potassium 1,3-dioxo-2,3-dihydro-1H-isoindol-2-ide

• ChemBase编号: 129076
• 分子式: C8H4KNO2
• 平均质量: 185.22116
• 单一同位素质量: 184.98791005
• SMILES: c1ccc2c(c1)C(=O)[N-]C2=O.[K+]
• Canonical SMILES: O=C1[N-]C(=O)c2c1cccc2.[K+]
• InChI: InChI=1S/C8H5NO2.K/c10-7-5-3-1-2-4-6(5)8(11)9-7;/h1-4H,(H,9,10,11);/q;+1/p-1
• InChIKey: FYRHIOVKTDQVFC-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: potassium 1,3-dioxo-2,3-dihydro-1H-isoindol-2-ide
• IUPAC传统名: potassium 1,3-dioxo-2H-isoindol-2-ide
• 别名: 苯邻二甲酰亚胺钾; Potassium phthalimide; Phthalimide potassium salt; Potassium phthalimide; Potassium 1,3-dioxoisoindolin-2-ide; potassium 1,3-dioxo-2,3-dihydro-1H-isoindol-2-ide

登记号

• CAS号: 1074-82-4
• EC号: 214-046-6
• MDL号: MFCD00005887
• Beilstein号: 3598719
• PubChem SID: 162223375
• PubChem CID: 3356745
• Chemspider ID: 10627162
• 维基百科标题: Potassium_phthalimide

理论计算性质

• Acid pKa: 8.402129
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 0.69284976
• LogD (pH = 7.4): 0.6526804
• Log P: 0.69342303
• 摩尔折射率: 38.5148 cm^3
• 极化性: 13.896068 Å^3
• 极化表面积: 43.37 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Soluble in water
• 外观: Light yellow solid
• 熔点: > 300 °C; >300°C
• 密度: 1.63
• 疏水性(logP): -0.09

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 危险公开号: 36/37/38
• 安全公开号: 26-37; R
• TSCA收录: 是
• GHS危险品标识: GHS07
• NFPA704:
  

  1

  2

  0
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A

产品相关信息

• 纯度: 95%; 95+%; 98+%

参考文献

• For an example of the classical Gabriel synthesis of primary amines from an alkyl halide by alkylation of potassium phthalimide followed by hydrolysis, see: Org. Synth. Coll., 2, 25 (1943). For use of the Gabriel reaction on Merrifield resin as the first step of a synthesis of a polymer-supported carbodiimide, see: Org. Synth. Coll., 6, 951 (1988). The phthalimide alkylation is often carried out in DMF. A liquid-liquid phase-transfer method using (n-Hexadecyl)tri-n-butylphosphonium bromide, L01335, as catalyst also gives excellent results: Synthesis, 389 (1976).
• The standard method for cleavage of the N-substituted phthalimide is with hydrazine hydrate, effective under milder conditions than acid or base hydrolysis. Other hydrazines and primary amines have also been successful, e.g. methylhydrazine or N,N-dimethylpropanediamine: Org. Synth. Coll., 9, 13, 16 (1998). Another technique involves borohydride reduction to the hydroxy amide, and liberation of the amine with acetic acid, with cyclization to phthalide: Tetrahedron Lett., 25, 2093 (1984). For suggested improvements to the cleavage conditions in the Gabriel synthesis, see: J. Org. Chem., 61, 8063 (1996). Review of the Gabriel reaction: Angew. Chem. Int. Ed., 7, 919 (1968).
• For an alternative approach to the formation of primary amines, see Dibenzylamine, A11554.