5117-07-7

Basic information

• Product Name: 5,5'-Dithiobis(1-phenyl-1H-tetrazole)
• Synonyms: 5,5’-dithiobis[1-phenyl-1h-tetrazol;DI-(1-PHENYL-TETRAZOLE-5-YL)-DISULFIDE;DI-(1-PHENYLTETRAZOLYL-5)-DISULFIDE;5,5'-DITHIOBIS(1-PHENYL-1H-TETRAZOLE);5,5'-DITHIO-BIS(1-PHENYLTETRAZOLE);1,1'-DIPHENYL-BISTETRAZOLE-5,5'-DISULFIDE;1,1-DIPHENYL-BISTETRAZOLE-5,5'-DISULFIDE;1-PHENYL-5-[(1-PHENYL-1H-TETRAZOL-5-YL)DITHIO]-1H-TETRAZOLE
• CAS NO: 5117-07-7
• Molecular Formula: C₁₄H₁₀N₈S₂
• Molecular Weight: 354.41
• EINECS: 225-852-2
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Tetrazoles
• Mol File: 5117-07-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 145 °C (dec.)(lit.)
• Boiling Point: 618.6 °C at 760 mmHg
• Flash Point: 327.9 °C
• Appearance: /
• Density: 1.59g/cm³
• Vapor Pressure: 3.15E-15mmHg at 25°C
• Refractive Index: 1.84
• PKA: -0.03±0.10(Predicted)
• CAS DataBase Reference: 5,5'-Dithiobis(1-phenyl-1H-tetrazole)(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5'-Dithiobis(1-phenyl-1H-tetrazole)(5117-07-7)
• EPA Substance Registry System: 5,5'-Dithiobis(1-phenyl-1H-tetrazole)(5117-07-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5117-07-7(Hazardous Substances Data)

Usage

Uses

5,5′-Dithiobis(1-phenyl-1H-tetrazole) may be used in the preparation of 5-(5-nitropyridin-2-yldithio)-1-phenyl-1H-tetrazole.

General Description

5,5′-Dithiobis(1-phenyl-1H-tetrazole) is an organic disulphide. Structure of 5,5′-dithiobis(1-phenyl-1H-tetrazole) is reported to have two 1-phenyl-1H-tetra-zole-5-thiol-ate units linked by an S-S disulfide bridge. The photo-cleavage of sulphur-sulphur double bond of 5,5′-dithiobis(1-phenyl-1H-tetrazole) has been investigated by the nanosecond-laser flash photolysis method. The C-S-S-C torsion angle for 5,5′-dithiobis(1-phenyl-1H-tetrazole has been reported to be 81.9(1)°.

InChI:InChI=1/C14H10N8S2/c1-3-7-11(8-4-1)21-13(15-17-19-21)23-24-14-16-18-20-22(14)12-9-5-2-6-10-12/h1-10H

Upstream product

• 86-93-1 1-Phenyl-1H-tetrazole-5-thiol 
• 103-72-0 phenyl isothiocyanate 
• 5351-69-9 4-Phenyl-3-thiosemicarbazide 
• 13078-30-3 5-anilino-1,2,3,4-thiatriazole 
• 86-93-1 1-phenyl-1H-tetrazole-5-thiol 

Downstream Products

• 220949-25-7 1-phenyl-5-tetrazolylsulfenyl bromide 
• 86-93-1 1-Phenyl-1H-tetrazole-5-thiol 
• 5378-52-9 phenyl-1H-tetrazole 
• 52431-86-4 5-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-phenyl-5-thiotetrazole 
• 331963-96-3 5-(cyclohexylthio)-1-phenyl-1H-tetrazole 

Relevant articles and documents

Copper-assisted desulfurization of 1-R-tetrazole-5-thiols under complexation

The interaction of 1-R-tetrazole-5-thiols with copper(II) chloride in solution was found to yield crystalline tetrazole complexes [CuCl2L2]n (L is 1-R-tetrazole, R = Me, Et, Bu) and [CuCl2L2]n·nMeCN (L is 1-phenyltetrazole). The observed transformation of 1-R-tetrazole-5-thiols into 1-R-tetrazoles presents the first examples of desulfurization of tetrazole-5-thiols under complexation. A possible pathway of desulfurization of 1-R-tetrazole-5-thiols is proposed. It includes initial oxidation of tetrazole-5-thiols by copper(II) ions into bis(tetrazol-5-yl)disulfanes, followed by copper-assisted oxidation by air oxygen. Obtained complexes [CuCl2L2]n and [CuCl2L2]n·nMeCN were found to be coordination polymers, 2D and 1D, respectively. In all them, 1-R-tetrazoles act as monodentate ligands coordinated to the metal via the tetrazole ring N4 atom, whereas chlorine atoms provide bidentate bridging coordination to generate polymeric structure.

Natural product inspired allicin analogs as novel anti-cancer agents

A series of novel analogs of Allicin (S-allyl prop-2-ene-1-sulfinothioate) present in garlic has been synthesized in high yield. Synthesized 23 compounds were evaluated against different breast cancer cells (MDA-MB-468 and MCF-7) and non-cancer cells (WI38). Four compounds (3f, 3h, 3m and 3u) showed significant cytotoxicity against cancer cells whereas nontoxic to the normal cells. Based on the LD50 values and selectivity index (SI), compound 3h (S-p-methoxybenzyl (p-methoxyphenyl)methanesulfinothioate) was considered as most promising anticancer agent amongst the above three compounds. Further bio-chemical studies confirmed that compound 3h promotes ROS generation, changes in mitochondrial permeability transition and induced caspase mediated DNA damage and apoptosis.

Efficient dye-sensitized solar cells with potential-tunable organic sulfide mediators and graphene-modified carbon counter electrodes

A new class of organic sulfide mediators with programmable redox properties is designed via density functional theory calculations and synthesized for efficient dye-sensitized solar cells (DSCs). Photophysical and electrochemical properties of these mediators derived from systematical functionalization of the framework with electron donating and withdrawing groups (MeO, Me, H, Cl, CF3, and NO2) are investigated. With this new class of organic mediators, the redox potential can be fine-tuned over a 170 mV range, overlapping the conventional I-/I3-couple. Due to the suitable interplay of physical properties and electrochemical characteristics of the mediator involving electron-donating MeO group, the DSCs based on this mediator behave excellently in various kinetic processes such as dye regeneration, electron recombination, and mass transport. Thus, the MeO derivative of the mediator is identified as having the best performance of this series of redox shuttles. As inferred from electrochemical impedance spectroscopy and cyclic voltammetry measurements, the addition of graphene into the normal carbon counter electrode material dramatically improves the apparent catalytic activity of the counter electrode towards the MeO derivative of mediator, resulting in N719 based DSCs showing a promising conversion efficiency of 6.53% under 100 mW·cm-2 simulated sunlight illumination. Copyright