Tetracyanoethylene - AR , CAS No.670-54-2

CAS: 670-54-2 Cat. No.: T113728 Molecular Weight: 128.09 Beilstein Registry Number: 1679885 EC Number: 211-578-0

GRADE & PURITY AR

Synonyms

J-200117 | TCNE | Tetrakyanethylen [Czech] | AI3-28756 | delta(sup 2,2')-Bimalononitrile | 1,1,2,2-ethenetetracarbonitrile | 1,1,2,2-Ethylenetetracarbonitrile # | BBL027360 | EINECS 211-578-0 | Percyanoethylene | Tetracyanoethylene, 98% | Tox21_202940 | E

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice,FedEx DG Service

Overview

Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability. Reactant for: Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes and TCBD derivatives Thermal addition reaction with alkynes One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds Synthesis of cobalt tetracyanoethylene films Biotransformation by Botrytis cinerea

Specifications

Synonyms

J-200117 | TCNE | Tetrakyanethylen [Czech] | AI3-28756 | delta(sup 2, 2')-Bimalononitrile | 1, 1, 2, 2-ethenetetracarbonitrile | 1, 1, 2, 2-Ethylenetetracarbonitrile # | BBL027360 | EINECS 211-578-0 | Percyanoethylene | Tetracyanoethylene, 98% | Tox21_202940 | E

Specifications & Purity

AR

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice, FedEx DG Service

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

Grade

AR

Names and Identifiers

• Canonical Smiles: C(#N)C(=C(C#N)C#N)C#N
• IUPAC Name: ethene-1,1,2,2-tetracarbonitrile
• InChIKey: NLDYACGHTUPAQU-UHFFFAOYSA-N
• INCHI: 1S/C6N4/c7-1-5(2-8)6(3-9)4-10
• Isomeric SMILES: C(#N)C(=C(C#N)C#N)C#N
• WGK Germany: 3
• RTECS: KM7300000
• UN Number: 2811
• Molecular Weight: 128.09
• Beilstein: 1679885
• Reaxy-Rn: 506867

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Organic cyanides

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Organic cyanides
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitriles
• Alternative Parents: Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Nitrile - Carbonitrile - Organopnictogen compound - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as nitriles. These are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
• External Descriptors: Not available

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: Soluble in methanol, benzene, toluene, water (hydrolyses to form HCN), and ether (slightly).,
• Sensitivity: Light and Moisture sensitive
• Boil Point(°C): 223°C
• Melt Point(°C): 198°C
• Molecular Weight: 128.090 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 128.012 Da
• Monoisotopic Mass: 128.012 Da
• Topological Polar Surface Area: 95.200 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 289.000
• 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

1. Cao Jianfei, Yin Zuodong, Pang Qi, Lu Yuexi, Nong Xiuqing, Zhang Jin Zhong.  (2021)  Modulating optical properties and interfacial electron transfer of CsPbBr3 perovskite nanocrystals via indium ion and chlorine ion co-doping.  JOURNAL OF CHEMICAL PHYSICS,  155  (23):   [PMID:34937354] [10.1063/5.0076037]

2. Xiu Chen, Ying Zhang, Jin Han, Linzhou Zhang, Suoqi Zhao, Chunming Xu, Quan Shi.  (2021)  Direct Nickel Petroporphyrin Analysis through Electrochemical Oxidation in Electrospray Ionization Ultrahigh-Resolution Mass Spectrometry.  ENERGY & FUELS,      [PMID:] [10.1021/acs.energyfuels.0c03785]

3. Guohua Jiang, Tengteng Jiang, Xia Li, Zheng Wei, Xiangxiang Du, Xiaohong Wang.  (2014)  Boronic acid functionalized N-doped carbon quantum dots as fluorescent probe for selective and sensitive glucose determination.  Materials Research Express,  1  (2): (025708).  [PMID:] [10.1088/2053-1591/1/2/025708]

4. Jinghang Li, Qi Shi, Chaoyu Song, Chenxi Shi, Yuguang Lv.  (2025)  Analysis of Tetracycline Modification Based on g-C3N4 Photocatalytic Degradation.  Inorganics,  13  (3): (77).  [PMID:] [10.3390/inorganics13030077]

5. Qi Shi, Siqi Huang, Qi Xi, Yanan Niu, Nuan Wen, Libo Du, Yuguang Lv, Tai Peng.  (2025)  Preparation and photocatalytic degradation of PTCN/SnS2/Ti3C2 QDs composites.  JOURNAL OF THE INDIAN CHEMICAL SOCIETY,      [PMID:] [10.1016/j.jics.2025.101921]