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D138401

Sigma-Aldrich

Dimethyl acetylenedicarboxylate

95%

Sinônimo(s):

Dimethyl 2-butynedioate

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About This Item

Fórmula linear:
CH3OCOC≡CCO2CH3
Número CAS:
762-42-5
Peso molecular:
142.11
Beilstein:
607063
Número CE:
212-098-4
Número MDL:
MFCD00008456
Código UNSPSC:
12352100
ID de substância PubChem:
24893421
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

Nível de qualidade

200

Ensaio

95%

Formulário

liquid

índice de refração

n20/D 1.447 (lit.)

p.e.

95-98 °C/19 mmHg (lit.)

densidade

1.156 g/mL at 25 °C (lit.)

cadeia de caracteres SMILES

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

InChI

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

chave InChI

VHILMKFSCRWWIJ-UHFFFAOYSA-N

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Descrição geral

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

Aplicação

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

Pictogramas

CorrosionExclamation mark
GHS05,GHS07

Palavra indicadora

Danger

Frases de perigo

H302,H314

Classificações de perigo

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

Código de classe de armazenamento

8A - Combustible corrosive hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

186.8 °F - closed cup

Ponto de fulgor (°C)

86 °C - closed cup

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
WXBF5513V
WXBF1728V
WXBD6221V
WXBD2674V
0000094025

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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
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
Dimethyl acetylenedicarboxylate: A versatile tool in organic synthesis
CG Neochoritis, et al.
Synthesis, 537-585 (2014)
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
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
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Questions

1–2 of 2 Questions  

  1. 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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  2. 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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