59156-21-7

Basic information

• Product Name: 2-(4-Nitrophenyl)thiophene
• Synonyms: 2-(4-NITROPHENYL)THIOPHENE
• CAS NO: 59156-21-7
• Molecular Formula: C₁₀H₇NO₂S
• Molecular Weight: 205.23
• Mol File: 59156-21-7.mol
• Article Data: 77

Chemical Properties

• Melting Point: 138 °C
• Boiling Point: 338.8 °C at 760 mmHg
• Flash Point: 158.7 °C
• Appearance: /
• Density: 1.315 g/cm³
• Vapor Pressure: 0.000188mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: 2-(4-Nitrophenyl)thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Nitrophenyl)thiophene(59156-21-7)
• EPA Substance Registry System: 2-(4-Nitrophenyl)thiophene(59156-21-7)

Safety Data

• Hazardous Substances Data: 59156-21-7(Hazardous Substances Data)

Usage

General Description

2-(4-Nitrophenyl)thiophene is a chemical compound with the molecular formula C10H7NO2S. It is a member of the thiophene family, which is a group of aromatic heterocyclic compounds containing a five-membered sulfur-containing ring. The presence of a nitro group in the phenyl ring makes this compound highly reactive and useful in various chemical reactions, particularly in the synthesis of other complex organic molecules. It also exhibits interesting electronic and optical properties, making it potentially useful in materials science and organic electronics. Additionally, the nitro group can be reduced to an amino group, providing the potential for further functionalization and diversification of its chemical properties.

InChI:InChI=1/C10H7NO2S/c12-11(13)9-5-3-8(4-6-9)10-2-1-7-14-10/h1-7H

Upstream product

• 188290-36-0 thiophene 
• 100-16-3 4-nitrophenylhydrazone 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 81745-84-8 2-thienylzinc chloride 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 88011-26-1 α-thienyl-mercury(II) bromide 
• 5980-89-2 di-[2]thienyl-mercury 
• 45438-80-0 2-thienylzinc bromide 
• 6165-68-0 thiophene boronic acid 
• 100-00-5 4-chlorobenzonitrile 
• 2786-07-4 2-thienyl lithium 
• 54663-78-4 tributyl(thien-2-yl)stannane 

Downstream Products

• 1052113-14-0 [5-(4-Nitro-phenyl)-thiophen-2-yl]-oxo-acetic acid ethyl ester 
• 1350699-19-2 2-(4-aminophenyl)-3',4'-ethylenedioxy-5,2'-bithiophene 
• 1350699-15-8 2-(4-nitrophenyl)-3',4'-ethylenedioxy-5,2'-bithiophene 
• 1087349-15-2 1-(5-iodothien-2-yl)-4-nitrobenzene 
• 1370333-07-5 4-(5-(4-(bis(4-tert-butylphenyl)amino)phenyl)thiophen-2-yl)benzaldehyde 
• 1370333-06-4 (N,N-di-tert-butylphenyl)-4-(thiophen-2-yl)aniline 
• 1370333-00-8 (E)-3-(4-(5-(4-(bis(4-tert-butylphenyl)amino)phenyl)thiophen-2-yl)phenyl)-2-cyanoacrylic acid 
• 80387-65-1 5-<4-(acetylamino)phenyl>-2-(methoxycarbonyl)thiophene 
• 80387-79-7 5-(4-nitrophenyl)thiophene-2-carboxylic acid 
• 80387-66-2 5-(4-Amino-phenyl)-thiophene-2-carboxylic acid methyl ester 
• 61100-12-7 methyl 5-(4-nitrophenyl)thiophene-2-carboxylate 
• 70010-48-9 1-(2-thienyl)-4-aminobenzene 

Relevant articles and documents

Tunable electrochemical switches based on ultrathin organic films

We have performed electroreduction of bisthienyl aminobenzene and thienyl aminobenzene diazonium salts on glassy carbon and polycrystalline gold and generated ultrathin organic films. This method allows covalent bonding between the corresponding aromatic

Triphenylamine derivatives and the lithium-ion capture of [3.3]cyclophane used in organic dye-sensitized solar cells

Four novel organic dyes (H-1, H-2, H-3, H-4) containing phenyl-thiophenyl-thiophenyl as a bridge unit were synthesized and effectively used for the fabrication of dye-sensitized solar cells (DSSCs). In both compounds, a triarylamine moiety and cyanoacryli

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis

Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.