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Dibutyl sulfide, also known as butyl sulfide, N-butyl sulfide, Di-n-butyl sulfide, or butylthiobutane, is a colorless to pale yellow clear liquid and a symmetric thioether. It is a volatile sulfur compound that can be used as a flavoring agent and is found in raw cabbage, cooked beef, and mushrooms.

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  • 544-40-1 Structure
  • Basic information

    1. Product Name: Dibutyl sulfide
    2. Synonyms: Dibutyl sulfide >=98.0% (GC);Butyl sulfide solution;BUTYLTHIOBUTANE;BUTYL SULFIDE;BUTYL SULPHIDE;'LGC' (4000);FEMA 2215;DIBUTYLTHIOETHER
    3. CAS NO:544-40-1
    4. Molecular Formula: C8H18S
    5. Molecular Weight: 146.29
    6. EINECS: 208-870-5
    7. Product Categories: sulfide Flavor;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
    8. Mol File: 544-40-1.mol
  • Chemical Properties

    1. Melting Point: −76 °C(lit.)
    2. Boiling Point: 188-189 °C(lit.)
    3. Flash Point: 170 °F
    4. Appearance: Clear colorless to very slightly yellow/Liquid
    5. Density: 0.838 g/mL at 25 °C(lit.)
    6. Vapor Density: 5.07 (vs air)
    7. Vapor Pressure: 5.17 mm Hg ( 37.7 °C)
    8. Refractive Index: n20/D 1.452(lit.)
    9. Storage Temp.: Store below +30°C.
    10. Solubility: N/A
    11. Water Solubility: Silghtly miscible with water. Miscible with olive oil and almond oil.
    12. Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
    13. Merck: 14,1590
    14. BRN: 1732829
    15. CAS DataBase Reference: Dibutyl sulfide(CAS DataBase Reference)
    16. NIST Chemistry Reference: Dibutyl sulfide(544-40-1)
    17. EPA Substance Registry System: Dibutyl sulfide(544-40-1)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38-41
    3. Safety Statements: 26-36/37/39-24/25-36
    4. RIDADR: 2810
    5. WGK Germany: 2
    6. RTECS: ER6417000
    7. F: 13
    8. TSCA: Yes
    9. HazardClass: 6.1(b)
    10. PackingGroup: III
    11. Hazardous Substances Data: 544-40-1(Hazardous Substances Data)

544-40-1 Usage

Uses

Used in Flavoring Agents:
Dibutyl sulfide is used as a flavoring agent due to its herbaceous, green, garlic, onion, and heavy odor. It contributes to the unique taste and aroma of various food products.
Used in Organic Synthesis:
Dibutyl sulfide serves as a solvent and reagent in organic synthesis, aiding in the production of specific compound classes such as property-enhancing additives, pharmacological drugs, chemical-resistant polymers, detergents, and rubber antioxidants.
Used in Agriculture:
Dibutyl sulfide is used as an agricultural intermediate, playing a crucial role in the development and application of various agricultural products.
Used as a Sulfiding Agent:
In the industry, dibutyl sulfide is utilized as a sulfiding agent, which is essential for various chemical processes and reactions.
Used in Refinery Catalysts:
Dibutyl sulfide is employed as a refinery catalyst, enhancing the efficiency and performance of refining processes in the petrochemical industry.
Used as a Lubricant Additive:
It is used as a lubricant additive, improving the properties and performance of lubricants used in various mechanical applications.
Used as a Gas Odorant:
Dibutyl sulfide serves as a gas odorant, helping to detect and identify gas leaks for safety purposes.
Used in Mining Applications:
It is used as a processing aid in mining applications, contributing to the efficiency and effectiveness of mining operations.
Used as an Internal Standard in X-ray Fluorescence Spectroscopy (XRF) Measurements:
Dibutyl sulfide is used as an internal standard in XRF measurements of sulfur in oils and other liquid hydrocarbon matrices, ensuring accurate and reliable results in sulfur content analysis.

References

[1] George A. Burdock (1996) Encyclopedia of Food and Color Additives, Band 1 [2] http://chemicalland21.com/specialtychem/NH/DIBUTYL%20SULFIDE.htm

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.

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

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

544-40-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L07599)  Di-n-butyl sulfide, 98%   

  • 544-40-1

  • 100ml

  • 347.0CNY

  • Detail
  • Alfa Aesar

  • (L07599)  Di-n-butyl sulfide, 98%   

  • 544-40-1

  • 500ml

  • 1389.0CNY

  • Detail
  • Aldrich

  • (51491)  Dibutylsulfide  ≥98.0% (GC)

  • 544-40-1

  • 51491-100ML

  • 567.45CNY

  • Detail
  • Aldrich

  • (51491)  Dibutylsulfide  ≥98.0% (GC)

  • 544-40-1

  • 51491-500ML

  • 2,217.15CNY

  • Detail
  • Aldrich

  • (B101796)  Dibutylsulfide  96%

  • 544-40-1

  • B101796-100ML

  • 291.33CNY

  • Detail
  • Aldrich

  • (B101796)  Dibutylsulfide  96%

  • 544-40-1

  • B101796-500ML

  • 1,152.45CNY

  • Detail

544-40-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Dibutyl sulfide

1.2 Other means of identification

Product number -
Other names 1-butylsulfanylbutane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:544-40-1 SDS

544-40-1Synthetic route

C16H27OS(1+)*BF4(1-)

C16H27OS(1+)*BF4(1-)

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

Conditions
ConditionsYield
With methylamine at 60℃; for 10h;A 100%
B n/a
butyl sulfoxide
2168-93-6

butyl sulfoxide

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
With N,N-dimethylthioformamide; sulfuric acid In acetone at 30℃; for 3h;99%
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran at 20℃; for 0.0166667h;99%
With 2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide In toluene for 6h; Heating;99%
1-bromo-butane
109-65-9

1-bromo-butane

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
With sodium sulfide; aluminum oxide In toluene at 90℃; for 20h;98%
With potassium ethyl xanthogenate at 120℃; for 12h; Inert atmosphere;95%
With hexamethyldisilathiane; sodium methylate In tetrahydrofuran for 2.5h; Ambient temperature;87%
1-bromo-butane
109-65-9

1-bromo-butane

1-butanethiol
109-79-5

1-butanethiol

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
Stage #1: n-butanethiol With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 1-bromo-butane In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
93%
In acetonitrile Ambient temperature; electrooxidation, supporting electrolyte Et4NBr; other organohalides, other sulfides;86%
With 0.3 N Et4Br In acetonitrile electrolysis; other thiols, other halides;86%
9,10-dihydro-10-methylacridine
4217-54-3

9,10-dihydro-10-methylacridine

butyl sulfoxide
2168-93-6

butyl sulfoxide

A

10-methylacridinium cation
13367-81-2

10-methylacridinium cation

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
With perchloric acid; water In acetonitrile at 24.9℃; for 20h; Mechanism; Rate constant; Irradiation; other dialkyl sulfoxides;A 92%
B 92%
n-Butyl chloride
109-69-3

n-Butyl chloride

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
With sodium sulfide; aluminum oxide In toluene at 90℃; for 20h;89%
n-Butyl chloride
109-69-3

n-Butyl chloride

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

dibutyl disulfide
629-45-8

dibutyl disulfide

C

di-n-butyl trisulfide
5943-31-7

di-n-butyl trisulfide

Conditions
ConditionsYield
With potassium hydroxide; sulfur; hydrazine hydrate In water at 50 - 70℃; for 0.5h;A 4.5%
B 87%
C 1.7%
With potassium hydroxide; hydrazine hydrate In water at 50 - 70℃; for 0.5h; Product distribution;
With potassium hydroxide; hydrazine hydrate In water at 50 - 70℃; for 0.5h;A 4.5 % Chromat.
B 87.0 % Chromat.
C 1.7 % Chromat.
1-butanethiol
109-79-5

1-butanethiol

bis-phenoxymethyl ether
3807-05-4

bis-phenoxymethyl ether

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

dibutyl disulfide
629-45-8

dibutyl disulfide

C

bis<(n-butylthio)methyl> ether
62609-74-9

bis<(n-butylthio)methyl> ether

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 150℃; for 5h;A n/a
B n/a
C 85%
butyl para-toluenesulfonate
778-28-9

butyl para-toluenesulfonate

dibutyl disulfide
629-45-8

dibutyl disulfide

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
With aluminium trichloride; zinc In water; acetonitrile at 65℃; for 15h;84%
Stage #1: dibutyl disulfide With aluminium trichloride; zinc In acetonitrile at 65℃; for 2h;
Stage #2: butyl para-toluenesulfonate In water; acetonitrile at 65℃; for 15h;
84%
n-Butyl chloride
109-69-3

n-Butyl chloride

3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

A

1-butanethiol
109-79-5

1-butanethiol

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

3-(butylthio)propionic acid
22002-73-9

3-(butylthio)propionic acid

D

butyl 3-(butylthio)propanoate
121118-59-0

butyl 3-(butylthio)propanoate

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 140℃; for 0.166667h; microwave irradiation; Further byproducts.;A n/a
B n/a
C 83%
D n/a
1-iodo-butane
542-69-8

1-iodo-butane

1-butanethiol
109-79-5

1-butanethiol

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
With sodium carbonate; PtCl2(dppm) In acetone Heating;80%
With sodium carbonate; PtCl2(dppm) In acetone for 24h; Heating;80%
B9H13*(n-butyl)2sulfide
99666-94-1

B9H13*(n-butyl)2sulfide

triphenylphosphine
603-35-0

triphenylphosphine

A

B9H13*triphenylphosphine
32235-80-6

B9H13*triphenylphosphine

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
In diethyl ether React. of starting compd., stiiring (2 h) at room temp.;A 80%
B n/a
1-bromo-butane
109-65-9

1-bromo-butane

3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

3-(butylthio)propionic acid
22002-73-9

3-(butylthio)propionic acid

C

butyl 3-(butylthio)propanoate
121118-59-0

butyl 3-(butylthio)propanoate

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 100℃; for 0.166667h; microwave irradiation;A n/a
B 78%
C n/a
S-butyl O-butyl dithiocarbonate
10226-07-0

S-butyl O-butyl dithiocarbonate

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

dibutyl disulfide
629-45-8

dibutyl disulfide

C

S,S'-di-n-butyl dithiocarbonate
55716-09-1

S,S'-di-n-butyl dithiocarbonate

Conditions
ConditionsYield
Aliquat 336 at 100℃; for 1.5h; Yields of byproduct given;A n/a
B n/a
C 76%
dibutyl disulfide
629-45-8

dibutyl disulfide

acetylene
74-86-2

acetylene

A

thiophene
188290-36-0

thiophene

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 400℃; for 0.0166667h; Product distribution; Mechanism; var. temp.;A 70.2%
B 2%
C 25.1%
C20H30NO2S(1+)*BF4(1-)

C20H30NO2S(1+)*BF4(1-)

A

pyrrolidine
123-75-1

pyrrolidine

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

N1,N2-dimethylphthalamide
19532-98-0

N1,N2-dimethylphthalamide

Conditions
ConditionsYield
With methylamine at 30℃; for 20h;A n/a
B 70%
C n/a
butyl sulfoxide
2168-93-6

butyl sulfoxide

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
With hexamethyldisilathiane In dichloromethane at 60℃;A 68%
B n/a
chloropropionic acid
107-94-8

chloropropionic acid

1-butanethiol
109-79-5

1-butanethiol

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

dibutyl disulfide
629-45-8

dibutyl disulfide

C

3-(butylthio)propionic acid
22002-73-9

3-(butylthio)propionic acid

D

C10H18O4S
1031756-20-3

C10H18O4S

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 1h; Heating;A n/a
B n/a
C 67%
D n/a
1-bromo-butane
109-65-9

1-bromo-butane

3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

3-(butylthio)propionic acid
22002-73-9

3-(butylthio)propionic acid

C

butyl 3-(butylthio)propanoate
121118-59-0

butyl 3-(butylthio)propanoate

D

butyl 3-mercaptopropionate
16215-21-7

butyl 3-mercaptopropionate

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 120℃; for 0.166667h; microwave irradiation; Further byproducts.;A n/a
B 59%
C n/a
D n/a
1-iodo-butane
542-69-8

1-iodo-butane

thiourea
17356-08-0

thiourea

A

butylhydrazine
3530-11-8

butylhydrazine

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

N,N-dibutylhydrazine
7422-80-2

N,N-dibutylhydrazine

D

dibutyl disulfide
629-45-8

dibutyl disulfide

Conditions
ConditionsYield
With hydrazine hydrate at 40 - 45℃; for 4.5h;A 51%
B n/a
C n/a
D n/a
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

bis(trifluoromethyl)trisulfide
372-06-5

bis(trifluoromethyl)trisulfide

A

octane
111-65-9

octane

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

dibutyl disulfide
629-45-8

dibutyl disulfide

D

1-[(trifluoromethyl)thio]butane
7412-26-2

1-[(trifluoromethyl)thio]butane

E

1-Trifluoromethyldisulfanyl-butane

1-Trifluoromethyldisulfanyl-butane

F

C5H9F3S3

C5H9F3S3

Conditions
ConditionsYield
at -78℃; Product distribution; other organolithium compounds;A 8.1%
B 48.4%
C 3.9%
D 7.3%
E 15.5%
F 3.5%
n-Butyl chloride
109-69-3

n-Butyl chloride

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

dibutyl disulfide
629-45-8

dibutyl disulfide

Conditions
ConditionsYield
With potassium hydroxide; sulfur; hydrazine hydrate In water at 50 - 70℃; for 0.5h;A 46%
B 34%
With potassium hydroxide; hydrazine hydrate In water at 50 - 70℃; for 0.5h;A 46.0 % Chromat.
B 34.0 % Chromat.
acetyl iodide
507-02-8

acetyl iodide

butyl sulfoxide
2168-93-6

butyl sulfoxide

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
at 20 - 70℃; Mechanism;A 45%
B 15%
dibutyl tetrasulfide
5943-36-2

dibutyl tetrasulfide

A

thiophene
188290-36-0

thiophene

B

5-methyl-[1,2]dithiole-3-thione
3354-40-3

5-methyl-[1,2]dithiole-3-thione

C

1-butanethiol
109-79-5

1-butanethiol

D

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
at 450℃; for 0.0236111h; Product distribution; Mechanism; thermolysis of var. dibutyl polysulfides (C4H9)Sn (n = 2, 3); var. temp.;A 37.9%
B 5.4%
C 26%
D 4.2%
1-iodo-butane
542-69-8

1-iodo-butane

S-(2-chloroprop-2-en-1-yl)isothiuronium chloride
1049094-01-0

S-(2-chloroprop-2-en-1-yl)isothiuronium chloride

A

butylhydrazine
3530-11-8

butylhydrazine

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

N,N-dibutylhydrazine
7422-80-2

N,N-dibutylhydrazine

D

dibutyl disulfide
629-45-8

dibutyl disulfide

Conditions
ConditionsYield
Stage #1: S-(2-chloroprop-2-en-1-yl)isothiuronium chloride With tellurium; hydrazine hydrate; potassium hydroxide at 35 - 45℃; for 4.5h;
Stage #2: 1-iodo-butane at 40 - 50℃; for 3h;
A 36%
B 0.61 g
C 0.5 g
D 0.81 g
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

triphenylsulfonium trifluoromethanesulfonate
66003-78-9

triphenylsulfonium trifluoromethanesulfonate

A

biphenyl
92-52-4

biphenyl

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

(n-butylthio)benzene
1126-80-3

(n-butylthio)benzene

D

diphenyl sulfide
139-66-2

diphenyl sulfide

Conditions
ConditionsYield
In tetrahydrofuran; hexane at 0℃; for 2h;A 31%
B n/a
C 26%
D 14%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

A

biphenyl
92-52-4

biphenyl

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

(n-butylthio)benzene
1126-80-3

(n-butylthio)benzene

D

diphenyl sulfide
139-66-2

diphenyl sulfide

Conditions
ConditionsYield
With triphenylsulfonium trifluoromethanesulfonate In tetrahydrofuran; hexane at 0℃; for 2h;A 31%
B n/a
C 26%
D 14%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

A

biphenyl
92-52-4

biphenyl

B

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C

butyl sulfoxide
2168-93-6

butyl sulfoxide

D

(n-butylthio)benzene
1126-80-3

(n-butylthio)benzene

E

diphenyl sulfide
139-66-2

diphenyl sulfide

F

1-(butylsulfinyl)benzene
13153-10-1

1-(butylsulfinyl)benzene

Conditions
ConditionsYield
In diethyl ether for 2h; Product distribution; Heating;A 10%
B 5%
C 9%
D 5%
E 22%
F 26%
dibutyl sulfone
598-04-9

dibutyl sulfone

Dibutyl sulfide
544-40-1

Dibutyl sulfide

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran at 65℃; for 8h;26%
S,S-dibutyl-N-p-tosylsulfilimine
17627-00-8

S,S-dibutyl-N-p-tosylsulfilimine

sodium p-thiocresolate
10486-08-5

sodium p-thiocresolate

A

Dibutyl sulfide
544-40-1

Dibutyl sulfide

B

dibutyl disulfide
629-45-8

dibutyl disulfide

C

n-butyl 4-methylphenyl sulfide
21784-96-3

n-butyl 4-methylphenyl sulfide

D

4-methylphenyl n-butyl disulfide
69187-12-8

4-methylphenyl n-butyl disulfide

E

toluene
108-88-3

toluene

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 26℃; Product distribution; Irradiation; 1. other light sources discussed; 2. other reaction times discussed.;A 19.2%
B 18%
C 15%
D 6%
E n/a
Dibutyl sulfide
544-40-1

Dibutyl sulfide

dibutyl sulfone
598-04-9

dibutyl sulfone

Conditions
ConditionsYield
With potassium permanganate; copper(II) sulfate In hexane for 25h; Product distribution; Mechanism; Heating; other reagents;100%
With Py3PMo12O40; dihydrogen peroxide; Aliquat 336 In water at 70℃; for 0.25h;100%
With tert.-butylhydroperoxide; [Mo2(O)4{[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2] In 1,2-dichloro-ethane for 0.583333h; Reflux;100%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

butyl sulfoxide
2168-93-6

butyl sulfoxide

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; tetrabutylammomium bromide In dichloromethane; water for 0.166667h; Ambient temperature;100%
With calcium hypochlorite In ethyl acetate for 1.5h; Heating;100%
With oxygen; isobutyraldehyde; tris(1,3-bis(p-methoxyphenyl)-1,3-propanedionato)nickel(II) In acetonitrile at 60℃; for 18h;100%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

1-decenyl(phenyl)(tetrafluoroborato)-λ3-iodane
102987-32-6

1-decenyl(phenyl)(tetrafluoroborato)-λ3-iodane

1-decynyl(dibutyl)sulfonium tetrafluoroborate

1-decynyl(dibutyl)sulfonium tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane at 25℃; for 2.5h;100%
trans-geranyl bromide
6138-90-5

trans-geranyl bromide

Dibutyl sulfide
544-40-1

Dibutyl sulfide

C18H35S(1+)*BF4(1-)

C18H35S(1+)*BF4(1-)

Conditions
ConditionsYield
With silver tetrafluoroborate In dichloromethane at 20℃; for 2h;100%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

isolavandulyl bromide
27934-32-3

isolavandulyl bromide

C18H35S(1+)*BF4(1-)

C18H35S(1+)*BF4(1-)

Conditions
ConditionsYield
With silver tetrafluoroborate In dichloromethane100%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

rhodium(III) chloride trihydrate

rhodium(III) chloride trihydrate

RhCl3(Bu2S)3
55425-73-5

RhCl3(Bu2S)3

Conditions
ConditionsYield
In methanol at 60 - 85℃; for 3h; Inert atmosphere; Glovebox;99.7%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

C16H27OS(1+)*BF4(1-)

C16H27OS(1+)*BF4(1-)

Conditions
ConditionsYield
With silver tetrafluoroborate In acetonitrile for 0.5h; Heating;99%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

dibutyl(imino)-λ6-sulfanone
22133-03-5

dibutyl(imino)-λ6-sulfanone

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 25℃; for 3h; chemoselective reaction;99%
With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 25℃; for 3h;99%
With ammonium hydroxide; [bis(acetoxy)iodo]benzene In methanol at 0℃; for 0.25h; Flow reactor; Green chemistry;87%
Multi-step reaction with 2 steps
1: tert.-butylhydroperoxide; copper(ll) bromide / water; acetonitrile / Inert atmosphere; Reflux
2: sodium azide; sulfuric acid / chloroform / 12 h / 0 - 45 °C / Inert atmosphere
View Scheme
Dibutyl sulfide
544-40-1

Dibutyl sulfide

A

N,N'-dimethylbenzylamine
103-83-3

N,N'-dimethylbenzylamine

B

butyl sulfoxide
2168-93-6

butyl sulfoxide

Conditions
ConditionsYield
With 2-hydroperoxyhexafluoro-2-propanol In dichloromethane at -78℃; for 2h;A n/a
B 98%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

A

dibutyl sulfone
598-04-9

dibutyl sulfone

B

butyl sulfoxide
2168-93-6

butyl sulfoxide

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol for 1h; Ambient temperature;A 1%
B 98%
With ; periodic acid In pyridine for 3.6h; Ambient temperature;A n/a
B 96%
With ; periodic acid In pyridine for 1.5h; Ambient temperature;A 95%
B 1%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

trifluoromethanesulfonic acid 2-fluoroethyl ester
95353-04-1

trifluoromethanesulfonic acid 2-fluoroethyl ester

dibutyl(2-fluoroethyl)sulfonium trifluoromethanesulfonate

dibutyl(2-fluoroethyl)sulfonium trifluoromethanesulfonate

Conditions
ConditionsYield
In neat (no solvent) at 60℃; for 15h; Inert atmosphere; Sealed tube;98%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

2,2-difluoroethyl triflate
74427-22-8

2,2-difluoroethyl triflate

tributylsulfonium trifluoromethanesulfonate

tributylsulfonium trifluoromethanesulfonate

Conditions
ConditionsYield
In neat (no solvent) at 100℃; for 24h; Inert atmosphere; Sealed tube;97%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

2,2-difluoroethyl triflate
74427-22-8

2,2-difluoroethyl triflate

C13H27F3O3S2

C13H27F3O3S2

Conditions
ConditionsYield
at 100℃; for 24h; Inert atmosphere;97%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

A

rans-2-pinanol

rans-2-pinanol

B

butyl sulfoxide
2168-93-6

butyl sulfoxide

Conditions
ConditionsYield
With pinanyl hydroperoxide In various solvent(s) at 80℃; for 6h;A 96.5%
B 95.3%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

phenyl acrylate
937-41-7

phenyl acrylate

C17H26O2S

C17H26O2S

Conditions
ConditionsYield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;95%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

[N-(p-tolylsulfonyl)imino]phenyliodinane
55962-05-5

[N-(p-tolylsulfonyl)imino]phenyliodinane

S,S-dibutyl-N-p-tosylsulfilimine
17627-00-8

S,S-dibutyl-N-p-tosylsulfilimine

Conditions
ConditionsYield
Cu(3,4,7,8-tetramethyl-1,10-phenanthroline)(PPh3)Br In acetonitrile at 20℃; for 0.5h;93%
With iodine In dichloromethane at 20℃; for 24h; Inert atmosphere;79%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

1,1,1,5,5,5-hexafluoroacetylacetone
1522-22-1

1,1,1,5,5,5-hexafluoroacetylacetone

silver(l) oxide
20667-12-3

silver(l) oxide

Ag(1,1,1,5,5,5-hexafluoroacetylacetonate)(SBu2)
159648-81-4

Ag(1,1,1,5,5,5-hexafluoroacetylacetonate)(SBu2)

Conditions
ConditionsYield
In diethyl ether N2-atmosphere, protecting from light; addn. of 1.1 equiv. of CF3COCH2COCF3 to Ag2O soln. (-20°C), addn. of 1.16 equiv. of SBu2 (after 15 min), stirring (-20°C, overnight); warming to room temp., filtration, solvent removal (vac.); elem. anal.;91.6%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

2,2-difluoroethyl triflate
74427-22-8

2,2-difluoroethyl triflate

dibutyl(2,2-difluoroethyl)sulfonium trifluoromethanesulfonate

dibutyl(2,2-difluoroethyl)sulfonium trifluoromethanesulfonate

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 24h; Inert atmosphere; Sealed tube;91%
silver hexafluoroantimonate

silver hexafluoroantimonate

chloromethyl(1,5-cyclooctadiene)platinum(II)

chloromethyl(1,5-cyclooctadiene)platinum(II)

Dibutyl sulfide
544-40-1

Dibutyl sulfide

[(1,5-cyclooctadiene)Pt(Me)(SnBu2)][SbF6]

[(1,5-cyclooctadiene)Pt(Me)(SnBu2)][SbF6]

Conditions
ConditionsYield
Stage #1: silver hexafluoroantimonate; chloromethyl(1,5-cyclooctadiene)platinum(II) In tetrahydrofuran for 0.25h; Schlenk technique; Darkness; Inert atmosphere;
Stage #2: Dibutyl sulfide In tetrahydrofuran for 2h; Schlenk technique; Darkness; Inert atmosphere;
91%
dicarbonylcyclopentadienylcobalt
12078-25-0

dicarbonylcyclopentadienylcobalt

Dibutyl sulfide
544-40-1

Dibutyl sulfide

η5-cyclopentadienyltris(di-n-butyl sulfide)cobalt(III) tetrafluoroborate

η5-cyclopentadienyltris(di-n-butyl sulfide)cobalt(III) tetrafluoroborate

Conditions
ConditionsYield
With ferrocenium(III) tetrafluoroborate In dichloromethane byproducts: (C5H5)2Fe; under Ar, 1 mmol of CpCo(CO)2 and 3 mmol of S(n-Bu)2 dissolved in CH2Cl2, treated with 2 mmol of Cp2FeBF4, reacted at room temp. for 10 min; ppt. filtered, washed with CH2Cl2, dried in vac., recrystd. from MeNO2/CH2Cl2 (as required); elem. anal.;90%
cyclopentadienyldicarbonyl(tetrahydrofuran)iron(II) tetrafluoroborate

cyclopentadienyldicarbonyl(tetrahydrofuran)iron(II) tetrafluoroborate

Dibutyl sulfide
544-40-1

Dibutyl sulfide

[(cyclopentadienyl)Fe(CO)2(S(n-C4H9)2)][BF4]
95247-77-1

[(cyclopentadienyl)Fe(CO)2(S(n-C4H9)2)][BF4]

Conditions
ConditionsYield
In dichloromethane to soln. of Fe complex in CH2Cl2 added ligand under Ar, stirred at roomtemp. for several h; filtered, concd. in vac., filtered in petroleum/Et2O, ppt. washed with Et2O and petroleum, dried in high vac., recrystd. (CH2Cl2/Et2O); elem. anal.;90%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

[(κ3-P,N,P-(4-Me-2-(iPr2P)-C6H3)2N)Rh(H)(Cl)]
691894-27-6

[(κ3-P,N,P-(4-Me-2-(iPr2P)-C6H3)2N)Rh(H)(Cl)]

(N(C6H3(CH3)P(CH(CH3)2)2)2)Rh(SBu(n)2)
1000020-67-6

(N(C6H3(CH3)P(CH(CH3)2)2)2)Rh(SBu(n)2)

Conditions
ConditionsYield
With NaOC(CH3)3 In benzene-d6 (Ar); Rh complex treated with ligand in C6D6, NaOC(CH3)3 added, reacted for 10 min; treated with H2O, evapd., extd. (ether), filtered, evapd., triturated with toluene, dried;90%
Dibutyl sulfide
544-40-1

Dibutyl sulfide

dibutyl sulfoxide-(18)O

dibutyl sulfoxide-(18)O

Conditions
ConditionsYield
With N-Bromosuccinimide; 18O-labeled water In methanol at 0 - 10℃;88%
hexamethyldisilathiane
3385-94-2

hexamethyldisilathiane

Dibutyl sulfide
544-40-1

Dibutyl sulfide

niobium pentachloride
10026-12-7

niobium pentachloride

C8H18Cl3NbS2

C8H18Cl3NbS2

Conditions
ConditionsYield
In dichloromethane for 0.5h; Inert atmosphere; Schlenk technique;88%

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.

Synthesis, IR/Raman, and quantum-chemical structural analysis of new octathiotetraphosphetane ammonium salts

Badeeva, Elena K.,Platova, Elena V.,Batyeva, Elvira S.,Kursheva, Lidiya I.,Zvereva, Elena E.,Vandyukov, Aleksander E.,Katsyuba, Sergey A.,Kovalenko, Valeryi I.,Sinyashin, Oleg G.

, p. 24 - 30 (2011)

New octathiotetraphosphetane ammonium salts are obtained based on the reaction of white phosphorus (P4) and elemental sulfur with aliphatic mercaptans in the presence of amines (morpholine, methylmorpholine, pyrrolidine, and N,N-dimethylbenzylamine). Both the salts and novel Cu(I) chloride complex with the pyperidinium salt of octathiotetraphosphetane are characterized by IR/Raman spectroscopy in combination with DFT methods. The comparative spectral analysis reveals clear spectral features, characteristic for a P4S 84- anion, which are present in IR and Raman spectra of all the compounds obtained.

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

Thioether preparation method

-

Paragraph 0063; 0064, (2017/02/28)

The invention provides a thioether preparation method. The thioether is prepared according to the reaction formula of a formula (1) or a formula (2), wherein the A1-R1-X1 and the A2-R2-X2 are arylhalostannyl derivatives, no transition metal catalysts are needed in the reaction, heavy metal pollution is avoided, the used sulfur sources (sulfide and elementary substance sulfur) are cheap and easy to obtain, operation is simple and efficient, the reaction condition is mild, the cost is low, safety is high, and the thioether preparation method is suitable for industrial production.

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.

One-Pot Intermolecular C–S Self-Coupling of Dimethyl Sulfoxide Promoted by Molybdenum Pentachloride

Bortoluzzi, Marco,Ferretti, Eleonora,Hayatifar, Mohammad,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano

, p. 3838 - 3845 (2016/08/19)

The reactions between MoCl5and 1–2 equiv. of a selection of sulfoxides at room temperature in dichloromethane as solvent were studied. The 1:1 molar reaction between MoCl5and dimethyl sulfoxide (DMSO) afforded the C–S coupling product [Me2SCH2SMe][MoOCl4] (1), which was isolated in 46 % yield and characterized by analytical and spectroscopic methods and by X-ray diffraction. MoOCl3, SMe2and HCl were identified as side products. The reactions between MoCl5and tetrahydrothiophene 1-oxide, nBu2SO, MePhSO or (PhCH2)2SO yielded the corresponding sulfides and, in the cases of (PhCH2)2SO and MePhSO, also C–S activation compounds. According to DFT calculations, the unusual formation of 1 is the consequence of thermodynamically feasible Cl/O interchange between MoCl5and DMSO, this being a prerequisite for successive C–H bond activation.

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.

Reaction mechanisms of thioetherification for mercaptans and olefins over sulfided Mo-Ni/Al2O3 catalysts

Shen, Zhibing,Ke, Ming,Yu, Pei,Hu, Haiqiang,Song, Zhaozheng,Jiang, Qingzhe

, p. 120 - 127 (2015/02/02)

The thioetherification reaction of 1-butanethiol and 1-hexene dissolved in n-hexane was investigatedover sulfided Mo-Ni/Al2O3catalysts. The experimental results showed the catalysts have good cat-alytic performance for thioetherification reaction, but the isomerization and hydrogenation reactions of olefins over the catalysts can inhibit thioetherification reaction. As reaction temperature increases,the isomerization and hydrogenation reactions of olefins increase rapidly, however, the inhibition of thioetherification reaction also increases. The sulfur distribution and molecular structures of sulfurcompounds in the products were analyzed by the gas chromatograph with sulfur chemiluminescencedetector (GC-SCD) and the gas chromatograph/mass spectra spectrometry (GC/MS). Two possible routesof thioetherification reaction could be observed. At low temperature, the major pathway involves a directaddition of 1-butanethiol to the terminal carbon of double bond of 1-hexene. In this mechanism, the mainproduct is anti-Markovnikov adduct. At a higher temperature, the C S bond of 1-butanethiol can be sub-sequently cleaved, and the adsorbed -SH species can be formed on the catalysts. On the same time,abundant 1-hexene can be absorbed on the catalysts, as well. Therefore, the adsorbed SH species canthen recombine with adsorbed 1-hexene to form new hexyl-mercaptans, which can continue to produceanother kind of thioether (di-hexyl sulfide) with adsorbed 1-hexene. Similar with the first reaction route,the thioether of the anti-Markonikov adduct still dominates in the product.

Unexpected reaction of 2-chloro-1-propen-3-yl isothiuronium chloride with potassium ditelluride: the first example of vicinal elimination of chlorine and sulfur-bearing moieties

Levanova, Ekaterina P.,Grabelnykh, Valentina A.,Elaev, Alexander V.,Albanov, Alexander I.,Klyba, Lyudmila V.,Russavskaya, Natalia V.,Tarasova, Olga A.,Rozentsveig, Igor B.,Korchevin, Nikolai A.

, p. 505 - 511,7 (2020/09/16)

2-Chloro-1-propen-3-yl isothiuronium chloride reacts with potassium ditelluride in hydrazine hydrate to afford elemental tellurium and allene. The latter is formed due to the vicinal elimination of chlorine and a sulfur-bearing moiety.

Aliphatic thioethers by s-alkylation of thiols via trialkyl borates

Gunes, Deniz,Sirkecioglu, Okan,Bicak, Niyazi

experimental part, p. 1685 - 1690 (2010/09/17)

A simple and convenient one-pot procedure is described for the synthesis of thioethers via boron esters. This procedure involves in-situ generation of alkyl sulfates by reaction of trialkyl borates with concentrated sulfuric acid and subsequent reaction with thiols in the presence of pyridine. The reactions with boron esters of primary or secondary alcohols proceed cleanly at 100C and afford aliphatic thioethers in reasonable yields (59-93%) within 24 h. Interestingly, the 1H NMR spectra of the products showed no sign of positional isomerisms. The method fails however with thiophenol and does not yield aromatic thioethers, due to electrophilic substitution at the phenyl ring. Copyright Taylor & Francis Group, LLC.

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