| Identification | More | [Name]
6-CHLOROCHROMAN-4-ONE | [CAS]
37674-72-9 | [Synonyms]
6-CHLORO-2,3-DIHYDRO-4H-CHROMEN-4-ONE
6-CHLORO-4-CHROMANONE
6-CHLOROCHROMAN-4-ONE
6-CHLOROCHROMANONE
BUTTPARK 35\07-32
TIMTEC-BB SBB003732
4H-1-Benzopyran-4-one, 6-chloro-2,3-dihydro-
6-Chloro-4-chromanone (6-Chlorochroman-4-one)
6-Chloro-2,3-dihydro-4H-1-benzopyran-4-one
6-Chloro-3,4-dihydro-2H-1-benzopyran-4-one | [EINECS(EC#)]
253-611-1 | [Molecular Formula]
C9H7ClO2 | [MDL Number]
MFCD00024070 | [Molecular Weight]
182.6 | [MOL File]
37674-72-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
97-102 °C(lit.) | [Boiling point ]
322.0±42.0 °C(Predicted) | [density ]
1.345±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in solvents. | [form ]
powder to crystal | [color ]
White to Yellow to Orange | [BRN ]
124218 | [InChIKey]
LLTDYHFVIVSQPJ-UHFFFAOYSA-N | [CAS DataBase Reference]
37674-72-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [HS Code ]
29329990 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
6-Chlorochroman-4-one is used as chemical, organic intermediates for pharmaceuticals. | [Synthesis]
General procedure for the synthesis of 6-chlorobenzodihydropyran-4-one from 3-(p-chlorophenoxy)propionic acid: 3-(p-chlorophenoxy)propionic acid (2 g, 10 mmol) was reacted with concentrated sulfuric acid (20 mL) with stirring for 1 hour at room temperature. After completion of the reaction, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed twice with saturated aqueous sodium bicarbonate and subsequently dried with magnesium sulfate. The dried organic phase was filtered and concentrated under reduced pressure. The crude product was purified by solvent recrystallization from ethyl acetate/hexane (1:5) mixture. The resulting crystals were collected by filtration, washed with hexane and dried to give the target product 6-chlorobenzodihydropyran-4-one (1 g, 55% yield): melting point 98-101 °C (literature value: 100-101 °C); 1H NMR (DMSO-d6) δ 2.82 (t, J=6.5 Hz, 2H, 3-H2), 4.56 (t, J=6.5 Hz, 2H, 2 -H2), 7.1 (d, J=8.9 Hz, 1H, 8-H), 7.6 (dd, J=8.9 Hz/2.7 Hz, 1H, 7-H), 7.68 (d, J=2.7 Hz, 1H, 5-H); 13C NMR (DMSO-d6) δ 36.8 (C-3), 66.9 (C-2), 120.3 (C-8) 122.0 (C-4a/C-6), 125.3 (C-5), 135.6 (C-7), 160.1 (C-8a), 190.6 (C-4). | [References]
[1] Chinese Journal of Chemistry, 2011, vol. 29, # 4, p. 757 - 764
[2] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 834 - 844
[3] Journal of the Indian Chemical Society, 1939, vol. 16, p. 639,644
[4] Journal of the Indian Chemical Society, 1957, vol. 34, p. 467,468
[5] Journal of the American Chemical Society, 1954, vol. 76, p. 5065,5067 |
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