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1,2-Bis(phenylthio)ethane is an organic compound that features two phenylthio groups attached to an ethane backbone. This unique structure endows it with specific chemical properties, making it a valuable intermediate in the synthesis of various materials.

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  • 622-20-8 Structure
  • Basic information

    1. Product Name: 1,2-BIS(PHENYLTHIO)ETHANE
    2. Synonyms: ([2-(Phenylsulfanyl)ethyl]sulfanyl)benzene;1,2-Di(phenylthio) ethane;Benzene, 1,1'-[1,2-ethanediylbis(thio)]bis-;Bis(phenylthio)ethane;Ethane, 1,2-bis(phenylthio)-;1,2-BIS(PHENYLTHIO)ETHANE;AKOS BBS-00004432;1,2-Bis(phenylthio)ethane,98%
    3. CAS NO:622-20-8
    4. Molecular Formula: C14H14S2
    5. Molecular Weight: 246.39
    6. EINECS: 210-723-5
    7. Product Categories: N/A
    8. Mol File: 622-20-8.mol
  • Chemical Properties

    1. Melting Point: 68 °C
    2. Boiling Point: 65 °C / 3mmHg
    3. Flash Point: 184.6 °C
    4. Appearance: /
    5. Density: 1.16 g/cm3
    6. Vapor Pressure: 1.48E-05mmHg at 25°C
    7. Refractive Index: 1.646
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. Water Solubility: Insoluble in water.
    11. BRN: 1877719
    12. CAS DataBase Reference: 1,2-BIS(PHENYLTHIO)ETHANE(CAS DataBase Reference)
    13. NIST Chemistry Reference: 1,2-BIS(PHENYLTHIO)ETHANE(622-20-8)
    14. EPA Substance Registry System: 1,2-BIS(PHENYLTHIO)ETHANE(622-20-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany:
    5. RTECS:
    6. TSCA: Yes
    7. HazardClass: STENCH
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 622-20-8(Hazardous Substances Data)

622-20-8 Usage

Uses

Used in Polymer Synthesis:
1,2-Bis(phenylthio)ethane is used as a key intermediate in the synthesis of bismaleimide resins, specifically APO-BMI. This resin is known for its high thermal stability and excellent mechanical properties, which are crucial for various applications.
Used in Aerospace Industry:
In the aerospace industry, 1,2-bis(phenylthio)ethane contributes to the production of syntactic foams. These foams are lightweight, yet possess high strength and stiffness, making them ideal for use in aircraft and spacecraft components. The incorporation of 1,2-bis(phenylthio)ethane in the synthesis of APO-BMI enhances the overall performance of these syntactic foams, ensuring their reliability and durability in demanding environments.

Check Digit Verification of cas no

The CAS Registry Mumber 622-20-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 2 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 622-20:
(5*6)+(4*2)+(3*2)+(2*2)+(1*0)=48
48 % 10 = 8
So 622-20-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H14S2/c1-3-7-13(8-4-1)15-11-12-16-14-9-5-2-6-10-14/h1-10H,11-12H2

622-20-8 Well-known Company Product Price

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  • Alfa Aesar

  • (L02019)  1,2-Bis(phenylthio)ethane, 98+%   

  • 622-20-8

  • 10g

  • 594.0CNY

  • Detail
  • Alfa Aesar

  • (L02019)  1,2-Bis(phenylthio)ethane, 98+%   

  • 622-20-8

  • 50g

  • 2254.0CNY

  • Detail

622-20-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2-Bis(phenylthio)ethane

1.2 Other means of identification

Product number -
Other names 2-phenylsulfanylethylsulfanylbenzene

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:622-20-8 SDS

622-20-8Relevant articles and documents

Nucleophilic Cleavage of the Ether Bond of Chlorex in the Chalcogenation with Diphenyl Dichalcogenides in the System Hydrazine Hydrate–KOH

Albanov, A. I.,Bogdanova, I. N.,Grabel?nykh, V. A.,Istomina, N. V.,Korchevin, N. A.,Nikonova, V. S.,Rozentsveig, I. B.,Russavskaya, N. V.,Sosnovskaya, N. G.

, p. 1760 - 1762 (2020/10/15)

Abstract: The synthesis of unsymmetrical pincer ligands by reactions of diphenyl disulfide and diphenyl diselenide with bis(2-chloroethyl) ether in the system hydrazine hydrate–KOH was accompanied by the formation of 1,2-bis(phenylsulfanyl)ethane, 1,2-bis(phenylselanyl)ethane, and 1-(phenylselanyl)-2-(phenylsulfanyl)ethane as by-products with an overall yield of 23% as a result of nucleophilic cleavage of the C–O–C bond in the initial ether.

Synthesis and characterization of dithioethers, and their RuII and RuIII complexes

Cheu, Elizabeth L.S.,Yapp, Donald T.T.,Patrick, Brian O.,James, Brian R.

, p. 49 - 54 (2019/05/24)

The syntheses of nine, new dithioethers of the type RS(CH2)xSR, where x = 2 or 3 and R is an alkyl chain, as well as the known x = 2, R = phenyl or cyclohexyl compounds, are reported. The known dithioethers react with RuCl3·3H2O to form trans-RuCl2(dithioether)2 complexes 1 (R = Ph) and 2 (R = C6H11), whereas from the other dithioethers RuCl2[RS(CH2)xSR]2(μ-Cl)2 complexes have been isolated, where x = 3, and R = Et (complex 3), nPr (complex 4), nBu (complex 5), and R = npentyl (complex 6). The complexes are well characterized, including X-ray structures for complexes 1–4. The interest in these compounds stems from oxidation of the dithioethers to the corresponding disulfoxides and their Ru complexes.

A Bulky Disulfoxide Ligand for Pd-Catalyzed Oxidative Allylic C-H Amination with 2,2,2-Trichloroethyl Tosyl Carbamate

Li, You-Gui,Li, Li,Yang, Ming-Yue,He, Gang,Kantchev, Eric Assen B.

, p. 4907 - 4917 (2017/05/12)

Challenging substrates and conditions in homogeneous catalysis pose stringent demands on the ligands used. A novel, bulky, 1-adamantyl-substituted disulfoxide ligand designed after a systematic evaluation of the electronic and steric properties of disulfoxide substituents permits the allylic oxidative C-N coupling reaction to proceed at lower catalyst loading while requiring a smaller excess of reagents. Additionally, this ligand improves the yields when TsNHCOOCH2CCl3, a novel reagent that permits deprotection of the products under both acidic and basic conditions, is used.

A highly efficient heterogeneous rhodium(I)-catalyzed C-S coupling reaction of thiols with polychloroalkanes or alkyl halides under mild conditions

Xia, Jianhui,Yao, Ruiya,Cai, Mingzhong

, p. 221 - 225 (2015/03/30)

Heterogeneous C-S coupling reaction of thiols with polychloroalkanes or alkyl halides was achieved at 30 or 80 °C in the presence of 5 mol% of an MCM-41-immobilized bidentate phosphine rhodium complex (MCM-41-2P-RhCl(PPh3)) and triethylamine, yielding a variety of formaldehyde dithioacetals, ethylenedithioethers and unsymmetric thioethers in good to excellent yields. This heterogeneous rhodium catalyst can be easily recovered and recycled by simple filtration of the reaction solution and used for at least 10 consecutive trials without significant loss of activity.

Palladium(ii)-1-phenylthio-2-arylchalcogenoethane complexes: Palladium phosphide nano-peanut and ribbon formation controlled by chalcogen and Suzuki coupling activation

Kumar Rao, Gyandshwar,Kumar, Arun,Saleem, Fariha,Singh, Mahabir P.,Kumar, Satyendra,Kumar, Bharat,Mukherjee, Goutam,Singh, Ajai K.

, p. 6600 - 6612 (2015/04/14)

The ligands PhSCH2CH2EAr (L1-L3; E = S, Se or Te) and their Pd-complexes [PdLCl2] (1-3) have been synthesized and authenticated with their 1H, 13C{1H}, 77Se{1H} and 125Te{1H} NMR spectra. Single crystal structures of 1 and 3 reveal the geometry of donor atoms around palladium as nearly square planar. Thermolysis of all three complexes in trioctylphosphine (TOP) at 350, 320 and 280 °C, respectively, results in a single phase of crystalline PdP2. The morphology of the phase varies with 'E' to some extent. The nanopeanuts (size ~30 and ~35 nm) were formed with 1 and 2 as precursor complexes. On using complex 3 as a precursor nanoribbons are formed. The preferential growth in the (202) plane in the case of all the three precursor complexes has been rationalized in terms of texture coefficient and average crystallite size. All three complexes and PdP2 NPs have been explored for Suzuki-Miyaura coupling of several aryl halides. Complexes 1 and 2 show good catalytic activity but complex 3 does not. The activity appears to result due to in situ generated palladium containing nanoparticles (NPs) in the case of 1 and 2. The formation of inactive large Pd aggregates in the case of 3 appears to be responsible for the difference. The PdP2 NPs have been found to show good catalytic activity and recyclability up to six reaction cycles. The results of the three phase test suggest the involvement of both homogeneous and heterogeneous pathways in the activation of Suzuki coupling. DFT based free energy calculations are consistent with the results of catalysis via Pd(0) protected with the ligand. This palladium may also be released from in situ generated NPs. In the case of 3, negligible reactivity may be due to non-release of Pd. This journal is

(η5-Cp)Rh(III)/Ir(III) complexes with bis(chalcogenoethers) (E, E′ Ligands: E = S/Se; E′ = S/Se): Synthesis, structure, and applications in catalytic oppenauer-type oxidation and transfer hydrogenation

Prakash, Om,Sharma, Kamal Nayan,Joshi, Hemant,Gupta, Pancham L.,Singh, Ajai K.

, p. 983 - 993 (2014/03/21)

The air- and moisture-insensitive half-sandwich complexes [(η5-Cp)Rh(L)Cl][PF6] (1-3) and [(η5- Cp)Ir(L)Cl][PF6] (4-6) have been prepared by reacting L = L1-L3 (1,2-bis(phenylthio)ethane (L1), 1-(phenylseleno)-2-(phenylthio)ethane (L2) and 1,2-bis(phenylseleno)ethane (L3)) with [(η5-Cp)RhCl(μ-Cl)] 2 and [(η5-Cp)IrCl(μ-Cl)]2, respectively, at room temperature followed by treatment with NH 4PF6. Their HR-MS and 1H, 13C{ 1H}, and 77Se{1H} NMR spectra have authenticated them. The single-crystal structures of 1-6 have been established by X-ray crystallography. Complexes 1-6 have been explored for catalytic Oppenauer-type oxidation of alcohols and transfer hydrogenation of ketones with 2-propanol. 3 and 6 were the most efficient in the two catalytic reactions (TON values up to 9.9 × 102 and 9.8 × 103, respectively) and were therefore investigated in detail. 3 is the first example of a Rh(III) species explored for Oppenauer-type oxidation. The catalysis appears to be homogeneous. In transfer hydrogenation it appears that one of the catalytic species is without a Cp* ring. DFT calculations indicate higher reactivity for Rh complexes in comparison to Ir complexes. This order has also been found for the two catalytic reactions experimentally. The calculated bond lengths/angles by DFT are generally consistent with the experimental values.

Silica-promoted facile synthesis of thioesters and thioethers: A highly efficient, reusable and environmentally safe solid support

Basu, Basudeb,Paul, Susmita,Nanda, Ashis K.

experimental part, p. 767 - 771 (2010/09/05)

An efficient, mild and rapid procedure for the acylation and alkylation of aromatic and aliphatic thiols mediated on a silica gel surface at room temperature is described. The protocol allows the protection of thiols under neutral heterogeneous conditions without requiring any bases or Lewis acids, and the silica gel used as the promoter can be recycled for several runs without any loss of activity.

A highly efficient carbon-sulfur bond formation reaction via microwave-assisted nucleophilic substitution of thiols to polychloroalkanes without a transition-metal catalyst

Cao, Yi-Ju,Lai, Yuan-Yuan,Cao, Hong,Xing, Xiao-Ning,Wang, Xiang,Xiao, Wen-Jing

, p. 1529 - 1533 (2007/10/03)

An efficient carbon-sulfur bond formation reaction has been developed under microwave irradiation. This reaction affords a novel and rapid synthesis of thioacetals and sulfides under mild conditions. This method is particularly noteworthy given its experimental simplicity and high generality, and no transition-metal catalysts were needed under our conditions.

Unexpected Hofmann elimination in the benzophenone-(phenylthio)acetic tetrabutylammonium salt photoredox system

Wrzyszczynski, Andrzej,Pietrzak, Marek,Bartoszewicz, Jarogniew,Kozubek, Halina,Hug, Gordon L.,Marciniak, Bronislaw,Paczkowski, Jerzy

, p. 11182 - 11183 (2007/10/03)

The triplet state of benzophenone was quenched by the tetrabutylammonium salt of (phenylthio)acetic acid in acetonitrile solutions. The quenching event, following laser flash photolysis, resulted in the formation of a transient ion pair consisting of the benzophenone radical anion and the tetrabutylammonium cation. Subsequently this ion pair decays with the quaternary ammonium cation undergoing a Hofmann elimination to form butane-1 and tributylamine, which were detected in steady-state irradiation. This appears to be the first report of an ion pair consisting of a benzophenone radical anion and an organic cation (nonradical), in addition to the first report of a photoinduced Hofmann elimination in quaternary ammonium ions. Copyright

Reactions of diorganyl disulfides with dihaloalkanes in basic reductive media. Synthesis of bis(organylthio)alkanes

Alekminskaya,Russavskaya,Korchevin,Deryagina

, p. 75 - 78 (2007/10/03)

A convenient preparative synthesis of bis(organylthio)alkanes was developed. It is based on alkylation with dihaloalkanes of solutions of diorganyl disulfides in the basic reductive system hydrazine hydrate-alkali. The generation of organylthiolate anions

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