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D138401

Sigma-Aldrich

Dimethyl acetylenedicarboxylate

95%

Synonym(s):

Dimethyl 2-butynedioate

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About This Item

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

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.

Application

Versatile dienophile used in Diels-Alder reactions.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H314

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

186.8 °F - closed cup

flash_point_c

86 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF1728V
WXBD6221V
WXBD2674V
0000094025
0000078831

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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.
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)
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
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