ChemicalBook CAS DataBase List 1518-16-7

1518-16-7

Name	7,7,8,8-Tetracyanoquinodimethane
CAS	1518-16-7
EINECS(EC#)	216-174-8
Molecular Formula	C12H4N4
MDL Number	MFCD00011664
Molecular Weight	204.19
MOL File	1518-16-7.mol

Synonyms

1,4-BIS(DICYANOMETHYLENE)-2,5-CYCLOHEXADIENE 1,4-BIS(DICYANOMETHYLENE)CYCLOHEXADIENE 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bispropanedinitrile 2,5-CYCLOHEXADIENE-1,4-DIYLIDENE-A,A'-DIMALONONITRILE (2,5-CYCLOHEXADIENE-1,4-DIYLIDENE)DIMALONONITRILE (2,5-CYCLOHEXADIENE-1,4-DIYLIDENE)MALONONITRILE 2,5-CYCLOHEXADIENE-DELTA1,ALPHA4,ALPHA'-DIMALONONITRILE 7,7,8,8-TETRACYANO-1,4-QUINODIMETHANE 7,7,8,8-TETRACYANOQUINODIMETHANE TCNQ TETRACYANODIMETHANOQUINONE TETRACYANO P-QUINODIMETHANE TETRACYANOQUINODIMETHANE TIMTEC-BB SBB000435 2,2’-(2,5-cyclohexadiene-1,4-diylidene)bis-propanedinitril 2,5-Cyclohexadiene-1,4-diylidene-alpha,alpha'-dimalononitrile 2,5-cyclohexadiene-delta(sup1,alpha:4,alpha)-dimalononitrile 2,5-Cyclohexadiene-delta(sup1alpha:4alpha)dimalononitrile 7,7,8,8-Tetracyano-1,4-chinodimethan 7,7,8,8-Tetracyano-1,4-quinodimethan

Chemical Properties

Appearance	orange to green crystalline powder
Melting point	287-289 °C (dec.) (lit.)
Boiling point	332.67°C (rough estimate)
density	1.3596 (rough estimate)
refractive index	1.5000 (estimate)
storage temp.	Sealed in dry,Room Temperature
form	Crystalline Powder
color	Orange-brown to green
Stability:	Stable. Incompatible with strong acids, strong bases, strong reducing agents, strong oxidizing agents.
Water Solubility	insoluble
semiconductor properties	N-type (mobility=10-5cm2/V·s)
λmax	395nm(CH3CN)(lit.)
BRN	611604
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
SMILES	C1(=C(C#N)C#N)C=CC(=C(C#N)C#N)C=C1 \|c:8,t:0\|
CAS DataBase Reference	1518-16-7(CAS DataBase Reference)
NIST Chemistry Reference	Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-(1518-16-7)
EPA Substance Registry System	1518-16-7(EPA Substance)
Odor	Dark yellow to brown crystals/powder

Safety Data

Symbol(GHS)	GHS06
Signal word	Danger
Hazard statements	H301+H311+H331
Precautionary statements	P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Hazard Codes	Xn,Xi
Risk Statements	R22:Harmful if swallowed. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . less more
Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . S36/37:Wear suitable protective clothing and gloves . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . less more
RIDADR	3276
WGK Germany	3
RTECS	GU4850000
Hazard Note	Irritant
TSCA	Yes
HazardClass	6.1
PackingGroup	II
HS Code	29269095
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral

Hazard Information

Description

7,7,8,8-tetracyanoquinodimethane (TCNQ), with a LUMO at 4.5 eV, is known for the charge-transfer salts formed by its radical anion TCNQ in?photovoltaic, light-emitting diodes, and organic field-effect transistor?devices. TCNQ and its derivatives?have been used as dopants, leading to an increase in hole mobility or to the lowering of injection?barriers. One classic example of such is the treatment of tetrathiafulvene (TTF), an electron donor with TCNQ. TFF and TCNQ form an ion pair, the TTF-TCNQ complex. This process of doping leads to the crystallisation of the ion pair into a one-dimensionally stacked polymer. This polymer consists of segregated stacks of cations and anions of the donors and the acceptors, respectively. The complex crystal is an organic semiconductor that exhibits metallic electric conductivity [1, 2].

Chemical Properties

orange to green crystalline powder

History

The first report on the electrical conductivity in an organic solid appeared in 1954, namely, a perylene—bromine complex with a room-temperature conductivity of 0.1 S cm?1. In 1960, the organic acceptor Tetracyanoquinodimethane (TCNQ; 7,7,8,8-Tetracyanoquinodimethane) was synthesized, as well as a great number of its conducting charge-transfer complexes and radical ion salts. In the 1970s, the organic donor TTF led to the first organic metal TTF-TCNQ. Its room-temperature conductivity (500 S cm?1) increases with a decrease in the temperature to the value of 6000 S cm?1 at 60 K, where a metal-insulator transition occurs[1].

Uses

7,7,8,8-Tetracyanoquinodimethane is an electron-acceptor molecule used to form charge-transfer superconductors. It is an effective catalyst used for the ?-chlorination of carboxylic acids using chlorosulfonic acid; the presence of TCNQ suppresses competing free-radical chlorination.

Definition

ChEBI: A quinodimethane that is p-quinodimethane in which the methylidene hydrogens are replaced by cyano groups.

Synthesis Reference(s)

Journal of the American Chemical Society, 84, p. 3370, 1962 DOI: 10.1021/ja00876a028
The Journal of Organic Chemistry, 48, p. 1366, 1983 DOI: 10.1021/jo00156a048

General Description

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.

References

[1] Tahar Abbaz. “Synthesis and electrochemical proprieties of novel unsymmetrical bis-tetrathiafulvalenes and electrical conductivity of their charge transfer complexes with tetracyanoquinodimethane (TCNQ).” International Journal of Molecular Sciences 13 7 (2012): 7872–7885.

Material Safety Data Sheet(MSDS)

Questions And Answer

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Wuhan Roche Technology Development Co., Ltd.

Telephone 19171595131

Website

Hubei Lidu New Material Technology Co., Ltd.

Telephone19307246857 19307246857

Websitehttp://www.liduxcl.com

Hubei Lidu New Material Technology Co., Ltd

Telephone 19307245857

Websitehttp://www.liduxcl.com

J & K SCIENTIFIC LTD.

Telephone18210857532 18210857532

Websitehttps://www.jkchemical.com

Meryer (Shanghai) Chemical Technology Co., Ltd.

Telephone4006356688 18621169109

Websitehttp://www.x-labseek.com/

Alfa Aesar

Telephone400-6106006

Websitehttp://chemicals.thermofisher.cn

TCI (Shanghai) Development Co., Ltd.

Telephone021-67121386

Websitehttps://www.tcichemicals.com/CN/zh/

Energy Chemical

Telephone021-021-58432009 400-005-6266

Websitehttp://www.energy-chemical.com

Jilin OLED Material Tech Co., Ltd

Telephone0431-85877181

Websitehttp://www.jl-oled.com

JinYan Chemicals(ShangHai) Co.,Ltd.

Telephone13817811078

Websitehttp://www.jingyan-chemical.com/

Shanghai Hanhong Scientific Co.,Ltd.

Telephone021-54306202 13764082696

Websitehttps://www.hanhongsci.com

Syntechem Co.,Ltd

Telephone

Websitehttp://www.syntechem.com/

HANSHANG CHEMICAL SCIENTIFIC LIMITED

Telephone021-50521775 15800962688

Websitehttp://www.hanshangchem.com

Tianjin heowns Biochemical Technology Co., Ltd.

Telephone400 638 7771

Websitehttp://www.heowns.com

Sinopharm Chemical Reagent Co,Ltd.

Telephone86-21-63210123

Websitehttp://www.reagent.com.cn

Beijing Yan Nuo XinCheng Chemical Co., Ltd.

Telephone86-10-82830276

Websitehttps://www.chemicalbook.com/ShowSupplierProductsList15334/0_EN.htm

Explovisual Technology Incorporation

Telephone+86 (519) 8829-2061

Websitehttp://www.explovisual.com

Spectrum Chemical Manufacturing Corp.

Telephone021-021-021-67601398-809-809-809 15221380277

Websitehttps://www.spectrumchemical.com/OA_HTML/index.jsp?minisite=10020&respid=22372&language=US

1of4

Related Products

Send Inquriy

1518-16-7

Chemical Properties

Safety Data

Hazard Information

Description

Chemical Properties

History

Uses

Definition

Synthesis Reference(s)

General Description

References

Material Safety Data Sheet(MSDS)

Questions And Answer

Applications

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Related Products