Thioacetic Acid Powder CAS 507-09-5

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Thioacetic acid powder, also known as thioacetic acid, is an organic compound, CAS 507-09-5, The chemical formula is c2h4os. Colorless and transparent liquid, with unpleasant and irritating odor, easily soluble in water, ethanol, ether, etc. It is not stable against oxidants and strong bases, and has corrosiveness and a slight tear inducing effect. In addition, it also has an uncomfortable foul odor and can form explosive mixtures with the air, so it must be sealed and stored in a fume hood when in use. Obtained by heating and refluxing acetic acd and phosphorus pentasulfide together. In organic synthesis, it is used as an acetylthio and thiol agent, for the preparation of cysteine and thiol carboxylic acd compounds, as well as for the synthesis of fungicides, polymer modifiers, and additives. Mainly used as chemical reagents, organic synthesis reagents, tear gas agents, etc.

There are four methods for preparing thioacetic acid in the laboratory:

1. Acetic acid reacts with phosphorus pentasulfide at 91 ℃ and is further refined by vacuum distillation. Can be made. 5CH3COOH+P2S5→CH3COSHC2H4OS+P2O5

It is obtained by CO thermal distillation of glacial aldehyde acid and pentathiodiphosphate. Add fine powdered phosphorus pentasulfide to glacial acetic acid. When heated to 91 ℃, thioacetic acid begins to evaporate. Explosion and boiling must be prevented during heating, and the distillation temperature shall not exceed 100 ℃. The distillate is re distilled once to get the finished product.

2. Acetyl chloride reacts with hydrogen sulfide, neutralizes with dilute alkali solution, and then rectifies and refines. Can be made.

3. Acetic anhydride reacts with hydrogen sulfide to produce thioacetic acid, and acetic acid is also a by-product.

4. Vinyl ketone can be directly prepared by reacting with hydrogen sulfide.

It has active chemical properties and strong reactivity. It can react with unsaturated aliphatic hydrocarbons and alcohols to prepare mercaptans.

CH₃COSH+CH₂＝CHCH₃→CH₃CH₂CH₂SHCH₃COSH+CH₃CH₂OH→CH₃CH₂SH

reacts with ethylene oxide to prepare acetylthioethanol.

CH₃COSH+(CH₂)₂O→CH₃COSCH₂CH₂OH

Soil improvement

 

Improve soil structure
Thioacetic acid powder can be used as a soil amendment to improve soil structure, increase soil fertility, enhance soil permeability and water retention, and provide a favorable soil environment for crop growth.

Remediation of polluted soil
Thioacetate salts have been used as stabilizers and preparation methods for soil remediation of mercury, arsenic, antimony, and bismuth contaminated soils, demonstrating good remediation effects. This indicates that thioacetic acid has certain potential for application in soil pollution control.

Feed additives

 

Improve the nutritional value of feed
Thioacetic acid, as a new type of feed additive, has attracted much attention in animal husbandry. It can improve the nutritional value of feed and increase the digestion and absorption rate of animals towards feed.

Promote animal growth
Thioacetic acd can also promote protein synthesis in animals, which is beneficial for their growth and development. Research has shown that adding an appropriate amount of thioacetic acd to feed can significantly improve the growth rate of animals.

 

Antioxidant and anti-inflammatory effects
Thioacetic acd also has antioxidant and anti-inflammatory effects, which can effectively alleviate animal stress reactions and reduce disease incidence. At the same time, it can also improve the intestinal environment of animals, reduce the growth of bad bacteria, and maintain intestinal health.

Improve feed conversion rate
Feed conversion rate is an important indicator for measuring feed utilization efficiency. After adding thioacetic acd, the nutrients in the feed are more easily digested and absorbed by animals, thereby improving feed conversion rate and reducing breeding costs.

Fruit and vegetable preservation

 

Inhibit discoloration of fruit and vegetable tissues
Thioacetate compounds can be used to inhibit discoloration of fruit and vegetable tissues and extend shelf life. For example, treating fresh cut potato shreds with thioacetic acid bran ester solution can effectively inhibit their browning and maintain their commercial value. The implementation example shows that the processed potato shreds can maintain their original color even after being left at room temperature for multiple days, while the control sample rapidly turns brown. Thioacetic acid has strong antibacterial effects and can inhibit the process of fruit and vegetable decay and browning, thereby extending the shelf life of fruits and vegetables.

Thioacetic acid, has the molecular formula C ₂ H ₄ OS, a molecular weight of 76.13, and a CAS number of 507-09-5. This light yellow liquid is relatively stable at room temperature, but it should be noted that it is not stable to oxidants and strong bases, and has corrosiveness and a slight tear inducing effect. In addition, it also has an uncomfortable foul odor and can form explosive mixtures with the air, so it must be sealed and stored in a fume hood when in use.

 

In the field of organic synthesis, thioacetic acd is a multifunctional reagent. It is often used as an acylating agent to convert alcohols into acetic acd thiol esters, as well as a sulfur-containing Michael addition nucleophile. Under the combined action of pH 3P and EtO ₂ CN=NCO ₂ Et, thioacetic acd can undergo Mitsunobu reactions with various primary and secondary alcohols, thereby generating acetic acd thiol esters. It is worth noting that when reacting with optically active secondary alcohols, esters with configuration inversion will be obtained. These esters can further undergo hydrolysis or oxidation reactions to generate corresponding thiol or sulfonic acid derivatives.

 

Under conventional conditions, thioacetic acid has not shown significant advantages as an acylation reagent compared to acetyl chloride and acetic anhydride. However, in certain specific situations, thioacetic acid can selectively acylate amino groups in the presence of hydroxyl groups. In addition, it can first reduce the azide group to an amino group, and then directly undergo acetylation reaction to obtain acetamide derivatives.

Thioacetic acid powder has shown wide applications in the Michael reaction, and can undergo conjugate addition with various Michael receptors to generate corresponding acetic acd thiol ester compounds. These receptors include alpha, beta unsaturated aldehydes, quinones, carboxylic acds and their derivatives esters and amides, as well as nitroalkenes. Specifically, when added with α, β - unsaturated aldehydes and ketones, acetic acid thiol ester compounds can be efficiently generated.

After the addition reaction between thioacetic acd and α, β - unsaturated carboxylic acd lactones, corresponding acetic acd thiol ester compounds will be generated. If there is an excess of thioacetic acid, it will also undergo 1,4-addition reaction with dienes in the molecule, resulting in the formation of diacetate thiol ester compounds. It is worth noting that the 1,4-addition reaction between thioacetic acd and diene belongs to the free radical addition type.

Thioacetic acid can also undergo addition reactions with nitroalkenes to produce acetic acid nitrothiol ester compounds.

Thioacetic acid not only participates in addition reactions, but also acts as a nucleophilic ring opening reagent, reacting with ternary heterocycles to obtain adjacent bifunctional compounds. Taking the reaction between thioacetic acid and nitrogen heterocyclic propane as an example, the reaction first generates the ring opening product - the acetate of ortho aminothiol. It is worth noting that this unstable ester will immediately undergo intramolecular acyl migration reaction, ultimately generating N-acetylaminothiol.
In the reaction between thioacetic acid and olefins, free radical addition is a crucial step that can generate acetic acid nitrothiol ester compounds. This addition reaction exhibits a certain degree of stereoselectivity, usually with cis acetic acid thiol ester as the main product. However, it is worth noting that these compounds are not stable and will further hydrolyze into the corresponding thiol compounds. Similarly, thioacetic acid can undergo free radical addition with alkynes to form vinyl mercaptan ester compounds. In the process of free radical addition, the yield of the reaction can be increased by adding initiators or light conditions. When using asymmetric olefins and alkynes as reaction substrates, the addition reaction exhibits a certain degree of regioselectivity. Due to following the free radical addition mechanism, this reaction typically generates anti Markovian products.

Thioacetic acid powder is a commonly used acylating agent and sulfur-containing Michael addition nucleophile for converting alcohols into acetic acid thiol esters. It is mainly used in organic synthesis to prepare acetic acid thiol ester compounds.
In the presence of Ph ∝ P and EtO ₂ CN=NCO ₂ Et, the reagent reacts with various primary and secondary alcohols to produce acetic acid thiol esters. When optically active secondary alcohols are used, esters with configuration inversion can be obtained. The obtained ester can be further hydrolyzed to generate corresponding thiols or oxidized to corresponding sulfonic acid derivatives.

Under normal conditions, thioacetic acid as an acylation reagent does not have significant advantages compared to acetyl chloride and acetic anhydride. But under certain conditions, thioacetic acid can selectively acylate amino groups in the presence of hydroxyl groups. Thioacetic acid can also first reduce the azide group to an amino group, and then directly acetylate it to obtain acetamide derivatives.

The most widely used application of thioacetic acid is as a Michael donor, which undergoes conjugate addition reactions with different Michael receptors. For example, addition reactions can occur with α, β - unsaturated aldehydes, ketones, quinones, carboxylic acids and their derivatives esters, amides, nitroalkenes, etc., to obtain corresponding acetic acid thiol ester compounds. Thioacetic acid undergoes addition reaction with α, β - unsaturated aldehydes and ketones to obtain the corresponding acetic acid thiol ester compounds.

Thioacetic acid undergoes addition reaction with α, β - unsaturated carboxylic acid lactones to obtain corresponding acetic acid thiol ester compounds. When thioacetic acid is excessive, the excess thioacetic acid will further undergo 1,4-addition reaction with dienes in the molecule to obtain corresponding diacetic acid thiol ester compounds. The 1,4-addition reaction between thioacetic acid and dienes belongs to free radical addition.

Thioacetic acid can undergo addition reactions with nitroalkenes to obtain corresponding acetic acid nitrothiol ester compounds.

Thioacetic acid can also act as a nucleophilic ring opening reagent to undergo ring opening reactions on ternary heterocycles, resulting in adjacent bifunctional compounds. For example, the reaction between thioacetic acid and nitrogen heterocyclic propane first yields the acetic acid ester of the ring opening product ortho aminothiol. Then, the unstable ester immediately undergoes intramolecular acyl migration reaction in situ, generating N-acetylaminothiol.

Thioacetic acid can undergo free radical addition with olefins to form corresponding acetic acid nitrothiol ester compounds. This addition reaction has a certain degree of stereoselectivity and mainly generates cis acetic acid thiol ester. But it is not very stable and hydrolyzes to obtain corresponding thiol compounds. Thioacetic acid can undergo free radical addition with alkynes to generate corresponding vinyl mercaptan ester compounds. When thioacetic acid undergoes free radical addition, the addition of a free radical initiator or under light conditions can increase the yield. When using asymmetric olefins and alkynes as substrates, the addition reaction exhibits a certain degree of regioselectivity. Due to the free radical addition mechanism, this reaction mainly generates anti Markovian products.

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