1,3-diethyl propanedioate

• ChemBase编号: 76796
• 分子式: C7H12O4
• 平均质量: 160.16778
• 单一同位素质量: 160.07355886
• SMILES: O=C(OCC)CC(=O)OCC
• Canonical SMILES: CCOC(=O)CC(=O)OCC
• InChI: InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
• InChIKey: IYXGSMUGOJNHAZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,3-diethyl propanedioate
• IUPAC传统名: diethyl malonate
• 别名: 胡萝卜酸二乙酯; 丙二酸二乙酯; Diethyl propane-1,3-dioate; Diethyl malonate; Malonic acid diethyl ester; Diethyl malonate; Propanedioic acid diethyl ester

登记号

• CAS号: 105-53-3
• EC号: 203-305-9
• MDL号: MFCD00009195
• Beilstein号: 774687
• 默克索引号: 143823
• PubChem SID: 24901030; 24894329; 162041698
• PubChem CID: 7761
• CHEBI ID: 391281
• CHEMBL: 177114
• Chemspider ID: 13863636
• FEMA编号: 2375
• 医学主题词(MeSH): Diethyl+malonate
• 美国药典/FDA物质标识码: 53A58PA183
• 维基百科标题: Diethyl_malonate
• 欧洲委员会编号: 2106
• Flavis Number: 9.49

理论计算性质

• Acid pKa: 12.359425
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.67428666
• LogD (pH = 7.4): 0.674282
• Log P: 0.6742868
• 摩尔折射率: 38.0232 cm^3
• 极化性: 15.247779 Å^3
• 极化表面积: 52.6 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: negligible in water
• 外观: colourless liquid
• 熔点: -50 °C (223 K); -50°C; -50°C; -51°C; -51--50 °C(lit.)
• 沸点: 198-200°C; 199 °C (472 K); 199 °C(lit.); 199°C
• 闪点: 194 °F; 200 °C; 90 °C; 90°C; 90°C(194°F)
• 密度: 1.05 g/cm^3, liquid; 1.055; 1.055 g/mL at 25 °C(lit.); 1.06 g/ml
• 折射率: 1.413; 1.4140; n20/D 1.413; n20/D 1.413(lit.); n20/D 1.414
• 蒸汽压: 1 mmHg ( 40 °C)
• 蒸汽密度: 5.52 (vs air)
• 感官: fruity

安全信息

• 保存注意事项: Irritant
• RTECS编号: OO0700000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+); 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 36; R:28-36/37/38
• 安全公开号: 26; S:28-29-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• 主要危害: Harmful (X), Flammable (F)
• GHS危险声明: H227; H319
• GHS警示性声明: P305 + P351 + P338
• 个人保护装置: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Regulation Compliance: FDA 21 CFR (172.515)

药理学性质

• 过敏源: no known allergens

产品相关信息

• 纯度: ≥97.0% (GC); ≥98%; ≥99.0% (GC); ≥99.5% (GC); 99%
• 级别: Halal; NI; puriss.; puriss. p.a.; purum; ReagentPlus®
• 有效期: (limited shelf life, expiry date on the label)
• 线性分子式: CH2(COOC2H5)2

详细说明

MP Biomedicals - 05206008

MP Biomedicals Rare Chemical collection

Sigma Aldrich - W237507

包装
1 kg in poly bottle
1 sample in glass bottle
10, 25 kg in poly drum

Sigma Aldrich - D97754

包装
1, 2.5 kg in poly bottle
500 g in poly bottle
25 g in glass bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

参考文献

• For phase-transfer monoalkylation of the active methylene group see, e.g. (18-crown-6): Synthesis, 37 (1977); and (BTEAC): Org. Prep. Proced. Int., 26, 469 (1994). Solid-liquid phase transfer alkylation has been promoted by microwave irradiation: Synth. Commun., 25,1761 (1995). Dialkylation can also occur in the presence of BTEAC: Synthesis, 54 (1985); Org. Synth. Coll., 7, 411 (1990), to give cyclopropane derivatives. Stereoselective alkylation has been achieved under particularly mild conditions with secondary alkyl mesylates in the presence of Cesium fluoride, 12885 in DMF; complete inversion occurs at the secondary alkyl carbon: J. Org. Chem., 60, 2627 (1995); see also: Synlett, 499 (1998).
• C-Acylation of malonic esters is normally carried out by reaction of the Mg derivative with an acid chloride. A convenient method using a combination of MgCl₂ and triethylamine was introduced by Rathke: J. Org. Chem., 50, 2622 (1985); see also Triethylamine, A12646 for discussion of this system:
  
• A number of procedures have been devised for the direct conversion of malonic esters to acetic esters (decarboalkoxylation), in a single step of which heating in wet DMSO is perhaps the simplest: J. Org. Chem., 43, 138 (1978). See also 1,4-Diazabicyclo[2.2.2]octane, A14003.
• Compare also Dimethyl malonate, A11007, Di-tert-butyl malonate, A12774, Dibenzyl malonate, A10844, and Isopropylidene malonate, A15603.
• Substituents can also be introduced by Michael addition; see e.g.: Org. Synth. Coll., 8, 467 (1993).
• Arylation occurs with aryl bromides in the presence of CuI: Gazz. Chim. Ital., 122, 511 (1992).