1,3-dimethyl propanedioate

• ChemBase编号: 85346
• 分子式: C5H8O4
• 平均质量: 132.11462
• 单一同位素质量: 132.04225874
• SMILES: O(C(=O)CC(=O)OC)C
• Canonical SMILES: COC(=O)CC(=O)OC
• InChI: InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3
• InChIKey: BEPAFCGSDWSTEL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,3-dimethyl propanedioate
• IUPAC传统名: dimethyl malonate
• 别名: 丙二酸二甲酯; Dimethyl malonate; Propanedioic acid dimethyl ester; Malonic acid dimethyl ester; Dimethyl malonate

登记号

• CAS号: 108-59-8
• EC号: 203-597-8
• MDL号: MFCD00008460
• Beilstein号: 774261
• 默克索引号: 146096
• PubChem SID: 24848281; 24882580; 24854457; 162072462
• PubChem CID: 7943
• Chemspider ID: 21106102
• 维基百科标题: Dimethyl_malonate

理论计算性质

• Acid pKa: 12.90322
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.039329175
• LogD (pH = 7.4): -0.03933052
• Log P: -0.039329156
• 摩尔折射率: 28.526 cm^3
• 极化性: 11.623122 Å^3
• 极化表面积: 52.6 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

• 溶解度: Slightly soluble in water
• 外观: Colorless liquid
• 熔点: -62 - -60°C; -62 °C(lit.); -62°C; -62°C
• 沸点: 180-181 °C(lit.); 180-181°C; 180–181 °C; 180-181°C
• 闪点: 185 °F; 85 °C; 85°C; 90°C(194°F)
• 密度: 1.154; 1.156; 1.156 g/mL at 25 °C(lit.)
• 折射率: 1.4130; n20/D 1.413; n20/D 1.413(lit.)
• 蒸汽密度: >1 (vs air)
• 疏水性(logP): 0.069

安全信息

• 保存注意事项: Irritant
• RTECS编号: OO0950000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 36/37/38
• 安全公开号: 15; 26-36
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H227; H315-H319-H335
• GHS警示性声明: P210-P280-P370+P378A-P403+P235-P501A; P261-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

产品相关信息

• 纯度: ≥96.0% (GC); ≥99%; 95%; 98%; 98+%
• 级别: purum
• 线性分子式: CH2(COOCH3)2

详细说明

Sigma Aldrich - 136441

包装
1 kg in glass bottle
250 g in glass bottle

参考文献

• For successive C-alkylation, using NaOMe/MeOH, followed by NaH/THF, see: Org. Synth. Coll., 8, 381 (1993). For Michael addition to ɑ?-unsaturated acids, catalyzed by the Li salt of L-proline, see: J. Chem. Soc., Chem. Commun., 1088 (1991). For Knoevenagel reaction with (R)-citronellal, catalyzed by piperidine/AcOH, to give the alkylidene derivative, see: Org. Synth. Coll., 9, 310 (1998).
• C-Arylation with ortho-nitroaryl halides can be accomplished with NaH in DMSO. The products can be readily converted to substituted oxindoles: Synthesis, 51 (1993):
  
• Arylation with benzene: Tetrahedron Lett., 27, 2763 (1986), and free-radical substitution with thiophene or furan at the 2-position: Heterocycles, 27, 2627 (1988), are promoted by Ce(IV) salts.
• See also Diethyl malonate, A15468.