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| | 6-BROMO-4-CHLOROQUINOLINE Basic information |
| Product Name: | 6-BROMO-4-CHLOROQUINOLINE | | Synonyms: | BUTTPARK 23\09-04;4-CHLORO-6-BROMOQUINOLINE;6-BROMO-4-CHLOROQUINOLINE;6-Bromo-4-chloroquinoline ,98%;6-Bromo-4-chloroquinoline ,97%;6-Bromo-4-chloro-1-azanaphthalene;4--6-broMinechlorinequinoline;Quinoline,6-bromo-4-chloro- | | CAS: | 65340-70-7 | | MF: | C9H5BrClN | | MW: | 242.5 | | EINECS: | | | Product Categories: | | | Mol File: | 65340-70-7.mol |  |
| | 6-BROMO-4-CHLOROQUINOLINE Chemical Properties |
| Melting point | 110-112℃ | | Boiling point | 314.6±22.0 °C(Predicted) | | density | 1.673±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Toluene | | form | solid | | pka | 2.76±0.16(Predicted) | | Appearance | White to light yellow Solid | | InChI | InChI=1S/C9H5BrClN/c10-6-1-2-9-7(5-6)8(11)3-4-12-9/h1-5H | | InChIKey | KJILYZMXTLCPDQ-UHFFFAOYSA-N | | SMILES | N1C2C(=CC(Br)=CC=2)C(Cl)=CC=1 |
| Hazard Codes | T | | Risk Statements | 25-20/22 | | Safety Statements | 45-36/37 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29334900 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Eye Irrit. 2
Skin Irrit. 2 |
| | 6-BROMO-4-CHLOROQUINOLINE Usage And Synthesis |
| Chemical Properties | Light yellow to yellow powder | | Uses | 6-Bromo-4-chloroquinoline belongs to the class of heterocyclic compounds and has been used in the synthesis of other compounds, such as pharmaceuticals.
| | Pharmaceutical Applications | 6-bromo-4-chloroquinoline is an important intermediate of Omipalisib[6].
Omipalisib (GSK2126458, GSK458) is a kind of highly selective, effective p110 α/β/gamma/delta and MTORC1/2 inhibitor is that one kind is mainly used for treating solid tumor, lymthoma, idiopathic pulmonary fibrosis and idiopathic pulmonary interstitial fibre The therapeutic agent of dimensionization. | | Synthesis | 4.1.8 Synthesis of 6-bromo-4-chloroquinoline (11)
To a 100 mL round bottom flask were sequentially added 6-bromo-4-hydroxyquinoline (10) (3.0 g, 13.45 mmol), phosphorus trichloride (20 mL) and N,N-dimethylformamide (0.5 mL). The reaction mixture was heated to reflux and stirred for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was slowly poured into ice water (100 mL) and stirring was continued for 1 hour. Subsequently, the pH of the mixture was adjusted with saturated aqueous sodium bicarbonate solution to 8. The reaction mixture was extracted with ethyl acetate, the organic phases were combined and dried with anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give the title compound 6-bromo-4-chloroquinoline (11) (2.75 g, 11.36 mmol, 84% yield) as a white solid.
1H NMR (500 MHz, DMSO-d6) δ 8.87 (d, J = 4.5 Hz, 1H, Ar-H), 8.32 (d, J = 2.0 Hz, 1H, Ar-H), 8.03 (d, J = 9.0 Hz, 1H, Ar-H), 7.99 (dd, J = 9.0, 2.0 Hz, 1H, Ar-H), 7.82 (d, J = 4.5 Hz, 1H, Ar-H).
ESI-MS: m/z = 242 [M + H]+. | | References | [1] Patent: US2006/63805, 2006, A1. Location in patent: Page/Page column 9
[2] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[3] Patent: US2015/320727, 2015, A1. Location in patent: Paragraph 0557; 0558
[4] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[5] Patent: WO2006/132739, 2006, A2. Location in patent: Page/Page column 48
[6] Patent: CN106432073B, 2016. |
| | 6-BROMO-4-CHLOROQUINOLINE Preparation Products And Raw materials |
| Raw materials | Ethyl acetate-->Diethyl ether-->N,N-Dimethylformamide-->Thionyl chloride-->Petroleum ether-->Sodium sulfate-->Acetone-->Sodium bicarbonate-->Hexane-->Diphenyl ether-->Biphenyl-->4-Bromoaniline-->Trimethoxymethane-->2,2-Dimethyl-1,3-dioxane-4,6-dione-->2-methylpentane-->2-Propenoic acid, 3-[(4-bromophenyl)amino]-, ethyl ester-->2-(P-TOLYLAMINOMETHYLENE)MALONIC ACID DIETHYL ESTER-->5-[(4-Bromophenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione ,98% |
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