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1518-16-7 molecular structure
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2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile

ChemBase ID: 77700
Molecular Formular: C12H4N4
Molecular Mass: 204.18696
Monoisotopic Mass: 204.04359615
SMILES and InChIs

SMILES:
N#CC(=c1ccc(=C(C#N)C#N)cc1)C#N
Canonical SMILES:
N#CC(=c1ccc(=C(C#N)C#N)cc1)C#N
InChI:
InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
InChIKey:
PCCVSPMFGIFTHU-UHFFFAOYSA-N

Cite this record

CBID:77700 http://www.chembase.cn/molecule-77700.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
IUPAC Traditional name
tetracyanoquinodimethane
Synonyms
(2,5-Cyclohexadiene-1,4-diylidene)-dimalononitrile
7,7,8,8-Tetracyanoquinodimethane
2,2'-(Cyclohexa-2,5-diene-1,4-diylidene)dipropane-1,3-dinitrile
TCNQ
Tetracyanoquinodimethane
(2,5-Cyclohexadiene-1,4-diylidene)
-dimalononitrile, 7,7,8,8-Tetracyanoquinodimethane
2,2'-(2,5-环己二烯-1,4-二基)丙二腈
7,7,8,8-四氰基对苯二醌二甲烷
7,7,8,8-四氰基对醌二甲烷
CAS Number
1518-16-7
EC Number
216-174-8
MDL Number
MFCD00011664
Beilstein Number
1427366
611604
PubChem SID
162042571
24849689
PubChem CID
73697
CHEBI ID
52445
Chemspider ID
66342
Wikipedia Title
Tetracyanoquinodimethane

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 0.7475403  LogD (pH = 7.4) 0.7475403 
Log P 0.7475403  Molar Refractivity 61.1884 cm3
Polarizability 20.516354 Å3 Polar Surface Area 95.16 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Apperance
green-coloured crystals expand Show data source
Melting Point
287-289 °C (dec.)(lit.) expand Show data source
287-289(dec.)°C expand Show data source
293.5–296 °C expand Show data source
ca 288°C dec. expand Show data source
Boiling Point
sublimes expand Show data source
Orbital energy
LUMO 4.6 eV expand Show data source
Semiconductor Properties
N-type (mobility=10-5 cm2/V·s) expand Show data source
Storage Warning
Harmful/Irritant expand Show data source
RTECS
GU4850000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
X expand Show data source
UN Number
UN3439 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
III expand Show data source
Risk Statements
20/21/22 expand Show data source
23/24/25 expand Show data source
Safety Statements
36/37 expand Show data source
36/37-45 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 + H311 + H331 expand Show data source
H331-H302-H312 expand Show data source
GHS Precautionary statements
P261-P280-P301 + P310-P311 expand Show data source
P261-P280-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Gene Information
human ... CAPN1(823)rat ... Capn1(29153), Nos1(24598) expand Show data source
Purity
≥98.0% (N) expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Empirical Formula (Hill Notation)
C12H4N4 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 157635 external link
Packaging
10 g in poly bottle
5 g in glass bottle
Application
Electron-acceptor molecule used to form charge-transfer superconductors.1
Sigma Aldrich - 87126 external link
Other Notes
Formation of charge-transfer complexes1

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Effective catalyst for the ɑ-chlorination of carboxylic acids using chlorosulfonic acid; the presence of TCNQ suppresses competing free-radical chlorination: J. Org. Chem., 48, 1364 (1983).
  • • Electron-acceptor, forming stable radical anions: J. Am. Chem. Soc., 82, 6408 (1960); 84, 3370, 3374 (1962).
  • • Forms charge-transfer complexes with electron-rich donors: J. Am. Chem. Soc., 95, 948 (1973).
  • • For a review of the differences between "metallic" and "non-metallic" salts of TCNQ, see: Acc. Chem. Res., 12, 79 (1979).
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PATENTS

PATENTS

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INTERNET

INTERNET

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