Product Name

  • Name

    Carprofen

  • EINECS 258-712-4
  • CAS No. 53716-49-7
  • Article Data20
  • CAS DataBase
  • Density 1.42 g/cm3
  • Solubility
  • Melting Point 186-188 °C
  • Formula C15H12ClNO2
  • Boiling Point 509.1 °C at 760 mmHg
  • Molecular Weight 273.719
  • Flash Point 261.7 °C
  • Transport Information UN 2811
  • Appearance Off-white crystalline solid
  • Safety 45-36-26
  • Risk Codes 25-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 53716-49-7 (Carprofen)
  • Hazard Symbols ToxicT, HarmfulXn
  • Synonyms (dl)-6-Chloro-a-methylcarbazole-2-acetic acid;2-(6-Chlorocarbazol-2-yl)propionicacid;6-Chloro-a-methyl-9H-carbazole-2-aceticacid;6-Chloro-a-methylcarbazole-2-aceticacid;C 5720;Carprodyl;Imadyl;Rimadyl;Ro 20-5720;Ro20-5720/000;
  • PSA 53.09000
  • LogP 4.16260

Synthetic route

methyl 9-benzoyl-2-(6-chlorocarbazol-2-yl)propanoate

methyl 9-benzoyl-2-(6-chlorocarbazol-2-yl)propanoate

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol at 80℃; for 1.5h;92%
ethyl 2-(6-chloro-9H-carbazol-2-yl)propanoate
52262-89-2

ethyl 2-(6-chloro-9H-carbazol-2-yl)propanoate

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 20℃; for 8h; Inert atmosphere; Schlenk technique;91%
With sodium hydroxide In methanol; water52%
2-(3-((4-chlorophenyl)amino)-4-chlorophenyl)propanoic acid

2-(3-((4-chlorophenyl)amino)-4-chlorophenyl)propanoic acid

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With triphenylphosphine; palladium dichloride; sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 10h; Reagent/catalyst; Inert atmosphere;91%
Stage #1: 2-(3-((4-chlorophenyl)amino)-4-chlorophenyl)propanoic acid With triphenylphosphine; nickel dichloride; palladium dichloride; sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere;
Stage #2: With acetic acid In N,N-dimethyl-formamide at 20℃; for 0.166667h;		87.9%
With triphenylphosphine; nickel dichloride; palladium dichloride; sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 10h; Reagent/catalyst; Inert atmosphere;87.9%
With triphenylphosphine; nickel dichloride; palladium dichloride; sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere;87.9%
methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate
52263-88-4

methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 50℃;90%
With sodium hydroxide In water for 4h; Reflux;88%
With potassium hydroxide for 1.5h; Heating; Yield given;
2-(3-((4-chlorophenyl)amino)-4-aminophenyl)propionic acid

2-(3-((4-chlorophenyl)amino)-4-aminophenyl)propionic acid

A

2-(6-chloro-9-nitroso-9H-carbazol-2-yl)propanoic acid

2-(6-chloro-9-nitroso-9H-carbazol-2-yl)propanoic acid

B

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Stage #1: 2-(3-((4-chlorophenyl)amino)-4-aminophenyl)propionic acid With toluene-4-sulfonic acid; orthoformic acid triethyl ester; copper(l) chloride In tetrahydrofuran; methanol for 0.5h;
Stage #2: With sodium nitrite In tetrahydrofuran; methanol at 35 - 40℃; for 1h;		A 88.2%
B 11.5%
carprofenate trimethylamine salt

carprofenate trimethylamine salt

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 60℃; for 1.5h; pH=3;82.7%
1-(6-chloro-2-(1-methoxy-1-oxopropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazol-1-ylidene)pyrrolidin-1-ium tetrafluoroborate

1-(6-chloro-2-(1-methoxy-1-oxopropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazol-1-ylidene)pyrrolidin-1-ium tetrafluoroborate

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With pyridine hydrochloride at 200℃; for 1h; Inert atmosphere;81.8%
2-(1-cyanoethyl)-6-chlorocarbazole
99203-00-6

2-(1-cyanoethyl)-6-chlorocarbazole

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With sodium hydroxide In ethylene glycol at 180 - 185℃; for 2.5h;75.9 g
2-(6-Chloro-9H-carbazol-2-yl)-2-trimethylsilanyloxy-propionitrile
99203-05-1

2-(6-Chloro-9H-carbazol-2-yl)-2-trimethylsilanyloxy-propionitrile

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; tin(ll) chloride 1.) 10 min, 2a.) RT, 18 h, 2b.) 100 deg C, 2.5 h; Yield given. Multistep reaction;
(6-chloro-2-carbazolyl)methylmalonic acid diethyl ester
71208-55-4

(6-chloro-2-carbazolyl)methylmalonic acid diethyl ester

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With hydrogenchloride In acetic acid
(6-chloro-1,2,3,4-tetrahydro-2-carbazolyl)methylmalonic acid diethyl ester
71208-54-3

(6-chloro-1,2,3,4-tetrahydro-2-carbazolyl)methylmalonic acid diethyl ester

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Cl2 / toluene / 4 h / 75 °C / 450.04 Torr
2: HCl / acetic acid
View Scheme
2-acetylcarbazole
23592-74-7

2-acetylcarbazole

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) (EtO)3PO, BF3*Et2O, 2.) trichloroisocyanuric acid, (EtO)3PO / 1.) 5 deg C, 15 min, 2a.) from 0 deg C to 5 deg C, 1.0 h, 2b.) RT, 4.0 h
2: 83 percent / ZnI2 / CHCl3 / 22 h / Heating
3: 1.) SnCl2, HOAc, 2.) conc. HCl / 1.) 10 min, 2a.) RT, 18 h, 2b.) 100 deg C, 2.5 h
View Scheme
1-(2-acetylcarbazol-9-yl)ethanone
23592-73-6

1-(2-acetylcarbazol-9-yl)ethanone

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 71 percent / trichloroisocyanuric acid / dimethylformamide / 5.5 h / Ambient temperature
2: 92 percent / NaOH / ethanol; H2O / 1.25 h / Heating
3: 83 percent / ZnI2 / CHCl3 / 22 h / Heating
4: 1.) SnCl2, HOAc, 2.) conc. HCl / 1.) 10 min, 2a.) RT, 18 h, 2b.) 100 deg C, 2.5 h
View Scheme
Multi-step reaction with 5 steps
1: 71 percent / trichloroisocyanuric acid / dimethylformamide / 5.5 h / Ambient temperature
2: 98 percent / NaBH4, 14 N NaOH / ethanol / 2 h / Heating
3: 99.8 percent / 4-dimethylaminopyridine / ethyl acetate / 3 h / Ambient temperature
4: dimethylsulfoxide / a) 97 deg C, 2.5 mmHg, b) from 130 deg C to 132 deg C, 9.5 h
5: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
Multi-step reaction with 5 steps
1: 71 percent / trichloroisocyanuric acid / dimethylformamide / 5.5 h / Ambient temperature
2: 98 percent / NaBH4, 14 N NaOH / ethanol / 2 h / Heating
3: 99.8 percent / 4-dimethylaminopyridine / ethyl acetate / 3 h / Ambient temperature
4: 1.) LiH / 1.) DMF, 50 deg C, 2.5 h, 2.) DMF, reflux, 5 h
5: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
9H-carbazole
86-74-8

9H-carbazole

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: conc. H2So4 / tetrachloroethene / 4 h / Heating
2: 71 percent / trichloroisocyanuric acid / dimethylformamide / 5.5 h / Ambient temperature
3: 92 percent / NaOH / ethanol; H2O / 1.25 h / Heating
4: 83 percent / ZnI2 / CHCl3 / 22 h / Heating
5: 1.) SnCl2, HOAc, 2.) conc. HCl / 1.) 10 min, 2a.) RT, 18 h, 2b.) 100 deg C, 2.5 h
View Scheme
Multi-step reaction with 6 steps
1: conc. H2So4 / tetrachloroethene / 4 h / Heating
2: 71 percent / trichloroisocyanuric acid / dimethylformamide / 5.5 h / Ambient temperature
3: 98 percent / NaBH4, 14 N NaOH / ethanol / 2 h / Heating
4: 99.8 percent / 4-dimethylaminopyridine / ethyl acetate / 3 h / Ambient temperature
5: dimethylsulfoxide / a) 97 deg C, 2.5 mmHg, b) from 130 deg C to 132 deg C, 9.5 h
6: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
Multi-step reaction with 6 steps
1: conc. H2So4 / tetrachloroethene / 4 h / Heating
2: 71 percent / trichloroisocyanuric acid / dimethylformamide / 5.5 h / Ambient temperature
3: 98 percent / NaBH4, 14 N NaOH / ethanol / 2 h / Heating
4: 99.8 percent / 4-dimethylaminopyridine / ethyl acetate / 3 h / Ambient temperature
5: 1.) LiH / 1.) DMF, 50 deg C, 2.5 h, 2.) DMF, reflux, 5 h
6: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
1-(6-chloro-9H-carbazol-2-yl)ethanone
92841-22-0

1-(6-chloro-9H-carbazol-2-yl)ethanone

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 83 percent / ZnI2 / CHCl3 / 22 h / Heating
2: 1.) SnCl2, HOAc, 2.) conc. HCl / 1.) 10 min, 2a.) RT, 18 h, 2b.) 100 deg C, 2.5 h
View Scheme
1-(6-chloro-9H-carbazol-2-yl)ethanol
92841-21-9

1-(6-chloro-9H-carbazol-2-yl)ethanol

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99.8 percent / 4-dimethylaminopyridine / ethyl acetate / 3 h / Ambient temperature
2: dimethylsulfoxide / a) 97 deg C, 2.5 mmHg, b) from 130 deg C to 132 deg C, 9.5 h
3: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
Multi-step reaction with 3 steps
1: 99.8 percent / 4-dimethylaminopyridine / ethyl acetate / 3 h / Ambient temperature
2: 1.) LiH / 1.) DMF, 50 deg C, 2.5 h, 2.) DMF, reflux, 5 h
3: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
6-chloro-2,9-diacetylcarbazole
99203-07-3

6-chloro-2,9-diacetylcarbazole

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / NaOH / ethanol; H2O / 1.25 h / Heating
2: 83 percent / ZnI2 / CHCl3 / 22 h / Heating
3: 1.) SnCl2, HOAc, 2.) conc. HCl / 1.) 10 min, 2a.) RT, 18 h, 2b.) 100 deg C, 2.5 h
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / NaBH4, 14 N NaOH / ethanol / 2 h / Heating
2: 99.8 percent / 4-dimethylaminopyridine / ethyl acetate / 3 h / Ambient temperature
3: dimethylsulfoxide / a) 97 deg C, 2.5 mmHg, b) from 130 deg C to 132 deg C, 9.5 h
4: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / NaBH4, 14 N NaOH / ethanol / 2 h / Heating
2: 99.8 percent / 4-dimethylaminopyridine / ethyl acetate / 3 h / Ambient temperature
3: 1.) LiH / 1.) DMF, 50 deg C, 2.5 h, 2.) DMF, reflux, 5 h
4: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
2-(1-acetoxyethyl)-6-chlorocarbazole
99202-99-0

2-(1-acetoxyethyl)-6-chlorocarbazole

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylsulfoxide / a) 97 deg C, 2.5 mmHg, b) from 130 deg C to 132 deg C, 9.5 h
2: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.) LiH / 1.) DMF, 50 deg C, 2.5 h, 2.) DMF, reflux, 5 h
2: 75.9 g / NaOH / ethane-1,2-diol / 2.5 h / 180 - 185 °C
View Scheme
2-(6-chloro-carbazol-2-yl)-acrylic acid
70929-08-7

2-(6-chloro-carbazol-2-yl)-acrylic acid

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
In ethanol13 mg. (32.3%)
2-(6-chloro-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoic acid

2-(6-chloro-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoic acid

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With pyridine hydrochloride at 230℃; for 3h; Inert atmosphere;
methyl 2-(6-chloro-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoate

methyl 2-(6-chloro-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoate

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
With pyridine hydrochloride at 200℃; for 3h; Inert atmosphere;
recorcinol
108-46-3

recorcinol

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: iodine / tetrahydrofuran; water / 20 °C
2: triethylamine / dichloromethane / 0 - 20 °C
3: phenylmagnesium bromide / toluene; diethyl ether / -30 - 20 °C
4: cesium fluoride / acetonitrile / 12 h / 20 °C
5: potassium carbonate; palladium diacetate; Trimethylacetic acid / 24 h / Reflux
6: sodium hydroxide; water / methanol / 50 °C
View Scheme
methyl 2-(3-((4-chlorophenyl)amino)phenyl)propanoate

methyl 2-(3-((4-chlorophenyl)amino)phenyl)propanoate

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; palladium diacetate; Trimethylacetic acid / 24 h / Reflux
2: sodium hydroxide; water / methanol / 50 °C
View Scheme
2-iodoresorcinol
41046-67-7

2-iodoresorcinol

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: phenylmagnesium bromide / toluene; diethyl ether / -30 - 20 °C
3: cesium fluoride / acetonitrile / 12 h / 20 °C
4: potassium carbonate; palladium diacetate; Trimethylacetic acid / 24 h / Reflux
5: sodium hydroxide; water / methanol / 50 °C
View Scheme
2-iodo-1,3-phenylene bis(trifluoromethanesulfonate)
514826-78-9

2-iodo-1,3-phenylene bis(trifluoromethanesulfonate)

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: phenylmagnesium bromide / toluene; diethyl ether / -30 - 20 °C
2: cesium fluoride / acetonitrile / 12 h / 20 °C
3: potassium carbonate; palladium diacetate; Trimethylacetic acid / 24 h / Reflux
4: sodium hydroxide; water / methanol / 50 °C
View Scheme
C17H25F3O5SSi

C17H25F3O5SSi

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: cesium fluoride / acetonitrile / 12 h / 20 °C
2: potassium carbonate; palladium diacetate; Trimethylacetic acid / 24 h / Reflux
3: sodium hydroxide; water / methanol / 50 °C
View Scheme
C17H15ClIO2(1+)*CF3O3S(1-)

C17H15ClIO2(1+)*CF3O3S(1-)

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(I) thiophene-2-carboxylate; triphenylphosphine; sodium azide; 1,10-Phenanthroline / N,N-dimethyl acetamide / 12 h / 100 °C / Inert atmosphere; Schlenk technique
2: sodium hydroxide / water; methanol
View Scheme
carbazole-2-oxalic acid methyl ester

carbazole-2-oxalic acid methyl ester

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuryl dichloride / 1,2-dichloro-ethane
2: hydrogenchloride; sodium hydroxide; sodium chloride; magnesium / tetrahydrofuran; ethanol; water
3: sulfuric acid / tetrahydrofuran
4: ethanol
View Scheme
6-chlorocarbazole-2-oxalic acid methyl ester

6-chlorocarbazole-2-oxalic acid methyl ester

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride; sodium hydroxide; sodium chloride; magnesium / tetrahydrofuran; ethanol; water
2: sulfuric acid / tetrahydrofuran
3: ethanol
View Scheme
methanol
67-56-1

methanol

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate
52263-88-4

methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 12h;100%
With toluene-4-sulfonic acid for 1h; Reflux;99%
With sulfuric acid98%
benzyl bromide
100-39-0

benzyl bromide

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

benzyl 2-(3-chloro-9H-carbazol-7-yl)propionate
166408-09-9

benzyl 2-(3-chloro-9H-carbazol-7-yl)propionate

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 2h;		98%
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 3h;		84%
With potassium carbonate In acetone at 20℃;
isoniazid
54-85-3

isoniazid

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

(RS)-1-(6-chloro-9H-carbazol-2-yl)-1-[5-(4-pyridyl)-1,3,4-oxadiazol-2-yl]ethane

(RS)-1-(6-chloro-9H-carbazol-2-yl)-1-[5-(4-pyridyl)-1,3,4-oxadiazol-2-yl]ethane

Conditions
ConditionsYield
With trichlorophosphate for 2.5h; Reflux;91%
2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

temozolomide
85622-93-1

temozolomide

methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate
52263-88-4

methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 60℃; for 6h; Sealed tube;88%
sodium acetate
127-09-3

sodium acetate

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

diethylaminoethyl 6-chloro-α-methyl-9H-carbazole-2-acetate acetate

diethylaminoethyl 6-chloro-α-methyl-9H-carbazole-2-acetate acetate

Conditions
ConditionsYield
Stage #1: 2-bromo-N,N-diethylethanamine hydrobromide; 2-(6-chloro-carbazol-2-yl)-propionic acid With C11H16NPol In chloroform at 20℃; for 5h; not specified;
Stage #2: sodium acetate In tetrahydrofuran; chloroform for 2h;		87.8%
sodium acetate
127-09-3

sodium acetate

2-bromo-N,N-diethylethanamine hydrobromide
1069-72-3

2-bromo-N,N-diethylethanamine hydrobromide

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

diethylaminoethyl 6-chloro-α-methyl-9H-carbazole-2-acetate acetate

diethylaminoethyl 6-chloro-α-methyl-9H-carbazole-2-acetate acetate

Conditions
ConditionsYield
Stage #1: 2-bromo-N,N-diethylethanamine hydrobromide; 2-(6-chloro-carbazol-2-yl)-propionic acid With triethylamine In chloroform at 20℃; for 5h;
Stage #2: sodium acetate for 2h;		87.8%
Stage #1: 2-bromo-N,N-diethylethanamine hydrobromide; 2-(6-chloro-carbazol-2-yl)-propionic acid With polymer bound triethylamine In chloroform at 20℃; for 5h;
Stage #2: sodium acetate for 2h;		87.8%
...Expand
2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

aniline
62-53-3

aniline

2-(6-chloro-9H-carbazol-2-yl)-N-phenylpropanamide

2-(6-chloro-9H-carbazol-2-yl)-N-phenylpropanamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With pyridine; 1,1'-carbonyldiimidazole at 20℃; for 2h;
Stage #2: aniline for 12h; Heating;		86%
2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

ethanolamine
141-43-5

ethanolamine

2-(6-chloro-9H-carbazol-2-yl)-N-(2-hydroxyethyl)propanamide
919730-73-7

2-(6-chloro-9H-carbazol-2-yl)-N-(2-hydroxyethyl)propanamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With pyridine; 1,1'-carbonyldiimidazole at 20℃; for 2h;
Stage #2: ethanolamine for 12h; Heating;		85%
2,6-dimethylphenyl isonitrile
119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

1-iodo-2-((2-methylallyl)oxy)benzene
156642-47-6

1-iodo-2-((2-methylallyl)oxy)benzene

2-(6-chloro-9H-carbazol-2-yl)-N-(2,6-dimethylphenyl)-N-(2-(3-methyl-2,3-dihydrobenzofuran-3-yl)acetyl)propanamide

2-(6-chloro-9H-carbazol-2-yl)-N-(2,6-dimethylphenyl)-N-(2-(3-methyl-2,3-dihydrobenzofuran-3-yl)acetyl)propanamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With tetrabutyl-ammonium chloride; caesium carbonate In water at 80℃; for 0.5h;
Stage #2: 1-iodo-2-((2-methylallyl)oxy)benzene With bis(dibenzylideneacetone)-palladium(0); catacxium A In water; toluene at 20℃; Inert atmosphere;
Stage #3: 2,6-dimethylphenyl isonitrile In water; toluene at 100℃; for 2h; chemoselective reaction;		73%
...Expand
methanesulfonamide
3144-09-0

methanesulfonamide

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

N-[2-(6-chloro-9H-carbazol-2-yl)-propionyl]-methanesulfonamide

N-[2-(6-chloro-9H-carbazol-2-yl)-propionyl]-methanesulfonamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 5℃; for 2h;
Stage #2: methanesulfonamide With 1,2-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 4h;		72%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

1,3-dioxoisoindolin-2-yl 2-(6-chloro-9H-carbazol-2-yl)propanoate

1,3-dioxoisoindolin-2-yl 2-(6-chloro-9H-carbazol-2-yl)propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 18h;68%
With diisopropyl-carbodiimide In dichloromethane
2-amino-3-chloropyridine
39620-04-7

2-amino-3-chloropyridine

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

2-(6-chloro-9H-carbazol-2-yl)-N-(3-chloropyridin-2-yl)propanamide

2-(6-chloro-9H-carbazol-2-yl)-N-(3-chloropyridin-2-yl)propanamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h;
Stage #2: 2-amino-3-chloropyridine In acetonitrile at 20℃; for 36h;		61%
carbon dioxide
1111-72-4

carbon dioxide

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

[13C]carprofen

[13C]carprofen

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 2h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;60%
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With caesium carbonate In methanol at 20℃; for 1h; Inert atmosphere;
Stage #2: carbon dioxide In dimethyl sulfoxide at 150℃; for 4h; Inert atmosphere; Cooling with liquid nitrogen;		10 mg
{(1R,2R)-cyclohexane-1,2-diamine}dichloridoplatinum(II)
38780-40-4, 52691-24-4, 61848-70-2, 61848-66-6, 61848-62-2

{(1R,2R)-cyclohexane-1,2-diamine}dichloridoplatinum(II)

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

C21H25Cl2N3O2Pt

C21H25Cl2N3O2Pt

Conditions
ConditionsYield
With sodium carbonate; silver nitrate In N,N-dimethyl-formamide at 20℃; for 24h; Darkness;56%
morpholine
110-91-8

morpholine

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

1-(6-chloro-9H-carbazol-2-yl)-2-morpholinoethane-1,2-dione

1-(6-chloro-9H-carbazol-2-yl)-2-morpholinoethane-1,2-dione

Conditions
ConditionsYield
With copper(l) iodide; Nb6O19(7-)*7K(1+)*H(1+)*13H2O; oxygen In dimethyl sulfoxide at 100℃;55%
4-iodoanisol
529-28-2

4-iodoanisol

2,6-dimethylphenyl isonitrile
119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

N-(2-(6-chloro-9H-carbazol-3-yl)propanoyl)-N-(2,6-dimethylphenyl)-2-methoxybenzamide

N-(2-(6-chloro-9H-carbazol-3-yl)propanoyl)-N-(2,6-dimethylphenyl)-2-methoxybenzamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With tetrabutyl-ammonium chloride; caesium carbonate In water at 80℃; for 0.5h; Inert atmosphere;
Stage #2: 4-iodoanisol With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In water; toluene at 100℃; for 0.5h; Inert atmosphere;
Stage #3: 2,6-dimethylphenyl isonitrile In water; toluene at 100℃; for 1.5h; Inert atmosphere;		52%
...Expand
2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

1-(6-chloro-9H-carbazol-2-yl)ethanol
92841-21-9

1-(6-chloro-9H-carbazol-2-yl)ethanol

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With dipotassium hydrogenphosphate; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In chloroform at 20℃; for 72h; Schlenk technique; Irradiation; Green chemistry;
Stage #2: With sodium tetrahydroborate In methanol; chloroform for 0.5h; Green chemistry;		51%
3-methylpyridin-2-ylamine
1603-40-3

3-methylpyridin-2-ylamine

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

2-(6-chloro-9H-carbazol-2-yl)-N-(3-methylpyridin-2-yl)propanamide

2-(6-chloro-9H-carbazol-2-yl)-N-(3-methylpyridin-2-yl)propanamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h;
Stage #2: 3-methylpyridin-2-ylamine In acetonitrile at 20℃; for 36h;		44%
2-Amino-3-bromopyridine
13534-99-1

2-Amino-3-bromopyridine

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

2-(6-chloro-9H-carbazol-2-yl)-N-(3-bromopyridin-2-yl)propanamide

2-(6-chloro-9H-carbazol-2-yl)-N-(3-bromopyridin-2-yl)propanamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h;
Stage #2: 2-Amino-3-bromopyridine In acetonitrile at 20℃; for 36h;		43%
2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

2-amino-3-trifluoromethylpyridine
183610-70-0

2-amino-3-trifluoromethylpyridine

2-(6-chloro-9H-carbazol-2-yl)-N-(3-(trifluoromethyl)pyridin-2-yl)propanamide

2-(6-chloro-9H-carbazol-2-yl)-N-(3-(trifluoromethyl)pyridin-2-yl)propanamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h;
Stage #2: 2-amino-3-trifluoromethylpyridine In acetonitrile at 20℃; for 36h;		41%
2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

2-(9H-carbazol-2-yl)propanoic acid
52263-68-0

2-(9H-carbazol-2-yl)propanoic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol; ethyl acetate under 760.051 Torr;40%
3-iodo-2-aminopyridine
104830-06-0

3-iodo-2-aminopyridine

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

2-(6-chloro-9H-carbazol-2-yl)-N-(3-iodopyridin-2-yl)propanamide

2-(6-chloro-9H-carbazol-2-yl)-N-(3-iodopyridin-2-yl)propanamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-carbazol-2-yl)-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h;
Stage #2: 3-iodo-2-aminopyridine In acetonitrile at 20℃; for 36h;		37%
(OC-6-33)-(diammine)dichloridodihydroxidoplatinum(IV)
125074-46-6, 31246-62-5, 31246-63-6, 31246-66-9, 53261-25-9

(OC-6-33)-(diammine)dichloridodihydroxidoplatinum(IV)

2-(6-chloro-carbazol-2-yl)-propionic acid
53716-49-7

2-(6-chloro-carbazol-2-yl)-propionic acid

C30H28Cl4N4O4Pt

C30H28Cl4N4O4Pt

Conditions
ConditionsYield
With triethylamine; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 48h; Darkness;30%

Carprofen Chemical Properties

Molecular Structure of Carprofen (CAS NO.53716-49-7):

IUPAC Name: 2-(6-chloro-9H-carbazol-2-yl)propanoic acid
Molecular formula: C15H12ClNO2
Molar mass: 273.714 g/mol
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 31.23 Å2
Index of Refraction: 1.731
Molar Refractivity: 77.01 cm3
Molar Volume: 192.6 cm3
Surface Tension: 65.1 dyne/cm
Density: 1.42 g/cm3
Flash Point: 261.7 °C
Enthalpy of Vaporization: 82.09 kJ/mol
Boiling Point: 509.1 °C at 760 mmHg
Vapour Pressure: 3.45E-11 mmHg at 25°C
EINECS: 258-712-4
Melting point: 186-188 °C
Appearence: Off-White Crystalline Solid
EINECS: 258-712-4
Product Categories: Active Pharmaceutical Ingredients; Heterocyclic Compounds; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals

Carprofen Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 165mg/kg (165mg/kg)   Medicamentos de Actualidad. Vol. 18, Pg. 170, 1982.
mouse LD50 oral 186mg/kg (186mg/kg)   Medicamentos de Actualidad. Vol. 18, Pg. 170, 1982.
mouse LD50 subcutaneous 267mg/kg (267mg/kg)   Medicamentos de Actualidad. Vol. 18, Pg. 170, 1982.
rat LD50 intraperitoneal 110mg/kg (110mg/kg)   Medicamentos de Actualidad. Vol. 18, Pg. 170, 1982.
rat LD50 oral 74mg/kg (74mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 251, 1977.
rat LD50 subcutaneous 190mg/kg (190mg/kg)   Medicamentos de Actualidad. Vol. 18, Pg. 170, 1982.

Carprofen Safety Profile

Poison by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cl− and NOx.
Hazard Codes: ToxicT,HarmfulXn
Risk Statements: 25-36/37/38-20/21/22 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 45-36-26 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811

Carprofen Specification

 Carprofen , with CAS number of 53716-49-7, can be called (+/-)-6-chloro-alpha-methylcarbazole-2-acetic acid ;  (+-)-9h-carbazole-2-aceticaci ; carprofeno;dl-6-chloro-alpha-methylcarbazole-2-aceticacid;imadyl . Carprofen (CAS NO.53716-49-7) is a non-steroidal anti-inflammatory drug that is used by veterinarians as a supportive treatment for the relief of arthritic symptoms in geriatric dogs. Carprofen can be used both short term, for joint pain or post-operative inflammation, or for day-to-day relief from the pain and inflammation associated with osteoarthritis, hip dysplasia, and other forms of joint deterioration . Carprofen can also be effective in reducing fever.

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