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| | 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN Basic information |
| Product Name: | 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN | | Synonyms: | 3-CHLORO-4-METHYLUMBELLIFERONE;3-CHLORO-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE;3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN;3-chloro-7-hydroxy-4-methyl-2h-1-benzopyran-2-on;3-chloro-7-hydroxy-4-methyl-2-benzopyrone;3-CHLORO-7-HYDROXY-4-METHYL-2H-1-BENZOPYRAN-2-ONE;3-Chloro-4-methyl-7-hydroxycoumarine;AKOS BBS-00008033 | | CAS: | 6174-86-3 | | MF: | C10H7ClO3 | | MW: | 210.61 | | EINECS: | 228-217-8 | | Product Categories: | Coumarins | | Mol File: | 6174-86-3.mol |  |
| | 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN Chemical Properties |
| Melting point | 240-244 °C (lit.) | | Boiling point | 405.8±45.0 °C(Predicted) | | density | 1.48±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | pka | 7.43±0.20(Predicted) | | form | Powder | | color | White to off-white | | λmax | 332nm(EtOH)(lit.) | | InChI | 1S/C10H7ClO3/c1-5-7-3-2-6(12)4-8(7)14-10(13)9(5)11/h2-4,12H,1H3 | | InChIKey | ODZHLDRQCZXQFQ-UHFFFAOYSA-N | | SMILES | CC1=C(Cl)C(=O)Oc2cc(O)ccc12 | | CAS DataBase Reference | 6174-86-3(CAS DataBase Reference) | | EPA Substance Registry System | 2H-1-Benzopyran-2-one, 3-chloro-7-hydroxy-4-methyl- (6174-86-3) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/37 | | WGK Germany | 3 | | TSCA | TSCA listed | | HS Code | 29329900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN Usage And Synthesis |
| Uses | Labelled Chlorferon is has α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Also used in the synthesis of fluorogenic substrates for the detection of bacterial β-Galactosidase. | | Definition | ChEBI: Chlorferron is an organochlorine compound. It is functionally related to a 4-methylumbelliferone. | | Synthesis | GENERAL STEPS: Resorcinol (2.0 g, 18.2 mmol) was dissolved in dioxane and the solution was cooled to 0 °C. Concentrated sulfuric acid (0.5 mL) was added slowly and dropwise at 25 °C. Subsequently, ethyl 2-chloroacetoacetate (2.8 g, 21.8 mmol) was added and the reaction mixture was heated to 60 °C and maintained at this temperature for 4 hours. After completion of the reaction, the mixture was poured into cold water, the precipitate was collected by filtration and dried under reduced pressure. Finally, the product was purified by recrystallization from methanol to give 3-chloro-7-hydroxy-4-methylcoumarin (6a) as white needle-like crystals. | | References | [1] Chemistry - A European Journal, 2012, vol. 18, # 32, p. 9901 - 9910
[2] Synthesis, 2006, # 11, p. 1895 - 1897
[3] Monatshefte fur Chemie, 2008, vol. 139, # 7, p. 805 - 808
[4] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 153 - 165
[5] Tetrahedron Letters, 2006, vol. 47, # 19, p. 3279 - 3281 |
| | 3-CHLORO-7-HYDROXY-4-METHYLCOUMARIN Preparation Products And Raw materials |
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