• 1. CXLVII.—Nitro-derivatives of m-cresol
  George Philip Gibson J. Chem. Soc. Trans. 1923 123 1269
• 2. Electrophilic aromatic substitution. Part 23. The nitration of phenol and the cresols in aqueous sulphuric acid
  Robert G. Coombes,John G. Golding,Panicos Hadjigeorgiou J. Chem. Soc. Perkin Trans. 2 1979 1451
• 3. Investigations on the gas-phase photolysis and OH radical kinetics of methyl-2-nitrophenols
  Iustinian Bejan,Ian Barnes,Romeo Olariu,Shouming Zhou,Peter Wiesen,Thorsten Benter Phys. Chem. Chem. Phys. 2007 9 5686
• 4. CLXXV.—Experiments on the migration of para-halogen atoms in phenols
  Ivan Richard Gibbs,Philip Wilfred Robertson J. Chem. Soc. Trans. 1914 105 1885
• 5. CXXI.—Mercuration of nitrohydroxybenzaldehydes
  Thomas Anderson Henry,Thomas Marvel Sharp J. Chem. Soc. Trans. 1924 125 1049

• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Nitrophenols

5-Methyl-2-Nitrophenol: A Comprehensive Overview

5-Methyl-2-nitrophenol, also known by its CAS number 700-38-9, is a compound of significant interest in various scientific and industrial applications. This compound is a derivative of phenol, with a methyl group attached at the 5-position and a nitro group at the 2-position. The combination of these substituents imparts unique chemical properties, making it a valuable molecule in fields such as pharmaceuticals, agrochemicals, and materials science.

The structure of 5-methyl-2-nitrophenol is characterized by the presence of two key functional groups: the nitro group (-NO?) and the methyl group (-CH?). The nitro group is a strong electron-withdrawing group, which significantly influences the electronic properties of the molecule. This makes 5-methyl-2-nitrophenol highly reactive in various chemical reactions, particularly in nucleophilic aromatic substitution and electrophilic substitution reactions. The methyl group, on the other hand, acts as an electron-donating group, balancing the electronic effects of the nitro group to some extent.

Recent studies have highlighted the potential of 5-methyl-2-nitrophenol as an intermediate in the synthesis of bioactive compounds. For instance, researchers have explored its role in the development of novel antibiotics and antifungal agents. The compound's ability to act as a precursor for more complex molecules has made it a valuable building block in organic synthesis. Additionally, its application in agrochemicals has been investigated, particularly in the development of herbicides and pesticides with improved efficacy and reduced environmental impact.

In terms of physical properties, 5-methyl-2-nitrophenol is a crystalline solid with a melting point of approximately 110°C. It is sparingly soluble in water but exhibits good solubility in organic solvents such as dichloromethane and ethyl acetate. These properties make it suitable for use in various chemical processes that require controlled solubility profiles.

The synthesis of 5-methyl-2-nitrophenol typically involves nitration of methyl-substituted phenols under controlled conditions. The reaction conditions are critical to ensure selective nitration at the desired position on the aromatic ring. Recent advancements in catalytic systems have enabled more efficient and selective synthesis methods, reducing byproduct formation and improving overall yield.

In terms of safety data, handling 5-methyl-2-nitrophenol requires standard precautions typical for chemicals with similar properties. It is important to note that prolonged exposure to skin or inhalation should be avoided due to potential health risks. Proper personal protective equipment (PPE) should be used during handling and storage.

The environmental impact of 5-methyl-2-nitrophenol has also been a topic of recent research. Studies have shown that under certain conditions, it can undergo biodegradation by microorganisms present in soil and water environments. This suggests that its environmental persistence is limited under natural conditions, which is reassuring for its use in agricultural applications.

In conclusion, 5-methyl-2-nitrophenol, with its unique chemical properties and versatile applications, continues to be an area of active research across multiple disciplines. Its role as an intermediate in organic synthesis, coupled with its potential in developing bioactive compounds and agrochemicals, underscores its importance in modern chemistry.

• 609-93-8(2,6-Dinitro-p-cresol (wetted with ca. 20% Water, containing 25g on a dry weight basis))
• 6265-07-2(2-Amino-4-methyl-6-nitrophenol)
• 38512-82-2(5-Methyl-2-nitroanisole)
• 61161-83-9(5-(hydroxymethyl)-2-nitrophenol)
• 89189-61-7(Phenol, methylnitro-)
• 101664-28-2(Phenol,5-ethyl-2-nitro-)
• 18062-89-0([1,1'-Biphenyl]-3-ol,4-nitro-)
• 16533-36-1(5-Methyl-2-nitrobenzene-1,3-diol)
• 18087-10-0(4,5-Dimethyl-2-nitrophenol)
• 68137-08-6(Phenol,3(or 4)-methyl-2-nitro- (9CI))