3-ethoxy-3-oxopropanoic acid

• ChemBase编号: 123201
• 分子式: C5H8O4
• 平均质量: 132.11462
• 单一同位素质量: 132.04225874
• SMILES: C(C(=O)O)C(=O)OCC
• Canonical SMILES: CCOC(=O)CC(=O)O
• InChI: InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)
• InChIKey: HGINADPHJQTSKN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-ethoxy-3-oxopropanoic acid
• IUPAC传统名: ethyl hydrogen malonate
• 别名: 丙二酸单乙酯; 丙二酸氢乙酯; Monoethyl malonate; 3-ethoxy-3-oxopropanoic acid; (Ethoxycarbonyl)acetic acid; 3-Ethoxy-3-oxopropanoic acid; Ethyl hydrogen malonate; Ethyl malonate; Monoethyl hydrogen malonate; mono-Ethyl malonate; ETHYL HYDROGEN MALONATE; Malonic acid monoethyl ester; Monoethyl malonate; Ethyl hydrogen malonate

登记号

• CAS号: 1071-46-1
• EC号: 213-992-7
• MDL号: MFCD00020490
• Beilstein号: 1758845
• PubChem SID: 24868159; 162217554
• PubChem CID: 70615

理论计算性质

• Acid pKa: 3.917031
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -1.4176992
• LogD (pH = 7.4): -3.0331244
• Log P: 0.17158474
• 摩尔折射率: 28.5055 cm^3
• 极化性: 11.39605 Å^3
• 极化表面积: 63.6 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Liquid
• 熔点: 200 - 202°C
• 沸点: 106.5 °C/3 mmHg(lit.); 106°C/3mm
• 闪点: >110°C(230°F); 113 °C; 235.4 °F
• 密度: 1.119; 1.119 g/mL at 25 °C(lit.)
• 折射率: 1.4295; n20/D 1.435(lit.)
• 疏水性(logP): 0.352

安全信息

• 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: 26-36; 26-37-60
• 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: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

产品相关信息

• 纯度: 90+%; 95%; 96%; 98%
• 杂质: <10% ethyl malonate, potassium salt
• 线性分子式: HO2CCH2CO2C2H5

详细说明

Sigma Aldrich - 445088

包装
5 g in glass bottle
Application
Reactant for:
• Preparation of tetramic acids via Dieckmann ring closure1
• Organocatalytic decarboxylative Doebner-Knoevenagel reactions2
• Conjugation to amino-modified oligonucleotides3
• Acylation reactions (acylation agent)4
• Indole glyoxylamides for potential Prion disease treatment5
• Knoevenagel condensation with aldehydes6
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 445088.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

参考文献

• Carbodiimide coupling with polymer-bound ɑ-amino acids has been used in the solid-phase synthesis of substituted tetramic acids; J. Org. Chem., 63, 4808 (1998).
• See also Ethyl potassium malonate, A10720.
• Half esters of malonic acid react with ɑ?-enals in pyridine/DMAP to give ɑ? δ-dienoic esters with good (E)-selectivity: Synthesis: 534 (1988).
• Reaction with alkyl chloroformates results in decarboxylation of the mixed anhydride in situ, providing a route to mixed ethyl alkyl malonates in high yield under very mild conditions: Tetrahedron Lett., 26, 1573 (1985).
• The O,ɑ-dilithio-derivative, formed with n-BuLi in THF, can be acylated with acid chlorides to give, on acidic work-up (in situ decarboxylation), ?-ketoesters directly in high yield: J. Org. Chem., 44, 310 (1979); Org. Synth. Coll., 7, 213 (1990). Similarly, alkylation of the dilithio-derivative provides a direct route to esters of substituted acetic acids: J. Org. Chem., 40, 2556 (1975).