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Merck
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Key Documents

D138401

Sigma-Aldrich

Dimethyl acetylenedicarboxylate

95%

동의어(들):

Dimethyl 2-butynedioate

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About This Item

Linear Formula:
CH3OCOC≡CCO2CH3
CAS Number:
Molecular Weight:
142.11
Beilstein:
607063
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

95%

형태

liquid

refractive index

n20/D 1.447 (lit.)

bp

95-98 °C/19 mmHg (lit.)

density

1.156 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C#CC(=O)OC

InChI

1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3

InChI key

VHILMKFSCRWWIJ-UHFFFAOYSA-N

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일반 설명

Dimethyl acetylenedicarboxylate (DMAD) is an ester utilized as a dienophile and a dipolarophile in cycloaddition reactions.

애플리케이션

Versatile dienophile used in Diels-Alder reactions.

픽토그램

CorrosionExclamation mark

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point (°F)

186.8 °F - closed cup

Flash Point (°C)

86 °C - closed cup

개인 보호 장비

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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이미 열람한 고객

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
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
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
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
Yi Li et al.
Polymers, 13(3) (2021-01-28)
Big spherulite structure and high crystallinity are the two main drawbacks of poly(butylene succinate) (PBS) and hinder its application. In this work, a new type of copolyester poly(butylene succinate-co-butylene acetylenedicarboxylate) (PBSAD) is synthesized. With the incorporation of acetylenedicarboxylate (AD) units

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