22796-26-5

Basic information

• Product Name: 2,3-dihydro-5,6-dimethyl-1,4-dithiin
• Synonyms: 2,3-dihydro-5,6-dimethyl-1,4-dithiin;1,4-Dithiin, 2,3-dihydro-5,6-dimethyl-;Einecs 245-225-7
• CAS NO: 22796-26-5
• Molecular Formula: C₆H₁₀S₂
• Molecular Weight: 146.2736
• EINECS: 245-225-7
• Mol File: 22796-26-5.mol

Chemical Properties

• Boiling Point: 228.3°Cat760mmHg
• Flash Point: 94.5°C
• Appearance: /
• Density: 1.086g/cm³
• Vapor Pressure: 0.112mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: 2,3-dihydro-5,6-dimethyl-1,4-dithiin(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dihydro-5,6-dimethyl-1,4-dithiin(22796-26-5)
• EPA Substance Registry System: 2,3-dihydro-5,6-dimethyl-1,4-dithiin(22796-26-5)

Safety Data

• Hazardous Substances Data: 22796-26-5(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Strong

Natural occurrence

Commonly found in garlic and other members of the Allium genus

Taste and odor characteristics

Sulfur-containing structure gives distinctive taste and odor

Health benefits

Potential antimicrobial, anti-inflammatory, and antioxidant properties

Potential uses

Natural food preservative and flavoring agent

InChI:InChI=1/C6H10S2/c1-5-6(2)8-4-3-7-5/h3-4H2,1-2H3

Upstream product

• 6008-81-7 2-ethyl-2-methyl-1,3-dithiolane 
• 513-86-0 3-hydroxy-2-butanon 
• 540-63-6 ethane-1,2-dithiol 
• 4091-39-8 3-chloro-2-butanone 
• 74637-13-1 1-(2-Methyl-[1,3]dithiolan-2-yl)-ethanol 
• 221047-35-4 2-[1(S)-hydroxyethyl]-2-methyl-1,3-dithiolane 
• 33266-07-8 2-acetyl-2-methyl-1,3-dithiolane 
• 69382-62-3 ethandithiol 
• 814-75-5 3-bromo-butanone 

Downstream Products

• 33266-07-8 2-acetyl-2-methyl-1,3-dithiolane 
• 55290-64-7 dimethipin 

Relevant articles and documents

Stereoselective azide introduction during 1,2-sulfur migration in α-hydroxyalkyldithioacetals

A series α-hydroxyalkyldithiolanes were reacted with a mixture of triphenylphosphine, diethyl azodicarboxylate and hydrazoic acid to give 2-azido-l,4-dithianes stereoselectively. Reduction of the azido group to an amine resulted in racemisation.

The Mechanism of the Mitsunobu Azide Modification and the Effect of Additives on the Rate of Hydroxyl Group Activation

The Mitsunobu azide modification has been studied by NMR using a hindered alcohol and the principle intermediates involved have been tentatively identified.The accelerated hydroxyl group activation in the presence of hydrazoic acid or of catalytic quantities of phenol gives us an insight into the reactivity of some of the intermediates involved in these reactions.

Synthesis of 2,3-dihydro-1,4-dithiins and 2-alkylidene-1,4-dithianes by 1,2-sulfur migration in 2-(1-hydroxyalkyl)-1,3-dithiolanes

2,3-Dihydro-1,4-dithiins and the isomeric 2-alkylidene-1,4-dithianes were synthesized from 1,2-diketones and alkyl pyruvates by kinetically controlled ring expansion of 2-(1-hydroxyalkyl)-1,3-dithiolanes with p-toluenesulfonyl chloride in pyridine. In addition, 2,3-dihydro-1,4-dithiins, the thermodynamic products, were formed exclusively by using p-toluenesulfonic acid in refluxing benzene. The 2-alkylidene-1,4-dithianes were readily isomerised to the corresponding 2,3-dihydro-1,4-dithiins. Similarly, 2,3-dimethyl-6,7-dihydro-5H-1,4-dithiepine and (+)-2-methylene-3-methyl-1,4-diethiepane were obtained from 2-[(S)-1-hydroxyethyl]-2-methyl-1,3-dithiane.

Preparation of Some Oxa- and Thia-decalins and -propellanes. Barriers to Conformational Interconversion

Reactions of 5,6-dihydro-2,3-dimethyl-1,4-dioxin, -1,4-oxathiin and -1,4-dithiin with bromine in the presence of 1,2-ethanediol, 2-mercaptoethanol and 1,2-ethanedithiol, respectively, afforded, in most cases, high yields of the corresponding oxa- and thia-decalins as cis-isomers only.Similar reactions of the bicyclic dihydrodioxins, 2,5-dioxabicyclodec-1(6)-ene and the sulfur analogues gave the corresponding propellanes in high yields.The barriers to conformational interconversion were obtained from variable temperature NMR spectra.Other examples of propellanes were obtained; addition of dihalocarbenes to the bicyclic dihydrodioxins furnished the corresponding dihalocyclopropane derivatives, and the photochemical addition of benzophenone gave the expected oxetane.

Reactivity of ethanediyl S,S-acetals; 2. Synthesis of 2,3-dihydro-1,4-dithiins

A new, reliable one-step synthesis of 2,3-dihydro-1,4-dithiins from ethanediyl S,S-acetal derivatives of carbonyl compounds is reported.

THE REACTION OF ETHANEDIYL S,S-ACETALS WITH HALOGENES

Cyclic thioacetals and thioketals (1,3-dithiolanes) are reported to react smoothly with halogens in a 1:1 molar ratio, at room temperature in anhydrous carbon tetrachloride.The mechanistic aspects of the reaction are considered and evidence is shown of the itermediacy of monocationic rather than the previously postulated dicatonic species in the cleavage reactions of 1,3-dithiolanes of aromatic ketones.

Method of making certain 2,3-dihydro-1,4-dithiins

A method of making certain 2,3-dihydro-1,4-dithiins of the following formula by the action of alpha-hydroxyketones (acyloins) of 1,2-dithiols: STR1 wherein R1 and R2 are hydrogen or alkyl having 1 to 6 carbon atoms or are joined together to form a ring with 3 or 4 methylene groups, and R3 and R4 are hydrogen or the same or different alkyl groups having 1 to 10 carbon atoms, which alkyl groups may be substituted with lower alkoxy groups.

Method of treating gastric ulcers using 5,6-dihydro-1,4-dithiinoxides

5,6-Dihydro-1,4-dithiinoxides, compositions containing the 5,6-dihydro-1,4-dithiinoxides as their active ingredient and methods useful in the treatment of gastric ulcers are disclosed.

Herbicidal method employing substituted dithin tetroxides

Regulation of the growth of plant life, including herbicidal, defoliant or desiccant effects, may be accomplished with certain 2,3-dihydro-1,4-dithiin 1,1,4,4-tetroxides of the formula STR1 wherein the R's have various values such as hydrogen, alkyl, etc. Certain of the compounds, such as 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide, are new chemicals, and are useful as pre-and post-emergent herbicides, and in harvest aid procedures, such as defoliation/desiccation of various crops, including cotton and potatoes.