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774642

Sigma-Aldrich

(Diethylamino)sulfur trifluoride solution

1.0 M in dichloromethane

Synonym(s):

DAST solution in dichloromethane

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About This Item

Empirical Formula (Hill Notation):
C4H10F3NS
CAS Number:
38078-09-0
Molecular Weight:
161.19
MDL number:
MFCD00000363
UNSPSC Code:
12352101
PubChem Substance ID:
329767703
NACRES:
NA.22

form

liquid

concentration

1.0 M in dichloromethane

density

1.303 g/mL at 25 °C

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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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.

Signal Word

Danger

Hazard Statements

H226,H314,H336,H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1A - STOT SE 3

Target Organs

Central nervous system

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

75.2 °F

Flash Point(C)

24 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kirihara, Masayuki
Tetrahedron Letters, 47(22), 3777-3777 (2006)
Nucleic acid related compounds. 79. Efficient conversions of thioethers to a-fluoro thioethers with DAST or DAST/antimony(III) chloride
The Journal of Organic Chemistry, 58(15), 3800-3800 (1993)
Sophie Canova et al.
Organic letters, 8(10), 2091-2094 (2006-05-05)
[reaction: see text] Treatment of beta,gamma-unsaturated monoprotected 1,2-diols with diethylaminosulfur trifluoride (DAST) allows the stereoselective formation of beta,gamma-unsaturated aldehydes in good yields and with a good transfer of chirality.
Enzyme-catalyzed reactions. 16. Preparation of (S)-2-fluoronitriles
Stelzer, U.; Effenberger, F.
Tetrahedron Asymmetry, 4, 161-161 (1993)
Stereoselective introduction of a trifluoromethyl group into an unsaturated system
Tellier, F.; Sauvetre, R.
Tetrahedron Letters, 32, 5963-5963 (1991)
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