5-Chloro-2-nitroanisole

Base Information

• Chemical Name: 5-Chloro-2-nitroanisole
• CAS No.: 6627-53-8
• Molecular Formula: C7H6ClNO3
• Molecular Weight: 187.583
• Hs Code.: 2909309090
• European Community (EC) Number: 229-594-1
• NSC Number: 60112
• UNII: SVY2LTV7GJ
• DSSTox Substance ID: DTXSID4064426
• Nikkaji Number: J5.205A
• Wikidata: Q72455667
• Mol file: 6627-53-8.mol

Synonyms:5-Chloro-2-nitroanisole;6627-53-8;4-Chloro-2-methoxy-1-nitrobenzene;4-Chloro-2-methoxynitrobenzene;2-Nitro-5-chloroanisole;Benzene, 4-chloro-2-methoxy-1-nitro-;Anisole, 2-nitro-5-chloro-;Anisole, 5-chloro-2-nitro-;5-Chloro-2-nitro-1-methoxybenzene;6227-53-8;SVY2LTV7GJ;EINECS 229-594-1;MFCD00007288;NSC 60112;NSC-60112;NSC60112;4-chloro-2-methoxy-1-nitro-benzene;UNII-SVY2LTV7GJ;SCHEMBL102625;DTXSID4064426;5-Chloro-2-nitroanisole, 97%;ABEUJUYEUCCZQF-UHFFFAOYSA-;5-chloro-2-nitrophenyl methyl ether;AB6852;2-METHOXY-4-CHLORONITROBENZENE;4-Chloro-2-methoxy-1-nitrobenzene #;AKOS005216326;AC-3778;AM62071;CS-W007477;PS-3461;4-chloro-2-(methyloxy)-1-nitrobenzene;SY026548;1-CHLORO-3-METHOXY-4-NITROBENZENE;FT-0636201;A19860;EN300-152625;AF-962/00506059;J-514956

Chemical Property of 5-Chloro-2-nitroanisole

Chemical Property:

• Appearance/Colour: slightly yellow to green crystalline powder
• Vapor Pressure: 0.00389mmHg at 25°C
• Melting Point: 70-72°C(lit.)
• Refractive Index: 1.559
• Boiling Point: 289.1 ºC at 760 mmHg
• Flash Point: 128.7 ºC
• PSA: 55.05000
• Density: 1.366 g/cm³
• LogP: 2.78000
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 187.0036207
• Heavy Atom Count: 12
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

5-Chloro-2-nitroanisole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)Cl)[N+](=O)[O-]
• 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. 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).

Technology Process of 5-Chloro-2-nitroanisole

There total 14 articles about 5-Chloro-2-nitroanisole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

sodium methylate (124-41-4) + 3,4-dinitro-chlorobenzene (610-40-2) → 4-chloro-2-nitroanisole (89-21-4) + 1-chloro-3-methoxy-4-nitrobenzene (6627-53-8)

Guidance literature:

In methanol; for 0.5h;

Reference yield:

5-chloro-2-nitrophenol (611-07-4) + methyl iodide (74-88-4) → 1-chloro-3-methoxy-4-nitrobenzene (6627-53-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

Reference yield:

2,4-dichloronitrobenzene (611-06-3) → 1-chloro-3-methoxy-4-nitrobenzene (6627-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1: water; sodium hydroxide / dimethyl sulfoxide / 16 h / 60 °C

2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C

With water; potassium carbonate; sodium hydroxide; In dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

1,4-dioxane

methanol

(5-chloro-2-nitro-phenyl)-phenyl sulfone

sodium methylate

Downstream raw materials:

2-methoxy-4-(methylsulfanyl)-1-nitrobenzene

bis-(3-methoxy-4-nitro-phenyl)-sulfide

2-methoxy-1-nitro-4-phenoxy-benzene

3-methoxy-6-nitro-phenol

Refernces

• 1、 -. "COVALENT INHIBITORS OF KRAS G12C". Paragraph 0461. . Retrieved 2014/09/30.
• 2、 Varenikova, S. F.,Nekhoroshev, A. A.,Sevbo, D. P.. "Methoxylation of 3,4-dinitrochloro(bromo)benzene". . p. 1651 - 1652. Retrieved 2007/10/02.