2-amino-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase编号: 85712
• 分子式: C8H6N2O2
• 平均质量: 162.14544
• 单一同位素质量: 162.04292744
• SMILES: N1(C(=O)c2c(cccc2)C1=O)N
• Canonical SMILES: NN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C8H6N2O2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H,9H2
• InChIKey: KSILMCDYDAKOJD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC传统名: 2-aminoisoindole-1,3-dione
• 别名: 氨基邻苯二甲胺，不对称; N-氨基邻苯二甲酰亚胺; N,N-Phthaloylhydrazine, unsym.; N-Aminophthalimide; 2-aminoisoindoline-1,3-dione

登记号

• CAS号: 1875-48-5
• EC号: 217-505-9
• MDL号: MFCD00005895
• Beilstein号: 383756
• PubChem SID: 24850729; 162072828
• PubChem CID: 74645

理论计算性质

• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 0.39687458
• LogD (pH = 7.4): 0.39694643
• Log P: 0.39694735
• 摩尔折射率: 43.7989 cm^3
• 极化性: 15.594562 Å^3
• 极化表面积: 63.4 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

• 熔点: 200-202 °C(lit.); ca 195°C dec.

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 36/37/38; 36/37/38-42/43
• 安全公开号: 22-26-36/37-45; 26-36
• TSCA收录: 否
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H317-H319-H334-H335; H315-H319-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338-P342 + P311; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ~90% (HPLC); 90%; 94%; 97%
• 级别: technical; technical grade
• Empirical Formula (Hill Notation): C8H6N2O2

详细说明

Sigma Aldrich - 178314

Other Notes
残留物为邻苯二甲酰肼
包装
25 g in poly bottle
5 g in glass bottle
Application
用于手性 N-烯酰基磺内酰胺的氮杂环丙烷反应。1

Sigma Aldrich - 09251

Analysis Note
典型红外波段 1715 和 1776cm-1

参考文献

• May be oxidized with lead(IV) acetate to "phthalimidonitrene", which adds to alkenes to give aziridines. The phthalimido group can be cleaved with hydrazine hydrate: J. Chem. Soc. (C), 576 (1970); J. Am. Chem. Soc., 92, 1784 (1970); Helv. Chim. Acta,55, 1276 (1972); Org. Synth. Coll., 6, 56 (1988). Addition to cyclopentadienes leads to substituted pyridines after ring-opening with base: Heterocycles, 22, 1369 (1984). Addition to the (racemic) acrylic ester below shows an extremely high facial selectivity, adding to the less hindered side (290:1): Helv. Chim. Acta, 72, 1095 (1989).
  
• Aziridination has also been achieved in high yield by electrochemical oxidation: J. Am. Chem. Soc., 124, 530 (2002).