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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

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

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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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.
Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes
M. Hudlicky
Org. React., 35, 513-513 (1988)
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)
Nucleic acid related compounds. 79. Efficient conversions of thioethers to α-fluoro thioethers with DAST or DAST/antimony(III) chloride
The Journal of Organic Chemistry, 58, 3800-3800 (1993)
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