(acetyloxy)(phenyl)-$l^{3}-iodanyl acetate

• ChemBase编号: 91440
• 分子式: C10H11IO4
• 平均质量: 322.09641
• 单一同位素质量: 321.97020683
• SMILES: [I](c1ccccc1)(OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[I](c1ccccc1)OC(=O)C
• InChI: InChI=1S/C10H11IO4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7H,1-2H3
• InChIKey: ZBIKORITPGTTGI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (acetyloxy)(phenyl)-$l^{3}-iodanyl acetate; (acetyloxy)(phenyl)-λ^3-iodanyl acetate
• IUPAC传统名: phenyliodosodiacetate; (acetyloxy)(phenyl)-λ^3-iodanyl acetate
• 别名: 二乙酸亚碘酰苯; 二乙酸亚碘酰苯; 碘苯二乙酸酯; 碘苯二乙酸; (Diacetoxyiodo)benzene; Iodobenzene diacetate; (acetyloxy)(phenyl)-$l^{3}-iodanyl acetate; (Diacetoxyiodo)benzene; DIB; Iodosobenzene diacetate; Iodobenzene I,I-diacetate; Iodosobenzene I,I-diacetate; (Diacetoxyiodo)benzene

登记号

• CAS号: 3240-34-4
• EC号: 221-808-1
• MDL号: MFCD00008692
• Beilstein号: 1879369
• PubChem SID: 24858980; 162078139; 24850764
• PubChem CID: 76724

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 2.1789038
• LogD (pH = 7.4): 2.1789038
• Log P: 2.1789038
• 摩尔折射率: 62.2473 cm^3
• 极化性: 25.908724 Å^3
• 极化表面积: 52.6 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 159-161°C; 159-163°C; 161-163 °C; 161-163 °C(lit.)

安全信息

• 保存注意事项: Irritant/Light Sensitive/Keep Cold; Light Sensitive
• RTECS编号: DA3525000
• 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: 26-37
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥98.0% (AT); 96%; 98%; 98+%
• 级别: purum
• 线性分子式: C6H5I(O2CCH3)2

详细说明

Sigma Aldrich - 178721

Application
Unactivated sp3 C-H bonds of both oxime and pyridine substrates undergo highly regio- and chemoselective Pd(II)-catalyzed oxygenation with PhI(OAc)2 as a stoichiometric oxidant.
橙花醇转化为橙花醛的 TEMPO 氧化反应中的化学计量氧化剂。1用作铑催化的烯烃与氨基磺酸酯进行氮杂环丙化反应中的氧化剂。2
用于合成各种杂环化合物的试剂。
用于室温下钯催化的吲哚的 2-芳基化反应。
Rh2(esp)2: An Exceptionally Efficient and Selective Catalyst for C-H Amination
包装
1 kg in glass bottle
5, 25, 100 g in glass bottle

Sigma Aldrich - 31490

Other Notes
用于邻二醇的裂解、羟基化以及许多其他氧化反应的试剂，综述1；热不稳定亚碘酰苯的制备2
Application
Rh2(esp)2: An Exceptionally Efficient and Selective Catalyst for C-H Amination

参考文献

• Versatile oxidizing and acetoxylating agent.
• For a review of the ɑ-functionalization of carbonyl compounds by hypervalent iodine reagents, see: Contemp. Org. Synth., 2, 121 (1995).
• Hydrazine hydrate is oxidized to the useful cis-reducing agent diimide: Synth. Commun., 17, 703 (1987).
• Converts primary aliphatic amides to amines, by Hofmann degradation: J. Org. Chem., 44, 1746 (1979); Synthesis, 266 (1981); 31 (1983). For use in the synthesis of ?-alanine derivatives, see: J. Org. Chem., 62, 6918 (1997); for reaction scheme, see N(ɑ)-Benzyloxycarbonyl-L-asparagine, L08592.
• In the presence of triethyl orthoformate, aryl ethyl ketones undergo a rearrangement to ɑ-methyl arylacetates: Synthesis, 231 (1984):
  
• Similarly, in the presence of an orthoformate and sulfuric acid, flavanones undergo a 1,2-aryl shift to give 2-aryl-2,3-dihydrobenzofuran-3-carboxylates: Bull. Chem. Soc. Jpn., 68, 1168 (1995). However, iodosobenzene diacetate alone oxidizes flavanones to flavones: J. Chem. Res. (Synop.), 213 (1995). For a review of the use of the reagent in heterocyclic synthesis, see: Synlett, 221 (1994).
• Useful reagent for mild, rapid cleavage of 1,3-dithianes to the parent carbonyl compounds: Syn. Commun., 30, 4081 (2000).
• In combination with iodine, forms the acyl hypoiodite, which adds to alkenes: Bull. Chem. Soc. Jpn., 41, 1476 (1968), iodinates alkylbenzenes: J. Am. Chem. Soc., 90, 6187 (1968), and effects the decarboxylative iodination of aromatic carboxylic acids: Synth. Commun., 18, 1327 (1988).
• See cis,cis-1,5-Cyclooctadiene, B21196, for an intramolecular cyclization reaction.
• For use in the Pd(II)-catalyzed functionalization of sp² and sp³ C-H bonds, see: J. Am. Chem. Soc., 126, 2300 (2004).
• Treatment with aqueous NaOH gives the useful selective oxidant iodosobenzene (iodosylbenzene): Org. Synth. Coll., 5, 658 (1973).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 657 (2006). For reviews of the use of polyvalent iodine compounds in organic synthesis, see: Synthesis, 709 (1984); Acc. Chem. Res., 19, 244 (1986); Chem. Rev., 96, 1123 (1996). For a monograph, see: A Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, N.Y. (1992).