544-40-1 Usage
Description
Dibutyl sulfide (also named as butyl sulfide; N-butyl sulfide; Di-n-butyl sulfide; butylthiobutane), a colorless to pale yellow clear liquid, is a symmetric thioether. Dibutyl sulfide is found in raw cabbage, boiled and cooked beef, and some varieties of mushroom.
Dibutyl sulfide is typically used as a flavoring agent. As a thioether, dibutyl sulfide has applications in organic synthesis as a solvent as well as a reagent. It is used to synthesize specific compound classes including property-enhancing additives, pharmacological drugs, chemical resistant polymers, detergents, and rubber antioxidants. Dibutyl sulfide can also be used as an agricultural intermediate, a sulfiding agent, a refinery catalyst, a lubricant additive, a gas odorant, and a processing aid in mining applications. Furthermore, it can be used as an internal standard in X-ray fluorescence spectrometry (XRF) measurements of sulfur in oils and other liquid hydrocarbon matrices.
References
[1] George A. Burdock (1996) Encyclopedia of Food and Color Additives, Band 1
[2] http://chemicalland21.com/specialtychem/NH/DIBUTYL%20SULFIDE.htm
Chemical Properties
Butyl sulfide has an herbaceous, green, garlic, onion, heavy odor.
Occurrence
Reported found in raw cabbage, cooked beef and mushrooms.
Uses
Di-n-butyl sulfide is generally used as an agricultural intermediate, a sulfiding agent, a refinery catalyst, a lubricant additive, a gas odorant and a processing aid in mining applications. It finds application as an internal standard in X-ray fluorescence spectrometry (XRF) measurements of sulfur in oils and other liquid hydrocarbon matrices.
Preparation
From butyl bromide and sodium sulfide in boiling ethanol; according to some authors two forms exist, exhibiting different
boiling points but identical solubilities in various solvents; both forms are insoluble in water.
Aroma threshold values
Recognition: 0.88 ppb
Synthesis Reference(s)
Journal of the American Chemical Society, 73, p. 2251, 1951 DOI: 10.1021/ja01149a096Tetrahedron Letters, 29, p. 4477, 1988 DOI: 10.1016/S0040-4039(00)80527-4
General Description
Butyl sulfide is a volatile sulfur compound that can be used as a flavoring agent.
Biochem/physiol Actions
Taste at 5 ppm
Purification Methods
Wash the sulfide with aqueous 5% NaOH, then water. Dry with CaCl2 and distil it from sodium. [Beilstein 1 IV 1559.]
Check Digit Verification of cas no
The CAS Registry Mumber 544-40-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 4 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 544-40:
(5*5)+(4*4)+(3*4)+(2*4)+(1*0)=61
61 % 10 = 1
So 544-40-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H18S/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3
544-40-1Relevant articles and documents
FLUORENONE KETYL ANIONS GENERATED IN HYDROCARBON MEDIA BY PHASE TRANSFER CATALYSIS
Cazianis, Constantine T.,Screttas, Constantinos G.
, p. 165 - 168 (1983)
Fluorenone ketyl anions with the counterions Bun3S(1+), Bun4N(1+) and (n-C12H25)3(CH3)N(1+) have been generated in benzene by decomposing fluorenopinacol with the relevant alkylammonium or alkylsulphonium base, under phase-transfer catalytic conditions.The recorded ESR spectra in the hydrocarbon medium exhibit a marked cation dependence.The phenomenon is interpreted on the basis of spin density transfer from the anion to the magnetic nuclei of the cation.The implications to the phase transfer catalysis are discussed.
Catalytic dehydrogenation of amines to imines and the in-situ reduction of sulfoxides into sulfides
Li, Bo,Liu, Bing,Liu, Xixi,Wang, Wei,Wang, Yanxin,Xiang, Nian,Zhang, Zehui
, p. 81 - 88 (2021/07/30)
The catalytic acceptorless dehydrogenation of primary amines into imines and H2 represents one of the most important organic transformations, and the in-situ utilization of the generated H2 for chemical reduction reactions has never
Cd(II)-MOF-IM: Post-synthesis functionalization of a Cd(II)-MOF as a triphase transfer catalyst
Wang, Jian-Cheng,Ma, Jian-Ping,Liu, Qi-Kui,Hu, Yu-Hong,Dong, Yu-Bin
supporting information, p. 6989 - 6992 (2016/06/09)
A robust and porous Cd(ii)-MOF based on a bent imidazole-bridged ligand was synthesized and post-synthetically functionalized with linear alkyl chains to afford imidazolium salt (IM)-type triphase transfer catalysts for organic transformations. The imidazolium salt decorated Cd(ii)-MOF-IM exhibits typical solid phase transfer catalytic behavior for the azidation and thiolation of bromoalkane between aqueous/organic phases. Moreover, they can be easily recovered and reused under the PTC conditions. Cd(ii)-MOF-IM herein created a versatile family of solid phase transfer catalysts for promoting a broad scope of reactions carried out in a biphasic mixture of two immiscible solvents.
Oxidation and halogenation of divinyl selenide. first synthesis of divinyl selenoxide
Kurkutov,Potapov,Amosova
, p. 624 - 627 (2016/07/06)
Efficient procedure was developed for the preparation of divinyl selenoxide in 92% yield by oxidation of divinyl selenide with sodium periodate. At the action of S-nucleophiles on the divinyl selenoxide it is reduced to divinyl selenide. The reaction of divinyl selenide with an equimolar amount of sulfuryl chloride or bromine led to halogenation products at the selenium atom: divinylselenium dichloride and divinylselenium dibromide. A rearrangement was discovered of divinylselenium dibromide into vinyl(1,2-dibromoethyl)-selenide. The hydrolysis of divinylselenium dichloride results in divinyl selenide.
