16689-02-4

Basic information

• Product Name: 5-NITROTHIOPHENE-2-CARBONITRILE
• Synonyms: 2-CYANO-5-NITROTHIOPHENE;AKOS 92290;5-CYANO-2-NITROTHIOPHENE;5-NITRO-2-THIOPHENECARBONITRILE;5-NITROTHIOPHENE-2-CARBONITRILE;BUTTPARK 121\04-20;5-NITROTHIOPHENE-2-CARBONITRILE, 98+%;2-Nitrothiophene-5-carbonitrile
• CAS NO: 16689-02-4
• Molecular Formula: C₅H₂N₂O₂S
• Molecular Weight: 154.15
• EINECS: -0
• Product Categories: Heterocyclic Compounds;Thiophen;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes
• Mol File: 16689-02-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 42-46 °C
• Boiling Point: 273.9 °C at 760 mmHg
• Flash Point: 119.4 °C
• Appearance: /
• Density: 1.5 g/cm³
• Vapor Pressure: 0.00558mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: 2-8°C
• BRN: 123934
• CAS DataBase Reference: 5-NITROTHIOPHENE-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITROTHIOPHENE-2-CARBONITRILE(16689-02-4)
• EPA Substance Registry System: 5-NITROTHIOPHENE-2-CARBONITRILE(16689-02-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37/39
• RIDADR: UN 3439 6.1/PG 3
• WGK Germany: 3
• F: 10-13-23
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 16689-02-4(Hazardous Substances Data)

Usage

General Description

5-Nitrothiophene-2-carbonitrile is a chemical compound with the molecular formula C6H3N3O2S. It is a nitro-substituted thiophene derivative, containing a nitro group and a cyano group on the 2-position of the thiophene ring. It is commonly used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and organic compounds. The compound is a yellow crystalline solid with a characteristic odor and is stable under normal conditions. It is important to handle this chemical with care as it is considered toxic and may cause irritation to the skin, eyes, and respiratory system. Additional safety measures, such as wearing protective clothing and using proper ventilation, should be taken when handling 5-Nitrothiophene-2-carbonitrile.

InChI:InChI=1/C5H2N2O2S/c6-3-4-1-2-5(10-4)7(8)9/h1-2H

Upstream product

• 1003-31-2 thiophene-2-carbonitrile 
• 4521-33-9 5-nitro-2-thiophenecarboxaldehyde 
• 6030-18-8 5-nitrothiophene-2-carbaldehyde oxime 
• 57784-57-3 (Z)-thiophene-2-carbaldehyde oxime 
• 14289-24-8 5-nitrothiophene-2-carboxaldehyde diacetate 
• 98-03-3 thiophene-2-carbaldehyde 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 6277-18-5 2-iodo-5-nitrothiophene 
• 143-33-9 sodium cyanide 
• 87997-11-3 5-nitro-2-thienyltrimethylammonium bromide 
• 104416-19-5 5-nitrothiophene-2-aldoxime 

Downstream Products

• 207849-74-9 (5-fluorothiophen-2-yl)formyl chloride 
• 4377-58-6 5-fluorothiophene-2-carboxylic acid 
• 876516-60-8 5-(2-methylphenyloxy)-thiophen-2-carbonitrile 
• 1359763-59-9 5-(3-trifluoromethylphenyloxy)-thiophen-2-carbonitrile 
• 1187947-31-4 [Ru(η5-C5H5)(1,2-bis(diphenylphosphino)ethane)(5-nitrothiophene-2-carbonitrile)]PF6 
• 944457-18-5 [Fe(η5-cyclopentadienyl(1,2-bis(diphenylphosphino)ethane)(5-nitrothiophene-2-carbonitrile)]PF6 
• 849806-14-0 5-p-Tolyloxy-thiophene-2-carbonitrile 
• 32415-91-1 5-fluorothiophene-2-carbonitrile 
• 849811-49-0 5-(3-benzyloxy-phenoxy)-thiophene-2-carbonitrile 
• 849806-09-3 5-phenoxythiophene-2-carbonitrile 
• 849811-48-9 5-(3-bromophenoxy)-thiophene-2-carbonitrile 
• 849806-10-6 5-(4-fluoro-phenoxy)-thiophene-2-carbonitrile 
• 849806-06-0 5-(3-fluorophenoxy)thiophene-2-carbonitrile 
• 52532-63-5 2-cyano-5-aminothiophene 

Relevant articles and documents

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

An efficient synthesis of nitriles from aldoximes using diethyl phosphorocyanidate under mild conditions

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Efficient transformation of aldoximes to nitriles using 2-chloro-1-methylpyridinium iodide under mild conditions

Various (aliphatic, aromatic, and heterocyclic aromatic) types of aldoximes were converted into the corresponding nitriles in good to excellent yields using 2-chloro-1-methylpyridinium iodide (CMPI) as a dehydrating agent under mild conditions.