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D138401

Sigma-Aldrich

Dimethyl acetylenedicarboxylate

95%

Synonym(s):

Dimethyl 2-butynedioate

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₹3,474.83
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5 G
₹3,474.83
25 G
₹7,674.93

About This Item

Linear Formula:
CH3OCOC≡CCO2CH3
CAS Number:
762-42-5
Molecular Weight:
142.11
Beilstein:
607063
EC Number:
212-098-4
MDL number:
MFCD00008456
UNSPSC Code:
12352100
PubChem Substance ID:
24893421
NACRES:
NA.22

₹3,474.83

Available to ship on25 April 2025Details

Request a Bulk Order

Quality Level

200

Assay

95%

form

liquid

refractive index

n20/D 1.447 (lit.)

bp

95-98 °C/19 mmHg (lit.)

density

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

InChI key

VHILMKFSCRWWIJ-UHFFFAOYSA-N

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General description

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

Application

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

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5513V
WXBF1728V
WXBD6221V
WXBD2674V
0000094025

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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.
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
Huan-Rui Pan et al.
The Journal of organic chemistry, 75(19), 6644-6652 (2010-09-14)
The facile three-component reactions of N,N-substituted imidazo[1,5-a]pyridine carbenes, namely imidazo[1,5-a]pyridin-3-ylidenes, with aldehydes and DMAD or allenoates were disclosed. Both reactions proceeded via tandem nucleophilic addition, [3 + 2]-cycloaddition, and ring transformation to produce different 4-[(2-pyridyl)methyl]aminofuran derivatives generally in moderate yields.
Vijay Nair et al.
Organic letters, 7(21), 4625-4628 (2005-10-08)
[reaction: see text] The pyridine-mediated reaction of dimethyl acetylenedicarboxylate and cyclobutene-1,2-diones affords selective access to either hexasubstituted benzene derivatives or cyclopentenedione derivatives depending on the concentration of pyridine.
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  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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