ethyl 2-cyanoacetate

• ChemBase编号: 85658
• 分子式: C5H7NO2
• 平均质量: 113.11458
• 单一同位素质量: 113.04767847
• SMILES: N#CCC(=O)OCC
• Canonical SMILES: CCOC(=O)CC#N
• InChI: InChI=1S/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3
• InChIKey: ZIUSEGSNTOUIPT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethyl 2-cyanoacetate
• IUPAC传统名: ethyl cyanoacetate
• 别名: 氰乙酸乙酯; 氰基乙酸乙酯; Ethyl cyanoacetate; Cyanoacetic acid ethyl ester; Ethyl cyanoacetate; ethyl 2-cyanoacetate

登记号

• CAS号: 105-56-6
• EC号: 203-309-0
• MDL号: MFCD00001940
• Beilstein号: 605871
• 默克索引号: 143786
• PubChem SID: 24894436; 24865300; 162072774
• PubChem CID: 7764

理论计算性质

• Acid pKa: 8.98093
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.22939037
• LogD (pH = 7.4): 0.21830069
• Log P: 0.22953361
• 摩尔折射率: 27.4848 cm^3
• 极化性: 10.614262 Å^3
• 极化表面积: 50.09 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: -22 °C(lit.); -22°C; -23°C; -23°C
• 沸点: 208°C; 208-210 °C(lit.); 208-210°C; 208-210°C
• 闪点: 109 °C; 109°C; 109°C(228°F); 228.2 °F
• 密度: 1.0560 g/ml; 1.063; 1.063 g/mL at 25 °C(lit.)
• 折射率: 1.4180; n20/D 1.418; n20/D 1.418(lit.)
• 蒸汽压: 1 mmHg ( 67.8 °C)
• 蒸汽密度: 3.9 (vs air)

安全信息

• 保存注意事项: Harmful
• RTECS编号: AG4110000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 20/21/22; 36; R:36
• 安全公开号: 23-26; 36/37; S:26
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332; H319
• GHS警示性声明: P261-P305+P351+P338; P280
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

产品相关信息

• 纯度: ≥98%; ≥98.0% (GC); ≥99%; ≥99.5% (GC); 95+%; 97%; 98+%
• 级别: analytical standard; purum
• 有效期: (limited shelf life, expiry date on the label)
• 线性分子式: NCCH2COOC2H5

详细说明

Sigma Aldrich - 241202

包装
50 g in glass bottle

Sigma Aldrich - E18425

包装
1 kg in glass bottle
5, 250 g in glass bottle

参考文献

• For use in the synthesis of pyrrole derivatives, see p-Toluenesulfonylmethyl isocyanide, A14312.
• Stereoselective alkylation of the active methylene has been accomplished under particularly mild conditions with secondary alkyl mesylates in the presence of CsF in DMF; complete inversion occurs at the secondary alkyl carbon: J. Org. Chem., 60, 2627 (1995).
• Arylation by aryl iodides is promoted by copper(I) iodide: Synthesis, 67 (1983); J. Org. Chem., 58, 7606 (1993); or trans-Dichlorobis(triphenylphosphine)palladium(II), 10491: Synthesis, 506 (1985).
• For examples of Knoevenagel condensations of cyanoacetic esters with carbonyl compounds, see: Org. Synth. Coll., 3, 385, 399 (1955); 4, 93, 463 (1963); review: Org. React., 15, 204 (1967). Knoevenagel condensation with aromatic aldehydes has also been carried out under acidic conditions, for example, good yields have been obtained with ZnCl₂: Tetrahedron Lett., 32, 5821 (1991).