D138401
丁炔二酸二甲酯
95%
别名:
Dimethyl 2-butynedioate
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关于此项目
线性分子式:
CH3OCOC≡CCO2CH3
化学文摘社编号:
分子量:
142.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-098-4
Beilstein/REAXYS Number:
607063
MDL number:
Assay:
95%
Form:
liquid
InChI key
VHILMKFSCRWWIJ-UHFFFAOYSA-N
InChI
1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
SMILES string
COC(=O)C#CC(=O)OC
assay
95%
form
liquid
Quality Level
refractive index
n20/D 1.447 (lit.)
bp
95-98 °C/19 mmHg (lit.)
density
1.156 g/mL at 25 °C (lit.)
General description
乙炔二羧酸二甲酯 (DMAD)是一种酯，可用作环加成反应中的二烯亲和物和亲偶极物。
Application
用于 Diels-Alder 反应的多功能亲二烯体。
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B
存储类别
8A - Combustible corrosive hazardous materials
flash_point_f
186.8 °F - closed cup
flash_point_c
86 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Yuanyuan Chen et al.
Journal of the American Chemical Society, 129(35), 10773-10784 (2007-08-19)
Recently, it was reported that both dienylfurans and dienylisobenzofurans could react with dimethyl acetylenedicarboxylate (DMAD) to give [8+2] cycloadducts. Understanding these [8+2] reactions will aid the design of additional [8+2] reactions, which have the potential for the synthesis of 10-membered
Cheng Ma et al.
The Journal of organic chemistry, 70(22), 8919-8923 (2005-10-22)
[reaction: see text] A facile preparation of 3-aminofuran derivatives via multicomponent reactions of thiazole carbenes, aldehydes, and dimethyl acetylenedicarboxylate (DMAD) is reported. In this process, the thiazole carbenes, generated in situ from thiazolium salts, reacted with aldehydes and DMAD at
Shunmin He et al.
Nature communications, 10(1), 2219-2219 (2019-05-19)
A long-standing question in the field of embryogenesis is how the zygotic genome is precisely activated by maternal factors, allowing normal early embryonic development. We have previously shown that N6-methyladenine (6mA) DNA modification is highly dynamic in early Drosophila embryos
Qiuping Ding et al.
The Journal of organic chemistry, 74(2), 921-924 (2008-12-06)
Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoximes, DMAD, and bromine are described, which afford the unexpected isoquinoline-based azomethine ylides in good to excellent yields. The products could be further elaborated via palladium-catalyzed cross-coupling reactions to generate highly functionalized isoquinoline-based stable
Dimethyl acetylenedicarboxylate: A versatile tool in organic synthesis
CG Neochoritis, et al.
Synthesis, 537-585 (2014)
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