1600-44-8

Basic information

• Product Name: Tetramethylene sulfoxide
• Synonyms: TETRAMETHYLENE SULFOXIDE;TETRAMETHYLENE SULPHOXIDE;tetrahydro-thiophen1-oxide;Tetrametylene sulfoxide;Thiolane 1-oxide;Thiophane 1-oxide;Thiophane monoxide;Thiophane oxide
• CAS NO: 1600-44-8
• Molecular Formula: C₄H₈OS
• Molecular Weight: 104.17
• EINECS: 216-493-2
• Mol File: 1600-44-8.mol
• Article Data: 129

Chemical Properties

• Boiling Point: 235-237 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.158 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0123mmHg at 25°C
• Refractive Index: n20/D 1.52(lit.)
• Water Solubility: Fully miscible in water.
• BRN: 105274
• CAS DataBase Reference: Tetramethylene sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetramethylene sulfoxide(1600-44-8)
• EPA Substance Registry System: Tetramethylene sulfoxide(1600-44-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: XN0830000
• TSCA: T
• Hazardous Substances Data: 1600-44-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

In a comparative study of aromatic fluorodenitration with Potassium fluoride, in several dipolar aprotic solvents, a much faster reaction rate was observed with DMSO or tetramethylene sulfoxide than with the more commonly used Sulfolane.

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.]

InChI:InChI=1/C4H8OS/c5-6-3-1-2-4-6/h1-4H2

Upstream product

• 110-01-0 thiophene 
• 67-66-3 chloroform 
• 110-22-5 diacetyl peroxide 
• 25862-08-2 dibenzyl selenoxide 
• 94-36-0 dibenzoyl peroxide 
• 100-68-5 methyl-phenyl-thioether 
• 132882-85-0 RuCl₂(tmso)4 
• 420-04-2 CYANAMID 
• 50578-18-2 S,S-tetramethylenesulfoximide 
• 66021-66-7 p-TolSO₂NO 
• 126-33-0 sulfolane 
• 70284-20-7 N-bromo-N-potassio-p-toluenesulfonamide 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 117122-94-8 1,1-dibromo-tetrahydro-1λ⁴-thiophene 

Downstream Products

• 110-01-0 thiophene 
• 57872-24-9 1,1,2,3,4,5-hexahydro-1-<<(4-methylphenyl)sulfonyl>imino>tiophene 1-oxide 
• 74-85-1 ethene 
• 287-23-0 cyclobutane 
• 106-98-9 1-butylene 
• 187737-37-7 propene 
• 74-84-0 ethane 
• 74-86-2 acetylene 
• 75-19-4 cyclopropane 
• 106-99-0 buta-1,3-diene 
• 126-33-0 sulfolane 
• 16122-64-8 1,3-bis-(3-chloro-phenyl)-[1,3]diazetidine-2,4-dione 
• 127279-90-7 C₁₁H₁₅OS⁽¹⁺⁾*F₆P^(1-) 

Relevant articles and documents

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

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.

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

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

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.

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

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

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

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.