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D138401

Sigma-Aldrich

Dimethyl acetylenedicarboxylate

95%

Sinonimo/i:

Dimethyl 2-butynedioate

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5 G
CHF 30.30
25 G
CHF 93.50

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5 G
CHF 30.30
25 G
CHF 93.50

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

CHF 30.30

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Livello qualitativo

200

Saggio

95%

Stato

liquid

Indice di rifrazione

n20/D 1.447 (lit.)

P. ebollizione

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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Categorie correlate

Descrizione generale

Dimethyl acetylenedicarboxylate (DMAD) is an ester utilized as a dienophile and a dipolarophile in cycloaddition reactions.[1]

Applicazioni

Versatile dienophile used in Diels-Alder reactions.[2][3][4]

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
WXBF5513V
WXBF1728V
WXBD6221V
WXBD2674V
0000094025

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Sigma-Aldrich

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Dicyclopentadiene

Ethyl 4,4,4-trifluoro-2-butynoate 97%

Sigma-Aldrich

401455

Ethyl 4,4,4-trifluoro-2-butynoate

Jing Sun et al.
ACS combinatorial science, 13(4), 421-426 (2011-05-17)
A protocol has been developed for the efficient synthesis of structurally diverse 3,4-dihydropyridin-2(1H)-ones and 3,4-dihydro-2H-pyrans via four-component reactions of arylamines, acetylenedicarboxylate, aromatic aldehydes and cyclic 1,3-diketones. The selective formation of the very different pyridinone or pyran derivatives depends on the
Guan-Wu Wang et al.
Organic & biomolecular chemistry, 4(22), 4063-4064 (2007-02-23)
The novel multicomponent reaction of [60]fullerene with dimethyl acetylenedicarboxylate and isoquinoline, quinoline or substituted quinolines was investigated. This type of reaction presents the first example of a 1,4-dipolar cycloaddition reaction in fullerene chemistry.
Steven E Wheeler et al.
Journal of the American Chemical Society, 132(10), 3304-3311 (2010-02-18)
Stereoselective Diels-Alder cycloadditions that probe substituent effects in aryl-aryl sandwich complexes were studied experimentally and theoretically. Computations on model systems demonstrate that the stereoselectivity in these reactions is mediated by differential pi-stacking interactions in competing transition states. This allows relative
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
Dimethyl acetylenedicarboxylate: A versatile tool in organic synthesis
CG Neochoritis, et al.
Synthesis, 537-585 (2014)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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