dimethyl(methylidene)azanium iodide

• ChemBase编号: 127300
• 分子式: C3H8IN
• 平均质量: 185.00679
• 单一同位素质量: 184.97014726
• SMILES: C[N+](=C)C.[I-]
• Canonical SMILES: C[N+](=C)C.[I-]
• InChI: InChI=1S/C3H8N.HI/c1-4(2)3;/h1H2,2-3H3;1H/q+1;/p-1
• InChIKey: VVDUZZGYBOWDSQ-UHFFFAOYSA-M

名称和登记号

名称

• IUPAC标准名: dimethyl(methylidene)azanium iodide
• IUPAC传统名: dimethyl(methylidene)azanium iodide
• 别名: N,N-二甲基亚甲基碘化胺; Eschenmoser 盐; N,N-二甲基亚甲基碘化铵; (N,N-二甲基)亚甲基碘化铵; Eschenmoser's salt; N,N-Dimethylmethyleneammonium iodide; Eschenmoser’s salt; N,N-Dimethylmethyleneiminium iodide; N,N-Dimethylmethyleneiminium iodide; Eschenmoser's iodide salt; (N,N-Dimethyl)methyleneammonium iodide

登记号

• CAS号: 33797-51-2
• EC号: 251-680-2
• MDL号: MFCD00011810
• Beilstein号: 3594966; 1731022
• 默克索引号: 143251
• PubChem SID: 162221621; 24852854; 24865478
• PubChem CID: 2724133
• Chemspider ID: 2006292
• 维基百科标题: Eschenmoser's_salt

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): -3.7471042
• LogD (pH = 7.4): -3.7471042
• Log P: -3.7471042
• 摩尔折射率: 29.3724 cm^3
• 极化性: 7.276546 Å^3
• 极化表面积: 3.01 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: decomp. in water
• 外观: colorless hygroscopic crystals
• 熔点: 116°C; 219 °C (dec.)(lit.); 235-240 °C (dec.); ca 240°C dec.

安全信息

• 保存注意事项: Moisture & Light Sensitive
• 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; R36/37/38
• 安全公开号: 26-36; 26-37; S26 S36
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0% (AT); 97%; 98%
• 级别: purum
• 线性分子式: CH2=N+(CH3)2I-

详细说明

Sigma Aldrich - 214914

包装
10, 50 g in glass bottle
Application
多种合成应用的有效试剂，1,2尤其是用于氨甲基化反应；3,4酮转化为 α,β-不饱和烯酮的反应。5

Sigma Aldrich - 40769

Other Notes
供直接使用的"Mannich 试剂"1,2,3,4：羰基的 α-亚甲基化作用以及与烯烃进行烯反应

参考文献

• Crystalline salt of the Mannich intermediate, used by Eschenmoser to introduce a dimethylaminomethyl group into the corrin nucleus: Angew. Chem. Int. Ed., 10, 330 (1971). Enolates of ketones, esters and lactones give the Mannich bases from which the ɑ-methylene derivatives can be prepared by quaternization and elimination: Tetrahedron Lett., 1621 (1977). Malonate esters are converted to ɑ-substituted acrylates: J. Am. Chem. Soc., 104, 6787 (1982); 108, 8068 (1986); J. Chem. Soc., Chem. Commun., 480 (1989).
• The dimethylaminomethylenation of phenols gives high yields and shows a high ortho-regioselectivity: Synthesis, 906 (1983). Indoles are converted almost quantitatively to their 3-dimethylaminomethyl derivatives: Heterocycles, 14, 55 (1980).