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235253

Sigma-Aldrich

二乙胺基三氟化硫

95%

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别名:
DAST, 二乙氨基三氟化硫
线性分子式:
(C2H5)2NSF3
CAS号:
38078-09-0
分子量:
161.19
Beilstein:
1849066
EC 号:
253-771-2
MDL编号:
MFCD00000363
PubChem化学物质编号:
24854092
NACRES:
NA.22

质量水平

100

检测方案

95%

形式

liquid

bp

30-32 °C/3 mmHg (lit.)

密度

1.22 g/mL at 25 °C (lit.)

储存温度

2-8°C

SMILES字符串

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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相关类别

一般描述

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。

应用

  • 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。

替代产品

产品编号
说明
价格

719439

XtalFluor-E®

719447

XtalFluor-M®

象形图

FlameCorrosion
GHS02,GHS05

警示用语：

Danger

危险声明

H226 - H242 - H314

危险分类

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

补充剂危害

EUH014

储存分类代码

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

闪点(°F)

73.4 °F

闪点(°C)

23 °C

个人防护装备

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

法规信息

危险化学品

分析证书(COA)

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索取COA

  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)
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)
P G Hultin et al.
Carbohydrate research, 322(1-2), 14-25 (2000-01-12)
We have made thioglycoside donors for the 4,6-dideoxy-L-lyxo-hexopyranosyl ('4-deoxy-L-rhamnosyl') and 4-deoxy-4-fluoro-L-rhamnosyl monosaccharide residues. The preparation of the deoxyfluororhamnose was not straightforward, and revealed some unexpected behavior of the diethylaminosulfur trifluoride (DAST) reagent. The new glycosyl donors were used to synthesize
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
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.
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商品

Diethylaminosulfur Trifluoride (DAST)

Diethylaminosulfur trifluoride (DAST) is ideal for nucleophilic fluorination and has been used in selective fluorinations of alcohols, alkenols, carbohydrates, ketones, sulfides, epoxides, thioethers, and cyanohydrins.

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