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235253

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/REAXYS Number:
1849066
EC Number:
253-771-2
MDL number:
MFCD00000363
UNSPSC Code:
12352101
PubChem Substance ID:
24854092
NACRES:
NA.22

Quality Level

100

assay

95%

form

liquid

bp

30-32 °C/3 mmHg (lit.)

density

1.22 g/mL at 25 °C (lit.)

functional group

amine

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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General description

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

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.

replaced by

Referencia del producto
Descripción
Precios

719439

XtalFluor-E®

719447

XtalFluor-M®

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH014

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk_germany

WGK 3

flash_point_f

73.4 °F

flash_point_c

23 °C

ppe

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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Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes
M. Hudlicky
Org. React., 35, 513-513 (1988)
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.
Stereoselective introduction of a trifluoromethyl group into an unsaturated system
Tellier, F.; Sauvetre, R.
Tetrahedron Letters, 32, 5963-5963 (1991)
Recent advances in nucleophilic fluorination reactions of organic compounds using Deoxofluor and DAST
RP Singh, et al.
Synthesis, 2002, 2561-2578 (2002)
M Kirihara et al.
Chemical & pharmaceutical bulletin, 48(2), 220-222 (2000-03-08)
Diethylaminosulfur trifluoride reacted with cyclic ketoximes bearing substituent(s) that can stabilize a carbocation to cause fluorinative fragmentation, affording fluorinated carbonitrile. Ketoximes lacking such substituents afforded complex mixtures. However, the introduction of a sulfur functionality, which can stabilize a carbocation and
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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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