235253
(Diethylamino)sulfur trifluoride
95%
Sinonimo/i:
DAST, Diethylaminosulfur trifluoride
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About This Item
Formula condensata:
(C2H5)2NSF3
Numero CAS:
Peso molecolare:
161.19
Beilstein:
1849066
Numero CE:
Numero MDL:
Codice UNSPSC:
12352101
ID PubChem:
NACRES:
NA.22
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Livello qualitativo
Saggio
95%
Forma fisica
liquid
P. eboll.
30-32 °C/3 mmHg (lit.)
Densità
1.22 g/mL at 25 °C (lit.)
Gruppo funzionale
amine
Temperatura di conservazione
2-8°C
Stringa SMILE
CCN(CC)S(F)(F)F
InChI
1S/C4H10F3NS/c1-3-8(4-2)9(5,6)7/h3-4H2,1-2H3
CSJLBAMHHLJAAS-UHFFFAOYSA-N
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Descrizione generale
Diethylamino sulfur trifluoride (DAST) is a fluorinating reagent used in the synthesis of fluorinated compounds and ring-opening reactions.
Applicazioni
- 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.
Sostituito da
N° Catalogo
Descrizione
Determinazione del prezzo
Avvertenze
Danger
Indicazioni di pericolo
Classi di pericolo
Eye Dam. 1 - Flam. Liq. 3 - Self-react. D - Skin Corr. 1A
Rischi supp
Codice della classe di stoccaggio
5.2 - Organic peroxides and self-reacting hazardous materials
Classe di pericolosità dell'acqua (WGK)
WGK 3
Punto d’infiammabilità (°F)
73.4 °F
Punto d’infiammabilità (°C)
23 °C
Dispositivi di protezione individuale
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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A J Phillips et al.
Organic letters, 2(8), 1165-1168 (2000-05-11)
[formula: see text] A mild and highly efficient cyclization of beta-hydroxy amides to oxazolines is described using DAST and Deoxo-Fluor reagents. A one-pot protocol for the synthesis of oxazoles from beta-hydroxy amides is also presented.
P G Hultin et al.
Carbohydrate research, 322(1-2), 14-25 (2000-01-12)
We have made thioglycoside donors for the 4,6-dideoxy-L-lyxo-hexopyranosyl ('4-deoxy-L-rhamnosyl') and 4-deoxy-4-fluoro-L-rhamnosyl monosaccharide residues. The preparation of the deoxyfluororhamnose was not straightforward, and revealed some unexpected behavior of the diethylaminosulfur trifluoride (DAST) reagent. The new glycosyl donors were used to synthesize
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
Aurélien Bigot et al.
Organic letters, 13(2), 192-195 (2010-12-15)
The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of α,α-disubstituted-α-acylaminoketones. The resulting fluorooxazolines can be ring-opened or selectively substituted by a range of nucleophiles to provide in high yields
Jindřich Karban et al.
Organic & biomolecular chemistry, 10(2), 394-403 (2011-11-16)
A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4-dianhydropyranoses yielded solely products of skeletal rearrangement resulting from migration of the tetrahydropyran oxygen (educts of D-altro and D-talo configuration) or of the 1,6-anhydro bridge
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