2444-49-7

Basic information

• Product Name: diallyl tetrasulphide
• Synonyms: diallyl tetrasulphide;Tetrasulfide, di-2-propenyl;diallyl tetrasulfide;Bis(2-propenyl) pertetrasulfide;Bis(allylthio) persulfide;Di(2-propenyl) pertetrasulfide;Diallyl pertetrasulfide;ICD-1585
• CAS NO: 2444-49-7
• Molecular Formula: C₆H₁₀S₄
• Molecular Weight: 210.4036
• EINECS: 219-485-7
• Mol File: 2444-49-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 279.2 °C at 760 mmHg
• Flash Point: 120.9 °C
• Appearance: /
• Density: 1.211 g/cm³
• Vapor Pressure: 0.00692mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: diallyl tetrasulphide(CAS DataBase Reference)
• NIST Chemistry Reference: diallyl tetrasulphide(2444-49-7)
• EPA Substance Registry System: diallyl tetrasulphide(2444-49-7)

Safety Data

• Hazardous Substances Data: 2444-49-7(Hazardous Substances Data)

Usage

Uses

Diallyl Tetrasulfide is a mitotic inhibitor and apoptosis inducers. An anti-carcinogenic agent.Also, it is derived from Allyl Bromide (A549655), which is used as a reagent in the synthesis of Resveratrol derivatives. Resveratrol (R150000) is a minor constitutent of wine, correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion and progression.

InChI:InChI=1/C6H10S4/c1-3-5-7-9-10-8-6-4-2/h3-4H,1-2,5-6H2

Synthetic route

3-chloroprop-1-ene (107-05-1) → diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7)

Conditions	Yield
With sulfur; potassium hydroxide; water In tetrahydrofuran for 2h; Ambient temperature;	A 30% B 10%

prop-2-ene-1-thiol (870-23-5) → diallyl tetrasulfide (2444-49-7)

Conditions	Yield
With diethyl ether; sodium ethanolate beim Behandeln anschliessend mit Dischwefeldichlorid in Petrolaether;

diallyl disulphide (2179-57-9) → 3-vinyl-4H-<1,2>-dithiin (62488-53-3) + diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7)

Conditions	Yield
at 50℃; for 168h; Further byproducts given;	A 0.7 % Chromat. B 3 % Chromat. C 9.7 % Chromat. D 0.47 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 5-methyl-4,7-dithiadeca-1,9-diene (820-30-4)

Conditions	Yield
at 80℃; for 240h; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.45 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 2‐ethenyl‐4H‐1,3‐dithiine (80028-57-5)

Conditions	Yield
at 50℃; for 168h; Further byproducts given;	A 3 % Chromat. B 9.7 % Chromat. C 0.47 % Chromat. D 0.3 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 4-methyl-1,2,3-trithiolane

Conditions	Yield
at 80℃; for 240h; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.68 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 5-methyl-1,2,3,4-tetrathiane

Conditions	Yield
at 80℃; for 240h; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.42 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 7-methyl-4,5,8-trithiaundeca-1,10-diene

Conditions	Yield
at 80℃; for 240h; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.86 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 7-methyl-4,5,6,9,10-pentathiatrideca-1,12-diene

Conditions	Yield
at 80℃; for 240h; Yield given. Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D n/a

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 8-methyl-4,5,6,9,10-pentathiatrideca-1,12-diene

Conditions	Yield
at 80℃; for 240h; Yield given. Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D n/a

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 2-(2',3'-dithia-5'-hexenyl)-3,4-dihydro-2H-thiopyran

Conditions	Yield
at 80℃; for 240h; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 2.3 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 2-(2'-<3',4'-dihydro-2H-thiopyranyl>)-4H-<1,3>-dithiin

Conditions	Yield
at 80℃; for 240h; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.2 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 2-(2',3',4'-trithia-6'-heptenyl)-3,4-dihydro-2H-thiopyran

Conditions	Yield
at 80℃; for 240h; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.7 % Chromat.

diallyl disulphide (2179-57-9) → diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + 3-(2',3',4'-trithia-6'-heptenyl)-3,4-dihydro-2H-thiopyran

Conditions	Yield
at 80℃; for 240h; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 5.5 % Chromat. D 0.25 % Chromat.

allyl bromide (106-95-6) → diallyl disulphide (2179-57-9) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7)

Conditions	Yield
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;

3-chloroprop-1-ene (107-05-1) → diallyl disulphide (2179-57-9) + diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7)

Conditions	Yield
Stage #1: With sodium sulfide; sodium hydroxide; sulfur; polyethylene glycol In water at 45 - 60℃; under 1173.78 Torr; Stage #2: 3-chloroprop-1-ene In water at 45 - 50℃; under 915.2 - 4897.34 Torr; Product distribution / selectivity; continuous process;
Stage #1: With sodium sulfide; sodium hydroxide; sulfur In water at 45 - 60℃; under 1173.78 Torr; Stage #2: 3-chloroprop-1-ene In water at 45 - 50℃; under 915.2 - 4897.34 Torr; Product distribution / selectivity; continuous process;

allicin (539-86-6) → diallyl disulphide (2179-57-9) + diallyl sulphide (592-88-1) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + bis-2-propenyl pentasulfide (118686-45-6)

Conditions	Yield
With sulfur; dibutylamine at 60 - 70℃; for 1h; Product distribution / selectivity;

allicin (539-86-6) → diallyl disulphide (2179-57-9) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7)

Conditions	Yield
at 60 - 70℃; for 1h; Product distribution / selectivity;

allicin (539-86-6) → diallyl disulphide (2179-57-9) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + bis-2-propenyl pentasulfide (118686-45-6)

Conditions	Yield
at 70℃; for 1h; Product distribution / selectivity;
With sulfur at 60 - 70℃; for 1h; Product distribution / selectivity;

allicin (539-86-6) → diallyl disulphide (2179-57-9) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + bis-2-propenyl pentasulfide (118686-45-6) + diallyl hexasulfide (137443-18-6)

Conditions	Yield
With sulfur at 60 - 70℃; for 1h; Product distribution / selectivity;

allicin (539-86-6) → diallyl disulphide (2179-57-9) + diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + bis-2-propenyl pentasulfide (118686-45-6) + diallyl hexasulfide (137443-18-6) + diallyl heptasulfide (139693-24-6)

Conditions	Yield
With sulfur at 70℃; for 1h; Product distribution / selectivity;

allicin (539-86-6) → diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7)

Conditions	Yield
at 70℃; for 1h; Product distribution / selectivity;

allicin (539-86-6) → diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + bis-2-propenyl pentasulfide (118686-45-6) + diallyl hexasulfide (137443-18-6) + diallyl heptasulfide (139693-24-6)

Conditions	Yield
With sulfur at 70℃; for 1h; Product distribution / selectivity;

allicin (539-86-6) → diallyl trisulfide (2050-87-5) + diallyl tetrasulfide (2444-49-7) + bis-2-propenyl pentasulfide (118686-45-6) + diallyl heptasulfide (139693-24-6)

Conditions	Yield
With sulfur at 70℃; for 1h; Product distribution / selectivity;

diallyl tetrasulfide (2444-49-7) + zinc → diallyl sulphide (592-88-1)

copper(II) bromide dihydrate + diallyl tetrasulfide (2444-49-7) → 3CuBr*diallyltetrasulfide

Conditions	Yield
In ethanol Electrochem. Process; diallyltetrasulfide added to a soln. of CuBr2*2H2O in EtOH, placed into glass reservoir, copper electrodes mounted via air tight seal, system maintained for 20 h under an applied tension of alternating current (50 Hz, 0.2 V, 0.1 mA); crystn. on electrodes;

Upstream product

• 539-86-6 allicin 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 2179-57-9 diallyl disulphide 
• 870-23-5 prop-2-ene-1-thiol 

Downstream Products

• 592-88-1 diallyl sulphide 

Relevant articles and documents

From symmetrical tetrasulfides to trisulfide dioxides: Via photocatalysis

A straightforward strategy involving photocatalysis has been established for accessing trisulfide dioxides from readily achieved symmetrical tetrasulfides. Stern-Volmer analysis and radical quenching experiments demonstrated the occurrence of a single electron transfer between the photocatalyst and sulfinic acid. Bioactive molecules such as the antihypertensive drug captopril, allicin derivatives, amino acids and terpenes were efficiently and reversibly linked through sulfur-sulfur covalent bonds. Furthermore, flow-setup syntheses of trisulfide dioxides were successfully achieved on the gram scale, indicating the great potential of the developed protocol for practical industrial applications. This journal is

PROCESS FOR PRODUCING DIALLYL DISULFIDE

The invention provides a process for forming diallyl disulfide. The process comprises A) mixing together sulfur and at least one alkali metal sulfide in an initial aqueous medium in which at least about 90 volume percent of said aqueous medium is water, such that a disulfide source is formed in said initial aqueous medium thereby forming a disulfide source-conatining aqueous medium, and B) mixing together at least a portion of said disulfide source-containing aqueous medium and at lease one allyl halide selected from allyl cloride, allyl bromide, or a mixture of any two or all three of these, in the absence of any additional solvent other than water, at a temperature in the range of about 40?C to about 60?C, such that diallyl disulfide is formed.

A New Use of the Tetrahydrofuran/Powdered Potassium Hydroxide System: Convenient α-Sulfenylation of Ketones and Preparation of Dialkyl Polysulfides

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