822-84-4

Basic information

• Product Name: 3-nitrothiophene
• Synonyms: Thiophene, 3-nitro-; 3-Nitrothiophene; 5-17-01-00313 (Beilstein Handbook Reference); BRN 0110656
• CAS NO: 822-84-4
• Molecular Formula: C₄H₃NO₂S
• Molecular Weight: 129.1371
• EINECS: 212-502-9
• Mol File: 822-84-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 78.5°C
• Boiling Point: 225°C
• Flash Point: 90.5°C
• Appearance: /solid
• Density: 1.426 (estimate)
• Vapor Pressure: 0.125mmHg at 25°C
• Refractive Index: 1.5130 (estimate)
• CAS DataBase Reference: 3-nitrothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-nitrothiophene(822-84-4)
• EPA Substance Registry System: 3-nitrothiophene(822-84-4)

Safety Data

• Hazardous Substances Data: 822-84-4(Hazardous Substances Data)

Usage

General Description

3-Nitrothiophene is an organic compound with the chemical formula C4H3NO2S. It is a bright yellow crystalline solid with a slightly fruity odor, and is insoluble in water but soluble in organic solvents. 3-Nitrothiophene is commonly used as an intermediate in the pharmaceutical and agrochemical industries, as well as in the synthesis of various fine chemicals. It is known to be a mild irritant to the skin, eyes, and respiratory system, and should be handled with care. The compound is also known to undergo various reactions, such as nitration and reduction, resulting in different derivatives with potential applications in various fields.

InChI:InChI=1/C4H3NO2S/c6-5(7)4-1-2-8-3-4/h1-3H

Upstream product

• 188290-36-0 thiophene 
• 81975-00-0 2-bromo-4-nitro-thiophene 
• 2161-96-8 2-bromo-3-nitrothiophene 
• 89283-24-9 5-bromo-4-nitro-thiophene-2-carboxylic acid 
• 40358-04-1 4-nitrothiophene-2-sulphonyl chloride 
• 89283-80-7 3-nitrothiophene-2-carboxylic acid 
• 38611-19-7 3-nitro-2-trimethylsilylthiophene 
• 6165-69-1 Thien-3-ylboronic acid 
• 1192-06-9 3-thienyl lithium 
• 13138-70-0 4-nitro-2-thiophenecarboxylic acid 
• 91-22-5 quinoline 

Downstream Products

• 42602-67-5 N-(thiophen-3-yl)acetamide 
• 79128-75-9 N-Thiophen-3-yl-benzamide 
• 2160-51-2 2,5-dibromo-3-nitro-thiophene 
• 5347-12-6 2,4-dinitrothiophene 
• 175731-00-7 2-dichloromethyl-3-nitrothiophene 
• 80313-09-3 2-amino-3-nitrothiophene 
• 193144-26-2 (Z,Z)-1-(S)-α-methylbenzylamino-4-methylthio-2-nitro-1,3-butadiene 
• 193144-25-1 (Z,Z)-1-cyclohexylamino-4-methylthio-2-nitro-1,3-butadiene 
• 17721-06-1 3-aminothiophene 

Relevant articles and documents

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

Ipso-nitration of arylboronic acids with bismuth nitrate and perdisulfate

An efficient and one pot synthetic method of ipso-nitration of arylboronic acids has been developed. The high efficiency, general applicability, and broader substrate scope including heterocycles and functional groups make this method advantageous. Due to its simplicity, we expect to find application of this method in synthesis.

Facile synthesis of 3-nitro-2-substituted thiophenes

A new approach to 3-nitro-2-substituted thiophenes has been developed. Exposure of commercially available 1,4-dithane-2,5-diol to nitroalkenes in the presence of 20% triethylamine results in a tandem Michael?intramolecular Henry reaction to form the corresponding tetrahydrothiophene. Subsequent microwave irradiation on acidic alumina in the presence of chloranil effects the solvent free dehydration and aromatization to form 3-nitro-2-substituted thiophenes cleanly and rapidly. A simple workup procedure removes the requirement for purification by chromatography in most cases.