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Diethylaminosulfur trifluoride CAS 38078-09-0 DAST

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  • Appearance: Yellow liquid
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Diethylaminosulfur trifluoride Supplement
38078-09-0

Basic Info of Diethylaminosulfur trifluoride

What is Diethylaminosulfur trifluoride?

Diethylaminosulfur trifluoride, commonly abbreviated DAST, is a widely used fluorination reagent in organic synthesis, and it is a member of the (dihydrocarbylamino)sulfur trifluoride family. DAST is a nucleophilic fluorination reagent, which can convert hydroxy compounds to monofluoro compounds, aldehydes and ketones to difluoro compounds, and has no effect on the carbonyl groups of carboxylic acids and their derivatives.

DAST is a liquid. It can be stored at room temperature or in a refrigerator for a long time under dry conditions. DAST will decompose at 90 °C, and there is a danger of explosion if improperly handled. However, DAST is one of the most widely used fluorinated reagents due to its simplicity and versatility.

Diethylaminosulfur trifluoride Uses

  1. Diethylaminosulfur trifluoride (DAST) is used as a fluorinating agent and a fluorinating agent on anticancer drugs. For example, react with alcohol to obtain corresponding fluoroalkane; react with acid chloride to obtain corresponding acid fluoride; react with aldehyde or ketone to obtain geminal difluoride; react with sulfoxide to obtain α-fluorosulfide, and then use perchlorobenzoic acid Oxidation gives α-fluorosulfoxide.
  2. Diethylaminosulfur Trifluoride is a very useful fluorinating agent in chemical synthesis. Diethylaminosulfur Trifluoride is also used as a reagent in the preparation of 2-thiazolines from (1,2)-thioam ido-alcohols.
  3. Diethylaminosulfur trifluoride (DAST) is used as a precursor to prepare 2,6-dimethoxybenzoyl fluoride and 2-thiazolines. It is a useful fluorinating agent used for a variety of compounds including alcohols, thioethers, alkenols and cyanohydrins. It also serves as a catalyst for Friedel-Crafts allylation reaction using tertiary cyclopropyl silyl ethers and in the rearrangement of homoallylic alcohols to unsaturated aldehydes. It plays an important role for gem difluorination of ketopipecolinic acids.

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Synthesis of Diethylaminosulfur Trifluoride

DAST converts alcohols to corresponding alkyl fluorides and aldehydes and unimpeded ketones to acyclic difluorides. Carboxylic acid only reacts with acyl fluoride (sulfur tetrafluoride affects the conversion of -co2 h → -cf 3). DAST is preferred over the more classical gaseous SF 4 because it is easier to handle as a liquid. A slightly thermally stable compound is morpho DAST. Acid unstable substrates are less likely to be rearranged and eliminated because DAST is less susceptible to acid contamination. The reaction temperature is also mild – alcohols usually react at -78 ° C and ketones at about 0 ° C.

DAST is prepared by the reaction of diethylaminotrimethylsilane and sulfur tetrafluoride:
Et 2 NSiMe 3 + SF 4 → Et 2 NSF 3 + Me 3 SiF
The initial paper required using trichlorofluoromethane (Freon-11) as a solvent, which has been outlawed by the Montreal Method and also is no more available as a commercial chemical. Ether is an eco-friendly substitute that can be made use of without minimizing manufacturing. As a result of the dangers associated with the prep work of DAST (glass etching, possibility of exothermic events), it is generally bought from commercial sources.

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