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Sigma-Aldrich

(Diethylamino)sulfur trifluoride

technical, packed in PTFE bottles, ≥90% (NMR)

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:
57648628
NACRES:
NA.22

grade

technical

Assay

≥90% (NMR)

quality

packed in PTFE bottles

bp

30-32 °C/3 mmHg (lit.)

density

1.22 g/mL at 25 °C (lit.)

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.

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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

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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Stereoselective introduction of a trifluoromethyl group into an unsaturated system
Tetrahedron Letters, 32, 5963-5963 (1991)
M Wenckens et al.
Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 52(4), 503-507 (1998-04-29)
It is documented that specific types of sterol play a major role in the resumption of meiosis in oocytes from mice in vitro. 4,4-Dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol (FF-MAS) isolated from human follicular fluid and 4,4-dimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol (T-MAS) isolated from bull
E Poirot et al.
Carbohydrate research, 334(3), 195-205 (2001-08-22)
Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-alpha-D-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl
Bruno Anxionnat et al.
The Journal of organic chemistry, 77(14), 6087-6099 (2012-06-13)
As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope
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.
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