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| CAS No.: | 531-81-7 |
|---|---|
| Name: | Coumarin-3-carboxylic acid |
| Article Data: | 163 |
| Molecular Structure: | |
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| Formula: | C10H6O4 |
| Molecular Weight: | 190.155 |
| Synonyms: | 1,2-Benzopyran-3-carboxylicacid, 2-keto- (3CI);2-Oxo-2H-1-benzopyran-3-carboxylic acid;2H-1-Benzopyran-2-one-3-carboxylic acid;3-Carboxycoumarin;3-Carboxylcoumarin;Coumarin-3-carboxylic acid;G 1;G 1 (rodenticide);NSC 14797;NSC 44926;NSC53239; |
| EINECS: | 208-518-0 |
| Density: | 1.493 g/cm3 |
| Melting Point: | 189-192 ºC(lit.) |
| Boiling Point: | 388.6 °C at 760mmHg |
| Flash Point: | 162.7 °C |
| Solubility: | Water Solubility : 13 g/L (37 ºC) |
| Appearance: | light brown crystalline powder |
| Hazard Symbols: |
 T,  Xi
|
| Risk Codes: | 25 |
| Safety: | 36/37/39-45-28A |
| Transport Information: | UN 2811 |
| PSA: | 67.51000 |
| LogP: | 1.49120 |
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Specification
The IUPAC name of Coumarin-3-carboxylic acid is 2-oxochromene-3-carboxylic acid . With the CAS registry number 531-81-7, it is also named as 2-Oxobenzopyran-3-carboxylic acid ; 3-Carboxycoumarin ; 5-18-08-00323 (Beilstein Handbook Reference) ; AI3-36066 ; G 1 (The rodenticide) (VAN) ; Malonic acid, salicylidene-, delta-lactone ; 2-Oxo-2H-chromene-3-carboxylic acid ; 2H-1-Benzopyran-3-carboxylic acid, 2-oxo- . It is a pharmaceutical intermediate. Coumarin-3-carboxylic acid was used as a detector for hydroxyl radicals (.OH) in aqueous solution. This method is quantitative, sensitive, specific and therefore accurate. It has an excellent potential for use in biological systems.
The Coumarin-3-carboxylic acid can be obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. It is also prepared by 2-oxo-2H-chromene-3-carboxylic acid ethyl ester , 2-hydroxy-benzaldehyde and malonic acid .
The Coumarin-3-carboxylic acid can be used in many organic synthesis. For example: 1. It reacts with 5,6-diamino-3-methyl-1-phenyl-1H-pyrimidine-2,4-dione to get 2-oxo-2H-chromene-3-carboxylic acid (6-amino-3-methyl-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide . 2. It reacts with 3-amino-4-hydroxy-chromen-2-one to obtain 2-(3-coumarinyl)-coumarino(3',4':4,5)oxazole .
The Coumarin-3-carboxylic acid is toxic if swallowed. If you want to contact the product, you must wear suitable protective clothing, gloves and eye/face protection. After contact with skin, wash immediately with plenty of soap-suds. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
The other characteristics of this product can be summarized as: (1)#H bond acceptors: 4 ; (2)#H bond donors: 1 ; (3)#Freely Rotating Bonds: 1 ; (4)Index of Refraction: 1.639 ; (5)Molar Refractivity: 45.86 cm3 ; (6)Molar Volume: 127.3 cm3 ; (7)Polarizability: 18.18×10-24 cm3 ; (8)Surface Tension: 66.8 dyne/cm ; (9)Enthalpy of Vaporization: 67.28 kJ/mol ; (10)Vapour Pressure: 9.77E-07 mmHg at 25°C. People can use the following data to convert to the molecule structure. SMILES: O=C(O)C\1=C\c2c(OC/1=O)cccc2; InChI: InChI=1/C10H6O4/c11-9(12)7-5-6-3-1-2-4-8(6)14-10(7)13/h1-5H,(H,11,12).
The following is the toxicity data which has been tested.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02594, | |
| rat | LD50 | oral | 200mg/kg (200mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 260, 1947. |