trifluoromethanesulfonyl trifluoromethanesulfonate

• ChemBase编号: 99630
• 分子式: C2F6O5S2
• 平均质量: 282.1388192
• 单一同位素质量: 281.90913442
• SMILES: S(=O)(=O)(C(F)(F)F)OS(=O)(=O)C(F)(F)F
• Canonical SMILES: FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F
• InChI: InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
• InChIKey: WJKHJLXJJJATHN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: trifluoromethanesulfonyl trifluoromethanesulfonate
• IUPAC传统名: trifluoromethanesulfonyl trifluoromethanesulfonate; triflic anhydride
• 别名: 三氟甲烷磺酸酐 溶液; 三氟甲磺酸酐 溶液; 三氟甲烷磺酸酐; 三氟甲磺酸酐; 三氟甲烷磺酸酐; Triflic anhydride; Trifluoromethanesulphonic anhydride 99%; Perfluoromethanesulfonic anhydride solution; Triflic anhydride solution; Trifluoromethanesulfonic anhydride solution; Trifluoromethanesulfonic anhydride; Perfluoromethanesulfonic Anhydride; Tirflic Anhydride; Triflate Anhydride; Triflic Acid Anhydride; Trifluoromethanesulfonic Acid Anhydride; Trifluoromethanesulfonic Anhydride; Trifluoromethylsulfonic Acid Anhydride; Trifluoromethylsulfonic Anhydride; Trifluoromethanesulfonic Anhydride

登记号

• CAS号: 358-23-6
• EC号: 206-616-8
• MDL号: MFCD00000408
• Beilstein号: 1813600
• PubChem SID: 24889545; 162085893; 24850557
• PubChem CID: 67749

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 2.8943794
• LogD (pH = 7.4): 2.8943794
• Log P: 2.8943794
• 摩尔折射率: 30.1848 cm^3
• 极化性: 14.092987 Å^3
• 极化表面积: 77.51 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: -80°C; -80°C
• 沸点: 81-83 °C(lit.); 81-83°C; 81-83°C
• 闪点: none°C
• 密度: 1.359 g/mL at 25 °C; 1.677; 1.677 g/mL at 25 °C(lit.); 1.720
• 折射率: 1.3210; 1.3212; n20/D 1.321(lit.); n20/D 1.402
• 蒸汽压: 8 mmHg ( 20 °C)
• 蒸汽密度: 5.2 (vs air)

安全信息

• 保存注意事项: Corrosive/Harmful/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS编号: PB2772000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 2922; 3265; UN3265
• 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): 2; II
• 危险公开号: 14-22-35; 14-22-35-40; 14-34
• 安全公开号: 26-36/37/39-43-45; 26-36/37/39-45; 8-26-30-36/37/39-45-60
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H314; H314-H318; H314-H351
• GHS警示性声明: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; 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 2922 8/PG 2; UN 3265 8/PG 2
• 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: ≥98.0% (T); ≥99%; 95+%; 98%
• 浓度: 1 M in methylene chloride
• 级别: purum
• 线性分子式: (CF3SO2)2O
• Empirical Formula (Hill Notation): C2F6O5S2

详细说明

Apollo Scientific Ltd - PC7420

Packaged in Safebreak bottles

Sigma Aldrich - 704083

包装
25, 100 mL in glass bottle
Application
Catalyst for synthesis of Bacteroides fragilis zwitterionic polysaccharide Ai tetrasaccharide repeating unit via glycosylation1Reagent for stereoselective synthesis of mennosazide methyl uronate donors2Activator for direct glycosylation with anomeric hydroxy sugars3

Sigma Aldrich - 176176

Application
关于三氟甲磺酸酐、酸和酯在精细化学和制药合成上的催化应用的综述。4
广泛用于合成烷基和乙烯基三氟甲基磺酸酯的试剂。
Catalyst for glycosylation for synthesis of polysaccharides1Reagent for stereoselective synthesis of mannosazide methyl uronate donors2Activator for direct glycosylation with anomeric hydroxy sugars3
包装
1 kg in glass bottle
50, 250, 500 g in glass bottle
5, 10 g in ampule

Sigma Aldrich - 91737

Other Notes
亲电子三氟甲磺酰基的来源。综述4,5,6,7,8
Application
Catalyst for glycosylation for synthesis of polysaccharides1Reagent for stereoselective synthesis of mannosazide methyl uronate donors2Activator for direct glycosylation with anomeric hydroxy sugars3

Toronto Research Chemicals - T790520

Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group.

参考文献

• Cai, D. et al.: Org. Synth., 10, 112 (2004)
• For examples of preparation of alkyl and aryl triflates, and use of the latter in the Stille coupling reaction, see: Org. Synth. Coll., 6, 324 (1988); 9, 553 (1998). Alkyl triflates undergo solvolysis reactions between five and seven powers of ten times more rapidly than the corresponding halides or tosylates: J. Am. Chem. Soc., 97, 6478 (1975); Angew. Chem. Int. Ed., 9, 521 (1970). For a review of the chemistry of triflate esters, see: Synthesis, 85 (1982).
• Enolizable carbonyl compounds in the presence of base can be converted to vinyl (enol) triflates: Synthesis, 85 (1982); Org. Synth. Coll., 6, 757 (1988). For conditions employing preferred base, 2,6-Di-tert-butyl-4-methylpyridine, L14143, see: Org. Synth. Coll., 8, 97, 126 (1993). Enol triflates behave as a source of vinyl cations. For reviews, see: Angew. Chem. Int. Ed., 17, 333 (1978); Acc. Chem. Res., 11, 107 (1978); 15, 348 (1982); 21, 147 (1988).
• For formation of keteniminium triflates, see N,N-Dimethylacetamide, A10924.
• The Ritter reaction is normally most successful with tertiary alcohols. In contrast, a useful variation allows conversion of primary or secondary alcohols to amides in good yield: Tetrahedron Lett., 30, 581 (1989):
  
• For use in the Vilsmeier formylation of less active substrates, see N,N-Dimethylformamide, A13547.
• Triflic anhydride has also been found to promote the nitration of arenes, even deactivated ones, under mild conditions: Synthesis, 1087 (1992).
• For a review of chemical transformations induced by the reagent, see: Tetrahedron, 56, 3077 (2000). For a brief feature on uses in synthesis, see: Synlett, 390 (2004).