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)
A E Lloyd et al.
Nucleic acids symposium series, (27)(27), 185-186 (1992-01-01)
Pyrimidine nucleosides (or their 5'-aldehydes) when treated with DAST give O2,5'-(fluoro)-anhydronucleosides. If this is prevented by blocking N-3 or O4, the desired 5'-deoxy-5'-(di)-fluoronucleoside is accompanied by the production of a compound resulting from migration of the base following scission of
Yasser M Loksha et al.
Archiv der Pharmazie, 342(9), 501-506 (2009-07-29)
1-Substiuted 6-(3-cyanobenzoyl) and [(3-cyanophenyl)fluoromethyl]-5-ethyl-uracils were synthesized and evaluated in cell-based assays against HIV-1 wild-type and its clinically relevant non-nucleoside reverse transcriptase inhibitor (NNRTI)-resistant mutants. Some of the synthesized compounds showed activity against HIV-1 wild-type in the same range as Emivirine
E Poirot et al.
Carbohydrate research, 334(3), 195-205 (2001-08-22)
Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-alpha-D-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl
M Wenckens et al.
Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 52(4), 503-507 (1998-04-29)
It is documented that specific types of sterol play a major role in the resumption of meiosis in oocytes from mice in vitro. 4,4-Dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol (FF-MAS) isolated from human follicular fluid and 4,4-dimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol (T-MAS) isolated from bull
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