32059-75-9

Basic information

• Product Name: Thiophene, 3-methyl-2-nitro- (6CI, 8CI, 9CI)
• Synonyms: Thiophene, 3-methyl-2-nitro- (6CI, 8CI, 9CI);3-Methyl-2-nitrothiophene
• CAS NO: 32059-75-9
• Molecular Formula: C₅H₅NO₂S
• Molecular Weight: 143.165
• Product Categories: NITRO;Thiophens
• Mol File: 32059-75-9.mol

Chemical Properties

• Boiling Point: 219.5 °C at 760 mmHg
• Flash Point: 86.6 °C
• Appearance: /
• Density: 1.337 g/cm³
• CAS DataBase Reference: Thiophene, 3-methyl-2-nitro- (6CI, 8CI, 9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene, 3-methyl-2-nitro- (6CI, 8CI, 9CI)(32059-75-9)
• EPA Substance Registry System: Thiophene, 3-methyl-2-nitro- (6CI, 8CI, 9CI)(32059-75-9)

Safety Data

• Hazardous Substances Data: 32059-75-9(Hazardous Substances Data)

Upstream product

• 616-44-4 3-Methylthiophene 
• 609-40-5 2-nitrothiophene 
• 75-16-1 methylmagnesium bromide 
• 14282-78-1 4-methylthiophene-2-carboxylic acid 
• 36034-99-8 4-methyl-5-nitrothiophene-2-carboxylic acid 

Downstream Products

• 41057-04-9 2-nitro-3-thiophenecarbaldehyde 
• 98027-62-4 3-hydroxymethyl-2-nitro-thiophene 
• 91544-07-9 4,4'-dimethyl-5,5'-dinitro-2,2'-bithienyl 

Relevant articles and documents

Effect of base on alkyltriphenylphosphonium salts in polar aprotic solvents

When arylmethyl phosphonium salts are treated with a base (e.g., t-BuOK or NaH) they homocouple to form symmetric 1,2-diarylethenes. In some cases, dilution and (or) use of excess base lead to very high yields of the product. This reaction is solvent sensitive: the reaction occurs only when polar aprotic solvents such as acetonitrile or DMSO are used. Other alkyl phosphonium salts (e.g., ethoxycarbonylmethyltriphenylphosphonium bromide and n- butyltriphenylphosphonium bromide) form a ylid (when an α-carbonyl group is present) or lose a phenyl group to form alkyldiphenylphosphine oxides when treated with the base. Mechanistic investigation of the homocoupling reaction indicates that the reaction proceeds through a ylid that acts as a nucleophile on an unreacted phosphonium salt. The resulting adduct undergoes elimination to form the observed product. The EIZ ratio seems to depend on the amount of the base used and the phosphonium salt involved.

A convenient synthesis of symmetric 1,2-diarylethenes from arylmethyl phosphonium salts

Symmetric ethenyldithiophenes are important intermediates for synthesis of photochromic materials and organic conductors. When acetonitrile is used as a solvent, 3-methylthiophenylphosphonium salts form symmetric ethenyldithiophenes in the presence of a strong base (e.g., NaH, tBuOK) in moderate to high yields. This homocoupling reaction is faster than a Wittig reaction with aromatic ketones in acetonitrile. Our study shows that the presence of polar aprotic solvents promotes the homocoupling reaction.

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.