42297-94-9

Basic information

• Product Name: 2-Methyl-5-nitrothiophene
• Synonyms: 2-Methyl-5-nitrothiophene; 2-Nitro-5-methylthiophene
• CAS NO: 42297-94-9
• Molecular Formula: C₅H₅NO₂S
• Molecular Weight: 143.1637
• Product Categories: Thiophens
• Mol File: 42297-94-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 233.4 °C at 760 mmHg
• Flash Point: 95 °C
• Appearance: /
• Density: 1.337 g/cm³
• CAS DataBase Reference: 2-Methyl-5-nitrothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-5-nitrothiophene(42297-94-9)
• EPA Substance Registry System: 2-Methyl-5-nitrothiophene(42297-94-9)

Safety Data

• Hazardous Substances Data: 42297-94-9(Hazardous Substances Data)

Usage

General Description

2-Methyl-5-nitrothiophene is a chemical compound with the molecular formula C5H5NO2S. It is a yellow liquid with a molecular weight of 143.17 g/mol. The compound is used in organic synthesis as a building block for various pharmaceutical and agrochemical products. It is also used as an intermediate in the production of insecticides and herbicides. 2-Methyl-5-nitrothiophene is known for its strong, unpleasant odor and should be handled with care due to its potential hazardous properties. Additionally, it is important to take measures to avoid exposure to the compound, as it can be harmful if ingested, inhaled, or comes into contact with the skin.

Upstream product

• 554-14-3 2-Methylthiophene 
• 1918-79-2 2-methylthiophene-5-carboxylic acid 
• 609-40-5 2-nitrothiophene 
• 75-16-1 methylmagnesium bromide 
• 591-09-3 nitro acetate 
• 20898-85-5 (5-nitrothiophen-2-yl)methanol 
• 4521-33-9 5-nitro-2-thiophenecarboxaldehyde 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 78771-28-5 2-Methyl-3,5-dinitrothiophene 
• 222557-94-0 2-{[4-Bis(acetoxyethyl)phenyl]ethenyl}-3,5-dinitrothiophene 
• 166887-84-9 2-(bromomethyl)-5-nitrothiophene 

Relevant articles and documents

Cleavage of 5-Nitro-2-(trimethylsilylmethyl)thiophene by Methanolic Sodium Methoxide. U.V. Spectroscopic and Solvent Isotope Effect Evidence for Generation of the Anion (1-)

The reaction of 5-nitro-2-(trimethylsilylmethyl)thiophene with NaOMe-MeOH involves generation of the observable anion (1-) with a solvent isotope effect k(MeOH)/k(MeOD) of 0.5, followed by protonation of the anion with a solvent isotope effect of 10; the results confirm that cleavages of RSiMe3 compounds by NaOMe-MeOH involve separation of the anions R(1-), and that the isotope effect in the reaction of R(1-) with MeOH depends greatly on the degree of conjugative delocalization of the negative charge, not just on the acidity of RH.

Synthesis of dinitro-substituted furans, thiophenes, and azoles

Direct nitration of the corresponding mononitro furans with fuming nitric acid, thiophenes with acetyl nitrate, and thiazoles with trifluoroacetyl nitrate, gave dinitro-substituted furans, thiophenes, and thiazoles. The nitrations of 2-alkylthiophenes wit

ALKYLATION ORIENTATION RULES IN CONJUGATE ADDITION OF GRIGNARD REAGENTS TO NITROPYRROLE AND NITROTHIOPHENE SYSTEMS

Conjugate addition of various Grignard reagents to 1-alkyl-2-nitropyrroles and to 2-nitrothiophene has been investigated. 1-Alkyl-2-nitropyrroles undergo alkylation at 3 and 5 positions with prevalence of the latter isomer.On the contrary, in the 2-nitrothiophene system, formation of the 3-isomer prevails.In both systems, a bulkier Grignard reagent favours the 5-isomer formation.This trend can be reversed increasing steric hindrance exerted by the 1-substituent of 2-nitropyrrole. 1-(Tri-isopropylsilyl)-3-nitropyrrole and 3-nitrothiophene give exclusively the 2-isomer.This reaction allows 2-alkyl-3-nitrothiophenes and pyrroles to be synthesized with a one-pot procedure instead of the classical multi stage reaction.