2-(3-benzoyl-phenyl)-thiopropionic acid S-methyl ester
ketoprofen
Conditions | Yield |
---|---|
With potassium hydroxide In acetone for 2h; Heating; | 100% |
(S)-2-(3-Benzoyl-phenyl)-propionic acid (S)-1-carbamoylmethyl-4,4-dimethyl-2-oxo-pyrrolidin-3-yl ester
ketoprofen
Conditions | Yield |
---|---|
With potassium trimethylsilonate In tetrahydrofuran at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With palladium diacetate; catacxium A In 1,4-dioxane at 100℃; for 20h; | 99% |
With palladium diacetate; catacxium A In 1,4-dioxane at 100℃; for 20h; | 99% |
With hydrogenchloride; water; palladium diacetate; catacxium A In 1,4-dioxane at 100℃; under 30003 Torr; for 20h; regioselective reaction; | 99 %Chromat. |
3-(3-benzoylphenyl)butan-2-one
ketoprofen
Conditions | Yield |
---|---|
With sodium hypochlorite at 70℃; for 0.25h; | 95% |
With sodium hypochlorite Yield given; |
dimethyl 2-methyl-2-(3'-benzoyl)phenylpropanedioate
ketoprofen
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran at 25℃; for 24h; | 95% |
alpha-(m-benzoylphenyl)propionitrile
ketoprofen
Conditions | Yield |
---|---|
With sulfuric acid for 7h; Reflux; | 92.8% |
With sulfuric acid In water; toluene | |
With sodium hydroxide; sulfuric acid In water; toluene | |
With sulfuric acid In water; toluene | |
With sulfuric acid for 7h; Reflux; |
C18H20O3
ketoprofen
Conditions | Yield |
---|---|
Stage #1: C18H20O3 With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In acetonitrile at 5℃; for 2h; pH=9 - 10; Stage #2: With hydrogenchloride In ethanol; water at 70℃; for 1h; | 91% |
ketoprofen
Conditions | Yield |
---|---|
With nitric acid In 1,4-dioxane at 20℃; for 10h; | 90% |
With nitric acid In 1,4-dioxane at 20℃; for 10h; | 65.6% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In water; acetonitrile at 35℃; for 24h; aq. phosphate buffer; | 40% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water; acetone at 20℃; for 168h; Enzymatic reaction; | 13% |
S-butyl α-(3-benzoylphenyl)thiopropionate
ketoprofen
Conditions | Yield |
---|---|
With potassium hydroxide In acetone for 2h; Heating; | 89% |
neomenthyldiphenylphosphine
3-benzoylstyrene
sulfuric acid
pentan-3-one
ketoprofen
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; CO; CuCl2; palladium dichloride In tetrahydrofuran; water; toluene | 88% |
α-(3-benzylphenyl)-propionic acid
ketoprofen
Conditions | Yield |
---|---|
With potassium permanganate; sulfuric acid; triethylamine In water; 1,2-dichloro-ethane at 20℃; for 3.5h; Oxidation; | 86.5% |
With potassium permanganate; sulfuric acid; water for 4h; Reflux; | 2.5 g |
With potassium permanganate; sulfuric acid In water for 6h; Reflux; | 2.5 g |
With potassium permanganate; sulfuric acid In water for 4h; Reflux; | 2.5 g |
With potassium permanganate; sulfuric acid In water for 6h; Reflux; | 2.5 g |
ethyl 2-<3-benzoylphenyl>propionate
ketoprofen
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 1h; Heating; | 86% |
With potassium hydroxide; water for 2h; Heating; |
3-(1-carboxy-ethyl)-phenyl boronic acid
carbon monoxide
Phenyl triflate
ketoprofen
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium(II) trifluoroacetate In tert-butyl methyl ether at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling; | 86% |
3-(1-carboxy-ethyl)-phenyl boronic acid
carbon monoxide
toluene-4-sulfonic acid phenyl ester
ketoprofen
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl acetamide at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling; | 83% |
chloroacetic acid ethyl ester
(3-acetylphenyl)(phenyl)methanone
ketoprofen
Conditions | Yield |
---|---|
Stage #1: chloroacetic acid ethyl ester; (3-acetylphenyl)(phenyl)methanone With sodium ethanolate In ethanol Reflux; Stage #2: With sodium hydroxide In ethanol for 2h; Further stages; | 83% |
Stage #1: chloroacetic acid ethyl ester; (3-acetylphenyl)(phenyl)methanone With sodium ethanolate In ethanol for 3h; Reflux; Stage #2: With dihydrogen peroxide; acetic acid at 90℃; for 10h; | 60.1% |
Conditions | Yield |
---|---|
Stage #1: 3-bromobenzophenone With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene for 0.666667h; Inert atmosphere; Stage #2: 1,1-bis(trimethylsilyloxy)prop-1-ene In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 80℃; for 12h; Sealed tube; Inert atmosphere; | 81% |
2-(3-benzoylphenyl)acetonitrile
potassium carbonate
carbonic acid dimethyl ester
A
ketoprofen
B
alpha-(m-benzoylphenyl)propionitrile
Conditions | Yield |
---|---|
A 80% B n/a |
2-(3-benzoylphenyl)acetonitrile
carbonic acid dimethyl ester
A
ketoprofen
B
alpha-(m-benzoylphenyl)propionitrile
Conditions | Yield |
---|---|
With potassium carbonate | A 80% B n/a |
ketoprofen methyl ester
ketoprofen
Conditions | Yield |
---|---|
Stage #1: ketoprofen methyl ester With sodium hydroxide In methanol; water for 1h; Reflux; Stage #2: With hydrogenchloride In water pH=2; | 73.5% |
diphenyl N-<2-(3-benzoylphenyl)-1-pyrrolidinopropylidene>phosphoramidate
ketoprofen
Conditions | Yield |
---|---|
With potassium hydroxide In ethylene glycol for 6h; Heating; | 72% |
2-methyl-3-(5-oxo-5-phenylpentyl)maleic anhydride
ketoprofen
Conditions | Yield |
---|---|
With pyridine hydrochloride at 230℃; for 6h; | 72% |
ketoprofen
Conditions | Yield |
---|---|
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile for 1.25h; Ambient temperature; | 72% |
5-benzoylbenzothiophene-3-carboxylic acid
A
ketoprofen
B
α-(3-benzylphenyl)-propionic acid
C
Dihydroketoprofen
Conditions | Yield |
---|---|
With sodium hydroxide; nickel In ethanol for 1h; Heating; | A 29% B n/a C 56.9% |
carbon monoxide
3-ethynylbenzophenone
A
ketoprofen
B
3-(m-benzoyl-phenyl)-propionic acid
Conditions | Yield |
---|---|
With potassium hydroxide; polyethylene glycol (PEG-400); potassium cyanide; nickel cyanide; cobalt(II) chloride In toluene at 90℃; under 760 Torr; for 24h; | A 55% B 2% |
3-benzoyl-α-chloro-propiophenone
A
1-(3-benzoylphenyl)propan-1-one
B
ketoprofen
Conditions | Yield |
---|---|
With methyloxirane In water; acetone Irradiation; | A 30% B 45% |
ketoprofen
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water; acetone at 20℃; for 168h; Enzymatic reaction; | 24% |
3-Benzoyl-α-methylphenylessigsaeure-2-oxopropylester
ketoprofen
Conditions | Yield |
---|---|
With buffer pH 8.0 In acetonitrile at 37℃; half-life time of hydrolysis at different pH; |
2-(3-benzoylphenyl)acetonitrile
methyl iodide
A
ketoprofen
B
2-(3-benzoylphenyl)acetic acid
Conditions | Yield |
---|---|
With sodium hydroxide; hydroalcoholic 2N NaOH; tetra(n-butyl)ammonium hydrogensulfate 1.) water-methylene chloride, 10 min, 2.) reflux, 6 h; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
(i) nBuLi, Et2NH, HMPT, THF, (ii) (acid hydrolysis); Multistep reaction; |
methanol
ketoprofen
ketoprofen methyl ester
Conditions | Yield |
---|---|
With sulfuric acid at 50℃; for 8h; Reflux; | 100% |
With sulfuric acid at 50℃; for 8h; | 100% |
With sulfuric acid In acetonitrile at 80 - 85℃; | 99% |
ketoprofen
α-(3-benzylphenyl)-propionic acid
Conditions | Yield |
---|---|
With potassium hydroxide; hydrazine hydrate; diethylene glycol 1.) reflux, 1.5 h, 2.) 195 deg C, 4 h; | 100% |
With 10% palladium on activated charcoal; hydrogen In methanol |
ketoprofen
Conditions | Yield |
---|---|
In acetone at 20℃; for 0.166667h; | 100% |
In acetone at 20℃; for 0.166667h; | 100% |
ketoprofen
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.166667h; | 100% |
ketoprofen
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.166667h; | 100% |
In methanol at 20℃; for 0.166667h; | 100% |
ketoprofen
Conditions | Yield |
---|---|
In acetone at 20℃; for 0.166667h; | 100% |
ketoprofen
Conditions | Yield |
---|---|
In acetone at 20℃; for 0.166667h; | 100% |
In acetone at 20℃; for 0.166667h; | 100% |
ketoprofen
Conditions | Yield |
---|---|
In acetone at 20℃; for 0.166667h; | 100% |
In acetone at 20℃; for 0.166667h; | 100% |
In acetone at 20℃; for 0.166667h; | 100% |
In methanol at 20℃; for 0.5h; |
ketoprofen
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.166667h; | 100% |
ketoprofen
Conditions | Yield |
---|---|
In acetone at 20℃; for 0.166667h; | 100% |
ketoprofen
N-(tert-butyloxycarbonyl)-2-amino-2-(hydroxymethyl)propane-1,3-diol
Conditions | Yield |
---|---|
Stage #1: ketoprofen With triethylamine; dimethylphosphinothioic chloride In dichloromethane for 0.166667h; Cooling with ice; Stage #2: N-(tert-butyloxycarbonyl)-2-amino-2-(hydroxymethyl)propane-1,3-diol With dmap; ammonia; triethylamine In 1,4-dioxane; dichloromethane; water at 20℃; for 0.666667h; | 100% |
ketoprofen
ketoprofen chloride
Conditions | Yield |
---|---|
With phosphorus pentachloride In tetrachloromethane at 40℃; for 0.5h; | 99% |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; | 98% |
With thionyl chloride In dichloromethane for 3h; | 95% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 5h; | 99% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.75h; Cooling with ice; | 99% |
ketoprofen
N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester
3-[2(R,S)-(3-benzoyl-phenyl)-propionyloxy]-2(S)-tert-butoxycarbonylamino-butyric acid tert-butyl ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; | 98% |
Conditions | Yield |
---|---|
With (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate In tert-Amyl alcohol at 90℃; under 760.051 Torr; for 2h; | 98% |
With oxygen; palladium diacetate; potassium hydrogencarbonate; p-benzoquinone In tert-Amyl alcohol at 85℃; under 760.051 Torr; for 48h; regioselective reaction; |
ketoprofen
ethyl acrylate
Conditions | Yield |
---|---|
With (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; oxygen; palladium diacetate; potassium hydrogencarbonate In tert-Amyl alcohol at 90℃; under 760.051 Torr; for 2h; | 98% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; | 98% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Cooling with ice; | 98% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; | 87% |
Conditions | Yield |
---|---|
With sodium hydroxide In water for 0.5h; | 97% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h; Inert atmosphere; | 96.8% |
ketoprofen
S-ketoprofen
Conditions | Yield |
---|---|
96% | |
Multi-step reaction with 3 steps 1.1: oxalyl chloride / 12 h / 40 °C 2.1: rink amide linker modified polystyrene grafted crowns; piperidine; benzotriazolyloxy-tris(dimethylamino)phosphonium(1+) PF6(1-) / diisopropylethylamine / dimethylformamide / 12 h / 20 °C 2.2: triethylamine / tetrahydrofuran / 12 h / 0 °C 2.3: 104 mg / trifluoroacetic acid / CH2Cl2 / 0.67 h 3.1: LiOH / tetrahydrofuran; H2O / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: oxalyl chloride / 12 h / 40 °C 2.1: triethylamine; (S)-(3-OH-4,4-di-Me-2-oxopyrrolidin-1-yl)CH2COOH on resin / tetrahydrofuran / 0 °C 2.2: LiOH*H2O / tetrahydrofuran; H2O / 4 h / 20 °C View Scheme |
ketoprofen
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; | 96% |
(S)-Leu-OMe
ketoprofen
2-[2-(3-benzoylphenyl)propionylamino]-4-methylpentanoic acid methyl ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 20℃; | 94% |
ketoprofen
1,1'-carbonyldiimidazole
(S)-1-(2-(3-benzoylphenyl)propanoyl)imidazole
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; Inert atmosphere; | 94% |
The Ketoprofen, with the CAS registry number 22071-15-4, is also known as 2-(3-Benzoylphenyl)propionic acid; 2-(meta-Benzoylphenyl) propionic acid; Alrheumat. It belongs to the product categories of Pharmaceuticals;Lipid signaling;Pharmaceutical raw material.Its EINECS number is 244-759-8.This chemical's molecular formula is C16H14O3 and molecular weight is 254.28. What's more,Its systematic name is Ketoprofen.It is a White Crystalline Solid.And it is an ibuprofen-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.
Physical properties about Ketoprofen are:
(1)ACD/LogP: 2.911; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.62; (4)ACD/LogD (pH 7.4): -0.16; (5)ACD/BCF (pH 5.5): 4.93; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 46.90; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.592; (13)Molar Refractivity: 71.795 cm3; (14)Molar Volume: 212.246 cm3; (15)Surface Tension: 49.7709999084473 dyne/cm; (16)Density: 1.198 g/cm3; (17)Flash Point: 228.793 °C; (18)Enthalpy of Vaporization: 72.408 kJ/mol; (19)Boiling Point: 431.316 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.
Uses of Ketoprofen :
Ketoprofen is a common NSAID, antipyretic, and analgesic used in horses and other equines. It is also used as a mild painkiller in smaller animals, generally following surgical procedures. It is most commonly used for muscoskeletal pain, joint problems, and soft tissue injury, as well as laminitis. It does not treat the underlying problem, nor does it speed the healing process. It is also used to control fevers and prevent endotoxemia. However, they may mask the symptoms of the underlying problem, and therefore make diagnosis more difficult for a veterinarian.
Safety Information of Ketoprofen:
The Ketoprofen is toxic by inhalation,in contact with skin and if swallowed It is irritating to eyes, respiratory system and skin.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.When you use it ,wear suitable protective clothing, gloves and eye/face protection.In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES:CC(c1cccc(c1)C(=O)c2ccccc2)C(=O)O;
(2)Std. InChI:InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19);
(3)Std. InChIKey:DKYWVDODHFEZIM-UHFFFAOYSA-N.
The toxicity data of Ketoprofen as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | unreported | 300mg/kg/15D- (300mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: HEADACHE | New England Journal of Medicine. Vol. 300, Pg. 796, 1979. |
guinea pig | LD50 | intravenous | 450mg/kg (450mg/kg) | Journal de Pharmacologie. Vol. 2, Pg. 259, 1971. | |
guinea pig | LD50 | oral | 1300mg/kg (1300mg/kg) | Journal de Pharmacologie. Vol. 2, Pg. 259, 1971. | |
human | TDLo | oral | 714ug/kg (.714mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | Journal of Clinical Pharmacology. Vol. 24, Pg. 486, 1984. |
man | TDLo | oral | 5714ug/kg (5.714mg/kg) | Clinical Rheumatology. Vol. 10, Pg. 215, 1991. | |
man | TDLo | oral | 5714ug/kg (5.714mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" | Clinical Rheumatology. Vol. 10, Pg. 215, 1991. |
mouse | LD50 | intraperitoneal | 300mg/kg (300mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 11, Pg. 7, 1976. | |
mouse | LD50 | intravenous | 500mg/kg (500mg/kg) | Journal de Pharmacologie. Vol. 2, Pg. 259, 1971. | |
mouse | LD50 | oral | 360mg/kg (360mg/kg) | Polish Journal of Pharmacology and Pharmacy. Vol. 38, Pg. 107, 1986. | |
mouse | LD50 | subcutaneous | 550mg/kg (550mg/kg) | Journal de Pharmacologie. Vol. 2, Pg. 259, 1971. | |
rat | LD50 | intraperitoneal | 80mg/kg (80mg/kg) | Drugs in Japan Vol. 6, Pg. 265, 1982. | |
rat | LD50 | intravenous | 350mg/kg (350mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 222, 1978. | |
rat | LD50 | oral | 62400ug/kg (62.4mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 34, Pg. 280, 1984. | |
rat | LD50 | rectal | 84mg/kg (84mg/kg) | GASTROINTESTINAL: PERITONITIS GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE | Journal of Toxicological Sciences. Vol. 6, Pg. 209, 1981. |
rat | LD50 | subcutaneous | 100mg/kg (100mg/kg) | Journal de Pharmacologie. Vol. 2, Pg. 259, 1971. | |
women | TDLo | oral | 11mg/kg/12H-I (11mg/kg) | SKIN AND APPENDAGES (SKIN): SWEATING: OTHER CARDIAC: PULSE RATE BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Journal of Clinical Pyschopharmacology. Vol. 19, Pg. 95, 1999. |
women | TDLo | oral | 80mg/kg/10D-I (80mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | British Medical Journal. Vol. 292, Pg. 97, 1986. |
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