2-(2-Nitrovinyl)thiophene TCI N0787

Chemical Identity

CAS No.: 874-84-0
PubChem: CID 95586·SID 87558948
Formula: C6H5NO2S
Molecular weight: 155.18 g/mol
Purity: >98.0%(GC)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 2-(2-nitroethenyl)thiophene
SMILES: C1=CSC(=C1)C=C[N+](=O)[O-]
InChIKey: UTPOWFFIBWOQRK-UHFFFAOYSA-N

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2-(2-Nitrovinyl)thiophene (CAS 874-84-0) is a heteroaromatic nitroalkene. Its structure is a thiophene ring with a nitrovinyl group attached at the 2-position. TCI supplies it under product code N0787 as a heterocyclic building block for research laboratories. Nitroalkenes of this type are usually made by a Henry reaction between thiophene-2-carbaldehyde and nitromethane, followed by dehydration. In the laboratory, the compound serves as a Michael acceptor, a dienophile, and a precursor to thiophene-containing amines. This makes it a flexible starting material for organic synthesis.

The compound's usefulness comes from its electronic structure. The carbon–carbon double bond is conjugated with a nitro group, which makes it strongly electron-poor. Nucleophiles such as malonates, ketones, indoles, and thiols therefore attack it readily. For this reason, 2-(2-Nitrovinyl)thiophene is often used as a test substrate when chemists develop asymmetric Michael additions with organocatalysts. After the addition, the nitro group in the product can be reduced to an amine or converted into a carbonyl group, which opens many further transformations. The thiophene ring is also a common benzene bioisostere in medicinal chemistry.

In Indonesia, this material suits university research groups working in organocatalysis, synthetic methodology, and medicinal chemistry. Groups developing new asymmetric reactions can use it as a benchmark heteroaromatic substrate next to the more common phenyl analogues. Medicinal chemistry laboratories can use it to build thiophene-containing amines and related scaffolds for compound libraries. It is also useful for advanced undergraduate and postgraduate practical courses, where students can work through Michael additions, nitro-group reductions, and multistep synthesis with a single versatile heterocyclic starting material.

TCI brochures (PDF)

Thiophenes 2026-06-29 · p. 8

Related TCI products

Asymmetric organocatalytic Michael additions: the electron-poor nitrovinyl double bond reacts readily with malonates, ketones, and indoles, so the compound works well as a standard test substrate for new chiral catalysts.
Synthesis of thiophene-containing amines: after conjugate addition or direct reduction, the nitro group can be converted into an amine, giving access to thiophene-based amine building blocks for further derivatisation.
Cycloaddition chemistry as a dienophile: the conjugated nitroalkene acts as an activated dienophile, so researchers can build new ring systems that carry both a thiophene unit and a nitro handle.
Thiol conjugate addition studies: thiols add easily to the activated double bond, so the compound is useful for studying sulfa-Michael reactions and preparing sulfur-functionalised nitroalkane intermediates.
Medicinal chemistry scaffold design: the thiophene ring is a common benzene bioisostere, so this building block helps chemists prepare thiophene analogues of phenyl-containing lead structures for structure–activity studies.

Brand	TCI (product code N0787)
CAS number	874-84-0
Molecular formula	—
Purity	—
Category	Chemistry > Building Blocks > Heterocyclic Building Blocks
Pack sizes	available in TCI's standard pack sizes; please confirm current options with AMI Scientific
Physical form	see the TCI product specification and Certificate of Analysis
Storage	keep tightly closed in a cool, dry, dark place; follow the storage conditions on the TCI label and SDS

Store 2-(2-Nitrovinyl)thiophene in its original, tightly sealed container, in a cool, dry, well-ventilated place away from direct light and heat. Always follow the storage temperature on the TCI label and Safety Data Sheet. Keep it away from strong oxidising agents, strong bases, and reducing agents, because nitroalkenes are reactive electrophiles. Handle it in a fume hood and wear nitrile gloves, safety glasses, and a lab coat. Avoid breathing in dust or vapour and avoid contact with skin and eyes. Weigh only the amount you need, reseal the container promptly, and dispose of waste according to institutional chemical waste procedures.

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