Applications
ChemicalBook > CAS DataBase List > 7,7,8,8-Tetracyanoquinodimethane

7,7,8,8-Tetracyanoquinodimethane

Applications
Product Name
7,7,8,8-Tetracyanoquinodimethane
CAS No.
1518-16-7
Chemical Name
7,7,8,8-Tetracyanoquinodimethane
Synonyms
TCNQ;TETRACYANOQUINODIMETHANE;Tetracyanoquinodimethan;Tetracyano p-Quinone Dimethane;TIMTEC-BB SBB000435;7,7,8,8-Tetracyanoqu;tetracyano-quinodimetha;etracyanoquinodimethane;7,7,8,8-Tetracyanodimethan;cyclohexa-1,2,4,5-tetraene
CBNumber
CB6306980
Molecular Formula
C12H4N4
Formula Weight
204.19
MOL File
1518-16-7.mol
More
Less

7,7,8,8-Tetracyanoquinodimethane Property

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
Water Solubility 
insoluble
λmax
395nm(CH3CN)(lit.)
BRN 
611604
Stability:
Stable. Incompatible with strong acids, strong bases, strong reducing agents, strong oxidizing agents.
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
Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis- (1518-16-7)
More
Less

Safety

Hazard Codes 
Xn,Xi,T
Risk Statements 
22-20/21/22-23/24/25
Safety Statements 
22-24/25-36/37-26-36-45
RIDADR 
3276
WGK Germany 
3
RTECS 
GU4850000
Hazard Note 
Irritant
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29269095
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
157635
Product name
7,7,8,8-Tetracyanoquinodimethane
Purity
98%
Packaging
5g
Price
$108
Updated
2024/03/01
Sigma-Aldrich
Product number
157635
Product name
7,7,8,8-Tetracyanoquinodimethane
Purity
98%
Packaging
10g
Price
$155
Updated
2024/03/01
TCI Chemical
Product number
T0078
Product name
7,7,8,8-Tetracyanoquinodimethane
Purity
>98.0%(HPLC)(N)
Packaging
5g
Price
$63
Updated
2024/03/01
TCI Chemical
Product number
T0078
Product name
7,7,8,8-Tetracyanoquinodimethane
Purity
>98.0%(HPLC)(N)
Packaging
25g
Price
$215
Updated
2024/03/01
Alfa Aesar
Product number
A10779
Product name
7,7,8,8-Tetracyanoquinodimethane, 98%
Packaging
5g
Price
$115
Updated
2024/03/01
More
Less

7,7,8,8-Tetracyanoquinodimethane Chemical Properties,Usage,Production

Applications

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.
It also has been shown that TCNQ can effectively modify Cu or Ag surfaces. The formation of Cu-TCNQ and Ag-TCNQ enhances the work function of such electrodes and reduces the hole injection barrier dramatically. Furthermore, it improves electrode/organic layer contact, hence the reduction of contact resistances.
Tetracyanoquinodimethane (TCNQ) is also found to act as a p-type doping agent of graphene films due to its powerful electron-accepting capacity.

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.

7,7,8,8-Tetracyanoquinodimethane Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

7,7,8,8-Tetracyanoquinodimethane Suppliers

Austria 1 Belgium 1 China 152 Europe 3 France 1 Germany 4 India 5 Japan 6 South Korea 1 Switzerland 2 United Kingdom 13 United States 28 Global 217
Hubei Kanglide Bio-pharmaceutical Co., Ltd
Tel
19307248857
Email
1901338096@qq.com
Country
China
ProdList
506
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44688
Advantage
61
Jilin OLED Material Tech Co., Ltd
Tel
0431-85877181
Fax
0431-85804772
Email
sales@jl-oled.com
Country
China
ProdList
154
Advantage
68
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
9976
Advantage
60
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
XiaoGan ShenYuan ChemPharm co,ltd
Tel
15527768850
Email
1791901229@qq.com
Country
China
ProdList
8838
Advantage
52
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
Advantage
57
HANSHANG CHEMICAL SCIENTIFIC LIMITED
Tel
021-50521775 15800962688
Fax
86-21-58306291
Email
sales@hanshangchem.com
Country
China
ProdList
471
Advantage
57
Tianjin heowns Biochemical Technology Co., Ltd.
Tel
400 638 7771
Email
sales@heowns.com
Country
China
ProdList
14435
Advantage
57
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Beijing Yan Nuo XinCheng Chemical Co., Ltd.
Tel
86-10-82830276
Fax
86-10-82830276-1
Country
China
ProdList
284
Advantage
62
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
Explovisual Technology Incorporation
Tel
+86 (519) 8829-2061
Fax
+86 (519) 8829-2061
Email
explovisual@hotmail.com
Country
China
ProdList
296
Advantage
60
Spectrum Chemical Manufacturing Corp.
Tel
021-021-021-67601398-809-809-809 15221380277
Fax
021-57711696
Email
marketing_china@spectrumchemical.com
Country
China
ProdList
9658
Advantage
60
Chengdu Ai Keda Chemical Technology Co., Ltd.
Tel
4008-755-333 18080918076
Fax
028-86757656
Email
800078821@qq.com
Country
China
ProdList
9718
Advantage
55
Shanghai civi chemical technology co.,Ltd
Tel
86-21-34053660
Fax
86-21-34053661
Email
sale@labgogo.com
Country
China
ProdList
9865
Advantage
52
Thermo Fisher Scientific
Tel
800-810-5118
Fax
+86-10-84193589
Email
cnchemical@thermofisher.com
Country
China
ProdList
17770
Advantage
75
Beijing innoChem Science & Technology Co.,Ltd.
Tel
400-810-7969 010-59572699
Fax
010-59572688
Email
ningzi.li@inno-chem.com.cn
Country
China
ProdList
6134
Advantage
55
9ding chemical ( Shanghai) Limited
Tel
4009209199
Fax
86-021-52271987
Email
sales@9dingchem.com
Country
China
ProdList
22514
Advantage
55
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-400-6206333 18521732826
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
The future of Shanghai Industrial Co., Ltd.
Tel
021-61552785
Fax
021-55660885
Email
sales@shshiji.com
Country
China
ProdList
9545
Advantage
55
Shanghai Yolne Chemical Co., Ltd.
Tel
021-62960152
Fax
021-52212593
Email
934678158@qq.com
Country
China
ProdList
9899
Advantage
55
Zhengzhou HongSheng Pharmaceutical Co., Ltd.
Tel
0371-13526885213 15637198702
Fax
0371-63709726
Email
xpkchem@163.com
Country
China
ProdList
3991
Advantage
58
Chengdu HuaXia Chemical Reagent Co. Ltd
Tel
400-1166-196 13458535857
Fax
QQ：800101999
Email
cdhxsj@163.com
Country
China
ProdList
13350
Advantage
58
Finetech Industry Limited
Tel
027-87465837 19945049750
Fax
027-8777-2287
Email
sales@finetechnology-ind.com
Country
China
ProdList
9648
Advantage
58
Suzhou yacoo science co.,Ltd
Tel
0512-87182056 18013166090
Fax
0512-87182056
Email
lingling.qi@yacoo.com.cn
Country
China
ProdList
7295
Advantage
60
Shanghai Boka-chem Tech. Inc.
Tel
400-026-1533/(021) 6478-0600
Fax
+86 (21) 6459-2060
Email
sales@bokachem.com
Country
China
ProdList
876
Advantage
58
Shanghai Xingui Biotechnology Co., Ltd.
Tel
17501653715
Email
xingui2022@126.com
Country
China
ProdList
10021
Advantage
58
Shanghai Macklin Biochemical Co.,Ltd.
Tel
15221275939 15221275939
Fax
021-50706099
Email
shenlinxing@macklin.cn
Country
China
ProdList
16166
Advantage
55
Hubei Jusheng Technology Co.,Ltd
Tel
027-59599241 18871490274
Fax
027-59599241
Email
1400878000@qq.com
Country
China
ProdList
9958
Advantage
58
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51456
Advantage
80
Ningbo Materials-X Co., Ltd
Tel
0574-87487840-805 15888368997
Fax
0574-87485342
Country
China
ProdList
474
Advantage
55
Jilin Chinese Academy of Sciences - Yanshen Technology Co., Ltd
Tel
0431-0431-80514535 19917294565
Email
et@chemextension.com
Country
China
ProdList
3982
Advantage
55
Codow Chemical Co.,Ltd.
Tel
18620099427
Fax
+86-20-62619665
Email
amy@howeipharm.com
Country
China
ProdList
17687
Advantage
55
Nanjing Vital Chemical Co., Ltd.
Tel
025-87193546 18652950785
Fax
025-87193546
Email
chemweiao@163.com
Country
China
ProdList
9021
Advantage
60
Henan CoreyChem Co., Ltd
Tel
0371-86658258
Fax
0371-60996044
Email
info@coreychem.com
Country
China
ProdList
10453
Advantage
58
Shandong Xiya Chemical Co., Ltd.
Tel
4009903999 13395398332
Fax
0539-6365991
Email
sales@xiyashiji.com
Country
China
ProdList
20806
Advantage
60
Zhengzhou Acme Chemical Co., Ltd.
Tel
0371-0371-55629727 13323845623
Fax
037155629727
Email
2885676761@qq.com
Country
China
ProdList
10009
Advantage
58
Amadis Chemical Company Limited
Tel
571-89925085
Fax
0086-571-89925065
Email
sales@amadischem.com
Country
China
ProdList
131957
Advantage
58
Guangdong wengjiang Chemical Reagent Co., Ltd.
Tel
0751-2886750 13927877953
Fax
0751-2886750
Email
3005811397@qq.com
Country
China
ProdList
13320
Advantage
58
Suzhou Shanyang Pharmaceutical Technology Co.,
Tel
0512-63268889 18506119477
Email
82169840@qq.com
Country
China
ProdList
529
Advantage
58
Taian Jiaye Biotechnology Co.Ltd
Tel
13127280945
Email
285424065@qq.com
Country
China
ProdList
9976
Advantage
55
Wuhan EEChem Technologies Co., Ltd
Tel
0711-3617768 13308685235
Fax
0711-3616558
Email
lihongcai4360@sina.com
Country
China
ProdList
1378
Advantage
55
JinJin Le Chemical Co., Ltd
Tel
10106090
Email
jjlchem2@163.com
Country
China
ProdList
9981
Advantage
58
Shandong Ono Chemical Co., Ltd.
Tel
0539-6362799 20）
Fax
0539-6362799（To 20）
Country
China
ProdList
9998
Advantage
58
9ding chemical ( Shanghai) Limited
Tel
021-021-52271985 17721149837
Fax
+86 (21) 52271987
Email
sales@9dingchem.com
Country
China
ProdList
19800
Advantage
60
More
Less

View Lastest Price from 7,7,8,8-Tetracyanoquinodimethane manufacturers

Hubei Lidu New Material Technology Co., Ltd
Product
7,7,8,8-TETRACYANOQUINODIMETHANE 1518-16-7
Price
US $0.00-0.00/g
Min. Order
10g
Purity
98%
Supply Ability
20tons
Release date
2024-09-24
Zibo Hangyu Biotechnology Development Co., Ltd
Product
7,7,8,8-Tetracyanoquinodimethane 1518-16-7
Price
US $0.10-0.30/kg
Min. Order
1kg
Purity
98%
Supply Ability
20 tons
Release date
2024-01-20
Career Henan Chemical Co
Product
7,7,8,8-Tetracyanoquinodimethane 1518-16-7
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100KG
Release date
2020-01-08

1518-16-7, 7,7,8,8-TetracyanoquinodimethaneRelated Search:

Diphenylmethane Dibromomethane Methyl 4-cyanobenzoate Diiodomethane Methylene dithiocyanate 2,3-Dimethoxy-5-methyl-p-benzoquinone 4,4'-Methylenedianiline 4-Cyanobenzoyl chloride 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane 1,4-Benzoquinone p-Toluquinone Malononitrile (TCNQ)2 ISOQUINOLINE(N-N-BUTYL) 2-FLUORO-7,7,8,8-TETRACYANOQUINODIMETHANE 2,5-DIFLUORO-7,7,8,8-TETRACYANOQUINODIMETHANE 2,5-BIS(2-HYDROXYETHOXY)-7,7,8,8-TETRACYANOQUINODIMETHANE Tetrathiafulvalene - 7,7,8,8-Tetracyanoquinodimethane Complex,7,7,8,8-Tetracyanoquinodimethane Tetrathiafulvalene salt, TCNQ-TTF, TTF-TCNQ 2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE,2,5-DIMETHYL-7,7,8,8-TETRACYANOQUINODIMETHANE 97+%

  • TIMTEC-BB SBB000435
  • Tetracyano p-Quinone Dimethane
  • 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bismalononitrile
  • 2,5-Cyclohexadiene-delta(sup1alpha:4alpha)dimalononitrile
  • 7,7,8,8-Tetracyano-1,4-chinodimethan
  • 7,7,8,8-Tetracyano-1,4-quinodimethan
  • 7,7,8,8-Tetracyanodimethan
  • 7,7,8,8-Tetracyano-p-quinodimethane
  • 7,7,8,8-tetracyanoquinoedimethane
  • 7,7,8,8-tetracyanoquinonedimethane
  • 7,7,8,8-Tetracyanoquino-Dimeth
  • 7,7,8,8-Tetracyanoquinodimethane,98%TCNQ
  • Propanedinitrile, 2,2-(2,5-cyclohexadiene-1,4-diylidene)bis-
  • TCNQ/7,7'',8,8''-TETRACYANOQUINO-DIMETHANE
  • 7,7,8,8-TETRACYANOQUINODIMETHANE TCNQ
  • TCNQ/TETRACYANO-QUINODIMETHA
  • Tetracyanoquinodimethane: (Ultima Gold AB)
  • (2,5-Cyclohexadiene-1,4-diylidene)-dimalononitrile, TCNQ
  • 2-[4-(Dicyanomethylidene)-1-cyclohexa-2,5-dienylidene]propanedinitrile
  • 7,7,8,8-Tetracyanoquinodimethane,98%
  • (2,5-Cyclohexadiene-1,4-diylidene)
  • 7,7,8,8-Tetracyanoqu
  • 2,2'-(Cyclohexa-2,5-diene-1,4-diylidene)dipropane-1,3-dinitrile, TCNQ
  • 7,7,8,8-TetracyanoquinodiMethane, 98% 10GR
  • 1,4-Bis(dicyanomethylene)cyclohexadiene TCNQ
  • 2,2'-(Cyclohexa-2,5-diene-1,4-diylidene)diMalononitrile
  • cyclohexa-1,2,4,5-tetraene
  • cyclohexa-2,5-diene-1,4-diylidene-bis-malononitrile
  • Propanedinitrile,2,2’-(2,5-cyclohexadien-1,4-diylidene)bis-
  • Quinodimethan, tetracyano-
  • tetracyano-quinodimetha
  • Tetracyanoquinodimethan
  • 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
  • TCNQ
  • TETRACYANO P-QUINODIMETHANE
  • TETRACYANOQUINODIMETHANE
  • TETRACYANODIMETHANOQUINONE
  • 7,7,8,8-TETRACYANO-1,4-QUINODIMETHANE
  • 7,7,8,8-TETRACYANOQUINODIMETHANE
  • 7,7,8,8-TetracyanoquinodiMethane (purified by subliMation)
  • 7,7,8,8-TetracyanoquinodiMethane 98%
  • 2,5-Cyclohexadiene-1,4-diylidene-alpha,alpha'-dimalononitrile
  • 2,5-cyclohexadiene-delta(sup1,alpha:4,alpha)-dimalononitrile
  • 2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
  • 7,7,8,8-Tetracyanoquinonedimethane for synthesis
  • 2,2’-(2,5-cyclohexadiene-1,4-diylidene)bis-propanedinitril
  • 7,7,8,8-Tetracyanoquinodimethane&gt
  • 7,7,8,8-Tetracyanoquinodimethane, 98%, for synthesis
  • TCNQ 7,7,8,8-Tetracyanoquinodimethan
  • etracyanoquinodimethane
  • 7,7',8,8'-tetracyanoquinodimethane
  • 2,2'-(Cyclohexa-2,5-diene-1,4-diylidene)dimalononitrile