235253
(Diethylamino)sulfur trifluoride
95%
Synonym(s):
DAST, Diethylaminosulfur trifluoride
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About This Item
Linear Formula:
(C2H5)2NSF3
CAS Number:
Molecular Weight:
161.19
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
EC Number:
253-771-2
Beilstein/REAXYS Number:
1849066
MDL number:
Assay:
95%
Form:
liquid
Quality Level
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
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Flam. Liq. 3 - Self-react. D - Skin Corr. 1A
supp_hazards
Storage Class
5.2 - Organic peroxides and self-reacting hazardous materials
wgk
WGK 3
flash_point_f
73.4 °F
flash_point_c
23 °C
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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Articles
Diethylaminosulfur trifluoride (DAST) facilitates nucleophilic fluorination in selective reactions with alcohols, ketones, and other compounds.
Stereoselective introduction of a trifluoromethyl group into an unsaturated system
Tellier, F.; Sauvetre, R.
Tetrahedron Letters, 32, 5963-5963 (1991)
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
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.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 235253-1G | 04061838784971 |
| 235253-5G | 04061838784995 |
| 235253-125G | 04061838231222 |
| 235253-25G | 04061838784988 |