phenyl[(trifluoroacetyl)oxy]-$l^{3}-iodanyl 2,2,2-trifluoroacetate

• ChemBase编号: 8596
• 分子式: C10H5F6IO4
• 平均质量: 430.0391892
• 单一同位素质量: 429.91367596
• SMILES: O=C(C(F)(F)F)O[I](c1ccccc1)OC(=O)C(F)(F)F
• Canonical SMILES: O=C(C(F)(F)F)O[I](c1ccccc1)OC(=O)C(F)(F)F
• InChI: InChI=1S/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H
• InChIKey: PEZNEXFPRSOYPL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: phenyl[(trifluoroacetyl)oxy]-$l^{3}-iodanyl 2,2,2-trifluoroacetate; phenyl[(trifluoroacetyl)oxy]-λ^3-iodanyl 2,2,2-trifluoroacetate
• IUPAC传统名: phenyl[(trifluoroacetyl)oxy]-$l^{3}-iodanyl 2,2,2-trifluoroacetate; phenyl[(trifluoroacetyl)oxy]-λ^3-iodanyl 2,2,2-trifluoroacetate
• 别名: 二(三氟乙酰氧基)碘代苯; I,I-双(三氟乙酸)碘苯; [双(三氟乙酰氧基)碘]苯; [Bis(trifluoroacetoxy)iodo]benzene; [Bis(trifluoroacetoxy)iodo]benzene; [Bis(trifluoroacetoxy)](phenyl)iodane; Iodosobenzene bis(trifluoroacetate); BTI; PIFA; Iodobenzene I,I-bis(trifluoroacetate); [Bis(trifluoroacetoxy)iodo]benzene; (Bis(trifluoroacetoxy)iodo)benzene

登记号

• CAS号: 2712-78-9
• EC号: 220-308-0
• MDL号: MFCD00009672
• Beilstein号: 764767
• PubChem SID: 160971903; 24849220; 24853882
• PubChem CID: 102317
• Chemspider ID: 92428
• 维基百科标题: (Bis(trifluoroacetoxy)iodo)benzene

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 5.005431
• LogD (pH = 7.4): 5.005431
• Log P: 5.005431
• 摩尔折射率: 64.8731 cm^3
• 极化性: 25.709503 Å^3
• 极化表面积: 52.6 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

理化性质

• 熔点: 121-125 °C(lit.); 122-125 °C; 122-125°C; 122-125°C

安全信息

• 保存注意事项: IRRITANT, KEEP COLD, LIGHT SENSITIVE; Irritant/Light Sensitive/Moisture Sensitive/Keep Cold/Store under Argon; Moisture & Light Sensitive
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: false; 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥95.0% (AT); 97%
• 级别: purum
• 线性分子式: (CF3CO2)2IC6H5

详细说明

Apollo Scientific Ltd - PC0403

Used to estimate asparagine and glutamine in peptides and proteins.

Sigma Aldrich - 232130

包装
10, 50 g in glass bottle
Application
Reactant or reagent for:
• Pummerer-like reactions1,2
• Chemoselective deprotection of dimethoxybenzyl ethers3
• Mediating oxidative cycloisomerization4,5
• Tosyloxylation of anilides6
在酸性条件下用于酮的直接 α-羟基化反应。也可作为 4-烷基酚的对氟化试剂，可在吡啶氢氟酸盐（产品目录号184225）存在的条件下合成 4-氟环己-2,5-二烯酮。 用于 N-酰腙经氧化反应生成 1,3,4-噁二唑的试剂。促进苯乙烯胺环化反应生成 N-烷基吲哚或 N-芳基吲哚。

Sigma Aldrich - 15230

Other Notes
用于脱氢和氧化反应的试剂，综述7；酰胺直接转化成胺（Hofmann-型重排反应）的新型试剂，以及羧基端多肽测序的关键物质8；也可用于羰基的平稳脱硫缩醛化反应9
Application
Reactant or reagent for:
• Pummerer-like reactions1,2
• Chemoselective deprotection of dimethoxybenzyl ethers3
• Mediating oxidative cycloisomerization4,5
• Tosyloxylation of anilides6

参考文献

• Terminal alkynes are oxidized by PIFA to ɑ-hydroxy ketones: Tetrahedron Lett., 26, 3837 (1985).
• Hypervalent iodine oxidizing agent, cf Iodosobenzene diacetate, B24531. PIFA oxidizes hydroquinones and catechols to benzoquinones. In the presence of a nucleophile, 4-substituted phenols give the corresponding 4,4-disubstituted cyclohexadienone: J. Chem. Soc., Perkin 1, 1891 (1993); 2047 (1994), and refs. therein. In water, 1,4-dimethoxy aromatics undergo oxidative demethylation to p-quinones: Tetrahedron Lett., 42, 6899 (2001). In TFA, acetanilides can be hydroxylated in the p-position: J. Org. Chem., 67, 7424 (2002).
• Primary amides undergo a Hofmann-like rearrangement to amines, avoiding the harsh conditions often required for the classical method: J. Org. Chem., 49, 4272, 4277 (1984); Synth. Commun., 18, 1615 (1988); Org. Synth. Coll., 8, 132 (1993). Promotes the azidation of alkyl groups of p-alkylanisoles with TMS azide: Tetrahedron Lett., 32, 4321 (1991); J. Am. Chem. Soc., 116, 3684 (1994); Synlett, 427 (1994), and also the direct nucleophilic sulfenylation and thiocyanation of phenol ethers with thiols and TMS isothiocyanate respectively: Synlett, 211 (1995); J. Org. Chem., 60, 7144 (1995).
• Mediates the selective cyanation of electron-rich aromatics with Trimethylsilyl cyanide, A19598, e.g. indoles to 2-cyanoindoles: Org. Lett., 7, 537 (2005).
• For a brief feature on uses of this reagent in synthesis, see: Synlett, 2851 (2006). For a comprehensive review of polyvalent iodine compounds, see: Chem. Rev., 96, 1123 (1996).