Quality Level
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
SMILES string
CCN(CC)S(F)(F)F
InChI
1S/C4H10F3NS/c1-3-8(4-2)9(5,6)7/h3-4H2,1-2H3
InChI key
CSJLBAMHHLJAAS-UHFFFAOYSA-N
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Related Categories
General description
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.
replaced by
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Flam. Liq. 3 - Self-react. D - Skin Corr. 1A
Supplementary Hazards
Storage Class Code
5.2 - Organic peroxides and self-reacting hazardous materials
WGK
WGK 3
Flash Point(F)
73.4 °F
Flash Point(C)
23 °C
Personal Protective Equipment
Regulatory Information
Certificates of Analysis (COA)
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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 should Product 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)
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Articles
Diethylaminosulfur trifluoride (DAST) is ideal for nucleophilic fluorination and has been used in selective fluorinations of alcohols, alkenols, carbohydrates, ketones, sulfides, epoxides, thioethers, and cyanohydrins.
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