2-Methyl-5-nitroaniline

Base Information

• Chemical Name: 2-Methyl-5-nitroaniline
• CAS No.: 99-55-8
• Molecular Formula: C7H8N2O2
• Molecular Weight: 152.153
• Hs Code.: 29214300
• European Community (EC) Number: 202-765-8
• NSC Number: 8947
• UN Number: 2660
• UNII: 433MYH2DWM
• DSSTox Substance ID: DTXSID4020959
• Nikkaji Number: J95.089K
• Wikidata: Q27135494
• Metabolomics Workbench ID: 64835
• ChEMBL ID: CHEMBL324642
• Mol file: 99-55-8.mol

Synonyms:2-methyl-5-nitroaniline;5-nitro-2-toluidine;5-nitro-2-toluidine monohydrochloride;5-nitro-2-toluidine sulfate;5-nitro-ortho-toluidine

Chemical Property of 2-Methyl-5-nitroaniline

Chemical Property:

• Appearance/Colour: yellow powder
• Melting Point: 104-107 °C
• Refractive Index: 1.6276 (estimate)
• Boiling Point: 329.4 °C at 760 mmHg
• PKA: 2.34±0.10(Predicted)
• Flash Point: 153 °C
• PSA: 71.84000
• Density: 1.269 g/cm³
• LogP: 2.58980
• Storage Temp.: 2-8°C
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.058577502
• Heavy Atom Count: 11
• Complexity: 155
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

2-Methyl-5-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 23/24/25-40-52/53
• Safety Statements: 36/37-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: CC1=C(C=C(C=C1)[N+](=O)[O-])N
• Uses: 5-Nitro-o-toluidine is used in the synthesis of numerous dyes. 2-Methyl-5-nitroaniline may be employed as analytical standard for the surfactant mediated transformations (?254nm) of 2,4-dinitrotoluene.

Technology Process of 2-Methyl-5-nitroaniline

There total 31 articles about 2-Methyl-5-nitroaniline 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: 98.0%

2-iodo-1-methyl-4-nitrobenzene (7745-92-8) → 2-methyl-5-nitroaniline (99-55-8)

Guidance literature:

With ammonium hydroxide; In water; at 20 ℃; for 9h; Green chemistry;

DOI:10.1039/c9nj04981a

Reference yield: 97.0%

2-bromo-4-nitrotoluene (7745-93-9) → 2-methyl-5-nitroaniline (99-55-8)

Guidance literature:

With ammonium hydroxide; In water; at 20 ℃; for 9h; Green chemistry;

DOI:10.1039/c9nj04981a

Reference yield: 92.0%

2-nitro-4-amino-5-methylobenzoic acid (136833-45-9) → 2-methyl-5-nitroaniline (99-55-8)

Guidance literature:

With hydrogenchloride; Heating;

upstream raw materials:

2,4-dinitrotoluene

4-methylbenzene-1,3-diamine

N-(2-methylphenyl)acetamide

2-nitro-4-amino-5-methylobenzoic acid

Downstream raw materials:

2,2'-(5-Nitro-o-tolylimino)diethanol

2-Methyl-5-nitrofumaranilic acid

2-(2-methyl-5-nitrophenyl)isoindoline-1,3-dione

ethyl (2-methyl-5-nitrophenyl)carbamate

Refernces

Imatinib analogs as potential agents for PET imaging of Bcr-Abl and c-KIT expression at a kinase level

10.1016/j.bmc.2013.10.040

The research focused on the synthesis and evaluation of imatinib mesylate (STI-571) analogs as potential agents for PET imaging of Bcr-Abl and c-KIT expression at the kinase level. The study involved molecular modeling to predict binding configurations, followed by the synthesis of STI-571 and its analogs using various reactants such as 2-methyl-5-nitroaniline, cyanamide, and 3-acetylpyridine derivatives. Radiolabeling with [18F] and [131I] was performed to prepare PET imaging agents. In vitro kinase assays were conducted to assess the potency of the analogs in inhibiting Bcr-Abl and c-KIT kinase activities. The uptake rates of [18F]-STI-571 in K562 cells (expressing Abl) and U87WT cells (overexpressing c-KIT) were measured and compared with those in U87 cells. PET scans were conducted on tumor-bearing mice to visualize tumor uptake and contrast. The research utilized various analytical techniques, including HPLC, MS, NMR, and radio-TLC, to monitor reactions, assess radiochemical purity, and characterize compounds. The results showed that the [18F]-STI-571 analog could serve as a marker for sensitivity to Bcr-Abl and c-KIT inhibitors, potentially aiding in patient selection for targeted therapies.