255-55-0

Basic information

• Product Name: 1,4-DITHIINO[2,3-B]-1,4-DITHIIN, 97
• Synonyms: 1,4-DITHIINO[2,3-B]-1,4-DITHIIN, 97;1,4,5,8-Tetrathianaphthalene~TTN;1,4,5,8-Tetrathianaphthalene;1,4-Dithiino[2.3-b]-1,4-dithiine;1,4-DITHIINO[2,3-B]-1,4-DITHIIN 97%;1,4-Dithiino2,3-bü-1,4-dithiin, 97%
• CAS NO: 255-55-0
• Molecular Formula: C₆H₄S₄
• Molecular Weight: 204.35596
• Mol File: 255-55-0.mol

Chemical Properties

• Boiling Point: 242.7±40.0 °C(Predicted)
• Appearance: /
• Density: 1.61±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1,4-DITHIINO[2,3-B]-1,4-DITHIIN, 97(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DITHIINO[2,3-B]-1,4-DITHIIN, 97(255-55-0)
• EPA Substance Registry System: 1,4-DITHIINO[2,3-B]-1,4-DITHIIN, 97(255-55-0)

Safety Data

• Safety Statements: S23:Do not inhale gas/fumes/vapour/spray.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 255-55-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 783, 1988 DOI: 10.1002/jhet.5570250314

Upstream product

• 156-59-2 cis-1,2-Dichloroethylene 
• 54995-24-3 disodium 1,3-dithiol-2-thione-4,5-dithiolate 
• 68494-08-6 4,5-bis(benzoylthio)-1,3-dithiole-2-thione 
• 540-59-0 1,2-Dichloroethylene 
• 109538-80-9 1,3-dithiolo<4,5-b><1,4>dithiin-2-thione 

Downstream Products

• 31366-25-3 tetrathiafulvalene 
• 66946-49-4 bis(propylenedithio)tetrathiafulvalene 

Relevant articles and documents

Direct syntheses of tetrathiafulvalene and bis- (ethylenedithio)tetrathiafulvalene by a non-coupling route from 1,4,5,8- tetrathianaphthalene

1,4,5,8-Tetrathianaphthalene (2, TTN; 1,4,5,8-tetrathiatetralin) has been synthesized in one step from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione (1) and cis-dichloroethylene in high yield. TTN (2) is readily converted into tetrathiafulvalene (3, TTF) upon tetralithiation or bis(ethylenedithio)tetrathiafulvalene (4, BEDT-TTF) upon tetralithiation, sulfur insertion into the carbon lithium bond pairs and subsequent capping of the reactive intermediate with 1,2-dibromoethane. The rearrangement of TTN allows for a facile synthesis of TTF and a novel non-coupling route to BEDT- TTF.

Selective Metalations of 1,4-Dithiins and Condensed Analogues Using TMP-Magnesium and -Zinc Bases

TMPMgCl·LiCl and TMPZnCl·LiCl allow facile magnesiation and zincation, respectively, of the 1,4-dithiin scaffold, producing polyfunctionalized 1,4-dithiins. A subsequent metalation of these S-heterocycles can also be achieved with the same TMP bases, lead

On the mechanism of formation of 1,4,5,8-tetrathianaphthalene (TTN) from dimercaptoisotrithione (dmit) derivatives

The mechanism of formation of TTN (an important precursor to tetrathiafulvalene (TTF)) from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione is discussed. Contrary to previous reports, ethylenetetrathiolate is not an intermediate in this synthesis, whereas 4,5-vinylenedithio-1,3-dithiole-2- thione is likely to be. The latter is prepared by a new synthesis and converted into TTN in one step. (C) 2000 Elsevier Science Ltd.

An expedient, cost effective large scale synthesis of tetrathiafulvalene

TTF is synthesized (85% yield) in two steps from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione and isolated in high purity without the use of chromatography.

A New Improved Synthesis and X-Ray Crystal Structure of Dithiino-1,4-Dithiin

Dithiino-1,4-Dithiin (3) has been synthesised in high yield by a one-step procedure starting with sodium 1,3-dithiole-2-thione-4,5-dithiolate (2).The X-ray crystal structure shows non-planarity of the fused ring system as well as short intermolecular S...S contacts.