ethyl prop-2-ynoate

• ChemBase编号: 57995
• 分子式: C5H6O2
• 平均质量: 98.09994
• 单一同位素质量: 98.03677943
• SMILES: C(#C)C(=O)OCC
• Canonical SMILES: CCOC(=O)C#C
• InChI: InChI=1S/C5H6O2/c1-3-5(6)7-4-2/h1H,4H2,2H3
• InChIKey: FMVJYQGSRWVMQV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethyl prop-2-ynoate
• IUPAC传统名: ethyl propiolate
• 别名: 乙炔基羧酸乙酯; 丙炔酸乙酯; Ethyl propiolate; Ethyl acetylenecarboxylate; Ethyl propiolate; Ethyl propiolate; Ethyl prop-2-ynoate; Propiolic acid ethyl ester

登记号

• CAS号: 623-47-2
• EC号: 210-795-8
• MDL号: MFCD00009184
• Beilstein号: 878250
• PubChem SID: 24894572; 162062758; 24887914
• PubChem CID: 12182

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 0.91800505
• LogD (pH = 7.4): 0.91800505
• Log P: 0.91800505
• 摩尔折射率: 25.3017 cm^3
• 极化性: 9.635451 Å^3
• 极化表面积: 26.3 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 9°C; 9°C
• 沸点: 118-120°C; 118-120°C; 120 °C(lit.); 120°C
• 闪点: 23°C; 23°C(73°F); 25 °C; 77 °F
• 密度: 0.963; 0.968 g/ml; 0.968 g/mL at 25 °C(lit.)
• 折射率: 1.4120; n20/D 1.412(lit.); n20/D 1.413

安全信息

• 保存注意事项: Flammable/Toxic/Harmful/Lachrymatory/Keep Cold; KEEP COLD, LACHRYMATOR, TOXIC, FLAMMABLE
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3272; UN3272
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 10-36/37/38; R:10-36/37/38
• 安全公开号: 26-36; 26-37-60; S:16-20-25-26-37/39
• TSCA收录: false; 否
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Warning
• GHS危险声明: H226-H315-H319-H335
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• 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 3272 3/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥99.0% (GC); 97%; 98%; 99%
• 级别: purum
• 杂质: ≤0.1% DCADMA; ≤0.2% dichloromethane
• 线性分子式: HC≡CCO2C2H5

详细说明

MP Biomedicals - 05205878

MP Biomedicals Rare Chemical collection

Sigma Aldrich - E46607

Application
卤化衍生物，用作手性相转移催化剂作用下环状 β-酮酯直接、不对称炔基化反应的底物。1还可用于 Ph3P 促进的苯-1,2,3,5-四羧酸酯的一锅法、四组分合成。2
包装
5, 25, 100 g in glass bottle

Sigma Aldrich - 81869

Other Notes
合成 (Z)-2,3-二溴丙烯酸乙酯1

参考文献

• Regio- and stereospecific hydrohalogenation of propiolic acid derivatives is illustrated by the conversion of ethyl propiolate to (Z)-3-bromo-2-propenoate in the presence of LiBr + acetic acid in acetonitrile: J. Org. Chem., 57, 709 (1992); Org. Synth. Coll., 9, 412 (1998).
• n-BuLi gives the alkynyllithium derivative, stable at low temperatures: J. Org. Chem., 45, 28 (1980). For use in a sequence for the synthesis of butenolides, see: J. Am. Chem. Soc., 101, 1544 (1979):
  
• Conjugate addition of allylic alcohols in the presence of trimethylamine proceeds via an intermediate betaine and leads to allyl vinyl ethers which undergo the Claisen rearrangement to give δ-unsaturated aldehydes: J. Org. Chem., 48, 5406 (1983); Org. Synth. Coll., 8, 536 (1993):