diphenyliodanium chloride

• ChemBase编号: 103221
• 分子式: C12H10ClI
• 平均质量: 316.56527
• 单一同位素质量: 315.951576
• SMILES: [Cl-].[I+](c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)[I+]c1ccccc1.[Cl-]
• InChI: InChI=1S/C12H10I.ClH/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;/h1-10H;1H/q+1;/p-1
• InChIKey: RSJLWBUYLGJOBD-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: diphenyliodanium chloride
• IUPAC传统名: diphenyliodanium chloride
• 别名: 二苯基碘酰氯; 二苯氯化碘鎓,; DPI; NSC 134275; Diphenyliodonium chloride; DIPHENYLIODONIUM CHLORIDE

登记号

• CAS号: 1483-72-3
• EC号: 216-049-8
• MDL号: MFCD00011909
• Beilstein号: 3574977
• 默克索引号: 147464
• PubChem SID: 24866949; 162090445
• PubChem CID: 73870

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 4.5634055
• LogD (pH = 7.4): 4.5634055
• Log P: 4.5634055
• 摩尔折射率: 64.8948 cm^3
• 极化性: 28.086405 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 233-235 °C (subl.)(lit.); 233-235°C (sublimes); ca 230°C dec.

安全信息

• 保存条件: 2-8°C
• 保存注意事项: Light Sensitive
• RTECS编号: NN6651666
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811; UN2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 25-36/37/38
• 安全公开号: 26-36; 26-36/37-45
• TSCA收录: 是
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H335
• GHS警示性声明: P261-P301 + P310-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

产品相关信息

• 纯度: ~97%; ≥98.0% (AT); 98+%
• 线性分子式: (C6H5)2I+Cl-

详细说明

MP Biomedicals - 02150976

Phenylation reagent.
Purity: ~97%

Sigma Aldrich - 43088

Other Notes
用于亲电苯基化反应（如丙二酸酯和二硫代羧酸酯的反应）的试剂8,9,10
包装
5, 25 g in glass bottle
Application
Reactant for:
• Copper-catalyzed cross coupling reactions of purines and diaryliodonium salts1
• Synthesis of acetylenic arylselenides2
• Sonogashira coupling reactions for the preparation of aryl alkynes3
• C-H functionalization for synthesis of (arylmethylene)oxindoles4
• Arylation of anilines5
• Studies on the visible-light photosensitive system-dlourescein yellow-bis(di-Ph iodonium)6
• Investigating the properties of direct and sensitized photolysis of dispersed photoacid generators7

参考文献

• They are also useful phenylating agents for a variety of anions:
• Diphenyliodonium salts are widely used as photoinitiators for cationic polymerization: Macromolecules, 10, 1307 (1977); review: Adv. Polym. Sci., 62, 1 (1982).
• C-Phenylation of the anions derived from malonic esters, ?-keto esters and arylacetic esters: J. Org. Chem., 28, 714 (1963). Arylation of ketones: J. Org. Chem., 31, 4315 (1966). ?-Diketones can be arylated either as monoanions: Tetrahedron, 8, 49 (1960); J. Am. Chem. Soc., 84, 2819 (1962), or as dianions: J. Org. Chem., 29, 3514 (1964), where reaction occurs at the more reactive (terminal) carbon; see, e.g. (1-phenylation of 2,4-pentanedione): Org. Synth. Coll., 6, 928 (1988). For arylation of Grignard reagents and cyanide ion, see: J. Am. Chem. Soc., 75, 2708 (1953), and of nitro-compounds: J. Org. Chem., 28, 1424 (1963); 29, 2108 (1964). Other reactions reported include: O-Phenylation of aryloxides: J. Chem. Soc., 2645 (1961), alkoxides and oximes: J. Org. Chem., 40, 3010 (1975); 36, 1780 (1971); S-Phenylation of sulfides: J. Org. Chem., 36, 233 (1971); N-Phenylation of heterocycles: Tetrahedron, 1, 145 (1957); J. Org. Chem., 39, 2710 (1974).
• For reviews of polyvalent iodine compounds in organic synthesis, see: Synthesis, 709 (1984); Chem. Rev., 96, 1123 (1996). For monographs, see: A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, N.Y. (1992); A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego (1996).