二乙氨基三氟化硫

二乙氨基三氟化硫
	IUPAC名; N,N-Diethyl-S,S,S-trifluoro-λ4-sulfanamine
別名	二乙氨基三氟化硫; 二乙(三氟化硫)胺
識別
縮寫	DAST
CAS編號	38078-09-0
PubChem	123472
ChemSpider	110068
SMILES	FS(F)(F)N(CC)CC;
InChI	1/3C4H12NS.3FH/c31-3-6(5)4-2;;;/h33-5H2,1-2H3;31H/q3+1;;;/p-3;
InChIKey	OJRFYRBETDFODT-DFZHHIFOAR
性質
化學式	C4H10F3NS
摩爾質量	161.19 g·mol−1
外觀	無色油狀液體
密度	1.220 g/cm3
沸點	30—32 °C（86—90 °F；303—305 K）（3 mmHg）
溶解性（水）	反應
溶解性	和乙醇反應，可溶於乙腈
危險性
	GHS危險性符號;
GHS提示詞	Danger
H-術語	H226, H302, H312, H314, H332
P-術語	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+312, P301+330+331
主要危害	有腐蝕性，可燃，可以爆炸
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二乙基氨基三氟化硫，簡稱DAST^[2]是一種有機硫化合物，化學式 Et₂NSF₃。這種液體是一種氟化劑，用於合成有機氟化合物。二乙基氨基三氟化硫是無色的，但舊樣本會呈橙色。

Quick Facts 二乙氨基三氟化硫[1], 識別 ...

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製備

DAST可以由二乙基氨基三甲基矽烷和四氟化硫反應而成：^[3]

Et₂NSiMe₃ + SF₄ → Et₂NSF₃ + Me₃SiF

原論文使用三氯氟甲烷（氟利昂-11）作為溶劑，但這種化合物因為被蒙特利爾議定書禁用，不再作為商品化學品提供，現已使用乙醚作為替代溶劑。^[4]

用處

DAST在有機合成中用作氟化劑，可以把醇（ROH）和醛（RCHO）氟化成對應的氟代烴（RF和RCHF₂）。^[5]它和硫醚或亞碸反應，生成對應的α-氟代硫醚。^[6]^[7]^[8]

它也用作傅-克反應的催化劑。^[9]

危險和替代試劑

DAST加熱分解成極易爆炸的(NEt₂)₂SF₂，並產生四氟化硫氣體。為了儘量減少發生事故，存放DAST樣本時要保持在50 °C以下。^[10]雙(2-甲氧乙基)氨基三氟化硫（商品名Deoxo-Fluor）和四氟硼酸二氟(嗎啉基)化鋶（商品名XtalFluor-M）都是衍生自DAST的試劑，但較難爆炸。^[11]^[12]

參見

石川試劑（英語：Ishikawa reagent）
氨基硫烷的氟化反應（英語：Fluorination with aminosulfuranes）

參考資料

[1]
A. H. Fauq, "N,N-Diethylaminosulfur Trifluoride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
[2]
Middleton, William J. New fluorinating reagents. Dialkylaminosulfur fluorides. The Journal of Organic Chemistry. 1975-03-01, 40 (5): 574–578. ISSN 0022-3263. doi:10.1021/jo00893a007.
[3]
W. J. Middleton, E. M. Bingham "Diethylaminosulfur Trifluoride" Organic Syntheses, Coll. Vol. 6, p.440; Vol. 57, p.50. Online version （頁面存檔備份，存於互聯網檔案館）
[4]
L. N. Markovskij; V. E. Pashinnik; A. V. Kirsanov. Application of Dialkylaminosulfur Trifluorides in the Synthesis of Fluoroorganic Compounds. Synthesis. 1973, 1973 (12): 787–789. doi:10.1055/s-1973-22302.
[5]
Organo-Fluorine Compounds, B. Baasner, H. Hagemann, J. C. Tatlow (Hrsg.), Houben-Weyl/Thieme, Stuttgart, 2000.
[6]
McCarthy, James R.; Peet, Norton P.; LeTourneau, Michael E.; Inbasekaran, Muthiah. (Diethylamino)sulfur trifluoride in organic synthesis. 2. The transformation of sulfoxides to .alpha.-fluoro thioethers. Journal of the American Chemical Society (American Chemical Society (ACS)). 1985, 107 (3): 735–737. ISSN 0002-7863. doi:10.1021/ja00289a053.
[7]
Wnuk, Stanislaw F.; Robins, Morris J. Antimony(III) chloride exerts potent catalysis of the conversion of sulfoxides to .alpha.-fluoro thioethers with (diethylamino)sulfur trifluoride. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1990, 55 (15): 4757–4760. ISSN 0022-3263. doi:10.1021/jo00302a052.
[8]
Robins, Morris J.; Wnuk, Stanislaw F. Nucleic acid related compounds. 79. Efficient conversions of thioethers to .alpha.-fluoro thioethers with DAST or DAST/antimony(III) chloride. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1993, 58 (15): 3800–3801. ISSN 0022-3263. doi:10.1021/jo00067a009.
[9]
來源：Sigma-Aldrich Co., product no. 235253 .
[10]
Messina, P. A.; Mange, K. C.; Middleton, W. J. Aminosulfur trifluorides: relative thermal stability. Journal of Fluorine Chemistry. 1989, 42 (1): 137–143. doi:10.1016/S0022-1139(00)83974-3.
[11]
l'Heureux, A.; Beaulieu, F.; Bennett, C.; Bill, D. R.; Clayton, S.; Laflamme, F. O.; Mirmehrabi, M.; Tadayon, S.; Tovell, D.; Couturier, M. Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling†,‡. The Journal of Organic Chemistry. 2010, 75 (10): 3401–3411. PMC 2869536 . doi:10.1021/jo100504x.
[12]
Beaulieu, F.; Beauregard, L. P.; Courchesne, G.; Couturier, M.; Laflamme, F. O.; l』Heureux, A. Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents. Organic Letters. 2009, 11 (21): 5050–5053. PMC 2770860 . PMID 19799406. doi:10.1021/ol902039q.

[1] [1]
A. H. Fauq, "N,N-Diethylaminosulfur Trifluoride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.

[2] [2]
Middleton, William J. New fluorinating reagents. Dialkylaminosulfur fluorides. The Journal of Organic Chemistry. 1975-03-01, 40 (5): 574–578. ISSN 0022-3263. doi:10.1021/jo00893a007.

[3] [3]
W. J. Middleton, E. M. Bingham "Diethylaminosulfur Trifluoride" Organic Syntheses, Coll. Vol. 6, p.440; Vol. 57, p.50. Online version （頁面存檔備份，存於互聯網檔案館）

[4] [4]
L. N. Markovskij; V. E. Pashinnik; A. V. Kirsanov. Application of Dialkylaminosulfur Trifluorides in the Synthesis of Fluoroorganic Compounds. Synthesis. 1973, 1973 (12): 787–789. doi:10.1055/s-1973-22302.

[5] [5]
Organo-Fluorine Compounds, B. Baasner, H. Hagemann, J. C. Tatlow (Hrsg.), Houben-Weyl/Thieme, Stuttgart, 2000.

[6] [6]
McCarthy, James R.; Peet, Norton P.; LeTourneau, Michael E.; Inbasekaran, Muthiah. (Diethylamino)sulfur trifluoride in organic synthesis. 2. The transformation of sulfoxides to .alpha.-fluoro thioethers. Journal of the American Chemical Society (American Chemical Society (ACS)). 1985, 107 (3): 735–737. ISSN 0002-7863. doi:10.1021/ja00289a053.

[7] [7]
Wnuk, Stanislaw F.; Robins, Morris J. Antimony(III) chloride exerts potent catalysis of the conversion of sulfoxides to .alpha.-fluoro thioethers with (diethylamino)sulfur trifluoride. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1990, 55 (15): 4757–4760. ISSN 0022-3263. doi:10.1021/jo00302a052.

[8] [8]
Robins, Morris J.; Wnuk, Stanislaw F. Nucleic acid related compounds. 79. Efficient conversions of thioethers to .alpha.-fluoro thioethers with DAST or DAST/antimony(III) chloride. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1993, 58 (15): 3800–3801. ISSN 0022-3263. doi:10.1021/jo00067a009.

[Sigma-9] [9]
來源：Sigma-Aldrich Co., product no. 235253 .

[Messina_et_al_1989-10] [10]
Messina, P. A.; Mange, K. C.; Middleton, W. J. Aminosulfur trifluorides: relative thermal stability. Journal of Fluorine Chemistry. 1989, 42 (1): 137–143. doi:10.1016/S0022-1139(00)83974-3.

[l'Heureux_et_al_2010-11] [11]
l'Heureux, A.; Beaulieu, F.; Bennett, C.; Bill, D. R.; Clayton, S.; Laflamme, F. O.; Mirmehrabi, M.; Tadayon, S.; Tovell, D.; Couturier, M. Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling†,‡. The Journal of Organic Chemistry. 2010, 75 (10): 3401–3411. PMC 2869536 . doi:10.1021/jo100504x.

[Beaulieu_et_al_2009-12] [12]
Beaulieu, F.; Beauregard, L. P.; Courchesne, G.; Couturier, M.; Laflamme, F. O.; l』Heureux, A. Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents. Organic Letters. 2009, 11 (21): 5050–5053. PMC 2770860 . PMID 19799406. doi:10.1021/ol902039q.

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