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D138401

Sigma-Aldrich

Dimethyl acetylenedicarboxylate

95%

Sinónimos:

Dimethyl 2-butynedioate

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5 G
31,90 €
25 G
66,40 €

31,90 €

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5 G
31,90 €
25 G
66,40 €

About This Item

Fórmula lineal:
CH3OCOC≡CCO2CH3
Número de CAS:
762-42-5
Peso molecular:
142.11
Beilstein:
607063
Número CE:
212-098-4
Número MDL:
MFCD00008456
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24893421
NACRES:
NA.22

31,90 €

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Nivel de calidad

200

Ensayo

95%

Formulario

liquid

índice de refracción

n20/D 1.447 (lit.)

bp

95-98 °C/19 mmHg (lit.)

densidad

1.156 g/mL at 25 °C (lit.)

cadena SMILES

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

InChI

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

Clave InChI

VHILMKFSCRWWIJ-UHFFFAOYSA-N

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Descripción general

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

Aplicación

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

Pictogramas

CorrosionExclamation mark
GHS05,GHS07

Palabra de señalización

Danger

Frases de peligro

H302,H314

Clasificaciones de peligro

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

Código de clase de almacenamiento

8A - Combustible corrosive hazardous materials

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

186.8 °F - closed cup

Punto de inflamabilidad (°C)

86 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
WXBF5513V
WXBF1728V
WXBD6221V
WXBD2674V
0000094025

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Sigma-Aldrich

454338

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
Vijay Nair et al.
The Journal of organic chemistry, 71(6), 2313-2319 (2006-03-11)
The zwitterion formed by the reaction of dimethoxycarbene and DMAD adds efficiently to one of the carbonyl groups of 1,2-dicarbonyl compounds and anhydrides to generate dihydrofurans and spirodihydrofurans in good yields. In many cases, the carbene inserts into the C-C
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.
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
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
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Preguntas

1–2 de 2 Preguntas  

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

    1 respuesta

    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 respuesta

    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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