91137-27-8

Basic information

• Product Name: 1-METHYL-5-NITRONAPHTHALENE
• Synonyms: 1-METHYL-5-NITRONAPHTHALENE;Ccris 7757
• CAS NO: 91137-27-8
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.19466
• Mol File: 91137-27-8.mol

Chemical Properties

• Boiling Point: 324.6 °C at 760 mmHg
• Flash Point: 155.5 °C
• Appearance: /
• Density: 1.234g/cm³
• Vapor Pressure: 0.000461mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: 1-METHYL-5-NITRONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-5-NITRONAPHTHALENE(91137-27-8)
• EPA Substance Registry System: 1-METHYL-5-NITRONAPHTHALENE(91137-27-8)

Safety Data

• Hazardous Substances Data: 91137-27-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-5-NITRONAPHTHALENE is used as a chemical intermediate for the synthesis of pharmaceuticals, playing a crucial role in the development of new medications and therapeutic agents. Its unique structure allows for the creation of a wide range of drug molecules, potentially leading to innovative treatments and improved patient outcomes.
Used in Agrochemical Industry:
In the agrochemical sector, 1-METHYL-5-NITRONAPHTHALENE is utilized as an intermediate for the production of various agrochemicals. This includes the synthesis of pesticides, herbicides, and other crop protection agents, which are essential for maintaining agricultural productivity and ensuring food security.
Used as a Dye and Pigment Intermediate:
1-METHYL-5-NITRONAPHTHALENE is employed in the dye and pigment industry as an intermediate for the production of colorants. Its chemical properties enable the creation of a diverse array of dyes and pigments, which are used in various applications such as textiles, plastics, and paints, adding vibrancy and color to a multitude of products.
Safety Precautions:

InChI:InChI=1/C11H9NO2/c1-8-4-2-6-10-9(8)5-3-7-11(10)12(13)14/h2-7H,1H3

Upstream product

• 856212-37-8 8-methyl-4-nitro-[1]naphthylamine 
• 624-91-9 methyl nitrite 
• 90-12-0 1-Methylnaphthalene 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 130523-30-7 8-methylnaphthalene-1-amine 
• 873977-06-1 N-(8-methyl-4-nitro-[1]naphthyl)-acetamide 

Relevant articles and documents

NO2+ nitration mechanism of aromatic compounds: Electrophilic vs charge-transfer process

The nitration of methylnaphthalenes with NO2BF4 and NOBF4 was examined in order to shed light on the controversial aromatic nitration mechanism, electrophilic vs charge-transfer process. The NO2+ nitration of 1,8-dimethylnaphthalene showed a drastic regioselectivity change depending on the reaction temperature, where ortho-regioselectivity at -78 °C and para- regioselectivity at 0 °C were considered to reflect the electrophilic and the direct or alternative charge-transfer process, respectively, because the NO+ nitration through the same reaction intermediates as in the NO2+ nitration via a charge-transfer process resulted in para-regioselectivity regardless of the reaction temperature. The NO2+ nitration of redox potential methylnaphthalenes higher than 1,8-dimethylnaphthalene gave a similar ortho-regioselectivity enhancement to 1,8-dimethylnaphthalene at lower temperature, thus reflecting the electrophilic process. On the other hand, the NO2+ nitration of redox potential methylnaphthalenes lower than 1,8-dimethylnaphthalene showed para-regioselectivity similar to the NO+ nitration, indicating the direct or alternative charge-transfer process. In the presence of strong acids where the direct charge-transfer process will be suppressed by protonation, the ortho-regioselectivity enhancement was observed in the NO2+ nitration of 1,8-dimethylnaphthalene, suggesting that the direct charge-transfer process could be the main process to show para- regioselectivity. These experimental results imply that the NO2+ nitration proceeds via not only electrophilic but also direct charge-transfer processes, which has been considered to be unlikely because of the high energy demanding process of a bond coordination change between NO2+ and NO2. Theoretical studies at the MP2/6-31G(d) level predicted ortho- and para-regioselectivity for the NO2+ nitration via electrophilic and charge- transfer processes, respectively, and the preference of the direct charge- transfer process over the alternative one, which support the experimental conclusion.

Charge-transfer Nitration of Naphthalene and the Methylnaphthalenes. Part 1. Direct Comparison with Electrophilic Aromatic Nitrations

The various nitronaphthalenes formed in high yields from the selective photoexcitation of the EDA complexes of the naphthalene and methylnaphthalene donors (ArH) with the N-nitropyridinium and tetranitromethane acceptors are ascribed to charge-transfer nitration, arising as they do from the cation-radical pairs .+, NO2>.The nitration products from such an electron-transfer pathway are quantitatively compared with those from the electrophilic nitration (thermal), under otherwise the same conditions.The mechanistic implications to electrophilic aromatic substitution are discussed.

Nitration of Reactive Aromatics via Elelctron Transfer. V. On the Reaction between Nitrogen Dioxide and the Radical Cation Hexafluorophosphates of Some Methyl-substituted Naphthalenes

The coupling reactions of series of methylnaphthalene radical cation hexafluorophosphates with nitrogen dioxide were studied in dichloromethane at low temperatures.Yields of nitro derivatives were generally higher with the β-methyl than with the α-methyl-substituted naphthalenes and the isomer distributions were different from those obtained in electrophilic aromatic nitration and nitrous acid catalyzed nitration.This confirm an earlier suggestion that the coupling reaction is not an elementary step of either nitration process.The high regioselectivity of the coupling reation can only partly be correlated with UHF spin densities.Pyrene+. hexafluorophosphate does not yield nitropyrenes upon treatment with nitrogen dioxide.This confirm earlier suggestions that only radical cations of aromatics with Eo values >= 1.7 V will take part in a successful (exergonic) coupling reaction with nitrogen dioxide.