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235253

Sigma-Aldrich

(Diethylamino)sulfur trifluoride

(Diethylamino)sulfur trifluoride
1 of 1 reviewers received a sample product or took part in a promotion

95%

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:
24854092
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

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

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General description

Diethylamino sulfur trifluoride (DAST) is a fluorinating reagent used in the synthesis of fluorinated compounds and ring-opening reactions.[1]

Application

  • Fluorinating agent: reaction with alcohols and carbonyl compounds, Review[2][3]
  • Review on nucleophilic fluorination.[3]
  • Catalyst for Friedel-Crafts allylation using tertiary cyclopropyl silyl ethers[4] and the rearrangement of homoallylic alcohols to unsaturated aldehydes.[5]
  • Early introduction of a fluoromethyl group stabilizes the epoxide during further manipulations in the synthesis of 26-fluoro-epothilone.[6]
  • Fluorinating agent for a variety of compounds, including thioethers, alkenols, and cyanohydrins.[7][8][9]
  • Reagent for gem difluorination of ketopipecolinic acids.[10]

replaced by

Product No.
Description
Pricing

719439

XtalFluor-E®

719447

XtalFluor-M®

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR8353
SHBQ8478
SHBQ7881
SHBN7047
SHBM8882

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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.
Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes
M. Hudlicky
Org. React., 35, 513-513 (1988)
Recent advances in nucleophilic fluorination reactions of organic compounds using Deoxofluor and DAST
RP Singh, et al.
Synthesis, 2002, 2561-2578 (2002)
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Questions

1–6 of 6 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. How should Product 235253, (Diethylamino) sulfur trifluoride (DAST), be handled?

    1 answer

    1. This product is water reactive and should be kept under nitrogen and stored at 2-8°C. It can decompose to hydrofluoric acid upon contact with water,  which could etch glassware. We sell the product in plastic (Linear High Density Polyethylene) bottles.

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  4. What solvents are miscible with Product 235253, (Diethylamino) sulfur trifluoride (DAST)?

    1 answer

    1. Although Sigma-Aldrich doesn't test the solubility of this reagent, references suggest using a non-polar and non-basic solvent, which would reduce the potential for intermediate carbocation formation and subsequent structural rearrangements in the final product.

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  5. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  6. Where can I find references citing the use of Product 235253, (Diethylamino) sulfur trifluoride (DAST)?

    1 answer

    1. The following journals mention the use of this reagent. 1. J. Org. Chem. 58, 3800, (1993) 2. Tet. Lett. 32, 5963, (1991) 3. Tet. Asym. 4, 161, (1993) 4. Synthesis 17, 2561-2578, (2002) 5. Tet. Lett. 45, 1445-1447, (2004) 6. Tetrahedron Lett. 47, 3777, (2006) 7. Org. Lett. 8, 2091, (2006) 8. Synlett 4, 693-697, (2004)

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Reviews

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