1-Methoxy-4-methyl-2-nitrobenzene

Base Information

• Chemical Name: 1-Methoxy-4-methyl-2-nitrobenzene
• CAS No.: 119-10-8
• Molecular Formula: C8H9NO3
• Molecular Weight: 167.164
• Hs Code.: 29093090
• European Community (EC) Number: 204-296-4
• UNII: 3B4205T5ZM
• DSSTox Substance ID: DTXSID3029152
• Nikkaji Number: J154.679A
• Wikidata: Q27256991
• ChEMBL ID: CHEMBL3188546
• Mol file: 119-10-8.mol

Synonyms:4-Methyl-2-nitroanisole;119-10-8;1-methoxy-4-methyl-2-nitrobenzene;4-Methoxy-3-nitrotoluene;Anisole, 4-methyl-2-nitro-;Methyl 2-nitro-p-tolyl ether;Benzene, 1-methoxy-4-methyl-2-nitro-;EINECS 204-296-4;UNII-3B4205T5ZM;DTXSID3029152;3B4205T5ZM;MFCD00024540;2-Methoxy-5-methylnitrobenzene;4-methyl-2-nitroanisol;3-nitro-4-methoxytoluene;4-methyl-2-nitro-anisole;SCHEMBL317536;DTXCID409152;2-NITRO-4-METHYLANISOLE;CHEMBL3188546;4-Methyl-2-nitroanisole, 99%;STR08535;4-methyl-2-nitrophenol methyl ether;Tox21_201221;AKOS015890178;AC-1354;PS-4995;NCGC00248962-01;NCGC00258773-01;CAS-119-10-8;SY106192;2-METHOXY-5-METHYL-1-NITROBENZENE;J154.679A;METHYL 4-METHYL-2-NITROPHENYL ETHER;CS-0009464;FT-0619008;M1205;D72475;EN300-2010055;A804199;AJ-797/43492807;J-004066;Q27256991

Chemical Property of 1-Methoxy-4-methyl-2-nitrobenzene

Chemical Property:

• Vapor Pressure: 0.00384mmHg at 25°C
• Melting Point: 8-9 °C(lit.)
• Refractive Index: n20/D 1.557(lit.)
• Boiling Point: 289.36 °C at 760 mmHg
• Flash Point: 136.054 °C
• PSA: 55.05000
• Density: 1.181 g/cm³
• LogP: 2.43500
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (sparingly), DMSO (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 167.058243149
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxy-3-nitrotoluene >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)OC)[N+](=O)[O-]
• Uses: 4-Methyl-2-nitroanisole may be used in the synthesis of 1-dibromomethyl-4-methoxy-2-nitrobenzene.

Technology Process of 1-Methoxy-4-methyl-2-nitrobenzene

There total 40 articles about 1-Methoxy-4-methyl-2-nitrobenzene 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: 91.0%

p-methylanizole (104-93-8) → 4-methoxy-3-nitrotoluene (119-10-8)

Guidance literature:

With sodium nitrate; acetic acid; trifluoroacetic acid; at 20 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.1c02183

Reference yield: 90.0%

4-methyl-2-nitrophenol (119-33-5) + dimethyl sulfate (77-78-1) → 4-methoxy-3-nitrotoluene (119-10-8)

Guidance literature:

4-methyl-2-nitrophenol; With sodium hydroxide; In water;

dimethyl sulfate; With tetrabutylammomium bromide; In dichloromethane; water; at 10 - 25 ℃; for 10 - 12h;

Reference yield: 90.0%

4-methyl-2-nitrophenol (119-33-5) + methyl iodide (74-88-4) → 4-methoxy-3-nitrotoluene (119-10-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 12h; Ambient temperature;

upstream raw materials:

p-methylanizole

methanol

1-chloro-4-methyl-2-nitro-benzene

4-methyl-2-nitrophenol

Downstream raw materials:

4-methyl-2-nitrophenol

2,6-dinitro-4-methylanisole

(Z)-3-methoxy-6-methyl-4,6-dinitrocyclohexa-2,4-dienyl acetate

(Z)-3-methoxy-6-methyl-2,6-dinitrocyclohexa-2,4-dienyl acetate

Refernces

Replacing the terminal piperidine in ceritinib with aliphatic amines confers activities against crizotinib-resistant mutants including G1202R

10.1016/j.ejmech.2016.11.046

The research explores the development of new ALK inhibitors to address resistance issues in non-small cell lung cancer (NSCLC) patients. The study focuses on modifying ceritinib by replacing its piperidine fragment with diverse aliphatic amines to improve its efficacy against crizotinib-resistant mutants, particularly the highly resistant G1202R mutant. The researchers synthesized and evaluated a series of compounds, with compound 10 (KRCA-764) showing promising activities against both wild-type ALK and crizotinib-resistant mutants, including G1202R, with an IC50 of 1.8 nM. This compound also exhibited better pharmacokinetic profiles than ceritinib. Key chemicals involved in the synthesis included 4-methyl-2-nitroanisole, phenylthioacetonitrile, sodium hydroxide, Pd/C, and various amines. The study utilized enzymatic and cell-based assays to evaluate the inhibitory activities of the synthesized compounds, and molecular docking studies were performed to understand the binding modes. In vivo xenograft studies in mice demonstrated that compound 10 had similar potency to ceritinib, suggesting further optimization could lead to clinical candidates capable of overcoming ALK mutant resistance.