三フッ化N,N-ジエチルアミノ硫黄

三フッ化N,N-ジエチルアミノ硫黄[1]
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優先IUPAC名
N,N-Diethyl-S,S,S-trifluoro-λ4-sulfanamine
別称
diethyl(trifluorosulfido)amine
識別情報
略称 DAST
CAS登録番号 38078-09-0 チェック
PubChem 123472
ChemSpider 110068 ×
UNII 78622BV6IJ
EC番号 253-771-2
特性
化学式 C4H10F3NS
モル質量 161.19 g mol−1
外観 無色の油状
密度 1.220 g/cm3
沸点

30 ～ 32℃ (at 3 mmHg)

水への溶解度 水と反応する
溶解度 エタノールと反応する
危険性
GHSピクトグラム 可燃性腐食性物質急性毒性（低毒性）
GHSシグナルワード 危険(DANGER)
Hフレーズ H226, H302, H312, H314, H332
Pフレーズ P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+312, P301+330+331
主な危険性 腐食性、引火性、爆発性
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

三フッ化N,N-ジエチルアミノ硫黄 (さんフッかN,N-ジエチルアミノいおう、N,N-diethylaminosulfur trifluoride）は、有機合成化学においてフッ素化試薬として用いられる化合物。略称は DAST。市販品が入手可能。

調製

DAST はジエチルアミノトリメチルシランと四フッ化硫黄を低温で反応させて調製する[2]。

Et
2NSiMe
3 + SF
4 → Et
2NSF
3 + Me
3SiF

用途

DAST の反応性は四フッ化硫黄に似る。

アルコールをフッ化アルキルに変換する。

R–OH + DAST → R–F

ケトンやアルデヒドを二フッ化物に変える。

RC(=O)R' + DAST → RCF
2R'
RCHO + DAST → RCHF
2

用途

レーザーで励起して常温でテラヘルツ波を発振する有機非線形光学結晶として1から20THzの広帯域波長可変単色テラヘルツ光源としての用途が報告されている[3][4][5][6][7][8]。

参考文献

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

脚注

  1. ^ Fauq, Abdul H.; Singh, Rajendra P.; Meshri, Dayal T. (2006). “Diethylaminosulfurtrifluoride”. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd175.pub2. ISBN 0-471-93623-5 
  2. ^ Middleton, W. J.; Bingham E. M. "Diethylaminosulfur Trifluoride." Org. Synth., Coll. Vol. 6, p.440 (1988); Vol. 57, p.50 (1977). オンライン版
  3. ^ テラヘルツイメージングによる非破壊検査技術
  4. ^ Shibuya, Takayuki, et al. "Terahertz-wave generation using a 4-dimethylamino-N-methyl-4-stilbazolium tosylate crystal under intra-cavity conditions." Applied physics express 1.4 (2008): 042002.
  5. ^ Taniuchi, T., S. Okada, and H. Nakanishi. "Widely tunable terahertz-wave generation in an organic crystal and its spectroscopic application." Journal of applied physics 95.11 (2004): 5984-5988.
  6. ^ 斗内政吉, 鈴木正人, 川山巌 ほか、「有機非線形光学結晶を用いたフェムト秒光パルス励起テラヘルツ電磁波発生」 『レーザー研究』 2009年 37巻 5号 p.355-360, doi:10.2184/lsj.37.355, レーザー学会
  7. ^ 戒能俊邦、「有機非線形光学材料の素子応用 光サンプリング・電気光学サンプリングなど」 『応用物理』 1998年 67巻 10号 p.1125-1130, doi:10.11470/oubutsu1932.67.1125, 応用物理学会
  8. ^ 谷内哲夫, 四方潤一, 伊藤弘昌、「非線形光学効果による広帯域波長可変テラヘルツ電磁波放射」 『レーザー研究』 2002年 30巻 7号 p.365-369, doi:10.2184/lsj.30.365,レーザー学会

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