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235253 Aldrich

(Diethylamino)sulfur trifluoride

95%

Synonym: DAST, Diethylaminosulfur trifluoride

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Properties

Related Categories Chemical Synthesis, Fluorination, Fluorination Reagents, Synthetic Reagents
InChI Key   CSJLBAMHHLJAAS-UHFFFAOYSA-N
assay   95%
form   liquid
bp   30-32 °C/3 mmHg(lit.)
density   1.22 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Packaging

1, 5, 25 g in poly bottle

Application

• Fluorinating agent: reaction with alcohols and carbonyl compounds, Review
• Review on nucleophilic fluorination.
• Catalyst for Friedel-Crafts allylation using tertiary cyclopropyl silyl ethers and the rearrangement of homoallylic alcohols to unsaturated aldehydes.
• Early introduction of a fluoromethyl group stabilizes the epoxide during further manipulations in the synthesis of 26-fluoro-epothilone.
• Fluorinating agent for a variety of compounds, including thioethers, alkenols, and cyanohydrins.
• Reagent for gem difluorination of ketopipecolinic acids.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
Reacts violently with water.
RIDADR 
UN3225 - class 4.1 - Self-reactive liquid type D (DIETHYLAMINOSULFUR TRIFLUORIDE), HI: all
WGK Germany 
3
Flash Point(F) 
73.4 °F
Flash Point(C) 
23 °C

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
What solvents are miscible with Product 235253, (Diethylamino) sulfur trifluoride (DAST)?
Although Sigma-Aldrich doesn't test the solubility of this reagent, references suggest using a non-polar and non-basic solvent, which would reduce the potential for intermediate carbocation formation and subsequent structural rearrangements in the final product.
How shouldProduct 235253, (Diethylamino) sulfur trifluoride (DAST), be handled?
This product is water reactive and should be kept under nitrogen and stored at 2-8°C. It can decompose to hydrofluoric acid upon contact with water, which could etch glassware. We sell the product in plastic (Linear High Density Polyethylene) bottles.
Where can I find references citing the use of Product 235253, (Diethylamino) sulfur trifluoride (DAST)?
The following journals mention the use of this reagent.1. J. Org. Chem. 58, 3800, (1993)2. Tet. Lett. 32, 5963, (1991)3. Tet. Asym. 4, 161, (1993)4. Synthesis 17, 2561-2578, (2002)5. Tet. Lett. 45, 1445-1447, (2004)6.Tetrahedron Lett. 47, 3777, (2006)7. Org. Lett. 8, 2091, (2006)8.Synlett 4, 693-697, (2004)
How do I find price and availability?
There are several ways to find pricing and availability for our products.Once you log onto our website, you will find the price and availability displayed on the product detail page.You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 orview local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
My question is not addressed here, how can I contact Technical Service for assistance?
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Protocols & Articles

Articles

Reagents for Fluorination

The trifluoromethyl substituent has long been recognized for the positive influence it can have on the biological activity of molecules. Professor William Dolbier, Jr. (University of Florida) has dev...
Aldrich ChemFiles 2007, 7.1, 11.

Peer-Reviewed Papers
15

References

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