2-(hydroxymethyl)-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase编号: 71767
• 分子式: C9H7NO3
• 平均质量: 177.15678
• 单一同位素质量: 177.04259309
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)CO
• Canonical SMILES: OCN1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C9H7NO3/c11-5-10-8(12)6-3-1-2-4-7(6)9(10)13/h1-4,11H,5H2
• InChIKey: MNSGOOCAMMSKGI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(hydroxymethyl)-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC传统名: N-(hydroxymethyl)phthalimide
• 别名: N-羟甲基酞酰亚胺; N-羟甲基邻苯二甲酰亚胺; N-(羟甲基)邻苯二甲酰亚胺; 2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione; 2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione; (Phthalimid-1-yl)methanol; N-(Hydroxymethyl)phthalimide; Phthalimidomethanol; N-(Hydroxymethyl)phthalimide; 2-(Hydroxymethyl)isoindoline-1,3-dione; 2-(hydroxymethyl)-2,3-dihydro-1H-isoindole-1,3-dione

登记号

• CAS号: 118-29-6
• EC号: 204-241-4
• MDL号: MFCD00005899
• Beilstein号: 140946
• PubChem SID: 162037160; 24895627
• PubChem CID: 8354

理论计算性质

• Acid pKa: 13.904436
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 0.33709803
• LogD (pH = 7.4): 0.3370979
• Log P: 0.33709803
• 摩尔折射率: 45.3133 cm^3
• 极化性: 16.660858 Å^3
• 极化表面积: 57.61 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 140-145 °C; 140-147°C; 147 - 149°C; 147-149 °C(lit.); 147-149°C°C
• 疏水性(logP): 0.522

安全信息

• 保存注意事项: IRRITANT; Irritant
• RTECS编号: TI5270000
• 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% (HPLC); 95%; 97%; 98%
• 级别: purum
• Empirical Formula (Hill Notation): C9H7NO3

详细说明

Sigma Aldrich - H41803

包装
100 g in poly bottle
在有机溶剂中原位生成无水甲醛的安全试剂。2
Application
用于芳香烃在三氟甲磺酸中的酰胺甲基化反应。1

参考文献

• Used for the introduction of the phthalimidomethyl group by electrophilic substitution of aromatic compounds. For reviews on this amidomethylation reaction, see: Org. React., 14, 52 (1965); Synthesis, 49, (1970); 85, 181 (1984).
• In the presence of diethylamine, protection of carboxylic acids as phthalimidomethyl esters has been reported. The group can be cleaved with hydrazine in MeOH, by a variety of basic or acidic conditions: Rec. Trav. Chim., 82, 941 (1963), or with Zn in AcOH: Chem. Ind. (London), 1204 (1970).