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
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
EC Number:
253-771-2
Beilstein/REAXYS Number:
1849066
MDL number:
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
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Flam. Liq. 3 - Self-react. D - Skin Corr. 1A
supp_hazards
Storage Class
5.2 - Organic peroxides and self-reacting hazardous materials
wgk
WGK 3
flash_point_f
73.4 °F
flash_point_c
23 °C
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Regulatory Information
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S De Jonghe et al.
Bioorganic & medicinal chemistry letters, 9(21), 3159-3164 (1999-11-24)
Short-chain 3-fluoro-(dihydro)ceramide analogues are synthesized from L-serine using diethylaminosulfur trifluoride (DAST) as fluorinating agent. The apoptogenic activity of these compounds was measured in three different cell lines and compared with their hydroxylated counterparts.
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
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