D138401
Dimethyl acetylenedicarboxylate
95%
Synonym(s):
Dimethyl 2-butynedioate
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About This Item
Linear Formula:
CH3OCOC≡CCO2CH3
CAS Number:
Molecular Weight:
142.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-098-4
Beilstein/REAXYS Number:
607063
MDL number:
Assay:
95%
Form:
liquid
Quality Level
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
Related Categories
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.
signalword
Danger
hcodes
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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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
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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| D138401-5G | 04061833559727 |
| D138401-25G | 04061833559710 |
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