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2179-57-9 Usage

Identification

▼▲ CAS.No.:? 2179-57-9? FL.No.:? 12.008 FEMA.No.:? 2028 NAS.No.:? 2028 CoE.No.:? 485 EINECS.No.:? 218-548-6? JECFA.No.:? 572

Description

Different sources of media describe the Description of 2179-57-9 differently. You can refer to the following data:
1. Allyl disulfide has a characteristic garlic odor. It is used as a flavor enhancer, flavoring agent or adjuvant.
2. Diallyl disulfide is one of the major allergens in garlic (Al/ium sativum) and onions. Among patients who are patch-test positive to garlic, all 13 who were tested had positive reactions to diallyl sulfide 5% petrolatum.

Regulatory Status

CoE: Used provisionally. Food: 5 ppm FDA: 21 CFR 172.515 FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1999).

Usage

Reported uses (ppm): (FEMA, 1994) ▼▲ Food Category? Usual? Max.? Alcoholic beverages? 0.1 1 Baked goods? 9.09 13.16 Condiments, relishes? 13.82 15.21 Frozen dairy? 0.1 1 Gelatins, puddings? 0.5 1 Gravies? 2 6.5 Meat products? 9.4 13.1 Nonalcoholic beverages? 0.07 0.68 Soft candy? 0.5 1 Soups? 1 10

Natural occurrence

Main constituent of Allium sativum essential oil. Reported found in onion (Allium cipa, L.), garlic (Allium sativum L.), chive (Allium schoenoprasum L.), nira (Allium tuberosum rottl.), raw cabbage and caucas (Allium victoralis L.).

Chemical Properties

Different sources of media describe the Chemical Properties of 2179-57-9 differently. You can refer to the following data:
1. CLEAR YELLOW LIQUID
2. Allyl disulfide has a characteristic garlic odor. It is used as a flavor enhancer, flavoring agent or adjuvant

Occurrence

Main constituent of Allium sativum essential oil. Reported found in onion (Allium cipa, L.), garlic (Allium sativum L.), chive (Allium schoenoprasum L.), nira (Allium tuberosum rottl.), raw cabbage and caucas (Allium victoralis L.).

Uses

Different sources of media describe the Uses of 2179-57-9 differently. You can refer to the following data:
1. antineoplastic, antibacterial, apoptosis inducer, insecticide
2. Diallyldisulfide has a range of uses varying from a Cytocrome P450 inhibitor to vasorelaxant and hypotensive. Being in the class of organosulfur compounds, it carries chemopreventive characteristics .
3. Diallyl disulfide is one of the three principallow-molecular-weight allergens of garlic. Allylpropyl disulfide and allicin are the other allergens.

Definition

ChEBI: An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.

Preparation

By oxidation of allyl mercaptan with iodine in the presence of pyridine and ethanol; from sodium allyl thiosulfate with potassium hydroxide.

Aroma threshold values

Detection: 4.3 to 30 ppb; Recognition: 80 ppb

Taste threshold values

Taste characteristics at 2 ppm: green onion and garlic-like with meaty nuances

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 615, 1966 DOI: 10.1021/jo01340a520Synthetic Communications, 25, p. 3573, 1995 DOI: 10.1080/00397919508015492

General Description

Allyl disulfide is naturally found in Allium species such as garlic and onion. It is used as a flavoring agent in meat and condiments.

Biochem/physiol Actions

Organosulfur compound that is naturally found in garlic. Contributes to the pungent odor of crushed garlic. Anticancer agent and may provide protection against cardiovascular disease.

Contact allergens

Diallyldisulfide is one of the major allergens in garlic (Allium sativum) and onions. Among patients patch-testpositive to garlic, all 13 who were tested had positive reactions to diallyl sulfide 5% pet.

Purification Methods

Purify the disulfide by fractional distillation until the molar refractivity is in uniformly good agreement with the calculated value [Small et al. J Am Chem Soc 69 1710 1947]. It has also been purified by gas chromatography [retention times: Carson & Wong J Org Chem 24 175 1959, UV: Koch J Chem Soc 395 1949]. It is present in garlic. [Beilstein 1 IV 2098.]

Check Digit Verification of cas no

The CAS Registry Mumber 2179-57-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,7 and 9 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2179-57:
(6*2)+(5*1)+(4*7)+(3*9)+(2*5)+(1*7)=89
89 % 10 = 9
So 2179-57-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H12O4/c9-5-1-2-6(10)7-4(5)3-12-8(7)11/h4-7,9-10H,1-3H2

2179-57-9 Well-known Company Product Price

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  • Alfa Aesar

  • (L11106)  Diallyl disulfide, tech. 80%, remainder mainly diallyl sulfide and diallyl trisulfide   

  • 2179-57-9

  • 5g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (L11106)  Diallyl disulfide, tech. 80%, remainder mainly diallyl sulfide and diallyl trisulfide   

  • 2179-57-9

  • 25g

  • 522.0CNY

  • Detail
  • Alfa Aesar

  • (L11106)  Diallyl disulfide, tech. 80%, remainder mainly diallyl sulfide and diallyl trisulfide   

  • 2179-57-9

  • 100g

  • 1449.0CNY

  • Detail
  • USP

  • (1223209)  Allyldisulfide  United States Pharmacopeia (USP) Reference Standard

  • 2179-57-9

  • 1223209-5X0.5ML

  • 4,647.24CNY

  • Detail
  • Aldrich

  • (317691)  Allyldisulfide  technical grade, 80%

  • 2179-57-9

  • 317691-25G

  • 373.23CNY

  • Detail
  • Aldrich

  • (317691)  Allyldisulfide  technical grade, 80%

  • 2179-57-9

  • 317691-100G

  • 1,035.45CNY

  • Detail

2179-57-9SDS

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 diallyl disulfide

1.2 Other means of identification

Product number -
Other names 2-Propenyl disulfide

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:2179-57-9 SDS

2179-57-9Synthetic route

prop-2-ene-1-thiol
870-23-5

prop-2-ene-1-thiol

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With nanophase manganese (VII) oxide coated clay (NM7O coated clay) In toluene at 40℃; for 3h;99%
With water; dihydrogen peroxide In various solvent(s) at 20℃; for 0.166667h; Oxidation; Dimerization;94%
CoCl2 In acetonitrile Ambient temperature;90%
allyl bromide
106-95-6

allyl bromide

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With 1,2-bis(5-methylisoxazol-3-yl)hydrazine; sodium carbonate; thiourea In water; acetonitrile at 80℃; for 2h;95%
With sodium sulfide trihydrate; hexachloroethane at 20℃; for 0.833333h; Reagent/catalyst;93%
With Sodium thiosulfate pentahydrate; water; dimethyl sulfoxide at 50 - 60℃; for 3.5h; pH=< 3;91%
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With lithium sulfide; sulfur; cetyl trimethyl ammonium bromide In chloroform; water for 1h; Ambient temperature;95%
With 1,2-bis(5-methylisoxazol-3-yl)hydrazine; sodium carbonate; thiourea In water; acetonitrile at 80℃; for 3h;92%
With sodium sulfide trihydrate; hexachloroethane at 20℃; for 1h; Reagent/catalyst;91%
allyl bromide
106-95-6

allyl bromide

thiourea
17356-08-0

thiourea

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With tetrachloromethane; water; triethylamine In glycerol at 50℃; for 12h;94%
With sodium carbonate In water; acetonitrile at 80℃; for 3h;92%
allyl tosylate
4873-09-0

allyl tosylate

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With sodium carbonate; sulfur; thiourea In water at 70℃; for 5h; Green chemistry;90%
thiourea
17356-08-0

thiourea

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With sodium carbonate In water; acetonitrile at 80℃; for 3h;87%
allyl thiocyanate
764-49-8

allyl thiocyanate

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With samarium; titanium tetrachloride In tetrahydrofuran at 0℃;82%
S-allyl ethanethioate
23973-51-5

S-allyl ethanethioate

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
Stage #1: S-allyl ethanethioate With hydrogenchloride; water In methanol at 50℃;
Stage #2: With iodine In methanol; water at 0℃; for 0.75h;
82%
diallyl sulphide
592-88-1

diallyl sulphide

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With hydrogen sulfide; dimethyl sulfoxide at 50℃; for 3h;76.3%
Diallyl selenide
127699-25-6

Diallyl selenide

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

diallyl sulphide
592-88-1

diallyl sulphide

Conditions
ConditionsYield
With hydrogen sulfide In dimethyl sulfoxide at 40℃; for 3h;A 11%
B 50.8%
2-(allylthio)benzo[d]oxazole
50463-17-7

2-(allylthio)benzo[d]oxazole

chloroform
67-66-3

chloroform

A

benzoxazole
273-53-0

benzoxazole

B

diallyl disulphide
2179-57-9

diallyl disulphide

C

2-(1,1-dichloro-3-butenylthio)benzoxazole

2-(1,1-dichloro-3-butenylthio)benzoxazole

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide at 45 - 55℃; for 25h; Rearrangement; disproportionation;A 37%
B 21%
C n/a
2-(allylthio)-1H-benzimidazole
51389-04-9

2-(allylthio)-1H-benzimidazole

chloroform
67-66-3

chloroform

A

2-(allylthio)benzo[d]oxazole
50463-17-7

2-(allylthio)benzo[d]oxazole

B

diallyl disulphide
2179-57-9

diallyl disulphide

C

1,2-diallyl sulfanyl-1H-benzoimidazole
124530-69-4

1,2-diallyl sulfanyl-1H-benzoimidazole

D

2-(1,1-dichloro-3-butenylthio)benzimidazole

2-(1,1-dichloro-3-butenylthio)benzimidazole

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide at 45 - 55℃; for 18h; Rearrangement; substitution; disproportionation; allylation; Further byproducts given;A 5%
B 37%
C n/a
D n/a
2-allylmercapto-1,3-benzothiazole
22388-07-4

2-allylmercapto-1,3-benzothiazole

chloroform
67-66-3

chloroform

A

1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

B

diallyl disulphide
2179-57-9

diallyl disulphide

C

diallyl sulphide
592-88-1

diallyl sulphide

D

2-(1,1-dichloro-3-butenylthio)benzothiazole

2-(1,1-dichloro-3-butenylthio)benzothiazole

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide at 45 - 55℃; for 25h; Rearrangement; disproportionation; Further byproducts given;A 24%
B 24%
C 15%
D n/a
2-allylmercapto-1,3-benzothiazole
22388-07-4

2-allylmercapto-1,3-benzothiazole

chloroform
67-66-3

chloroform

A

1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

B

diallyl disulphide
2179-57-9

diallyl disulphide

C

diallyl sulphide
592-88-1

diallyl sulphide

D

2,2'-benzothiazolyl
4271-09-4

2,2'-benzothiazolyl

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide at 45 - 55℃; for 25h; Rearrangement; disproportionation; Further byproducts given;A 24%
B 24%
C 15%
D 2%
allyl iodid
556-56-9

allyl iodid

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With diethyl ether; sodium disulfide
With carbon disulfide; potassium hydroxide In dimethyl sulfoxide for 2h;0.5 g
allyl iodid
556-56-9

allyl iodid

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

bis-2-propenyl pentasulfide
118686-45-6

bis-2-propenyl pentasulfide

Conditions
ConditionsYield
With sodium tetrasulfide; diethyl ether
diphenyl-μ-disulfido-1,2-dithio-dicarbonimidic acid diallyl ester

diphenyl-μ-disulfido-1,2-dithio-dicarbonimidic acid diallyl ester

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
at 90 - 95℃;
allyl iodid
556-56-9

allyl iodid

Potassium 4,5,6,7-tetrahydroindole-2-carbodithioate

Potassium 4,5,6,7-tetrahydroindole-2-carbodithioate

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

allyl ester of 4,5,6,7-tetrahydro-2-indolyldithiocarboxylic acid

allyl ester of 4,5,6,7-tetrahydro-2-indolyldithiocarboxylic acid

Conditions
ConditionsYield
In dimethyl sulfoxide for 2h; Yield given. Yields of byproduct given;
S-allyl cysteine
21593-77-1, 49621-03-6

S-allyl cysteine

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

allicin
539-86-6

allicin

C

bis-2-propenyl thiosulfonate
29418-05-1

bis-2-propenyl thiosulfonate

D

sodium pyruvate
113-24-6

sodium pyruvate

Conditions
ConditionsYield
With nitrogen(II) oxide In water for 24h; Ambient temperature; Yield given. Yields of byproduct given;
S-allyl cysteine
21593-77-1, 49621-03-6

S-allyl cysteine

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

allicin
539-86-6

allicin

C

bis-2-propenyl thiosulfonate
29418-05-1

bis-2-propenyl thiosulfonate

D

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With nitrogen(II) oxide; trifluoroacetic acid In water for 5h; Mechanism; Ambient temperature; other time; also in absence of CF3COOH;
allicin
539-86-6

allicin

A

3-vinyl-4H-<1,2>-dithiin
62488-53-3

3-vinyl-4H-<1,2>-dithiin

B

diallyl disulphide
2179-57-9

diallyl disulphide

C

diallyl trisulfide
2050-87-5

diallyl trisulfide

D

2‐ethenyl‐4H‐1,3‐dithiine
80028-57-5

2‐ethenyl‐4H‐1,3‐dithiine

Conditions
ConditionsYield
In chloroform-d1 at 25℃; for 144h;A 0.008 g
B 0.03 g
C 0.01 g
D 0.015 g
allicin
539-86-6

allicin

A

3-vinyl-4H-<1,2>-dithiin
62488-53-3

3-vinyl-4H-<1,2>-dithiin

B

diallyl disulphide
2179-57-9

diallyl disulphide

C

diallyl trisulfide
2050-87-5

diallyl trisulfide

D

2‐ethenyl‐4H‐1,3‐dithiine
80028-57-5

2‐ethenyl‐4H‐1,3‐dithiine

E

(Z)-ajoene
92285-00-2

(Z)-ajoene

F

(E)-ajoene
92284-99-6

(E)-ajoene

Conditions
ConditionsYield
at 37℃; for 48h; Product distribution; other temperatures, other times;
2-propenyl ethaneimidothiolate hydrobromide
87234-43-3

2-propenyl ethaneimidothiolate hydrobromide

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With sodium hydroxide
benzyl chloride
100-44-7

benzyl chloride

N-methyl-N-<(2-propenylthio)methylene>methanaminium bromide
96989-38-7

N-methyl-N-<(2-propenylthio)methylene>methanaminium bromide

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

allyl(benzyl)sulfide
6937-97-9

allyl(benzyl)sulfide

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 10h;
chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

N-methyl-N-<(2-propenylthio)methylene>methanaminium bromide
96989-38-7

N-methyl-N-<(2-propenylthio)methylene>methanaminium bromide

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

ethyl 2-(allylthio)acetate
15224-05-2

ethyl 2-(allylthio)acetate

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 10h;
N-methyl-N-<(2-propenylthio)methylene>methanaminium bromide
96989-38-7

N-methyl-N-<(2-propenylthio)methylene>methanaminium bromide

diallyl disulphide
2179-57-9

diallyl disulphide

Conditions
ConditionsYield
With sodium hydroxide
N-methyl-N-<(2-propenylthio)methylene>methanaminium bromide
96989-38-7

N-methyl-N-<(2-propenylthio)methylene>methanaminium bromide

α-bromoacetophenone
70-11-1

α-bromoacetophenone

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

2-(allylthio)-1-phenylethan-1-one
64878-08-6

2-(allylthio)-1-phenylethan-1-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 10h;
allyl bromide
106-95-6

allyl bromide

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

diallyl trisulfide
2050-87-5

diallyl trisulfide

C

diallyl tetrasulfide
2444-49-7

diallyl tetrasulfide

Conditions
ConditionsYield
With polysulfide; tetraethylammonium perchlorate In N,N-dimethyl-formamide in situ electrochemical generation of polysulfide from carbon-sulfur cathode; Title compound not separated from byproducts;
N-allyl isothiocyanate
57-06-7

N-allyl isothiocyanate

A

diallyl disulphide
2179-57-9

diallyl disulphide

B

diallyl sulphide
592-88-1

diallyl sulphide

C

allyl thiocyanate
764-49-8

allyl thiocyanate

D

diallyl trisulfide
2050-87-5

diallyl trisulfide

E

N,N'-diallylthiourea
6601-20-3

N,N'-diallylthiourea

F

3H-1,2-dithiole

3H-1,2-dithiole

Conditions
ConditionsYield
In water at 100℃; for 1h; thermal degradation; var. pH;
diallyl disulphide
2179-57-9

diallyl disulphide

3,6-dihydro-[1,2]dithiine
17547-93-2

3,6-dihydro-[1,2]dithiine

Conditions
ConditionsYield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride at 90℃;100%
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum In benzene-d6 at 20℃; for 1h; Product distribution; further catalyst, variation of the reaction time; catalytic ring-closing metathesis of further acyclic dienes;77 % Spectr.
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum In benzene-d6 at 20℃; for 1h;77 % Spectr.
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane-d2 for 4h; Heating;100 % Spectr.
diallyl disulphide
2179-57-9

diallyl disulphide

allicin
539-86-6

allicin

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at -50 - -20℃; for 0.75h; Product distribution / selectivity; Inert atmosphere;96%
With Peroxyformic acid In methanol at 0℃; for 0.25h; Reagent/catalyst;92%
With peracetic acid; sodium carbonate In chloroform at 0℃; 1.) 30 min; 2.) 30 min;90%
diallyl disulphide
2179-57-9

diallyl disulphide

prop-2-ene-1-thiol
870-23-5

prop-2-ene-1-thiol

Conditions
ConditionsYield
With indium; ammonium chloride In ethanol for 1h; Reduction; Heating;95%
With magnesium In methanol; benzene for 1.66667h; Ambient temperature;83%
diallyl disulphide
2179-57-9

diallyl disulphide

3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

3-(prop-2-en-1-yldisulfanyl)propanoic acid
805983-04-4

3-(prop-2-en-1-yldisulfanyl)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; diethyl ether at 20℃; for 24h; Inert atmosphere;92%
With sodium hydroxide In methanol; diethyl ether at 25℃; for 24.5h; Inert atmosphere;84%
With sodium hydroxide In methanol; diethyl ether at 20℃; for 24h; Inert atmosphere;63%
With sodium hydroxide In methanol; diethyl ether; water at 20℃; for 24h;28%
With sodium hydroxide at 20℃; for 24h; Reflux; Inert atmosphere;
diallyl disulphide
2179-57-9

diallyl disulphide

allyl bromide
106-95-6

allyl bromide

allyl(4-(tert-butyl)phenyl)sulfane

allyl(4-(tert-butyl)phenyl)sulfane

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;89%
trimethoxysilane
2487-90-3

trimethoxysilane

diallyl disulphide
2179-57-9

diallyl disulphide

bis-(3-trimethoxysilylpropyl)-disulphide
35112-74-4

bis-(3-trimethoxysilylpropyl)-disulphide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; cyclo-octa-1,5-diene In dichloromethane-d2 at 20℃; for 6h; Reagent/catalyst;89%
diallyl disulphide
2179-57-9

diallyl disulphide

1,1-dibromo-2,2-dimethylcyclopropane
32264-50-9

1,1-dibromo-2,2-dimethylcyclopropane

1-bromo-2,2-dimethylcyclopropyl allyl sulfide
79306-32-4

1-bromo-2,2-dimethylcyclopropyl allyl sulfide

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; diethyl ether 2 h, < -95 deg C, 1.5 h;78%
diallyl disulphide
2179-57-9

diallyl disulphide

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

S-allyl diphenylphosphinothioate

S-allyl diphenylphosphinothioate

Conditions
ConditionsYield
In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; Sealed tube;78%
1-vinyl-3,4,5-tribromo-1H-pyrazole
923035-87-4

1-vinyl-3,4,5-tribromo-1H-pyrazole

diallyl disulphide
2179-57-9

diallyl disulphide

5-allylthio-3,4-dibromo-1-vinylpyrazole

5-allylthio-3,4-dibromo-1-vinylpyrazole

Conditions
ConditionsYield
Stage #1: 1-vinyl-3,4,5-tribromo-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0333333h;
Stage #2: diallyl disulphide In tetrahydrofuran; hexane at -78 - 20℃; for 2h;
77%
diallyl disulphide
2179-57-9

diallyl disulphide

4-t-butylbenzenethiol
2396-68-1

4-t-butylbenzenethiol

A

allyl(4-(tert-butyl)phenyl)sulfane

allyl(4-(tert-butyl)phenyl)sulfane

B

bis(4-tert-butylphenyl)disulfide
7605-48-3

bis(4-tert-butylphenyl)disulfide

C

C13H18S2

C13H18S2

Conditions
ConditionsYield
With triethylamine In methanol at 40℃;A n/a
B 20%
C 75%
diallyl disulphide
2179-57-9

diallyl disulphide

4-mercaptobenzoic acid
1074-36-8

4-mercaptobenzoic acid

allyl (4-carboxyphenyl)disulfide
1166842-03-0

allyl (4-carboxyphenyl)disulfide

Conditions
ConditionsYield
With triethylamine at 60℃; for 8h; pH=4;74.3%
diallyl disulphide
2179-57-9

diallyl disulphide

4-t-butylbenzenethiol
2396-68-1

4-t-butylbenzenethiol

A

bis(4-tert-butylphenyl)disulfide
7605-48-3

bis(4-tert-butylphenyl)disulfide

B

C13H18S2

C13H18S2

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 40℃;A 71%
B 29%
diallyl disulphide
2179-57-9

diallyl disulphide

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

allyl phenyl thioether
5296-64-0

allyl phenyl thioether

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 25℃; for 30h; Inert atmosphere; Green chemistry;71%
diallyl disulphide
2179-57-9

diallyl disulphide

disulfide of 3-butyl-5-mercaptomethylisoxazoline

disulfide of 3-butyl-5-mercaptomethylisoxazoline

Conditions
ConditionsYield
With N-chloro-succinimide; triethylamine68%
diallyl disulphide
2179-57-9

diallyl disulphide

4-t-butylbenzenethiol
2396-68-1

4-t-butylbenzenethiol

allyl(4-(tert-butyl)phenyl)sulfane

allyl(4-(tert-butyl)phenyl)sulfane

Conditions
ConditionsYield
With triethylamine In methanol at 40℃; for 24h; Time;68%
diallyl disulphide
2179-57-9

diallyl disulphide

Isobutyl iodide
513-38-2

Isobutyl iodide

(E)-3-Allylsulfanyl-1-isobutylsulfanyl-propene
108140-96-1, 108140-97-2

(E)-3-Allylsulfanyl-1-isobutylsulfanyl-propene

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 2h;65.6%
4-bromo-1-phenyl-1H-pyrazole
15115-52-3

4-bromo-1-phenyl-1H-pyrazole

diallyl disulphide
2179-57-9

diallyl disulphide

C12H12N2S

C12H12N2S

Conditions
ConditionsYield
Stage #1: 4-bromo-1-phenyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h;
Stage #2: diallyl disulphide In tetrahydrofuran at 0 - 20℃;
65%
1-iodo-butane
542-69-8

1-iodo-butane

diallyl disulphide
2179-57-9

diallyl disulphide

1-((E)-3-Allylsulfanyl-propenylsulfanyl)-butane
169132-70-1

1-((E)-3-Allylsulfanyl-propenylsulfanyl)-butane

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 2h;61.2%
1.0 M-tetrahydrofuran

1.0 M-tetrahydrofuran

diallyl disulphide
2179-57-9

diallyl disulphide

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

2,5-bis(3-mercaptopropyl)-1,4-dithian

2,5-bis(3-mercaptopropyl)-1,4-dithian

Conditions
ConditionsYield
With bromine In tetrahydrofuran; dichloromethane; benzene61%
diallyl disulphide
2179-57-9

diallyl disulphide

4-mercaptobenzoic acid
1074-36-8

4-mercaptobenzoic acid

4-(allylthio)benzoic acid
16195-39-4

4-(allylthio)benzoic acid

Conditions
ConditionsYield
With triethylamine In methanol at 40℃; for 24h; Solvent;61%
9-(1'-β-D-ribofuranosyl)-8-ethyl-6-nitro-1,3-dideazaadenine

9-(1'-β-D-ribofuranosyl)-8-ethyl-6-nitro-1,3-dideazaadenine

diallyl disulphide
2179-57-9

diallyl disulphide

5'-allylthio-5'-deoxy-9-(1'-β-D-ribofuranosyl)-8-ethyl-6-nitro-1,3-dideazaadenine

5'-allylthio-5'-deoxy-9-(1'-β-D-ribofuranosyl)-8-ethyl-6-nitro-1,3-dideazaadenine

Conditions
ConditionsYield
With pyridine; triphenylphosphine at 20℃; for 24h;58%

2179-57-9Relevant articles and documents

Synthesis and preliminary evaluation of the anti-cancer activity on A549 lung cancer cells of a series of unsaturated disulfides

Olivito, Fabrizio,Amodio, Nicola,Di Gioia, Maria Luisa,Nardi, Monica,Oliverio, Manuela,Juli, Giada,Tassone, Pierfrancesco,Procopio, Antonio

, p. 116 - 119 (2019)

We synthesized a series of small symmetrical unsaturated disulfides by a multi-step reaction starting from organic alcohols, and we performed a preliminary test to evaluate the effect of these compounds on the viability of A549 lung cancer cells. The garlic-derived natural compound diallyl disulfide, known for its anticancer activity, was used as the lead compound in this study. We synthesized five DADS analogues having different carbon chain lengths and different positions of the double bonds. Two analogues exhibited a promising antitumor activity in vitro, and the allylic double bond did not seem to be the main driving force.

Oxidation of some organic thiols with tetramethylammonium fluorochromate(VI)

Imanieh,Ghamami,Mohammadi,Jangjoo

, p. 282 - 284 (2007)

Tetramethylammonium fluorochromate oxidizes alcohols to the corresponding aldehydes and ketones without polymerization of double bonds, overoxidation, and other side reactions. This reagent is effective for oxidation of thiols to disulfides.

Biocatalytic synthesis of diaryl disulphides and their bio-evaluation as potent inhibitors of drug-resistant Staphylococcus aureus

Saima,Soni, Isha,Lavekar, Aditya G.,Shukla, Manjulika,Equbal, Danish,Sinha, Arun K.,Chopra, Sidharth

, p. 171 - 178 (2019/01/04)

Staphylococcus aureus is a WHO Priority II pathogen for its capability to cause acute to chronic infections and to resist antibiotics, thus severely impacting healthcare systems worldwide. In this context, it is urgently desired to discover novel molecules to thwart the continuing emergence of antimicrobial resistance. Disulphide containing small molecules has gained prominence as antibacterials. As their conventional synthesis requires tedious synthetic procedure and sometimes toxic reagents, a green and environmentally benign protocol for their synthesis has been developed through which a series of molecules were obtained and evaluated for antibacterial activity against ESKAPE pathogen panel. The hit compound was tested for cytotoxicity against Vero cells to determine its selectivity index and time-kill kinetics was determined. The activity of hit was determined against a panel of S. aureus multi-drug resistant clinical isolates. Also, its ability to synergize with FDA approved drugs was tested as was its ability to reduce biofilm. We identified bis(2-bromophenyl) disulphide (2t) as possessing equipotent antimicrobial activity against S. aureus including MRSA and VRSA strains. Further, 2t exhibited a selectivity index of 25 with concentration-dependent bactericidal activity, synergized with all drugs tested and significantly reduced preformed biofilm. Taken together, 2t exhibits all properties to be positioned as novel scaffold for anti-staphylococcal therapy.

A rapid, efficient and green procedure for transformation of alkyl halides/ tosylates to organochalcogens in water

Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh

supporting information, p. 41 - 44 (2017/09/25)

A one-pot and efficient synthesis of dialkyl dichalcogenides (S, Se) in aqueous media under catalyst-free conditions using benzylic, allylic and primary halides with elemental sulfur and selenium has been developed. Also, this procedure was extended to preparation of trisulfides and triselenides from secondary and tertiary halides in same condition. In all cases, products can be obtained in good to excellent yield in short reactions time.

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