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| CAS No.: | 132-60-5 |
|---|---|
| Name: | CINCHOPHEN |
| Article Data: | 87 |
| Molecular Structure: | |
|
|
|
| Formula: | C16H11 N O2 |
| Molecular Weight: | 249.269 |
| Synonyms: | Cinchoninicacid, 2-phenyl- (8CI); 2-Phenyl-4-quinolinecarboxylic acid; 2-Phenylcinchonicacid; 2-Phenylcinchoninic acid; 4-Carboxy-2-phenylquinoline; Aciphenochinoline;Aciphenochinolinium; Agotan; Alutyl; Alutyo; Aminophan; Artam; Artexin; Atigoa;Atocin; Atofan; Atophan; Cinchophen; Cinchophene; Cinchophenic acid; Cinconal;Cincophen; Cincosal; Ikterosan; Mylofanol; NSC 2617; NSC 70178; Phenophan;Phenoquin; Polyphlogin; Quinofen; Quinophan; Quinophen; Rhematan; Rheumatan;Rheumin; Rheumine; Tervalon; Tophol; Tophosan; Traubofan; Vantyl; Viophan |
| Density: | 1.28g/cm3 |
| Melting Point: |
214-215 °C(lit.) |
| Boiling Point: | 456.9°Cat760mmHg |
| Flash Point: | 230.1°C |
| Solubility: | Insoluble in water |
| Hazard Symbols: |
|
| Risk Codes: | 22 |
| Safety: | 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. |
| PSA: | 50.19000 |
| LogP: | 3.60000 |
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| 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% |
- 88730-73-8
3-Hydroxy-3-(2-oxo-2-phenyl-ethyl)-1,3-dihydro-indol-2-one
- 132-60-5
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% |
- 117839-38-0
2-phenyl-4-quinolinecarboxaldehyde
A
- 29268-33-5
4-hydroxymethyl-2-phenylquinoline
B
- 132-60-5
cinchophen
| Conditions | Yield |
|---|---|
| With potassium hydroxide; ethanol; water | |
| With potassium hydroxide; ethanol; water |
- 31541-36-3, 34880-79-0, 56680-29-6
3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one
- 132-60-5
cinchophen
| Conditions | Yield |
|---|---|
| With hydrogenchloride; ethanol; water | |
| With ethanol; water; potassium carbonate |
| Conditions | Yield |
|---|---|
| With ethanol; acetic acid; aniline |
- 70097-13-1
2-(4-nitrophenyl)quinoline-4-carboxylic acid
- 132-60-5
cinchophen
| Conditions | Yield |
|---|---|
| beim Nitrieren; |
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Chemistry
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
Uses
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.
Production
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 .
Toxicity Data With Reference
| 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.
Safety Profile
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.
Specification
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.