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Merck
CN

235253

二乙胺基三氟化硫

95%

别名:

DAST, 二乙氨基三氟化硫

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线性分子式:
(C2H5)2NSF3
化学文摘社编号:
38078-09-0
分子量:
161.19
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24854092
EC Number:
253-771-2
Beilstein/REAXYS Number:
1849066
MDL number:
MFCD00000363

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产品名称

二乙胺基三氟化硫, 95%

InChI key

CSJLBAMHHLJAAS-UHFFFAOYSA-N

InChI

1S/C4H10F3NS/c1-3-8(4-2)9(5,6)7/h3-4H2,1-2H3

SMILES string

CCN(CC)S(F)(F)F

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

Quality Level

100

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相关类别

Application

  • 氟化剂：与醇和羰基化合物反应，综述
  • 关于亲核氟化的综述。
  • 在使用叔环丙基甲硅烷基醚进行Friedel-Crafts烯丙基化 和均聚醇重排成不饱和醛过程中的催化剂。
  • 在26-氟-埃坡霉素的合成中，氟甲基的早期引入可在进一步的操作过程中稳定环氧化物。
  • 可用于多种化合物（包括硫醚、链烯醇和氰醇）的氟化剂。
  • 用于酮基哌啶酸的宝石二氟化试剂。

General description

二乙氨基三氟化硫（DAST）是一种氟化试剂，用于合成含氟化合物和开环反应。

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH014

存储类别

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

法规信息

危险化学品
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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
SHBR8353
SHBQ8478
SHBQ7881
SHBN7047
SHBM8882

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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

    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.

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

    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.

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

    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)

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Recent advances in nucleophilic fluorination reactions of organic compounds using Deoxofluor and DAST
RP Singh, et al.
Synthesis, 2002, 2561-2578 (2002)
A J Phillips et al.
Organic letters, 2(8), 1165-1168 (2000-05-11)
[formula: see text] A mild and highly efficient cyclization of beta-hydroxy amides to oxazolines is described using DAST and Deoxo-Fluor reagents. A one-pot protocol for the synthesis of oxazoles from beta-hydroxy amides is also presented.
Jindřich Karban et al.
Organic & biomolecular chemistry, 10(2), 394-403 (2011-11-16)
A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4-dianhydropyranoses yielded solely products of skeletal rearrangement resulting from migration of the tetrahydropyran oxygen (educts of D-altro and D-talo configuration) or of the 1,6-anhydro bridge
Aurélien Bigot et al.
Organic letters, 13(2), 192-195 (2010-12-15)
The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of α,α-disubstituted-α-acylaminoketones. The resulting fluorooxazolines can be ring-opened or selectively substituted by a range of nucleophiles to provide in high yields
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)
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商品

Diethylaminosulfur Trifluoride (DAST)

Diethylaminosulfur trifluoride (DAST) facilitates nucleophilic fluorination in selective reactions with alcohols, ketones, and other compounds.

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