p-toluidine
106-49-0

p-toluidine

4-hydroxybenzaldehyde-linked-Wang-resin

4-hydroxybenzaldehyde-linked-Wang-resin

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / t-BuONa; (+)-BINAP / Pd(dba)2 / toluene / 110 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
N-(p-tolyl)-2-chloroacetamide
16634-82-5

N-(p-tolyl)-2-chloroacetamide

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: propan-2-ol / Heating
2: MeONa / methanol / 2 h / 85 °C
3: 82 percent / toluene / 80 - 90 °C
4: 80 percent / AlCl3 / 3 h / 170 °C
5: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-bromo-3-fluoro-chlorobenzene
309721-44-6

2-bromo-3-fluoro-chlorobenzene

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / t-BuONa; (+)-BINAP / Pd(dba)2 / toluene / 110 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
N-(2-chloro-6-fluoro-phenyl)-4-methylaniline
332903-74-9

N-(2-chloro-6-fluoro-phenyl)-4-methylaniline

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 82 percent / toluene / 80 - 90 °C
2: 80 percent / AlCl3 / 3 h / 170 °C
3: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
4-(2-chloro-6-fluorophenylamino)benzonitrile
817621-48-0

4-(2-chloro-6-fluorophenylamino)benzonitrile

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: HCl gas / ethyl acetate / 2.5 h / -5 - 0 °C
1.2: H2O / ethyl acetate / 36 h / 20 - 25 °C
2.1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C
3.1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
4.1: 82 percent / toluene / 80 - 90 °C
5.1: 80 percent / AlCl3 / 3 h / 170 °C
6.1: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
4-(2-chloro-6-fluoro-phenylamino)benzoic acid ethyl ester
817621-52-6

4-(2-chloro-6-fluoro-phenylamino)benzoic acid ethyl ester

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
1-(2-chloro-6-fluoro-phenyl)-5-methyl-1,4,5,6-tetrahydro-indol-2-one
817621-77-5

1-(2-chloro-6-fluoro-phenyl)-5-methyl-1,4,5,6-tetrahydro-indol-2-one

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / I2; DBU / xylene / 36 h / 155 °C
2: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-chloro-N-(2-chloro-6-fluoro-phenyl)-N-p-tolylacetamide
332903-78-3

2-chloro-N-(2-chloro-6-fluoro-phenyl)-N-p-tolylacetamide

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / AlCl3 / 3 h / 170 °C
2: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-(2-chloro-6-fluoro-phenoxy)-N-p-tolyl-acetamide

2-(2-chloro-6-fluoro-phenoxy)-N-p-tolyl-acetamide

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: MeONa / methanol / 2 h / 85 °C
2: 82 percent / toluene / 80 - 90 °C
3: 80 percent / AlCl3 / 3 h / 170 °C
4: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
4-(2-chloro-6-fluoro-phenylamino)benzimidic acid ethyl ester hydrochloride

4-(2-chloro-6-fluoro-phenylamino)benzimidic acid ethyl ester hydrochloride

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C
2: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C
3: 82 percent / toluene / 80 - 90 °C
4: 80 percent / AlCl3 / 3 h / 170 °C
5: 90 percent / aq. NaOH / ethanol; H2O / Heating
View Scheme
2-Amino-5-methylbenzoic acid
2941-78-8

2-Amino-5-methylbenzoic acid

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) acetate monohydrate / 1,4-dioxane / 25 °C
2: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux
3: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C
4: dimethyl sulfoxide / 1.5 h / Inert atmosphere
5: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
(2-chloro-6-fluorophenyl)boronic acid

(2-chloro-6-fluorophenyl)boronic acid

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) acetate monohydrate / 1,4-dioxane / 25 °C
2: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux
3: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C
4: dimethyl sulfoxide / 1.5 h / Inert atmosphere
5: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
C14H12Cl2FN

C14H12Cl2FN

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 1.5 h / Inert atmosphere
2: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
2-[(2-chloro-6-fluorophenyl)amino]-5-methyl-benzoic acid
619296-47-8

2-[(2-chloro-6-fluorophenyl)amino]-5-methyl-benzoic acid

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux
2: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C
3: dimethyl sulfoxide / 1.5 h / Inert atmosphere
4: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzenemethanol

2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzenemethanol

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C
2: dimethyl sulfoxide / 1.5 h / Inert atmosphere
3: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere
View Scheme
2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetonitrile
1403226-56-1

2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetonitrile

lumiracoxib
220991-20-8

lumiracoxib

Conditions
ConditionsYield
With water; barium(II) hydroxide In 1,4-dioxane for 30h; Reflux; Inert atmosphere;
methanol
67-56-1

methanol

lumiracoxib
220991-20-8

lumiracoxib

2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester
1175086-67-5

2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester

Conditions
ConditionsYield
Stage #1: methanol; lumiracoxib With hydrogenchloride In water for 8h; Reflux;
Stage #2: With sodium carbonate In water		89%
Stage #1: methanol; lumiracoxib With hydrogenchloride In water for 8h; Reflux;
Stage #2: With sodium hydrogencarbonate In water Cooling with ice; Saturated solution;		89%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;74%
lumiracoxib
220991-20-8

lumiracoxib

1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one
332903-83-0

1-(2-chloro-6-fluorophenyl)-5-methylindolin-2-one

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;85%
lumiracoxib
220991-20-8

lumiracoxib

2-{2-[(2-chloro-6-fluorophenyl)amine]-5-methylphenyl}acetohydrazide

2-{2-[(2-chloro-6-fluorophenyl)amine]-5-methylphenyl}acetohydrazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 8 h / Reflux
2: hydrazine hydrate / methanol / 24 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water / 8 h / Reflux
1.2: Cooling with ice; Saturated solution
2.1: hydrazine hydrate / methanol / 24 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C
2: hydrazine hydrate / ethanol / 1.5 h / Reflux
View Scheme
lumiracoxib
220991-20-8

lumiracoxib

2-{2-[(2-chloro-6-fluorophenyl)amine]-5-methylphenyl}-N-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)acetamide

2-{2-[(2-chloro-6-fluorophenyl)amine]-5-methylphenyl}-N-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 8 h / Reflux
2: hydrazine hydrate / methanol / 24 h / Reflux
3: acetic acid / 7 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water / 8 h / Reflux
1.2: Cooling with ice; Saturated solution
2.1: hydrazine hydrate / methanol / 24 h / Reflux
3.1: acetic acid / 7 h / Reflux
View Scheme
lumiracoxib
220991-20-8

lumiracoxib

C15H14ClFN2O2
1403226-61-8

C15H14ClFN2O2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C
2: potassium cyanide; water; hydroxylamine / methanol; tetrahydrofuran / 18 h / 20 °C
View Scheme
lumiracoxib
220991-20-8

lumiracoxib

C16H13ClFN3O2
1403226-62-9

C16H13ClFN3O2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C
2: hydrazine hydrate / ethanol / 1.5 h / Reflux
3: 1,1'-carbonyldiimidazole / tetrahydrofuran / 20 °C / Inert atmosphere
View Scheme

Lumiracoxib Chemical Properties

IUPAC  Name: 2-[2-(2-Chloro-6-fluoroanilino)-5-methylphenyl]acetic acid    
Empirical Formula: C15H13ClFNO2
Molecular Weight: 293.7206 
Classification Code: Analgesics ; Analgesics, Non-Narcotic ; Anti-Inflammatory Agents ; Anti-Inflammatory Agents, Non-Steroidal ; COX-2 Inhibitors ; Cyclooxygenase 2 Inhibitors ; Cyclooxygenase Inhibitors ; Enzyme Inhibitors ; Peripheral Nervous System Agents ; Sensory System Agents ; Treatment of rheumatoid arthritis, osteoarthritis, and pain prevention 
Freely Rotating Bonds: 4
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.628
Molar Refractivity: 76.45 cm3
Molar Volume: 215.3 cm3
Polarizability: 30.3×10-24 cm3
Surface Tension: 52.4 dyne/cm
Density: 1.363 g/cm3
Flash Point: 193.1 °C
Enthalpy of Vaporization: 68.12 kJ/mol
Boiling Point: 395.7 °C at 760 mmHg
Vapour Pressure: 5.68E-07 mmHg at 25°C 
The Cas Register Number of  Lumiracoxib is 220991-20-8.The chemical synonyms of  Lumiracoxib (CAS NO.220991-20-8) are Benzeneacetic acid, 2-((2-chloro-6-fluorophenyl)amino)-5-methyl-. Product categories of  Lumiracoxib (CAS NO.220991-20-8) are Aromatics Compounds ; Aromatics ; Intermediates  and  Fine Chemicals ; Pharmaceuticals . The molecular structure of  Lumiracoxib (CAS NO.220991-20-8) is
.

Lumiracoxib Uses

  Lumiracoxib (CAS NO.220991-20-8)  is used  as  COX-2  selective  inhibitor  non-steroidal  anti-inflammatory  drug.

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