81020-78-2

Basic information

• Product Name: 2-[(5-bromo-thiophen-2-yl)methylene]malononitrile
• Synonyms: 2-[(5-bromo-thiophen-2-yl)methylene]malononitrile;2-[(5-bromothiophen-2-yl)methylidene]propanedinitrile
• CAS NO: 81020-78-2
• Molecular Formula: C₈H₃BrN₂S
• Molecular Weight: 239.09182
• EINECS: -0
• Mol File: 81020-78-2.mol

Chemical Properties

• Melting Point: 157-158 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• Boiling Point: 358.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.718±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-[(5-bromo-thiophen-2-yl)methylene]malononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(5-bromo-thiophen-2-yl)methylene]malononitrile(81020-78-2)
• EPA Substance Registry System: 2-[(5-bromo-thiophen-2-yl)methylene]malononitrile(81020-78-2)

Safety Data

• Hazardous Substances Data: 81020-78-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-[(5-bromo-thiophen-2-yl)methylene]malononitrile is used as a reagent in organic synthesis for its capacity to engage in various chemical reactions, facilitating the creation of a broad spectrum of organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-[(5-bromo-thiophen-2-yl)methylene]malononitrile is utilized as a building block for the development of new pharmaceutical products. Its unique chemical properties and reactivity make it a promising candidate for the synthesis of novel therapeutic agents.
Used in Agrochemicals:
2-[(5-bromo-thiophen-2-yl)methylene]malononitrile is also employed in the agrochemical industry, where it serves as a key component in the synthesis of various agrochemicals, potentially contributing to the development of new pesticides or other agricultural chemicals.
Used in Materials Science:
Within the realm of materials science, 2-[(5-bromo-thiophen-2-yl)methylene]malononitrile is applied in the research and development of new materials. Its unique structure and properties may contribute to the creation of innovative materials with specific applications in various industries.
The potential applications of 2-[(5-bromo-thiophen-2-yl)methylene]malononitrile are broad and underscore its importance as a versatile chemical entity in multiple scientific and industrial domains.

Upstream product

• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 109-77-3 malononitrile 

Downstream Products

• 1453857-37-8 2-amino-4-(5-bromothiophen-2-yl)-5-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbonyl)-1H-pyrrole-3-carbonitrile 
• 1453857-35-6 6-(5-bromothiophen-2-yl)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[4,3-b]pyridine-5-carbonitrile 
• 153308-35-1 5-(2,2-dicyanovinyl)-2,2'-bithiophene 

Relevant articles and documents

Radical Rearrangement of Aryl/Alkylidene Malononitriles via Aza Michael Addition/Decynoformylation/Addition Sequence: An Access to α-Aminonitriles and α-Aminoamides

An efficient, safe, and environmentally friendly tertiary butyl hydrogen peroxide (TBHP)-mediated rearrangement of aryl/alkylidene malononitrile with anilines has been developed with in situ generation of HCN as the cyanide source for the synthesis of sub

Trans-A2B2 porphyrin derivative, and preparation method and application thereof

The invention discloses a trans-A2B2 porphyrin derivative, and a preparation method and an application thereof. The preparation method comprises the following steps: carrying out a reaction on 4-alkoxybenzaldehyde and pyrrole under the catalysis of trifluoroacetic acid to synthesize 5-substituted dipyrrylmethane; carrying out a cyclization reaction on the obtained 5-substituted dipyrrylmethane and 5-bromo-2-thiophenecarboxaldehyde under the action of trifluoroacetic acid and dichlorodicyan benzoquinone to form a porphyrin ring main body; connecting the thiophene alpha position of the porphyrin ring with a boronic acid pinacol ester group through using a Suzuki coupling reaction to modify the porphyrin ring; and carrying out the Suzuki coupling reaction on bromodicyanovinyl oligothiophene prepared in the early stage and the modified porphyrin ring under the catalysis action of palladium to obtain the final product. The trans-A2B2 porphyrin derivative is hopeful to become a high-efficiency organic photovoltaic battery donor material due to the unique molecular structure and large conjugated system.

Dicyanovinyl-substituted oligothiophenes: Structure-property relationships and application in vacuum-processed small molecule organic solar cells

Efficient synthesis of a series of terminally dicyanovinyl (DCV)-substituted oligothiophenes, DCVnT 1-6, without solubilizing side chains synthesized via a novel convergent approach and their application as electron donors in vacuum-processed m-i-p-type planar and p-i-n-type bulk heterojunction organic solar cells is described. Purification of the products via gradient sublimation yields thermally highly stable organic semiconducting materials in single crystalline quality which allows for X-ray structure analysis. Important insights into the packing features and intermolecular interactions of these promising solar cell materials are provided. Optical absorption spectra and electrochemical properties of the oligomers are investigated and valuable structure-property relationships deduced. Photovoltaic devices incorporating DCVnTs 4-6 showed power conversion efficiencies up to 2.8% for planar and 5.2% for bulk heterojunction organic solar cells under full sun illumination (mismatch corrected simulated AM 1.5G sunlight). The 5.2% efficiency shown here represents one of the highest values ever reported for organic vacuum-deposited single heterojunction solar cells.

Structure-property relationship of acceptor-substituted oligothiophenes

A series of oligothiophenes that are end-capped with dicyanovinyl (DCV) and 1,3,2-(2H)-dioxaborine (DOB) moieties has been prepared using standard procedures. Their optoelectronic properties have been investigated by cyclic voltammetry and optical absorption. The optical absorption has been measured both in solution and thin film state.

Synthesis and properties of fluorene or carbazole-based and dicyanovinyl-capped n-type organic semiconductors

Dicyanovinyl-substituted compounds as electron transport materials are rarely studied, especially oligomers. A new series of fluorene or carbazole-based and dicyanovinyl-capped oligomers consisting of benzene or thiophene segments were synthesized using t

Synthesis of donor-acceptor substituted oligothiophenes by Stille coupling

A synthesis of donor-acceptor-substituted oligothiophenes by Stille coupling is described. The 5′-estanyl derivatives, readily prepared from 5-alkoxy- and 5-amino-2,2′-bithiophenes 7 were coupled with the appropriate aryl or heteroaryl bromides to give th