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D138401

Sigma-Aldrich

Dimethyl acetylenedicarboxylate

95%

Sinonimo/i:

Dimethyl 2-butynedioate

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About This Item

Formula condensata:
CH3OCOC≡CCO2CH3
Numero CAS:
762-42-5
Peso molecolare:
142.11
Beilstein:
607063
Numero CE:
212-098-4
Numero MDL:
MFCD00008456
Codice UNSPSC:
12352100
ID PubChem:
24893421
NACRES:
NA.22

Livello qualitativo

200

Saggio

95%

Forma fisica

liquid

Indice di rifrazione

n20/D 1.447 (lit.)

P. eboll.

95-98 °C/19 mmHg (lit.)

Densità

1.156 g/mL at 25 °C (lit.)

Stringa SMILE

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

InChI

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

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Descrizione generale

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

Applicazioni

Versatile dienophile used in Diels-Alder reactions.

Pittogrammi

CorrosionExclamation mark
GHS05,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H302,H314

Classi di pericolo

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

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

186.8 °F - closed cup

Punto d’infiammabilità (°C)

86 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
WXBD6221V
WXBD2674V
0000094025
0000078831
0000064929

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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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