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Tetramethylene sulfoxide, also known as DMSO2, is a clear colorless to yellow liquid with unique chemical properties. It is a derivative of dimethyl sulfoxide (DMSO) and is known for its ability to act as a solvent in various chemical reactions.

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  • 1600-44-8 Structure
  • Basic information

    1. Product Name: Tetramethylene sulfoxide
    2. Synonyms: TETRAMETHYLENE SULFOXIDE;TETRAMETHYLENE SULPHOXIDE;tetrahydro-thiophen1-oxide;Tetrametylene sulfoxide;Thiolane 1-oxide;Thiophane 1-oxide;Thiophane monoxide;Thiophane oxide
    3. CAS NO:1600-44-8
    4. Molecular Formula: C4H8OS
    5. Molecular Weight: 104.17
    6. EINECS: 216-493-2
    7. Product Categories: N/A
    8. Mol File: 1600-44-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 235-237 °C(lit.)
    3. Flash Point: >230 °F
    4. Appearance: Clear colorless to yellow/Liquid
    5. Density: 1.158 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0123mmHg at 25°C
    7. Refractive Index: n20/D 1.52(lit.)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. Water Solubility: Fully miscible in water.
    11. BRN: 105274
    12. CAS DataBase Reference: Tetramethylene sulfoxide(CAS DataBase Reference)
    13. NIST Chemistry Reference: Tetramethylene sulfoxide(1600-44-8)
    14. EPA Substance Registry System: Tetramethylene sulfoxide(1600-44-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS: XN0830000
    6. TSCA: T
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1600-44-8(Hazardous Substances Data)

1600-44-8 Usage

Uses

Used in Chemical Synthesis:
Tetramethylene sulfoxide is used as a solvent in the field of chemical synthesis for its ability to facilitate faster reaction rates in certain processes. For instance, in a comparative study of aromatic fluorodenitration with Potassium fluoride, a much faster reaction rate was observed when using Tetramethylene sulfoxide as a solvent, as opposed to the more commonly used Sulfolane.
Used in Pharmaceutical Industry:
Tetramethylene sulfoxide is used as a solvent in the pharmaceutical industry for its potential to enhance the solubility and bioavailability of certain drugs. Its unique properties make it a valuable component in the development of new medications and drug formulations.
Used in Research and Development:
In the field of research and development, Tetramethylene sulfoxide is used as a solvent for its ability to improve the efficiency of various chemical reactions. This can lead to advancements in the synthesis of new compounds and materials, as well as a better understanding of reaction mechanisms.
Used in Environmental Applications:
Tetramethylene sulfoxide can be used in environmental applications, such as the treatment of wastewater or the removal of pollutants, due to its solvent properties and ability to interact with various contaminants.
Used in Material Science:
In material science, Tetramethylene sulfoxide can be utilized as a solvent for the synthesis of novel materials with specific properties, such as improved conductivity or enhanced stability. Its unique chemical characteristics make it a valuable asset in the development of advanced materials for various applications.

Synthesis Reference(s)

Journal of the American Chemical Society, 63, p. 2939, 1941 DOI: 10.1021/ja01856a021The Journal of Organic Chemistry, 50, p. 1787, 1985 DOI: 10.1021/jo00210a055Synthetic Communications, 24, p. 2393, 1994 DOI: 10.1080/00397919408010545

Purification Methods

Shake the oxide with BaO for 4 days, then distil it from CaH2 under reduced pressure. [Beilstein 17 III/IV 36, 17/1 V 38.]

Check Digit Verification of cas no

The CAS Registry Mumber 1600-44-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,0 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1600-44:
(6*1)+(5*6)+(4*0)+(3*0)+(2*4)+(1*4)=48
48 % 10 = 8
So 1600-44-8 is a valid CAS Registry Number.
InChI:InChI=1/C4H8OS/c5-6-3-1-2-4-6/h1-4H2

1600-44-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Alfa Aesar

  • (A17502)  Tetrahydrothiophene 1-oxide, 97%   

  • 1600-44-8

  • 10g

  • 351.0CNY

  • Detail
  • Alfa Aesar

  • (A17502)  Tetrahydrothiophene 1-oxide, 97%   

  • 1600-44-8

  • 50g

  • 1496.0CNY

  • Detail
  • Aldrich

  • (T22403)  Tetrahydrothiophene1-oxide  96%

  • 1600-44-8

  • T22403-25G

  • 1,007.37CNY

  • Detail

1600-44-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetramethylene sulfoxide

1.2 Other means of identification

Product number -
Other names thiolane 1-oxide

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:1600-44-8 SDS

1600-44-8Relevant articles and documents

Mn(III)-catalyzed oxidation of sulfides to sulfoxides with hydrogen peroxide

Hosseinpoor, Farideh,Golchoubian, Hamid

, p. 5195 - 5197 (2006)

Sulfides were selectively oxidized to the corresponding sulfoxides in good yields with hydrogen peroxide using a manganese(III) Schiff-base complex as a catalyst in glacial acetic acid as solvent under mild conditions.

Unexpected synthesis of an Au2In2 tetrametallatricyclic complex from α-aminophosphines and formation of Au-In-P and Ag-In-P nanomaterials

Chen, Hsiao Wei,Andy Hor,Pattacini, Roberto,Braunstein, Pierre

, p. 16242 - 16246 (2015)

Four Au-(μ-phosphinite)-In units assemble to form an unprecedented Au2In2 12-membered metallacycle which intersects at the In centres an 8-membered ring containing two In-μ-phosphinate linkages, resulting in a tricyclic structure. Thermal treatment of this complex and of its Ag(i) analog affords Au-In-P and Ag-In-P nanomaterials, respectively.

New heteropolyacids as catalysts for the selective oxidation of sulfides to sulfoxides with hydrogen peroxide

Romanelli, Gustavo P.,Vázquez, Patricia G.,Tundo, Pietro

, p. 75 - 78 (2005)

Pyridinium salts of Keggin-type molybdovanadophosphates proved to be highly active catalysts for the hydrogen peroxide oxidation of sulfides to the corresponding sulfoxide and sulfone derivatives. High conversion and high selectivity for sulfoxide were observed.

Ammonium bromide as an effective and viable catalyst in the oxidation of sulfides using nitro urea and silica sulfuric acid

Ghorbani-Choghamarani,Zamani

, p. 142 - 148 (2011)

A new catalytic method for the chemoselective oxidation of sulfides to the sulfoxides has been studied. A variety of dialkyl, alkylaryl and diaryl sulfides were subjected to the oxidation reaction by a mixture of nitro urea, derived from urea nitrate, silica sulfuric acid (SiO2-OSO3H) and catalytic amounts of ammonium bromide in CH2Cl2 at room temperature.

Dioxygen-Copper Reactivity: A Hydroperoxo-Dicopper(II) Complex

Karlin, Kenneth D.,Cruse, Richard W.,Gultneh, Yilma

, p. 599 - 600 (1987)

A hydroperoxo-dicopper(II) complex (3) can be prepared by (a) direct protonation of a peroxo-dicopper(II) complex (2), (b) oxygenation of a ligand-protonated form of the dicopper(I) precursor of (2), and (c) reaction of hydrogen peroxide with a hydroxo-bridged dicopper(II) complex (5); (3) reacts quantitatively with triphenylphosphine or tetrahydrothiophene to give (5) and oxygenated products.

Surface decorated magnetic nanoparticles with Mn-porphyrin as an effective catalyst for oxidation of sulfides

Shokoohi, Saeedeh,Rayati, Saeed

, p. 8 - 18 (2021/07/19)

Mn-porphyrin complex was anchored coordinatively to silica-coated surface of magnetic nanoparticles (SMNP). Afterward, a heterogeneous nanocatalyst (Fe3O4@SiO2-MnTCPP) has been characterized by Fourier transform infrared (FT-IR), ultraviolet-visible (UV-vis) spectroscopy, powder X-ray diffraction (XRD), scanning electron microscopy (SEM), vibrating sample magnetometry (VSM), thermogravimetric analysis (TGA), and transmission electron microscope (TEM). A thermal stability up to around 350°C was verified for prepared nanocatalyst based on thermogravimetric analysis. Finally, the catalytic performance of magnetically recoverable Mn-catalyst was exploited in the green oxidation of different sulfides with urea hydrogen peroxide (UHP) in the presence of imidazole as co-catalyst in ethanol under heterogeneous conditions. The eco-friendly property of ethanol strongly induced us to employ it as the reaction solvent in this oxidation system. Complete conversion (≥99) of sulfides to the corresponding sulfoxide or sulfones was obtained for ethyl phenyl sulfide, phenyl vinyl sulfide, diallyl sulfide, thiocyanatoethane, 2-ethyl mercaptoethanol and tetrahydrothiophene. Moreover, the recovered catalysts keep constant conversion yield up to at least three cycles.

Synthesis and characterization of magnetic Fe3O4@Creatinine@Zr nanoparticles as novel catalyst for the synthesis of 5-substituted 1H-tetrazoles in water and the selective oxidation of sulfides with classical and ultrasonic methods

Ghadermazi, Mohammad,Moeini, Nazanin,Molaei, Somayeh

, (2021/12/03)

Tetrazoles and sulfoxide compounds have a wide range of applications in industries and are of great expectation to be environmentally friendly and cost-effective. This paper reports the introduction of zirconium supported on Fe3O4 na

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

Cao, Zhong-Yan,Li, Xiaolong,Lu, Hao,Wang, Panpan,Wang, Shengqiang,Xu, Xiaobo,Yan, Leyu,Yang, A-Xiu

supporting information, p. 8691 - 8695 (2021/10/22)

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

Copper based on diaminonaphthalene-coated magnetic nanoparticles as robust catalysts for catalytic oxidation reactions and C-S cross-coupling reactions

Yarmohammadi, Nasrin,Ghadermazi, Mohammad,Mozafari, Roya

, p. 9366 - 9380 (2021/03/16)

In this work, the immobilization of copper(ii) on the surface of 1,8-diaminonaphthalene (DAN)-coated magnetic nanoparticles provides a highly active catalyst for the oxidation reaction of sulfides to sulfoxides and the oxidative coupling of thiols to disulfides using hydrogen peroxide (H2O2). This catalyst was also applied for the one-pot synthesis of symmetrical sulfidesviathe reaction of aryl halides with thiourea as the sulfur source in the presence of NaOH instead of former strongly basic and harsh reaction conditions. Under optimum conditions, the synthesis yields of sulfoxides, symmetrical sulfides, and disulfides were about 99%, 95%, and 96% respectively with highest selectivity. The heterogeneous copper-based catalyst has advantages such as the easy recyclability of the catalyst, the easy separation of the product and the less wastage of products during the separation of the catalyst. This heterogeneous nanocatalyst was characterized by FESEM, FT-IR, VSM, XRD, EDX, ICP and TGA. Furthermore, the recycled catalyst can be reused for several runs and is economically effective.

Trisaminomethane–cobalt complex supported on Fe3O4 magnetic nanoparticles as an efficient recoverable nanocatalyst for oxidation of sulfides and C–S coupling reactions

Ashraf, Muhammad Aqeel,Liu, Zhenling,Peng, Wan-Xi

, (2019/11/16)

In this work, trisaminomethane–cobalt complex immobilized onto the surface of Fe3O4 magnetic nanoparticles was successfully prepared via a simple and inexpensive procedure. The prepared nanocatalyst was considered a robust and clean nanoreactor catalyst for the oxidation and synthesis of sulfides under green conditions. This ecofriendly heterogeneous catalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffractometry, energy-dispersive X-ray spectroscopy, inductively coupled plasma-atomic emission spectroscopy, thermogravimetric analysis, vibrating sample magnetometry, X-ray mapping, scanning electron microscopy, and transmission electron microscopy techniques. Use of green medium, easy separation and workup, excellent reusability of the nanocatalyst, and short reaction time are some outstanding advantages of this method.

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