4159-03-9

Basic information

• Product Name: 2,5-DIPHENYL-1,4-DITHIIN
• Synonyms: 2,5-DIPHENYL-1,4-DITHIIN
• CAS NO: 4159-03-9
• Molecular Formula: C₁₆H₁₂S₂
• Molecular Weight: 268.39648
• Mol File: 4159-03-9.mol

Chemical Properties

• Boiling Point: 412.9°Cat760mmHg
• Flash Point: 209.7°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 1.2E-06mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: 2,5-DIPHENYL-1,4-DITHIIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIPHENYL-1,4-DITHIIN(4159-03-9)
• EPA Substance Registry System: 2,5-DIPHENYL-1,4-DITHIIN(4159-03-9)

Safety Data

• Hazardous Substances Data: 4159-03-9(Hazardous Substances Data)

Usage

Chemical family

Dithiin family

Type of compound

Cyclic organic compound

Structure

Two carbon atoms and two sulfur atoms forming a four-membered ring

Usage

Organic synthesis

Potential applications

Pharmaceutical industry

Unique properties

Structure and properties of the compound

Biological activities

Potential anti-cancer agent

InChI:InChI=1/C16H12S2/c1-3-7-13(8-4-1)15-11-18-16(12-17-15)14-9-5-2-6-10-14/h1-12H

Upstream product

• 532-27-4 1-chloroacetophenone 
• 536-74-3 phenylacetylene 
• 34066-54-1 2,5-Diphenyl-1,4-dithiinsulphoxide 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 7783-06-4 hydrogen sulfide 
• 70-11-1 α-bromoacetophenone 
• 6484-28-2 2-methyl-4(3H)-quinazolinethione 
• 6039-85-6 sodium phenacyl thiosulphate 
• 31737-18-5 2-(4-quinazolinylthio)acetophenone 
• 103896-70-4 2,5-diphenyl-1,4-dithiin-1-(N-tosyl)imide 
• 87273-09-4 ω-<4-(2,6-dimethylpyrimidinyl)thio>-acetophenone 
• 96304-21-1 ω-(2-methyl-4-quinazolinylthio)-acetophenone 
• 89991-26-4 ω-(6-methyl-4-pyrimidinylthio)-acetophenone 

Downstream Products

• 40753-18-2 (E)-4-Phenyl-2-(phenylmethylene)-1,3-dithiole 
• 20965-10-0 3,5-diphenylthiophene-2-carbaldehyde 
• 7111-79-7 [1,1';2'1'']terphenyl-4',5'-dicarboxylic acid dimethyl ester 
• 130287-12-6 2,4-dinitro-3,5-diphenylthiophene 
• 6317-70-0 2-bromo-5-nitro-3,6-diphenyl-[1,4]dithiin 
• 76629-84-0 2-bromo-4-nitro-3,5-diphenyl-thiophene 
• 75195-50-5 3-bromo-2,5-diphenyl-1,4-dithiin 1,1-dioxide 
• 76629-82-8 2,4-Diphenyl-3-nitrothiophene 
• 59156-16-0 2-nitro-3,5-diphenyl-thiophene 
• 874511-97-4 2,4-dibromo-3,5-diphenyl-thiophene 
• 103896-71-5 2-formyl-2,4-diphenyl-1,3-dithiole 
• 3328-86-7 2,4-diphenylthiophene 
• 124-38-9 carbon dioxide 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Development of a synthesis of diphenylthiophenes via a one-pot reaction of phenylacetylene and sulfur

The one-pot synthesis of a mixture of diphenylthiophenes 1 and 2 from the reaction of phenylacetylene and sulfur under various reaction conditions was studied. Potential intermediates and a reaction pathway are postulated. Copyright Taylor & Francis Inc.

REACTIONS OF ELEMENTAL SULFUR AND SELENIUM WITH SOME ACETYLENIC COMPOUNDS. FORMATION OF THIOPHENES AND SELENOPHENES

The reaction of 3-butyn-2-one with elemental sulfur at 205-215 deg C in benzene in a stainless autoclave afforded 2,4- and 2,5-diacetylthiophenes in 43percent and 22percent yields, respectively. Under similar conditions, the reaction with elemental selenium gave 2,4- and 2,5-diacetylselenophenes in 32percent and 29percent yields, respectively. Diphenylacetylene reacted with sulfur and selenium to produce tetraphenylthiophene (78percent) and tetraphenylselenophene (38percent), respectively. The reaction of di(2-thienyl)acetylene with sulfur provided tetra(2-thienyl)thiophene in 57percent yield. The reactionof dimethyl acetylenedicarboxylate with sulfur in the presence of diphenylacetylene afforded 2,3-bis(methoxycarbonyl)-4,5-diphenylthiophene (29percent) and tetrakis(methoxycarbonyl)thiophene (15percent). On the basis of these results, the mechanism for the formation of thiophenes and selenophenes is discussed.

THERMOLYSIS AND PHOTOLYSIS OF S-SUBSTITUTED 2,5-DIPHENYL-1,4-DITHIINS

The thermolysis of 2,5-diphenyl-1,4-dithiin-1-oxide (4) in the liquid phase induced rearrangement to 2-formyl-2,4-diphenyl-1,3-dithiole (7) and extrusion of sulfur oxide to give 2,4-diphenylthiophene (2a) as well as deoxygenation to 2,5-diphenyl-1,4-dithi

Kinetics of Dethionylation of 1,4-Dithiin-1-oxides in Different Solvents

The kinetics of dethionylation of 1,4-dithiin-1-oxides (I-III) in polar solvent like DMSO, sulfolane and chloroform have been studied spectrophotometrically.The reaction shows a pseudo-first order dependence in the substrate.The rate constants for II and III are higher than that of I under similar conditions.The activation parameters suggest an increased solvation in the transition state than in the ground state of the substrate.

EXTRUSION REACTIONS-VII. FORMATION OF 2,5-DIARYL-1,4-DITHIINS AND 2-ACETONYL THIAZOLES

ω-(2,6-Dimethyl-4-pyrimidinylthio-(4), 2-methyl-4-quinazolinylthio-(9), and 4-oxo-2-quinazolinylthio)-(10) acetophenones with hydrochloric or perchloric acid provide 2,5-diaryl-1,4-dithiins (7) whereas ω-(6-methyl-4-pyrimidinylthio)acetophenones (11) with aq HCl/HClO4 or POCl3 followed by hydrolysis provide 1-(4-aryl-2-thiazolyl)-2-propanones (12).Likewise, 2-(6-methyl-4-pyrimidinylthio)cyclohexanone (13) give the thiazole derivative (14).

HETEROCYCLES IN ORGANIC SYNTHESIS. PART V. A SYNTHESIS OF 2,5-DIARYL-1,4-DITHIINS

ω-(2-Methyl-4-quinazolinylthio or 2,6-dimethyl-4-pyrimidinylthio or 4-oxo-2-quinazolinylthio)acetophenones on treatment with hydrochloric or perchloric acid provide 2,5-diaryl-1,4-dithiins.

SKELETAL REARRANGEMENT OF 2,5-DIARYL-1,4-DITHIIN-1-OXIDES INDUCED BY HYDROCHLORIC ACID

Treatment of 2,5-diphenyl-1,4-dithiin-1-oxide with hydrochloric acid in dioxane caused a novel skeletal rearrangement to give 2-benzoyl-4-phenyl-1,3-dithiole together with the deoxygenation products.The reaction with gaseous hydrogen chloride in methanol

THERMAL AND PHOTOCHEMICAL REARRANGEMENTS OF 1,4-DITHIIN Sulfoxides

Thermolysis of 2,5-diphenyl-1,4-dithiin-1-oxide afforded 2-formyl-2,4-diphenyl-1,3-dithiole, which was obtained also in photolysis along with another rearranged product, 2-benzoyl-4-phenyl-1,3-dithiole.