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31366-25-3

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31366-25-3 Usage

Chemical Properties

ORANGE TO BROWNISH CRYSTALS OR CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 31366-25-3 differently. You can refer to the following data:
1. Electron donor for supramolecular synthesis,1 charge-transfer complex synthesis2 with 7,7,8,8-tetracyanoquinodimethane (cat. no. 157635), and for electron transfer to diazonium salts.3
2. Molecular sensors; radical catalyst.
3. Tetrathiafulvalene, holds wide application in HPLC, NMR. This heterocyclic compound contributed to the development of molecular electronics. They are used as a organic super conductors.

General Description

Tetrathiafulvalene (TTF) is an electron-donor which consists of oligomers, dendrimers and polymers which can be used in the formation of redox macromolecules.

Purification Methods

Recrystallise it from cyclohexane/hexane under an argon atmosphere [Kauzlarich et al. J Am Chem Soc 109 4561 1987]. [Beilstein 19/11 V 380.]

Check Digit Verification of cas no

The CAS Registry Mumber 31366-25-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,3,6 and 6 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 31366-25:
(7*3)+(6*1)+(5*3)+(4*6)+(3*6)+(2*2)+(1*5)=93
93 % 10 = 3
So 31366-25-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H4S4/c1-2-8-5(7-1)6-9-3-4-10-6/h1-4H

31366-25-3 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (L19229)  Tetrathiafulvalene, 97%   

  • 31366-25-3

  • 250mg

  • 547.0CNY

  • Detail
  • Alfa Aesar

  • (L19229)  Tetrathiafulvalene, 97%   

  • 31366-25-3

  • 1g

  • 1523.0CNY

  • Detail
  • Aldrich

  • (183180)  Tetrathiafulvalene  97%

  • 31366-25-3

  • 183180-250MG

  • 981.63CNY

  • Detail
  • Aldrich

  • (183180)  Tetrathiafulvalene  97%

  • 31366-25-3

  • 183180-1G

  • 2,543.58CNY

  • Detail

31366-25-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name tetrathiafulvalene

1.2 Other means of identification

Product number -
Other names TTF

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:31366-25-3 SDS

31366-25-3Synthetic route

4-bromotetrathiafulvalene
57223-41-3

4-bromotetrathiafulvalene

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

Conditions
ConditionsYield
With n-butyllithium In diethyl ether for 3h; Heating;100%
1,4,5,8-tetrathianaphthalene
255-55-0

1,4,5,8-tetrathianaphthalene

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 0.5h; Heating;99%
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3h;75%
With lithium diisopropyl amide In tetrahydrofuran70%
With lead(IV) acetate; sodium dithionite 1.) CF3COOH, 0 deg C; Yield given. Multistep reaction;
With potassium tert-butylate In tetrahydrofuran for 0.5h; Product distribution; Further Variations:; Reagents; Temperatures; Heating;
1,3-Dithiolium iodide
1863-66-7

1,3-Dithiolium iodide

triphenyl[4,5-bis(2'-cyanoethylsulfanyl)-1,3-dithiol-2-yl]phosphonium tetrafluoroborate

triphenyl[4,5-bis(2'-cyanoethylsulfanyl)-1,3-dithiol-2-yl]phosphonium tetrafluoroborate

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

4,5-bis(2-cyanoethylsulfanyl)tetrathiafulvalene
186139-70-8

4,5-bis(2-cyanoethylsulfanyl)tetrathiafulvalene

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 5℃; for 3h; Inert atmosphere;A 2.68 g
B 90%
1,3-Dithiolium iodide
1863-66-7

1,3-Dithiolium iodide

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

Conditions
ConditionsYield
With triethylamine In acetonitrile for 1h; Ambient temperature;85%
1-<1-(2,3-dihydrobenzofuran-3-yl)ethyl>tetrathiafulvalen-1-ium tetrafluoroborate

1-<1-(2,3-dihydrobenzofuran-3-yl)ethyl>tetrathiafulvalen-1-ium tetrafluoroborate

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

2,3-dihydro-3-(1-hydroxyethyl)benzofuran

2,3-dihydro-3-(1-hydroxyethyl)benzofuran

Conditions
ConditionsYield
In acetone for 1h; Ambient temperature;A 25%
B 63%
hexafluorophosphate de 1,3-dithiolium

hexafluorophosphate de 1,3-dithiolium

hexafluorophosphate de 4-methyl-1,3-dithiolium

hexafluorophosphate de 4-methyl-1,3-dithiolium

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

dimethyltetrathiafulvalene
54397-97-6

dimethyltetrathiafulvalene

C

monomethyltetrathiafulvalene
54397-94-3

monomethyltetrathiafulvalene

Conditions
ConditionsYield
With triethylamine; acetonitrileA 18%
B 31%
C 51%
tetrakis(methoxycarbonyl)tetrathiafulvalene
26314-39-6

tetrakis(methoxycarbonyl)tetrathiafulvalene

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

(Z)-[2,2']Bi[[1,3]dithiolylidene]-4,4'-dicarboxylic acid dimethyl ester
51751-18-9

(Z)-[2,2']Bi[[1,3]dithiolylidene]-4,4'-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With lithium chloride In N,N-dimethyl-formamide at 170℃; for 2.5h;A 50%
B 10%
C16H16NO2S5(1+)*BF4(1-)

C16H16NO2S5(1+)*BF4(1-)

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

3-((Z)-2-Azido-vinylsulfanylmethyl)-1-methanesulfonyl-2,3-dihydro-1H-indole

3-((Z)-2-Azido-vinylsulfanylmethyl)-1-methanesulfonyl-2,3-dihydro-1H-indole

Conditions
ConditionsYield
With sodium azide In acetoneA 49%
B 36%
1-[(2,3-dihydrobenzofuran-3-yl)methyl]tetrathiafulvalen-1-ium tetrafluoroborate

1-[(2,3-dihydrobenzofuran-3-yl)methyl]tetrathiafulvalen-1-ium tetrafluoroborate

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

3-((Z)-2-Azido-vinylsulfanylmethyl)-2,3-dihydro-benzofuran

3-((Z)-2-Azido-vinylsulfanylmethyl)-2,3-dihydro-benzofuran

Conditions
ConditionsYield
With sodium azide In acetoneA 45%
B 46%
C3H4S2*BF4(1-)*H(1+)

C3H4S2*BF4(1-)*H(1+)

4,5-bis(acetylthiomethyl)-1,3-dithiolium tetrafluoroborate

4,5-bis(acetylthiomethyl)-1,3-dithiolium tetrafluoroborate

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

2,3,6,7-tetrakis(acetylthiomethyl)tetrathiafulvalene
204076-18-6

2,3,6,7-tetrakis(acetylthiomethyl)tetrathiafulvalene

C

2,3-bis(acetylthiomethyl)tetrathiafulvalene
408316-59-6

2,3-bis(acetylthiomethyl)tetrathiafulvalene

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 20℃; for 3h; Product distribution; Further Variations:; Reagents; time;A 23%
B 18%
C 44%
C17H17O3S4(1+)*BF4(1-)

C17H17O3S4(1+)*BF4(1-)

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

[3-((Z)-2-Azido-vinylsulfanylmethyl)-4-methoxy-2,3-dihydro-benzofuran-6-yl]-methanol

[3-((Z)-2-Azido-vinylsulfanylmethyl)-4-methoxy-2,3-dihydro-benzofuran-6-yl]-methanol

Conditions
ConditionsYield
With sodium azide In acetoneA 21%
B 41%
1,3-dithiol-2-thione
930-35-8

1,3-dithiol-2-thione

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

Conditions
ConditionsYield
With dicobalt octacarbonyl In toluene for 0.5h; Heating;35%
at 80℃; under 3000240 Torr; for 6h; Product distribution; trimethyl phosphite; different pressure;30%
With phosphorous acid trimethyl ester at 80℃; under 3000240 Torr; for 6h;30%
1,3-dithiol-2-thione
930-35-8

1,3-dithiol-2-thione

4-formyl-5-(diethoxymethyl)-1,3-dithiole-2-thione
87258-15-9

4-formyl-5-(diethoxymethyl)-1,3-dithiole-2-thione

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

tetraformyltetrathiafulvalene-bis(diethyl acetal)
87258-16-0

tetraformyltetrathiafulvalene-bis(diethyl acetal)

C

tetraformyltetrathiafulvalene-bis(diethyl acetal)
87258-17-1

tetraformyltetrathiafulvalene-bis(diethyl acetal)

D

5-Diethoxymethyl-[2,2']bi[[1,3]dithiolylidene]-4-carbaldehyde

5-Diethoxymethyl-[2,2']bi[[1,3]dithiolylidene]-4-carbaldehyde

Conditions
ConditionsYield
With dicobalt octacarbonyl In toluene 40 deg C, 0.5 h; reflux, 5 h;A n/a
B n/a
C n/a
D 27%
1,3-dithiol-2-thione
930-35-8

1,3-dithiol-2-thione

azulenodithiocarbonate

azulenodithiocarbonate

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

C19H18S4

C19H18S4

Conditions
ConditionsYield
With triethyl phosphite at 110 - 120℃; Inert atmosphere;A n/a
B 25%
1,3-dithiol-2-thione
930-35-8

1,3-dithiol-2-thione

C11H6OS2
1451059-78-1

C11H6OS2

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

C14H8S4

C14H8S4

Conditions
ConditionsYield
With triethyl phosphite at 110 - 120℃; Inert atmosphere;A n/a
B 22%
CpMn(CO)2PMe3
12276-09-4

CpMn(CO)2PMe3

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

C5H5MnCO(P(CH3)3)C(S)2(CCOOCH3)2

C5H5MnCO(P(CH3)3)C(S)2(CCOOCH3)2

Conditions
ConditionsYield
With CS2 In tetrahydrofuran Irradiation (UV/VIS); (N2); soln. of Mn complex was photolyzed for 1,25 h, then (CCOOMe)2 wasadded; sepn. by TL chromy.;A 6%
B 20%
1,3-dithiol-2-one
2314-40-1

1,3-dithiol-2-one

4,5-ethylenedioxy-1,3-dithiole-2-thione
128457-00-1

4,5-ethylenedioxy-1,3-dithiole-2-thione

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

bis(ethylenedioxy)tetrathiafulvalene
120120-58-3

bis(ethylenedioxy)tetrathiafulvalene

C

4,5-ethylenedioxy-tetrathiafulvalene
128346-58-7

4,5-ethylenedioxy-tetrathiafulvalene

Conditions
ConditionsYield
With triethyl phosphite at 65℃; for 6h;A n/a
B n/a
C 3%
1,3-dithiol-2-thione
930-35-8

1,3-dithiol-2-thione

4,5-Ethylenedithio-1,3-dithiole-2-thione
59089-89-3

4,5-Ethylenedithio-1,3-dithiole-2-thione

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

bis(ethylenedithio)tetrathiofulvalene
66946-48-3

bis(ethylenedithio)tetrathiofulvalene

C

ethylenedithiotetrathiafulvalene
97307-49-8

ethylenedithiotetrathiafulvalene

Conditions
ConditionsYield
With phosphorous acid trimethyl ester In neat (no solvent) Heating;
1,3-dithiol-2-thione
930-35-8

1,3-dithiol-2-thione

2,5,7,9-tetrathiabicyclo[4.3.0]non-1(6)-en-8-one
74962-29-1

2,5,7,9-tetrathiabicyclo[4.3.0]non-1(6)-en-8-one

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

bis(ethylenedithio)tetrathiofulvalene
66946-48-3

bis(ethylenedithio)tetrathiofulvalene

C

ethylenedithiotetrathiafulvalene
97307-49-8

ethylenedithiotetrathiafulvalene

Conditions
ConditionsYield
triethyl phosphite;
1,3-dithiol-2-thione
930-35-8

1,3-dithiol-2-thione

4,5-Bis-[2-(tert-butyl-diphenyl-silanyloxy)-ethylsulfanyl]-[1,3]dithiol-2-one
160409-45-0

4,5-Bis-[2-(tert-butyl-diphenyl-silanyloxy)-ethylsulfanyl]-[1,3]dithiol-2-one

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

4,5-Bis-[2-(tert-butyl-diphenyl-silanyloxy)-ethylsulfanyl]-[2,2']bi[[1,3]dithiolylidene]

4,5-Bis-[2-(tert-butyl-diphenyl-silanyloxy)-ethylsulfanyl]-[2,2']bi[[1,3]dithiolylidene]

C

4,4',5,5'-tetrakis<2-(tert-butyldiphenylsilyloxy)ethylthio>tetrathiafulvalene
160409-46-1

4,4',5,5'-tetrakis<2-(tert-butyldiphenylsilyloxy)ethylthio>tetrathiafulvalene

Conditions
ConditionsYield
With triethyl phosphite In neat (no solvent) at 130℃; for 5h; Title compound not separated from byproducts;
tetrathiafulvalenium radical cation
35079-56-2

tetrathiafulvalenium radical cation

7,7,8,8-tetracyanoquinodimethane radical anion
1518-16-7

7,7,8,8-tetracyanoquinodimethane radical anion

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

7,7',8,8'-tetracyanoquinodimethane
1518-16-7

7,7',8,8'-tetracyanoquinodimethane

Conditions
ConditionsYield
In dimethyl sulfoxide; acetonitrile at 11℃; Equilibrium constant; Rate constant;
In acetonitrile at 20℃; Equilibrium constant;
1,3-Dithiolium tetrafluoroborate
53059-75-9

1,3-Dithiolium tetrafluoroborate

5,6-Dihydro-1,3-dithiolo<4,5-b><1,4>dithiin-2-ium Tetrafluoroborate

5,6-Dihydro-1,3-dithiolo<4,5-b><1,4>dithiin-2-ium Tetrafluoroborate

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

bis(ethylenedithio)tetrathiofulvalene
66946-48-3

bis(ethylenedithio)tetrathiofulvalene

C

ethylenedithiotetrathiafulvalene
97307-49-8

ethylenedithiotetrathiafulvalene

Conditions
ConditionsYield
With trimethylamine
1,3-Dithiolium tetrafluoroborate
53059-75-9

1,3-Dithiolium tetrafluoroborate

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

Conditions
ConditionsYield
With triethylamine In acetonitrile
With triethylamine In acetonitrile
hexafluorophosphate de 1,3-dithiolium-2-triphenylphosphonium
135303-55-8

hexafluorophosphate de 1,3-dithiolium-2-triphenylphosphonium

hexafluorophosphate de 4-methyl-1,3-dithiolium

hexafluorophosphate de 4-methyl-1,3-dithiolium

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

dimethyltetrathiafulvalene
54397-97-6

dimethyltetrathiafulvalene

C

monomethyltetrathiafulvalene
54397-94-3

monomethyltetrathiafulvalene

D

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With n-butyllithium 1.) THF, hexane; Yield given. Multistep reaction. Yields of byproduct given;
[2,2']Bi[[1,3]dithiolylidene]
35079-56-2, 31366-25-3

[2,2']Bi[[1,3]dithiolylidene]

2,3-dichloro-5,6-dicyano-1,4-benzoquinone anion radical
84-58-2

2,3-dichloro-5,6-dicyano-1,4-benzoquinone anion radical

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

2,3-dicyano-5,6-dichloro-p-benzoquinone
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In acetonitrile at 25℃; Equilibrium constant;
C8H2O4S4(1-)*K(1+)
111480-39-8, 111480-40-1

C8H2O4S4(1-)*K(1+)

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

Conditions
ConditionsYield
In nitromethane
internal salts of the radical-cation of tetrathiafulvalenecarboxylic acid
75960-01-9

internal salts of the radical-cation of tetrathiafulvalenecarboxylic acid

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

Conditions
ConditionsYield
In nitromethane for 0.5h;
hexafluorophosphate de 1,3-dithiolium

hexafluorophosphate de 1,3-dithiolium

hexafluorophosphate de 4-methyl-1,3-dithiolium-2-triphenylphosphonium
141192-76-9

hexafluorophosphate de 4-methyl-1,3-dithiolium-2-triphenylphosphonium

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

dimethyltetrathiafulvalene
54397-97-6

dimethyltetrathiafulvalene

C

monomethyltetrathiafulvalene
54397-94-3

monomethyltetrathiafulvalene

Conditions
ConditionsYield
With n-butyllithium 1.) hexane; Yield given. Multistep reaction. Yields of byproduct given;
tetrakis(trimethylsilyl)tetrathiafulvalene
96913-54-1

tetrakis(trimethylsilyl)tetrathiafulvalene

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

Conditions
ConditionsYield
With potassium carbonate; potassium hydrogencarbonate In tetrahydrofuran; ethanol for 2h; Ambient temperature;65 mg
tetrathiafulvalenium radical cation
35079-56-2

tetrathiafulvalenium radical cation

chloranil anion radical
118-75-2

chloranil anion radical

A

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

B

chloranil
118-75-2

chloranil

Conditions
ConditionsYield
In acetonitrile at 20℃; Equilibrium constant;
para-dinitrobenzene
100-25-4

para-dinitrobenzene

tetrathiafulvalene
31366-25-3

tetrathiafulvalene

1,4-Dinitro-benzene; compound with [2,2']bi[[1,3]dithiolylidene]
83868-36-4

1,4-Dinitro-benzene; compound with [2,2']bi[[1,3]dithiolylidene]

Conditions
ConditionsYield
In toluene Ambient temperature;100%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

2-(1,3-dithiol-2-yl)-1,3-dithiol-1-ium tetrafluoroborate

2-(1,3-dithiol-2-yl)-1,3-dithiol-1-ium tetrafluoroborate

Conditions
ConditionsYield
With tetrafluoroboric acid In chloroform for 0.5h; Ambient temperature;100%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

C10H20NO2(1+)*F6Sb(1-)

C10H20NO2(1+)*F6Sb(1-)

A

4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical
95407-69-5

4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical

B

bis-1,3-dithiolium hexafluoroantimonate

bis-1,3-dithiolium hexafluoroantimonate

Conditions
ConditionsYield
In acetonitrile for 0.0166667h; Ambient temperature;A 93%
B 100%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

tributyltin chloride
1461-22-9

tributyltin chloride

(n-buthylstannyl)tetrathiafulvalene
139698-09-2

(n-buthylstannyl)tetrathiafulvalene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2.5h; Stille Cross Coupling;100%
With LiC4H9 In tetrahydrofuran reaction of tetrathiafulvalene with butyllithium in THF at -78°C, addn. of tributyltin chloride, warming to room temp.; chromy. on deactivated alumina;75%
Stage #1: tetrathiafulvalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

copper(ll) bromide
7789-45-9

copper(ll) bromide

C6H4S4(2+)*CuBr3(2-)
77662-00-1

C6H4S4(2+)*CuBr3(2-)

Conditions
ConditionsYield
In acetonitrile To a soln. of CuBr2 in CH3CN was added dropwise with stirring a soln. of ligand in warm CH3CN;; ppt. was washed with CH3CN, vac.-dried; elem. anal.;;100%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

N,N'-Dicyano-1,4-benzoquinonediimine
98507-05-2, 90508-34-2, 90508-35-3

N,N'-Dicyano-1,4-benzoquinonediimine

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit N,N'-Dicyan-1,4-benzochinondiimin (1:1)
98515-29-8, 97954-66-0

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit N,N'-Dicyan-1,4-benzochinondiimin (1:1)

Conditions
ConditionsYield
In acetonitrile at 60℃;99%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

2-Chlor-N,N'-dicyan-1,4-benzochinondiimin
98507-08-5

2-Chlor-N,N'-dicyan-1,4-benzochinondiimin

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit 2-Chlor-N,N'-dicyan-1,4-benzochinondiimin (1:1)
98507-34-7

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit 2-Chlor-N,N'-dicyan-1,4-benzochinondiimin (1:1)

Conditions
ConditionsYield
In acetonitrile at 20℃;99%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

(E,E)-2,3-Dichlor-N,N'-dicyan-1,4-benzochinondiimin
105381-60-0

(E,E)-2,3-Dichlor-N,N'-dicyan-1,4-benzochinondiimin

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2,3-Dichlor-N,N'-dicyan-1,4-benzochinondiimin (1:1)
110375-35-4

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2,3-Dichlor-N,N'-dicyan-1,4-benzochinondiimin (1:1)

Conditions
ConditionsYield
In acetonitrile at 20℃;99%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

(E,E)-2-Brom-5-chlor-N,N'-dicyan-1,4-benzochinondiimin
110375-21-8

(E,E)-2-Brom-5-chlor-N,N'-dicyan-1,4-benzochinondiimin

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2-Brom-5-chlor-N,N'-dicyan-1,4-benzochinondiimin (1:1)
110375-37-6

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2-Brom-5-chlor-N,N'-dicyan-1,4-benzochinondiimin (1:1)

Conditions
ConditionsYield
In acetonitrile at 20℃;99%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

dodecamethylcarba-closo-dodecaborate
183679-26-7

dodecamethylcarba-closo-dodecaborate

[tetrathiafulvalene(1+)](closo-dodecamethylcarboranate)

[tetrathiafulvalene(1+)](closo-dodecamethylcarboranate)

Conditions
ConditionsYield
In dichloromethane pptn. (hexane);99%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

9-dicyanomethylene-2,4,7-trinitrofluorene
1172-02-7

9-dicyanomethylene-2,4,7-trinitrofluorene

acetone
67-64-1

acetone

C16H5N5O6*C6H4S4*0.5C3H6O

C16H5N5O6*C6H4S4*0.5C3H6O

Conditions
ConditionsYield
at 20℃;99%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

(E,E)-2-Chlor-N,N'-dicyan-5-methyl-1,4-benzochinondiimin
105381-59-7

(E,E)-2-Chlor-N,N'-dicyan-5-methyl-1,4-benzochinondiimin

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2-Chlor-N,N'-dicyan-5-methyl-1,4-benzochinondiimin (1:1)
110375-31-0

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2-Chlor-N,N'-dicyan-5-methyl-1,4-benzochinondiimin (1:1)

Conditions
ConditionsYield
In acetonitrile at 82℃;98%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

(E,E)-2,5-Dichlor-N,N'-dicyan-1,4-benzochinondiimin
97954-67-1

(E,E)-2,5-Dichlor-N,N'-dicyan-1,4-benzochinondiimin

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2,5-Dichlor-N,N'-dicyan-1,4-benzochinondiimin (1:1)
97954-68-2

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2,5-Dichlor-N,N'-dicyan-1,4-benzochinondiimin (1:1)

Conditions
ConditionsYield
In acetonitrile at 82℃;98%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

N,N'-dicyano-2-methoxy-5-trifluoromethyl-1,4-benzoquinonediimine

N,N'-dicyano-2-methoxy-5-trifluoromethyl-1,4-benzoquinonediimine

N,N'-dicyano-2-methoxy-5-trifluoromethyl-1,4-benzoquinonediimine/tetrathiafulvalene

N,N'-dicyano-2-methoxy-5-trifluoromethyl-1,4-benzoquinonediimine/tetrathiafulvalene

Conditions
ConditionsYield
In acetonitrile98%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

carbon dioxide
124-38-9

carbon dioxide

2-(1,3-dithiol-2-ylidene)-1,3-dithiole-4-carboxylate lithium

2-(1,3-dithiol-2-ylidene)-1,3-dithiole-4-carboxylate lithium

Conditions
ConditionsYield
With lithium diisopropyl amide In diethyl ether at -78 - 20℃; for 13h;96%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

(E,E)-2,5-Dibrom-N,N'-dicyan-1,4-benzochinondiimin
105381-61-1

(E,E)-2,5-Dibrom-N,N'-dicyan-1,4-benzochinondiimin

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2,5-Dibrom-N,N'-dicyan-1,4-benzochinondiimin (1:1)
110375-38-7

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit (E,E)-2,5-Dibrom-N,N'-dicyan-1,4-benzochinondiimin (1:1)

Conditions
ConditionsYield
In acetonitrile at 20℃;96%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

4-methoxy-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate

4-methoxy-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate

A

4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical
95407-69-5

4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical

B

C6H4S4(1+)*BF4(1-)

C6H4S4(1+)*BF4(1-)

Conditions
ConditionsYield
In acetonitrile for 0.0166667h; Ambient temperature;A n/a
B 95%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

gold(III) chloride trihydrate

gold(III) chloride trihydrate

C6H4S4(1+)*AuCl2(1-)
77662-01-2

C6H4S4(1+)*AuCl2(1-)

Conditions
ConditionsYield
In ethanol A soln. of ligand in warm EtOH was added with stirring to a soln. of HAuCl4*3H2O in EtOH;; ppt. was washed with EtOH, dried under high vac.; elem. anal.;;95%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

4-Methoxy-2,2,6,6-tetramethyl-1-oxo-piperidinium; nitrate

4-Methoxy-2,2,6,6-tetramethyl-1-oxo-piperidinium; nitrate

A

4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical
95407-69-5

4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical

B

C6H4S4(1+)*NO3(1-)

C6H4S4(1+)*NO3(1-)

Conditions
ConditionsYield
In acetonitrile for 0.0166667h; Ambient temperature;A n/a
B 93%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

2-chloro-N,N'-dicyano-5-methoxy-1,4-benzoquinonediimine

2-chloro-N,N'-dicyano-5-methoxy-1,4-benzoquinonediimine

2-chloro-N,N'-dicyano-5-methoxy-1,4-benzoquinonediimine/tetrathiafulvalene

2-chloro-N,N'-dicyano-5-methoxy-1,4-benzoquinonediimine/tetrathiafulvalene

Conditions
ConditionsYield
In acetonitrile at 60℃;93%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

3-bromopropyl acetate
592-33-6

3-bromopropyl acetate

bis[4,5-bis(3-acetoxypropylseleno)-1,3-dithiole-2-ylidene]
797034-99-2

bis[4,5-bis(3-acetoxypropylseleno)-1,3-dithiole-2-ylidene]

Conditions
ConditionsYield
Stage #1: tetrathiafulvalene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃;
Stage #2: With selenium In tetrahydrofuran; hexane at -78 - 0℃;
Stage #3: 3-bromopropyl acetate In tetrahydrofuran; hexane
93%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

gold(III) chloride trihydrate

gold(III) chloride trihydrate

C6H4S4(2+)*2AuCl4(1-)
77662-02-3

C6H4S4(2+)*2AuCl4(1-)

Conditions
ConditionsYield
In acetonitrile A soln. of ligand in CH3CN was added with stirring to a soln. of HAuCl4*3H2O in CH3CN;; ppt. was filtered under N2, washed with dry CH3CN, dried under high vac.; elem. anal.;;93%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

trimethylsilyl bis(trifluoromethanesulfonyl)imide
82113-66-4

trimethylsilyl bis(trifluoromethanesulfonyl)imide

C6H4S4(1+)*C2F6NO4S2(1-)

C6H4S4(1+)*C2F6NO4S2(1-)

Conditions
ConditionsYield
With xenon fluoride In dichloromethane at -78 - -40℃; for 2h;93%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

C68H104Ir4N20O8Pd4(8+)*8CF3O3S(1-)

C68H104Ir4N20O8Pd4(8+)*8CF3O3S(1-)

C68H104Ir4N20O8Pd4(8+)*8CF3O3S(1-)*C6H4S4

C68H104Ir4N20O8Pd4(8+)*8CF3O3S(1-)*C6H4S4

Conditions
ConditionsYield
In methanol for 24h;93%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

1,3-di-p-tolylbenzo[c]furan
62422-95-1

1,3-di-p-tolylbenzo[c]furan

C28H22OS4

C28H22OS4

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Diels-Alder Cycloaddition; Inert atmosphere; Reflux;93%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

3-Brom-2,5-bis(cyanimino)-2,5-dihydro-6-(methylthio)thieno<3,2-b>thiophen
139041-03-5

3-Brom-2,5-bis(cyanimino)-2,5-dihydro-6-(methylthio)thieno<3,2-b>thiophen

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit 3-Brom-2,5-bis(cyanimino)-2,5-dihydro-6-(methylthio)thieno<3,2-b>thiophen
141043-79-0

2-(1,3-Dithiol-2-yliden)-1,3-dithiol, CT-Komplex mit 3-Brom-2,5-bis(cyanimino)-2,5-dihydro-6-(methylthio)thieno<3,2-b>thiophen

Conditions
ConditionsYield
In acetonitrile Heating;92%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

tetrathiafulvalene chloride

tetrathiafulvalene chloride

Conditions
ConditionsYield
With thionyl chloride In dichloromethane92%
tetrathiafulvalene
31366-25-3

tetrathiafulvalene

4-methoxy-2,2,6,6-tetramethyl-1-oxopiperidinium perchlorate

4-methoxy-2,2,6,6-tetramethyl-1-oxopiperidinium perchlorate

A

4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical
95407-69-5

4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical

B

Tetrathiafulvalenium Perchlorate

Tetrathiafulvalenium Perchlorate

Conditions
ConditionsYield
In acetonitrile for 0.0166667h; Ambient temperature;A n/a
B 92%

31366-25-3Relevant articles and documents

Ysuedo et al.

, p. 1728 (1979)

Preparation of Methyl Chalcogenated Derivatives of 1,4,5,8-Tetrathiatetralin

Nakatsuji, Shin'ichi,Amano, Yoshiki,Kawamura, Haruki,Anzai, Hiroyuki

, p. 841 - 842 (1994)

Tetrakis(methylthio)-1,4,5,8-tetrathiatetralin 4 and tetrakis(methylseleno)-1,4,5,8-tetrathiatetralin 6 is successfully prepared by the reaction of tetrathiatetralin (TTT) 2 with lithium diissopropylamide and MeSSMe or MeSeSeMe in diethyl ether and a remarkable solvent effect is observed in the analogous reaction in tetrahydrofuran to give tetrakis(methylthio)tetrathiafulvalene 5 by a novel rearrangement.

Melby et al.

, p. 2456 (1974)

Fabre et al.

, p. 4033,4034,4035 (1977)

Wudl et al.

, p. 1453 (1970)

An ESR Study of the Radical Cations of Tetrathiafulvalene (TTF) and Electron Donors Containing the TTF Moiety

Cavara, Luka,Gerson, Fabian,Cowan, Dwaine O.,Lerstrup, Knud

, p. 141 - 152 (1986)

Hyperfine data and g factors are reported for the radical cations of tetrathiafulvalene (TTF; 1) and of its derivatives 2-13.From the intense satellite spectra of 1+. - 13+. not only the coupling constants of the 33S isotopes in the TTF moiety could be determined, but also, in favourable cases, those of the 13C isotopes in the central double bond.The former values range from 0.370 (8+.) to 0.470 mT (4+.) and the latter from 0.255 (8+.) to 0.360 mT (4+.) in the radical cations of bis(ethylenedithio)-TTF (8+.) and tetracyano-TTF (4+.).The radical cation of TTF (1+.) exhibits intermediate values, 0.425 for the 33S and 0.285 mT for the 13C isotopes.The spin population in 1+. - 13 +. resides, to a large extent, in the central S2C = CS2 part of the ?-system.It tends to increase (decrease) by substitution with electron-accepting (donating) groups in the 2,3,6,7-positions of TTF.

A Redox-Active Tetrathiafulvalene [2]Pseudorotaxane: Spectroelectrochemical and Cyclic Voltammetric Studies of the Highly-Reversible Complexation/Decomplexation Process

Devonport, Wayne,Blower, Mark A.,Bryce, Martin R.,Goldenberg, Leonid M.

, p. 885 - 887 (1997)

The complexation of TTF 2 and cyclobis(paraquat-p-phenylene) 14+ has been studied by cyclic voltammetry and by spectroelectrochemistry: shifts in the redox potentials for the TTF and the 14+ components of 45 and 30 mV, respectively, occur upon complexation. Decomplexation of 2.14+ upon oxidation of the TTF unit to the cation radical species has been monitored by spectroelectrochemistry. The complexation/decomplexation process is highly reversible over at least 10 electrochemical cycles, and this process is accompanied by a color change of the solution from dark green (complexed) to pale brown (uncomplexed) which is clearly visible to the naked eye.

Siedle,Johannesen

, p. 2002 (1975)

Engler et al.

, p. 5909,5910, 5911, 5915 (1977)

A systematic study of the variation of tetrathiafulvalene (TTF), TTF+ and TTF2+ reaction pathways with water in the presence and absence of light

Adeel, Shaimaa M.,Li, Qi,Nafady, Ayman,Zhao, Chuan,Siriwardana, Amal I.,Bond, Alan M.,Martin, Lisandra L.

, p. 49789 - 49795 (2014)

The chemistry of the strongly electron donating tetrathiafulvalene (TTF) molecule is exceptionally well known, but detailed knowledge of the chemistry of its technologically important one (TTF+) and two (TTF2+) electron oxidised redox partners is limited. In this paper, the different pathways that apply to the reaction of TTF, TTF+ and TTF2+ with water have been identified in the absence and presence of light. On the basis of data obtained by transient and steady state voltammetric methods in CH3CN (0.1 M Bu4NPF6) containing 10% (v/v) H2O, TTF is shown to participate in an acid base equilibrium reaction with HTTF+, with H2O acting as the proton donor. In contrast, TTF+ generated by one electron bulk oxidative electrolysis of TTF remains unprotonated and fully stable in the presence of 10% H2O in the dark. However, when this cation radical is exposed to white or blue (λ = 425 nm) light, TTF+ is photoreduced to TTF, with oxidation of water to give oxygen (detected by a Clark electrode) and protons that react with TTF to give HTTF+ as the counter reaction. Again emphasising important reaction pathway differences associated with each redox level, TTF2+ generated by bulk two electron oxidative electrolysis of TTF reacts rapidly with water, even in the dark, to give TTF+, protons, HTTF+ and oxygen as the products.

Azulene-based tetrathiafulvalenes: Preparation and their electron-donating ability

Sato, Ohki,Saito, Takahito,Aoki, Masami,Sakai, Atsushi

, p. 1254 - 1260 (2019/11/14)

The condensation reaction of dithiocarbonates derived from azuleno- and guaiazulenopentathiepin with vinylene trithiocarbonate and the ethylenedithio derivative in triethyl phosphite afforded azulene-based tetrathiafulvalenes [Az-TTF, Az-(EDT)TTF, GAz-TTF and GAz-(EDT)TTF], respectively. The vinylene derivatives (Az-TTF and GAz-TTF) showed slightly higher electron-donating ability than the corresponding ethylenedithio ones [Az-(EDT)TTF and GAz-(EDT)TTF] by CV measurement. GAz-TTFs produced charge transfer complexes with tetracyanoquinodimethane, respectively.

Charging a Li-O2 battery using a redox mediator

Chen, Yuhui,Freunberger, Stefan A.,Peng, Zhangquan,Fontaine, Olivier,Bruce, Peter G.

, p. 489 - 494 (2013/07/25)

The non-aqueous Li-air (O2) battery is receiving intense interest because its theoretical specific energy exceeds that of Li-ion batteries. Recharging the Li-O2 battery depends on oxidizing solid lithium peroxide (Li2O2), which is formed on discharge within the porous cathode. However, transporting charge between Li 2O2 particles and the solid electrode surface is at best very difficult and leads to voltage polarization on charging, even at modest rates. This is a significant problem facing the non-aqueous Li-O2 battery. Here we show that incorporation of a redox mediator, tetrathiafulvalene (TTF), enables recharging at rates that are impossible for the cell in the absence of the mediator. On charging, TTF is oxidized to TTF+ at the cathode surface; TTF+ in turn oxidizes the solid Li2O 2, which results in the regeneration of TTF. The mediator acts as an electron-hole transfer agent that permits efficient oxidation of solid Li 2O2. The cell with the mediator demonstrated 100 charge/discharge cycles.

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