5-CHLORO-2-NITROANISOLE Chemical Properties

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

5-Chloro-2-nitroanisole (6627-53-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HS Code 

2909309090

MSDS

• Language:English Provider:SigmaAldrich

5-CHLORO-2-NITROANISOLE Usage And Synthesis

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 (1). 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 (2).

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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