Product Name

  • Name

    Coumarin-3-carboxylic acid

  • EINECS 208-518-0
  • CAS No. 531-81-7
  • Article Data163
  • CAS DataBase
  • Density 1.493 g/cm3
  • Solubility Water Solubility : 13 g/L (37 ºC)
  • Melting Point 189-192 ºC(lit.)
  • Formula C10H6O4
  • Boiling Point 388.6 °C at 760mmHg
  • Molecular Weight 190.155
  • Flash Point 162.7 °C
  • Transport Information UN 2811
  • Appearance light brown crystalline powder
  • Safety 36/37/39-45-28A
  • Risk Codes 25
  • Molecular Structure Molecular Structure of 531-81-7 (Coumarin-3-carboxylic acid)
  • Hazard Symbols ToxicT, IrritantXi
  • 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;
  • PSA 67.51000
  • LogP 1.49120

Coumarin-3-carboxylic acid 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.

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