Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 50℃; for 4h; Suzuki-Miyaura coupling reaction; Inert atmosphere; | 96% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 140℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation; |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water for 0.208333h; microwave irradiation; | 95% |
Stage #1: indole-2,3-dione With cetyltrimethylammonium hydroxide In water at 20℃; for 0.166667h; Pfitzinger Quinoline Synthesis; Sonication; Green chemistry; Stage #2: acetophenone In water at 35℃; for 2.5h; Solvent; Reagent/catalyst; Temperature; Pfitzinger Quinoline Synthesis; Sonication; Green chemistry; | 95% |
With potassium hydroxide In ethanol at 50 - 60℃; for 14h; | 90% |
Conditions | Yield |
---|---|
With cesium fluoride In ethanol; water at 50℃; for 5h; Stille coupling; Inert atmosphere; | 92% |
3-Hydroxy-3-(2-oxo-2-phenyl-ethyl)-1,3-dihydro-indol-2-one
cinchophen
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid for 5h; Heating; | 90% |
With potassium hydroxide; ethanol |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 0.05h; Reagent/catalyst; Solvent; Microwave irradiation; Green chemistry; | 80% |
With ytterbium perfluorooctanoate In water for 3h; Doebner reaction; Reflux; | 72% |
In ethanol for 3h; Reflux; | 51% |
Conditions | Yield |
---|---|
Stage #1: benzaldehyde; 2-oxo-propionic acid With acetic acid for 1h; Reflux; Stage #2: With aniline for 8h; Reflux; | 62.2% |
2-phenyl-4-quinolinecarboxaldehyde
A
4-hydroxymethyl-2-phenylquinoline
B
cinchophen
Conditions | Yield |
---|---|
With potassium hydroxide; ethanol; water | |
With potassium hydroxide; ethanol; water |
3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one
cinchophen
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol; water | |
With ethanol; water; potassium carbonate |
Conditions | Yield |
---|---|
With ethanol; acetic acid; aniline |
2-(4-nitrophenyl)quinoline-4-carboxylic acid
cinchophen
Conditions | Yield |
---|---|
beim Nitrieren; |
N-[2-oxo-1-(2-oxo-indolin-3-yl)-2-phenyl-ethyl]-benzamide
cinchophen
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol |
Conditions | Yield |
---|---|
With ethanol |
ethanol
benzaldehyde
2-oxo-propionic acid
aniline
A
cinchophen
B
1,5-diphenyl-3-phenylimino-pyrrolidin-2-one
Conditions | Yield |
---|---|
With potassium hydroxide |
2-(2-acetamidophenyl)-N,N-diethyl-2-oxoacetamide
acetophenone
cinchophen
Conditions | Yield |
---|---|
With sodium hydroxide 1.) reflux, 1 h, 2.) reflux, 18 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid Heating; decomposition; |
cinchophen
Conditions | Yield |
---|---|
With chromium(III) oxide; sulfuric acid |
cinchophen
Conditions | Yield |
---|---|
With sulfuric acid at 130℃; |
hydrogenchloride
N-[2-oxo-1-(2-oxo-indolin-3-yl)-2-phenyl-ethyl]-benzamide
cinchophen
hydrogenchloride
ethanol
3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one
water
cinchophen
ethanol
3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one
water
cinchophen
Conditions | Yield |
---|---|
With sulfuric acid Reflux; | 100% |
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 0 - 20℃; for 13h; | 99% |
With thionyl chloride at 0℃; Reflux; | 84.9% |
cinchophen
3-amino-2-methyl-6-bromoquinazolin-4(3H)-one
2-Phenyl-quinoline-4-carboxylic acid (6-bromo-2-methyl-4-oxo-4H-quinazolin-3-yl)-amide
Conditions | Yield |
---|---|
With triethylamine; trichlorophosphate In toluene for 0.75h; Product distribution; Heating; other aromatic acids, also with 3-amino-2-methyl-4(3H)-quinazolone, influence of Et3N; | 99% |
With triethylamine; trichlorophosphate In toluene for 0.75h; Heating; | 99% |
cinchophen
Conditions | Yield |
---|---|
With tetramethylammonium trifluoromethanethiolate In dichloromethane at 25℃; for 2h; | 96% |
With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 95% |
With tetramethylammonium trifluoromethanethiolate In dichloromethane at 20℃; for 1h; | 89% |
cinchophen
3-(tert-butyldimethylsilyloxy)-17α-(3'-hydroxyprop-1'-ynyl)estradiol
3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate
Conditions | Yield |
---|---|
With dmap; N,N'-1,2-ethylenediylbis-(L-cysteine) diethyl ester dihydrochloride In dichloromethane at 0 - 20℃; for 2h; | 95% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; | 95% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 94.3% |
Conditions | Yield |
---|---|
With sulfuric acid for 0.166667h; microwave irradiation; | 94% |
With sulfuric acid Reflux; | 89% |
With sulfuric acid Fischer-Speier Esterification; Reflux; | 75% |
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h; | 94% |
cinchophen
2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside
2-Phenyl-quinoline-4-carboxylic acid 2-[(2S,4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 4.5h; Esterification; | 93% |
cinchophen
N,N-dimethylethylenediamine
N-[2-(dimethylamino)ethyl]-2-phenylquinoline-4-carboxamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 93% |
1-methyl-azetidin-3-amine
cinchophen
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 92.3% |
Conditions | Yield |
---|---|
Stage #1: cinchophen; aniline With benzotriazol-1-ol In N,N-dimethyl-formamide for 0.25h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 4h; Reagent/catalyst; Solvent; Temperature; | 90.1% |
With trichlorophosphate for 8h; Reflux; | 56% |
With Tetraethyl pyrophosphate; toluene | |
With Tetraethyl pyrophosphate |
cinchophen
2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-β-D-arabinohexopyranoside
2-Phenyl-quinoline-4-carboxylic acid 2-[(2R,4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 4.5h; Esterification; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 90% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 89.2% |
cinchophen
4-amino-N,N-dimethylaniline
N-(4-(dimethylamino)phenyl)-2-phenylquinoline-4-carboxamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 89% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 87% |
cinchophen
2-(2-amino-3-methoxyphenyl)-benzoxazole-4-carboxylic acid methyl ester
2-[3-methoxy-2-[(2-phenylquinoline-4-carbonyl)-amino]-phenyl]-benzoxazole-4-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: cinchophen With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Stage #2: 2-(2-amino-3-methoxyphenyl)-benzoxazole-4-carboxylic acid methyl ester With pyridine In dichloromethane | 86% |
Conditions | Yield |
---|---|
With PPA at 210 - 270℃; for 0.0416667h; microwave irradiation; | 85% |
With PPA | 70% |
cinchophen
2'-(tert-butyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazole]-7'(6'H)-one
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 12.5h; | 85% |
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 12h; | 85% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 48h; | 84% |
Conditions | Yield |
---|---|
With trichlorophosphate for 8h; Reflux; | 84% |
3-(hydroxymethyl)benzo[d]oxazol-2(3H)-one
cinchophen
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 5℃; for 2h; | 84% |
1,3,5-tripropyl-1,3,5-triazinane
tert-butylisonitrile
cinchophen
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 45℃; Ugi Condensation; | 83% |
Conditions | Yield |
---|---|
With trichlorophosphate for 8h; Reflux; | 82% |
Empirical Formula: C16H11NO2
Molecular Weight: 249.264 g/mol
EINECS: 205-067-1
Melting point: 214-215 °C(lit.)
Sensitive: Light sensitive
Index of Refraction: 1.682
Density: 1.28 g/cm3
Flash Point: 230.1 °C
Enthalpy of Vaporization: 75.55 kJ/mol
Boiling Point: 456.9 °C at 760 mmHg
Vapour Pressure: 3.84E-09 mmHg at 25 °C
Structure of Cinchophen (CAS NO.132-60-5):
IUPAC Name: 2-Phenylquinoline-4-carboxylic acid
Product Categories: API intermediates;Quinolinecarboxylic Acids
Cinchophen (CAS NO.132-60-5) has been used as antipyretic analgesic for acute and chronic arthritis, rheumatic pain, neuralgia, lumbago, gout, headache and so on.
First, having the preparation of isatin to be its sodium salt, and generated by the open-loop, and then with the cyclization of acetophenone to get Sim sodium , or with acetic acid or hydrochloric acid can be derived Xin-fen .
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | 1250mg/kg (1250mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. | |
human | LDLo | oral | 214mg/kg (214mg/kg) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 177, 1969. | |
man | LDLo | unreported | 74mg/kg (74mg/kg) | "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970. | |
mouse | LD50 | intraperitoneal | 200mg/kg (200mg/kg) | National Technical Information Service. Vol. AD691-490, | |
mouse | LD50 | subcutaneous | 350mg/kg (350mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 116, Pg. 154, 1958. | |
mouse | LDLo | oral | 1500mg/kg (1500mg/kg) | "Narkoseversuche mit Hoheren Alkoholen und Stickstoffderivaten, Dissertation," Leube, F., Pharmakologischen Institut der Universitat Tubingen, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. | |
rabbit | LDLo | unreported | 500mg/kg (500mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Journal of Pharmacology and Experimental Therapeutics. Vol. 74, Pg. 365, 1942. |
rat | LD50 | intravenous | 600mg/kg (600mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. | |
rat | LDLo | oral | 500mg/kg (500mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 260, 1947. |
Cinchophen (CAS NO.132-60-5) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.
A human poison by ingestion. An experimental poison by intraperitoneal and subcutaneous routes. Moderately toxic by an unspecified route. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes of Cinchophen (CAS NO.132-60-5): Xn
Risk Statements: 22
R22:Harmful if swallowed.
Safety Statements: 36/37/39-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
Cinchophen ,its cas register number is 132-60-5. It also can be called Cinchoninic acid, 2-phenyl- ; and 4-Quinolinecarboxylic acid, 2-phenyl- . 1g of the product can be dissolved in about 400ml chloroform, 100ml ether, 120ml of ethanol, almost insoluble in water. It is hazardous,so the first aid measures and others should be known. Such as: When on the skin: first,should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly,Get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.Notes to physician: Treat supportively and symptomatically.
In addition, Cinchophen (CAS NO.132-60-5) may discolor on exposure to light. It is not compatible with strong oxidizing agents, strong bases, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, carbon dioxide.
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