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D138401

Sigma-Aldrich

Dimethylacetylendicarboxylat

95%

Synonym(e):

Dimethyl-acetylendicarboxylat

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About This Item

Lineare Formel:
CH3OCOC≡CCO2CH3
CAS-Nummer:
762-42-5
Molekulargewicht:
142.11
Beilstein:
607063
EG-Nummer:
212-098-4
MDL-Nummer:
MFCD00008456
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24893421
NACRES:
NA.22

Assay

95%

Form

liquid

Brechungsindex

n20/D 1.447 (lit.)

bp

95-98 °C/19 mmHg (lit.)

Dichte

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

InChIKey

VHILMKFSCRWWIJ-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

Versatile dienophile used in Diels-Alder reactions.

Piktogramme

CorrosionExclamation mark
GHS05,GHS07

Signalwort

Danger

H-Sätze

H302,H314

Gefahreneinstufungen

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

Lagerklassenschlüssel

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flammpunkt (°F)

186.8 °F - closed cup

Flammpunkt (°C)

86 °C - closed cup

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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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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