774642
(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:
Molecular Weight:
161.19
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
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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[1][2]
- Review on nucleophilic fluorination.[2]
- Catalyst for Friedel-Crafts allylation using tertiary cyclopropyl silyl ethers[3] and the rearrangement of homoallylic alcohols to unsaturated aldehydes.[4]
- Early introduction of a fluoromethyl group stabilizes the epoxide during further manipulations in the synthesis of 26-fluoro-epothilone.[5]
- Fluorinating agent for a variety of compounds, including thioethers, alkenols, and cyanohydrins.[6][7][8]
- Reagent for gem difluorination of ketopipecolinic acids.[9]
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1A - STOT SE 3
Target Organs
Central nervous system
Supplementary Hazards
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
75.2 °F
Flash Point(C)
24 °C
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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)
Stereoselective introduction of a trifluoromethyl group into an unsaturated system
Tellier, F.; Sauvetre, R.
Tetrahedron Letters, 32, 5963-5963 (1991)
Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes
M. Hudlicky
Org. React., 35, 513-513 (1988)
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.
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