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235253

Sigma-Aldrich

(Diethylamino)sulfur trifluoride

95%

Synonym(s):

DAST, Diethylaminosulfur trifluoride

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About This Item

Linear Formula:
(C2H5)2NSF3
CAS Number:
38078-09-0
Molecular Weight:
161.19
Beilstein:
1849066
EC Number:
253-771-2
MDL number:
MFCD00000363
UNSPSC Code:
12352101
PubChem Substance ID:
24854092
NACRES:
NA.22

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

Product No.
Description
Pricing

719439

XtalFluor-E®

719447

XtalFluor-M®

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H242,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBR8353
SHBQ8478
SHBQ7881
SHBN7047
SHBM8882

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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
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)
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.
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
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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Articles

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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