31942
(Diethylamino)sulfur trifluoride
technical, packed in PTFE bottles, ≥90% (NMR)
Synonym(s):
DAST, Diethylaminosulfur trifluoride
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About This Item
Linear Formula:
(C2H5)2NSF3
CAS Number:
Molecular Weight:
161.19
Beilstein:
1849066
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
grade
technical
Assay
≥90% (NMR)
quality
packed in PTFE bottles
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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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.
recommended
Product No.
Description
Pricing
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
dust mask type N95 (US), Eyeshields, Gloves
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Stereoselective introduction of a trifluoromethyl group into an unsaturated system
Tetrahedron Letters, 32, 5963-5963 (1991)
Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes
M. Hudlicky
Org. React., 35, 513-513 (1998)
Po-Chiao Lin et al.
The Journal of organic chemistry, 74(11), 4041-4048 (2009-05-16)
When saccharides bearing a sulfur, selenium, or oxygen substituent at the anomeric center and an unprotected hydroxyl group either at C-4 or C-6 were subjected to fluorination with DAST in dichloromethane, a regioselective migration of the anomeric substituent to the
Synthesis of monodeoxyfluorinated, mucin-type oligosaccharide fragments.
R L Thomas et al.
Carbohydrate research, 165(2), c14-c16 (1987-08-01)
Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride. Part 2: The Friedel-Crafts allylation and cyclopropylation of electron-rich aromatic compounds
Kirihara, Masayuki, et al.
Tetrahedron Letters, 47, 3777-3777 (2006)
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