| Identification | More | [Name]
5-CHLORO-2-NITROANISOLE | [CAS]
6627-53-8 | [Synonyms]
4-CHLORO-2-METHOXYNITROBENZENE
5-CHLORO-2-NITROANISOLE
4-chloro-2-methoxy-1-nitro-benzen
4-Chloro-2-methoxynitrobenzene 98%
4-chloro-2-methoxy-1-nitro-benzene
4-Chloro-3-methoxy-1-nitrobenzene
5-CHLORO-2-NITROANISOLE 97% | [EINECS(EC#)]
229-594-1 | [Molecular Formula]
C7H6ClNO3 | [MDL Number]
MFCD00007288 | [Molecular Weight]
187.58 | [MOL File]
6627-53-8.mol |
| Chemical Properties | Back Directory | [Appearance]
SLIGHTLY YELLOW TO GREEN CRYSTALLINE POWDER | [Melting point ]
70-72 °C(lit.)
| [Boiling point ]
289.1±20.0 °C(Predicted) | [density ]
1.4219 (rough estimate) | [refractive index ]
1.6000 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, Ethyl Acetate | [form ]
Solid | [color ]
Yellow | [InChI]
InChI=1S/C7H6ClNO3/c1-12-7-4-5(8)2-3-6(7)9(10)11/h2-4H,1H3 | [InChIKey]
ABEUJUYEUCCZQF-UHFFFAOYSA-N | [SMILES]
C1([N+]([O-])=O)=CC=C(Cl)C=C1OC | [CAS DataBase Reference]
6627-53-8(CAS DataBase Reference) | [EPA Substance Registry System]
6627-53-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
2909309090 |
| Hazard Information | Back Directory | [Chemical Properties]
SLIGHTLY YELLOW TO GREEN CRYSTALLINE POWDER | [Uses]
5-Chloro-2-nitroanisole is involved in the synthesis of orally bioavailable anaplastic lymphoma kinases (ALK) inhibitors as anticancer drugs. In addition it is used in the synthesis of kinesin spindle
protein (KSP) inhibitors which are responsible for the spindle pole separation which occurs during mitosis in cancer cells. | [Synthesis]
To 5-chloro-2-nitrophenol (40 g, 0.23 mol) and iodomethane (49 g, 0.345 mol) in DMF (200 mL), K2CO3 (47.6 g, 0.345 mol) was added. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography (with petroleum ether as eluent) to afford the target product 2-nitro-5-chloroanisole (30 g, 70% yield). | [References]
[1] Liebigs Annalen der Chemie, 1988, p. 203 - 208
[2] Patent: US2014/288045, 2014, A1. Location in patent: Paragraph 0461
[3] Patent: WO2016/44772, 2016, A1. Location in patent: Paragraph 323 |
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