7,7,8,8-Tetracyanoquinodimethane（TCNQ） - ≥98% , CAS No.1518-16-7

CAS: 1518-16-7 Cat. No.: T106844 Molecular Weight: 204.19 Beilstein Registry Number: 1427366 EC Number: 216-174-8 PubChem CID: 73697

GRADE & PURITY ≥98%

Synonyms

EINECS 216-174-8 | MFCD00011664 | Q2135917 | Tetracyano-p-quinodimethane | 7,8,8-Tetracyano-p-quinodimethane | 2,5-Cyclohexadiene-1,4-diylidene-alpha,alpha'-dimalononitrile | 2,5-Cyclohexadiene-delta(sup 1,alpha:4,alpha)-dimalononitrile | 7,7,8,8-Tetracya

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

7,7,8, 8-tetracyano-p-benzoquinone dimethane (TNCQ) is a strong electron acceptor that has four cyanogroup and π-conjugated bonds to form charge transfer chains and ionic radical salts that are used primarily as p dopants in a variety of semiconductor manufacturing applications

Application：

7,7,8,8-Tetracyanoquinodimethane (TNCQ) is a strong electron acceptor as it has four cyano groups and π-conjugation bonds that form charge transferring chains and ion radical salts which are mainly used as p-dopants for the fabrication of a variety of semiconductor applications
Electron-acceptor molecule used to form charge-transfer superconductors.

Specifications

Synonyms

EINECS 216-174-8 | MFCD00011664 | Q2135917 | Tetracyano-p-quinodimethane | 7, 8, 8-Tetracyano-p-quinodimethane | 2, 5-Cyclohexadiene-1, 4-diylidene-alpha, alpha'-dimalononitrile | 2, 5-Cyclohexadiene-delta(sup 1, alpha:4, alpha)-dimalononitrile | 7, 7, 8, 8-Tetracya

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488184789
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488184789
• Canonical Smiles: C1=CC(=C(C#N)C#N)C=CC1=C(C#N)C#N
• IUPAC Name: 2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
• InChIKey: PCCVSPMFGIFTHU-UHFFFAOYSA-N
• INCHI: 1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
• Isomeric SMILES: C1=CC(=C(C#N)C#N)C=CC1=C(C#N)C#N
• WGK Germany: 3
• RTECS: GU4850000
• PubChem CID: 73697
• Molecular Weight: 204.19
• Beilstein: 1427366
• Reaxy-Rn: 611604

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Hydrocarbon derivatives
    • Class Quinodimethanes
      • Subclass P-quinodimethanes

• Kingdom: Organic compounds
• Superclass: Hydrocarbon derivatives
• Class: Quinodimethanes
• Subclass: P-quinodimethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: P-quinodimethanes
• Alternative Parents: Benzene and substituted derivatives Nitriles Organopnictogen compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: P-quinodimethane - Benzenoid - Monocyclic benzene moiety - Nitrile - Carbonitrile - Organic nitrogen compound - Organopnictogen compound - Organonitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as p-quinodimethanes. These are compounds containing a benzene ring conjugated to two methylidene groups at carbon atoms 1 and 4, respectively..
• External Descriptors: nitrile - alicyclic compound - quinodimethane

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Insoluble in water；oluble in tetrahydrofuran, dioxane
• Melt Point(°C): 287-289°C
• Molecular Weight: 204.190 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 204.044 Da
• Monoisotopic Mass: 204.044 Da
• Topological Polar Surface Area: 95.200 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 535.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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2. Qiuping Li, Nuan Wen, Wu Zhang, Liansheng Yu, Jinghui Shen, Shuxian Li, Yuguang Lv.  (2023)  Preparation of g-C3N4/TCNQ Composite and Photocatalytic Degradation of Pefloxacin.  Micromachines,  14  (5): (941).  [PMID:37241565] [10.3390/mi14050941]

3. Wu Yufeng, Wu Jianbo, Lin Yan, Liu Junchen, Pan Xiaolong, He Xian, Bi Ke, Lei Ming.  (2022)  Melamine sponge skeleton loaded organic conductors for mechanical sensors with high sensitivity and high resolution.  Advanced Composites and Hybrid Materials,  6  (1): (1-9).  [PMID:] [10.1007/s42114-022-00581-5]

4. Bing Han, Ruixiang Ma, Haihua Wang, Mi Zhou.  (2021)  High pressure investigations on TTF-TCNQ charge-transfer complexes.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:34740004] [10.1016/j.saa.2021.120541]

5. Jiaoyan Shi, Lipeng Wu, Qingya Sun, Fan Wu, Aming Xie.  (2021)  TTF-TCNQ derived N,S-codoped carbon with multiple macropores for excellent electromagnetic wave adsorption.  SYNTHETIC METALS,      [PMID:] [10.1016/j.synthmet.2021.116877]

6. Fengzhi Wang, Weisheng Lei, Xinhua Pan, Zhizhen Ye.  (2020)  Facile synthesis of graphitic carbon nitride via copolymerization of melamine and TCNQ for photocatalytic hydrogen evolution.  NANOTECHNOLOGY,  31  (47): (475406).  [PMID:32570221] [10.1088/1361-6528/ab9ed7]

7. Fengzhi Wang, Weisheng Lei, Xinhua Pan, Bin Lu, Zhizhen Ye.  (2020)  A nine-fold enhancement of visible-light photocatalytic hydrogen production of g-C3N4 with TCNQ by forming a conjugated structure.  RSC Advances,  10  (34): (20110-20117).  [PMID:35520418] [10.1039/C9RA10819J]

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