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Sigma-Aldrich

(Diethylamino)sulfur trifluoride

95%

Sinónimos:

DAST, Diethylaminosulfur trifluoride

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About This Item

Fórmula lineal:
(C2H5)2NSF3
Número de CAS:
38078-09-0
Peso molecular:
161.19
Beilstein:
1849066
Número CE:
253-771-2
Número MDL:
MFCD00000363
Código UNSPSC:
12352101
ID de la sustancia en PubChem:
24854092
NACRES:
NA.22

Nivel de calidad

100

Ensayo

95%

Formulario

liquid

bp

30-32 °C/3 mmHg (lit.)

densidad

1.22 g/mL at 25 °C (lit.)

grupo funcional

amine

temp. de almacenamiento

2-8°C

cadena SMILES

CCN(CC)S(F)(F)F

InChI

1S/C4H10F3NS/c1-3-8(4-2)9(5,6)7/h3-4H2,1-2H3

Clave InChI

CSJLBAMHHLJAAS-UHFFFAOYSA-N

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Descripción general

Diethylamino sulfur trifluoride (DAST) is a fluorinating reagent used in the synthesis of fluorinated compounds and ring-opening reactions.

Aplicación

  • 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.

sustituido por

Referencia del producto
Descripción
Precios

719439

XtalFluor-E®

719447

XtalFluor-M®

Pictogramas

FlameCorrosion
GHS02,GHS05

Palabra de señalización

Danger

Frases de peligro

H226,H242,H314

Clasificaciones de peligro

Eye Dam. 1 - Flam. Liq. 3 - Self-react. D - Skin Corr. 1A

Riesgos supl.

EUH014

Código de clase de almacenamiento

5.2 - Organic peroxides and self-reacting hazardous materials

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

73.4 °F

Punto de inflamabilidad (°C)

23 °C

Equipo de protección personal

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
SHBR8353
SHBQ8478
SHBQ7881
SHBN7047
SHBM8882

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Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

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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)
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
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
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
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Artículos

Diethylaminosulfur Trifluoride (DAST)

Diethylaminosulfur trifluoride (DAST) facilitates nucleophilic fluorination in selective reactions with alcohols, ketones, and other compounds.

Diethylaminosulfur Trifluoride (DAST)

Diethylaminosulfur trifluoride (DAST) facilitates nucleophilic fluorination in selective reactions with alcohols, ketones, and other compounds.

Diethylaminosulfur Trifluoride (DAST)

Diethylaminosulfur trifluoride (DAST) facilitates nucleophilic fluorination in selective reactions with alcohols, ketones, and other compounds.

Diethylaminosulfur Trifluoride (DAST)

Diethylaminosulfur trifluoride (DAST) facilitates nucleophilic fluorination in selective reactions with alcohols, ketones, and other compounds.

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