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31942

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/REAXYS Number:
1849066
EC Number:
253-771-2
MDL number:
MFCD00000363
UNSPSC Code:
12352101
PubChem Substance ID:
57648628
NACRES:
NA.22
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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[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]

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pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 3 - Self-react. D - Skin Corr. 1A

supp_hazards

EUH014

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk_germany

WGK 3

flash_point_f

73.4 °F

flash_point_c

23 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCBJ7670V
BCBJ4315V
BCBJ8916V
BCBG9807V
BCBF7001V

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Stereoselective introduction of a trifluoromethyl group into an unsaturated system
Tetrahedron Letters, 32, 5963-5963 (1991)
Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride. Part 2: The Friedel-Crafts allylation and cyclopropylation of electron-rich aromatic compounds
Kirihara, Masayuki, et al.
Tetrahedron Letters, 47, 3777-3777 (2006)
Synthesis of monodeoxyfluorinated, mucin-type oligosaccharide fragments.
R L Thomas et al.
Carbohydrate research, 165(2), c14-c16 (1987-08-01)
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.
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
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