diethyl(trifluoro-λ4-sulfanyl)amine

• ChemBase编号: 8505
• 分子式: C4H10F3NS
• 平均质量: 161.1891096
• 单一同位素质量: 161.04860499
• SMILES: CCN(CC)S(F)(F)F
• Canonical SMILES: CCN(S(F)(F)F)CC
• InChI: InChI=1S/C4H10F3NS/c1-3-8(4-2)9(5,6)7/h3-4H2,1-2H3
• InChIKey: CSJLBAMHHLJAAS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: diethyl(trifluoro-λ^4-sulfanyl)amine; diethyl(trifluoro-$l^{4}-sulfanyl)amine
• IUPAC传统名: diethylaminosulfur trifluoride
• 别名: 二乙胺基三氟化硫; 二乙氨基三氟化硫; DAST; (Diethylamino)sulphur trifluoride 97%; Diethylaminosulfur trifluoride; (Diethylamino)sulfur trifluoride; Diethylaminosulfur trifluoride; Diethylaminosulfur trifluoride; (Diethylamino)sulfur Trifluoride; (Diethylamino)sulphur Trifluoride; (Diethylamino)trifluorosulfur; (N,N-Diethylamino)sulfur Trifluoride; Diethylaminosulfate Trifluoride; Trifluoro(diethylamino)sulfur; (T-4)-(N-ethylethanaminato)trifluorosulfur

登记号

• CAS号: 38078-09-0
• EC号: 253-771-2
• MDL号: MFCD00000363
• Beilstein号: 1849066
• PubChem SID: 24859166; 160971812; 24854092
• PubChem CID: 123472

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.0079906
• LogD (pH = 7.4): 1.0079906
• Log P: 1.0079906
• 摩尔折射率: 33.6503 cm^3
• 极化性: 12.837758 Å^3
• 极化表面积: 3.24 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 30-32 °C/3 mmHg(lit.); 30-32°C/3mm; 30-32°C/3mm
• 闪点: 23 °C; 23°C; 23°C(73°F); 73.4 °F
• 密度: 1.22; 1.22 g/mL at 25 °C(lit.); 1.220; 1.23
• 折射率: 1.4115

安全信息

• 保存注意事项: Corrosive/Flammable/Hygroscopic/Moisture Sensitive/Keep Cold/Store under Argon; KEEP COLD, FLAMMABLE, CORROSIVE; Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 有毒(Toxic) (T)
• 联合国危险货物编号: 2920; UN2920
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 1; I
• 危险公开号: 10-14-20/21/22-34; 5-10-14-23-35
• 安全公开号: 16-26-36/37/39-45; 4-8-9-20-23-26-30-36/37/39-45-60
• TSCA收录: false; 否
• GHS危险品标识: GHS02; GHS05; GHS06; GHS07
• GHS警示词: Danger
• GHS危险声明: H226-H302 + H312 + H332-H314; H331-H314-H318-H226
• GHS警示性声明: P280-P303+P361+P353-P305+P351+P338-P310-P402; P280-P305 + P351 + P338-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 1
• 欧盟补充危害声明: Reacts violently with water.
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥90% (NMR); 95%; 97%
• 级别: technical
• 品质说明: packed in PTFE bottles
• 线性分子式: (C2H5)2NSF3

详细说明

Apollo Scientific Ltd - PC2563

Versatile fluorinating agent: JOC., 1975, 40, 574Has been reported to undergo explosive decomposition when heated above 90C.

Sigma Aldrich - 31942

Application

• Fluorinating agent: reaction with alcohols and carbonyl compounds, Review1,2
• Review on nucleophilic fluorination.2
• Catalyst for Friedel-Crafts allylation using tertiary cyclopropyl silyl ethers3 and the rearrangement of homoallylic alcohols to unsaturated aldehydes.4
• Early introduction of a fluoromethyl group stabilizes the epoxide during further manipulations in the synthesis of 26-fluoro-epothilone.5
• Fluorinating agent for a variety of compounds, including thioethers, alkenols, and cyanohydrins.6,7,8
• Reagent for gem difluorination of ketopipecolinic acids.9

Sigma Aldrich - 235253

Frequently Asked Questions
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包装
1, 5, 25, 250 g in poly bottle
Application

• Fluorinating agent: reaction with alcohols and carbonyl compounds, Review1,2
• Review on nucleophilic fluorination.2
• Catalyst for Friedel-Crafts allylation using tertiary cyclopropyl silyl ethers3 and the rearrangement of homoallylic alcohols to unsaturated aldehydes.4
• Early introduction of a fluoromethyl group stabilizes the epoxide during further manipulations in the synthesis of 26-fluoro-epothilone.5
• Fluorinating agent for a variety of compounds, including thioethers, alkenols, and cyanohydrins.6,7,8
• Reagent for gem difluorination of ketopipecolinic acids.9

Toronto Research Chemicals - D443670

Diethylaminosulfur Trifluoride is a very useful fluorinating agent in chemical synthesis. Diethylaminosulfur Trifluoride is also used as a reagent in the preparation of 2-thiazolines from (1,2)-thioamido-alcohols.

参考文献

• Giannini, G. et al.: Eur. J. Org. Chem., 11, 2411 (2004)
• Lafargue, P. et al.: Synlett, 2, 171 (2004)
• Convenient reagent for conversion, in the absence of base, of N-protected amino acids to the acyl fluorides: Lett. Pept. Sci., 2, 285 (1996); Indian J. Chem., 39, 384 (2000); compare Cyanuric fluoride, A15666. Review of peptide coupling via amino acid halides: Acc. Chem. Res., 29, 268 (1996). See also Appendix 6.
• In the presence of SbCl₃, promotes the fluoro-Pummerer rearrangement of sulfoxides: J. Am. Chem. Soc., 107, 735 (1985); Org. Synth.Coll., 9, 446 (1998):
  
• Direct conversion of thioethers to the ɑ-fluoro analogues has also been reported: J. Org. Chem., 58, 3800 (1993). Fluorination of thioesters leads to ɑɑ-difluoroethers: J. Org. Chem., 55, 768 (1990):
  
• See also 4-Morpholinylsulfur trifluoride, L19751.
• Reagent for conversion of alcohols to alkyl fluorides and carbonyl compounds to gem-difluorides, less prone to cause dehydration or rearrangement than SF₄: J. Org. Chem., 40, 574 (1975); Org. Synth. Coll., 6, 835 (1988); Eur. J. Org. Chem., 3177 (2000); Tetrahedron Lett, 44, 6661 (2003); reviews: Org. React., 35, 513 (1988); Austral. J. Chem., 54, 75 (2001); Synlett, 1130 (2006). Conversion of alcohols to fluorides has been accomplished with stereocontrol at the chiral center: Tetrahedron: Asym., 4, 161 (1993).
• Use of dichloromethane as solvent permits the selective monofluorination of sugars: J. Org. Chem., 48, 393 (1983). Glycosyl fluorides, which are useful building blocks for oligosaccharides: J. Am. Chem. Soc., 105, 2430 (1983), and C-glycosides, can be prepared by reaction of DAST with phenylthioglycosides: J. Am. Chem. Soc., 106, 4189 (1984). The reaction with diols can lead to difluorides, sulfite esters or cyclic ethers: J. Chem. Soc., Perkin 2, 861 (1995).