Page last updated: 2024-12-05
1,3-dicyanobenzene
Description
## 1,3-Dicyanobenzene: A Versatile Building Block in Research
1,3-dicyanobenzene, also known as *m*-dicyanobenzene, is an organic compound with the formula C8H4N2. It consists of a benzene ring with two cyano groups (-CN) attached at positions 1 and 3.
**Importance in Research:**
1,3-dicyanobenzene serves as a valuable building block in various research areas due to its unique properties and reactivity. Here are some key aspects:
* **Versatile Synthon:** Its two cyano groups offer multiple functionalization possibilities, enabling the synthesis of various organic molecules, including:
* **Polymers:** Its rigid structure and electron-withdrawing cyano groups contribute to the development of high-performance polymers with enhanced properties.
* **Metal-Organic Frameworks (MOFs):** The cyano groups act as strong ligands for metal ions, leading to the formation of porous materials with applications in gas storage, catalysis, and sensing.
* **Electronic Materials:** Its electron-deficient nature makes it suitable for applications in organic electronics, such as organic field-effect transistors (OFETs) and organic photovoltaic cells (OPVs).
* **Unique Reactivity:** The cyano groups can be easily modified through reactions like nucleophilic aromatic substitution, providing access to a vast array of derivatives with diverse functionalities.
* **Photophysical Properties:** Its strong electron-withdrawing nature leads to a significant red-shift in its absorption and emission spectra compared to benzene, making it suitable for optical applications.
* **Biological Activity:** Some derivatives of 1,3-dicyanobenzene exhibit potential biological activities, such as antimicrobial and anticancer properties.
**Specific Research Applications:**
* **Organic Synthesis:** 1,3-dicyanobenzene serves as a starting material for the synthesis of various nitrogen-containing heterocycles, pharmaceuticals, and dyes.
* **Material Science:** Its use in the synthesis of polymers, MOFs, and organic electronic materials is actively explored to improve their properties and expand their applications.
* **Catalysis:** Derivatives of 1,3-dicyanobenzene show potential as catalysts in various organic reactions.
* **Biochemistry and Medicine:** Research is ongoing to investigate the potential of its derivatives as drug candidates and therapeutic agents.
In summary, 1,3-dicyanobenzene is a versatile and valuable building block in various research areas, offering unique functionalities and reactivity for the development of novel materials, compounds, and applications.
1,3-dicyanobenzene: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|
| PubMed CID | 12276 |
| CHEMBL ID | 3182143 |
| CHEBI ID | 38218 |
| SCHEMBL ID | 9289 |
| MeSH ID | M0368772 |
Synonyms (60)
| Synonym |
|---|
| 1,3-benzendikarbonitril |
| unii-7g36n0292w |
| isoftalonitril |
| 7g36n0292w , |
| CHEBI:38218 , |
| benzene-1,3-dicarbonitrile |
| hsdb 5724 |
| einecs 210-933-7 |
| ccris 4132 |
| nitril kyseliny isoftalove [czech] |
| dinitrile of isophthalic acid |
| nsc 87880 |
| m-phthalodinitrile |
| isoftalonitril [czech] |
| ai3-25034 |
| isoftalodinitril [czech] |
| 1,3-benzendikarbonitril [czech] |
| 1,3-dicyanobenzene |
| isophthalonitrile |
| 626-17-5 |
| isophtalonitrile |
| wln: ncr ccn |
| 1,3-benzodinitrile |
| nsc87880 |
| m-dicyanobenzene |
| isoftalodinitril |
| 1,3-benzenedicarbonitrile |
| isophthalodinitrile |
| m-pdn |
| nsc-87880 |
| nitril kyseliny isoftalove |
| 3-cyanobenzonitrile |
| m-benzenedinitrile |
| inchi=1/c8h4n2/c9-5-7-2-1-3-8(4-7)6-10/h1-4 |
| 1,3-dicyanobenzene, 98% |
| I0158 |
| A833886 |
| NCGC00249051-01 |
| tox21_303190 |
| cas-626-17-5 |
| dtxcid207259 |
| dtxsid7027259 , |
| NCGC00257068-01 |
| NCGC00259025-01 |
| tox21_201474 |
| FT-0627453 |
| AKOS015890366 |
| meta-dicyanobenzene |
| 1,3-bis(cyano)benzene |
| 1,3-dicyanobenzene [hsdb] |
| SCHEMBL9289 |
| isopthalonitrile |
| J-503897 |
| m-cyanobenzonitrile |
| CHEMBL3182143 |
| mfcd00001795 |
| Q20966059 |
| EN300-91717 |
| CS-W013468 |
| E83004 |
Research Excerpts
Dosage Studied
| Excerpt | Relevance | Reference |
|---|
| "8% reduction at 100 mg/kg), six compounds, dosed at 50 mg/kg, produced reductions in inflammation comparable to this standard." | ( Synthesis and antiinflammatory evaluation of substituted isophthalonitriles, trimesonitriles, benzonitriles, and terephthalonitriles.
Battershell, RD; Goble, PH; Heilman, WP; Magee, TA; Pyne, WJ, 1978) | 0.26 |
Drug Classes (1)
| Class | Description |
|---|
| nitrile | A compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Protein Targets (4)
Potency Measurements
Bioassays (2)
| Assay ID | Title | Year | Journal | Article |
|---|
| AID1133373 | Toxicity in mouse assessed as overt effects | 1978 | Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
| Synthesis and antiinflammatory evaluation of substituted isophthalonitriles, trimesonitriles, benzonitriles, and terephthalonitriles. |
| AID1133366 | Antiinflammatory activity in Long Evans rat assessed as reduction of carrageenan-induced pedal edema at 200 mg/kg, po administered 1 hr prior to carrageenan challenge measured after 3 hrs relative to control | 1978 | Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
| Synthesis and antiinflammatory evaluation of substituted isophthalonitriles, trimesonitriles, benzonitriles, and terephthalonitriles. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (10)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|
| pre-1990 | 1 (10.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 5 (50.00) | 29.6817 |
| 2010's | 4 (40.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 24.16
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| Metric | This Compound (vs All) |
|---|
| Research Demand Index | 24.16 (24.57) | | Research Supply Index | 2.40 (2.92) | | Research Growth Index | 4.92 (4.65) | | Search Engine Demand Index | 23.28 (26.88) | | Search Engine Supply Index | 2.00 (0.95) |
| |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 10 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |