ethyl 2-isocyanoacetate

• ChemBase编号: 78318
• 分子式: C5H7NO2
• 平均质量: 113.11458
• 单一同位素质量: 113.04767847
• SMILES: [N+](#[C-])CC(=O)OCC
• Canonical SMILES: [C-]#[N+]CC(=O)OCC
• InChI: InChI=1S/C5H7NO2/c1-3-8-5(7)4-6-2/h3-4H2,1H3
• InChIKey: FPULFENIJDPZBX-UHFFFAOYSA-N

名称和登记号

名称

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

登记号

• CAS号: 2999-46-4
• EC号: 221-077-9
• MDL号: MFCD00000007
• Beilstein号: 3588613
• PubChem SID: 162043087; 24853557; 24881207
• PubChem CID: 533707

理论计算性质

• Acid pKa: 16.10355
• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): -1.9777237
• LogD (pH = 7.4): -1.9777237
• Log P: -1.9777237
• 摩尔折射率: 37.1139 cm^3
• 极化性: 11.067871 Å^3
• 极化表面积: 30.66 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

• 沸点: 194-196 °C(lit.); 194-196°C; 194-196°C
• 闪点: 183.2 °F; 84 °C; 84°C; 84°C(183°F)
• 密度: 1.035; 1.035 g/mL at 25 °C(lit.)
• 折射率: 1.4220; n20/D 1.418; n20/D 1.418(lit.)
• 疏水性(logP): -0.067

安全信息

• 保存注意事项: Moisture & Light Sensitive; Toxic/Moisture Sensitive/Light Sensitive/Store under Argon/Keep Cold
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2810; UN2810
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 20/21/22-36/37/38; 20/22
• 安全公开号: 9-26-36/37
• TSCA收录: 否
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H332; H331-H302-H312-H315-H319-H335-H227
• GHS警示性声明: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (GC); 95%; 98%
• 级别: purum
• 线性分子式: CNCH2COOCH2CH3

详细说明

Sigma Aldrich - 226319

Application
环化反应合成单体，用于制备吡咯类1,2、噁唑啉类3、苯二氮卓类4、噁唑类5 和咪唑类6。
General description
Material may darken upon storage
包装
5, 25 g in glass bottle

Sigma Aldrich - 58822

Caution
储存时可变为褐色
Other Notes
综述1,2；合成 α-氨基酸3

参考文献

• The method has been extended to nitroaromatics, leading to pyrroles and porphyrins fused with aromatic rings: J. Chem. Soc., Perkin 1, 417 (1996).
• Base-catalyzed Michael addition to nitroalkenes provides a route to substituted pyrroles, valuable as intermediates for porphyrin synthesis: J. Chem. Soc., Chem. Commun., 1098 (1985); Tetrahedron, 46, 7483, 7587 (1990); Org. Synth. Coll., 9, 242 (1998).
• The terminal carbon also undergoes nucleophilic attack on an acyl chloride to give an ɑ-keto imidoyl chloride, which cyclizes in base to a 2-acyl-5-ethoxy oxazole: Synth. Commun., 26, 1149 (1996).