61830-39-5

Basic information

• Product Name: 3,3'-DIINDOLYL DISULPHIDE
• Synonyms: 3,3'-DIINDOLYL DISULPHIDE;3,3'-Dithiobis-1H-indole;Diindol-3-yl Disulfide
• CAS NO: 61830-39-5
• Molecular Formula: C₁₆H₁₂N₂S₂
• Molecular Weight: 296.41
• Product Categories: Indole Derivatives;Sulfur & Selenium Compounds
• Mol File: 61830-39-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 218-220°C dec.
• Appearance: /
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly)
• CAS DataBase Reference: 3,3'-DIINDOLYL DISULPHIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-DIINDOLYL DISULPHIDE(61830-39-5)
• EPA Substance Registry System: 3,3'-DIINDOLYL DISULPHIDE(61830-39-5)

Safety Data

• Hazardous Substances Data: 61830-39-5(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Upstream product

• 26377-76-4 S-(3-indolyl)isothiourea hydrogeniodide 
• 120-72-9 indole 
• 480-94-4 1H-indole-3-thiol 
• 78-95-5 chloroacetone 
• 17356-08-0 thiourea 

Downstream Products

• 13839-92-4 5,10-dihydro[1,2,3,4]tetrathiocino[5,6-b:8,7-b']diindole 
• 916611-28-4 3,3'-dithiobis(1-phenylsulfonyl-1H-indole) 
• 956395-54-3 3,3'-dithiobis[1-(4-methylphenylsulfonyl)-1H-indole] 
• 916611-30-8 2-(1-phenylsulfonyl-1H-indol-3-yl)thio-1H-indole 

Relevant articles and documents

Structural characterization of di-indol-3-yl disulfide derivatives, potential antitumoral agents

Di-5-X-indol-3-yl disulfides (X = H 1, F 2, Br 3, I 4, OCH3 5) were synthesized and their solid state structures were probed by 13C CP/MAS NMR spectroscopy. All disulfides adopt a layered conformation and both indole rings in one molecule were assumed to have very similar structural parameters, which is in agreement with a simple spectral pattern. For compounds 1 and 5 X-ray diffraction results are also presented. In the crystals of 1 and 5, the packing of the molecules is stabilized by dissimilar weak intermolecular interactions: in 1 dominate the N1-H1?π intermolecular hydrogen bonds and in 5 the C2-H2?O10 intermolecular hydrogen bonds predominate. The di-5-fluoroindol-3-yl disulfide 2 and di-5-iodoindol-3-yl disulfide 4 were found to reduce considerably the growth of prostate cancer cell PC-3.

Synthesis of 3-(arylthio)indoles and related compounds by reactions of metalated aromatics or heterocycles with protected 3,3′-dithiobisindoles

An efficient and practical strategy for the synthesis of new 3-(arylthio)indoles and related compounds has been developed, involving cleavage of readily available protected 3,3′-dithiobisindoles with metalated aromatics or heterocycles. Georg Thieme Verla

Derivatives of 3-Mercaptoindole - Synthesis of a Potent Vasoconstrictor, 3-(2-Imidazolin-2-ylthio)indole (Tinazoline)

Indoles are oxidatively coupled with various cyclic and acyclic thioureas using iodine to give rise to 3-(2-imidazolin-2-ylthio)indole, 1-30, 32 and 36-40.Similar products 33, 34 and 35 are respectively obtained from benzindole, 1,6,6-trimethyl-4,5,6,7-tetrahydroindole and 7-azaindole, while alkylation of 3-mercaptoindole 44 with chlormethyl imidazoline leads to 31.Among the products so obtained, 3-(2-imidazolin-2-ylthio)indole is a potent vasoconstrictor and the hydrochloride salt forms the active ingredient of VarsylR. 3-Mercaptoindole (44) readily obtained by alkali treatment of S-(3-indolyl)isothiourea (36) is converted into amine derivatives 47 and 52 and to the acids 53-55.Acid-catalysed cyclisation of 55 affords the expected thiopyranone (57), as well as the interesting isomeric ketone (58).A mechanism is proposed for this novel rearrangement. 3-Mercaptoindole (44) is also converted to α-methylaminoacid (64) via the hydantoin (63). 3-Mercaptoindole-2-carboxylic acid (65) obtained from 10 is transformed to a variety of methylated derivatives 66-72.The amino acid 75 arising by the action of ethylenimine on 65 is esterified to 76 and cyclised to the condensed thiazepinone (77).