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D138401

Dimethyl acetylenedicarboxylate

Name: Dimethyl acetylenedicarboxylate
Brand: ALDRICH

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

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24893421

EC Number:

212-098-4

Beilstein/REAXYS Number:

607063

MDL number:

MFCD00008456

Assay:

95%

Form:

liquid

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Properties

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

Description

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

GHS05,GHS07

signalword

Danger

hcodes

H302,H314

pcodes

P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

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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Synthesis of 3,4-dihydropyridin-2(1H)-ones and 3,4-dihydro-2H-pyrans via Four-component reactions of aromatic aldehydes, cyclic 1,3-carbonyls, arylamines, and dimethyl acetylenedicarboxylate.

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

Novel multicomponent reaction of [60]fullerene: the first example of 1,4-dipolar cycloaddition reaction in fullerene chemistry.

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.

Probing substituent effects in aryl-aryl interactions using stereoselective Diels-Alder cycloadditions.

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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Global Trade Item Number

SKU	GTIN
D138401-5G	04061833559727
D138401-25G	04061833559710