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Merck
CN

A15207

Acetylenedicarboxylic acid

95%

Synonym(s):

2-Butynedioic acid

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About This Item

Linear Formula:
HOOCC≡CCOOH
CAS Number:
142-45-0
Molecular Weight:
114.06
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24890553
EC Number:
205-536-0
Beilstein/REAXYS Number:
878357
MDL number:
MFCD00004362
Assay:
95%
Form:
crystals

Key Documents

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InChI key

YTIVTFGABIZHHX-UHFFFAOYSA-N

InChI

1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)

SMILES string

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

assay

95%

form

crystals

mp

180-187 °C (dec.) (lit.)

storage temp.

2-8°C

Quality Level

200

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Application

Acetylenedicarboxylic acid is generally used to synthesize its ester derivatives, dimethyl acetylenedicarboxylate (DMAD) and dimethyl acetylenedicarboxylate, which are useful precursors in organic synthesis.
Some of the common applications are listed below:
  • Acetylenedicarboxylic acid and its ester derivatives can undergo Cu(I)-catalyzed radical addition with acetophenones to yield furan derivatives.
  • It is one of the shortest linear links used in the preparation of Covalent Organic Frameworks (COFs) and Metal Organic Frameworks (MOFs) like IRMOF-0.
  • Various hexaarylbenzenes can be built via oxidative cyclodehydrogenation of diaryl alkynes derived from acetylenedicarboxylic acid.
  • It can be used as a spacer while synthesizing molecular chains or dendrimers such as 2,3,8-trifunctionalized indenoquinoxaline dendrons and bisarylacetylene chromophores.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

267.8 °F

flash_point_c

131 °C

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG3995
BCBV9179
BCBP5048V
BCBF9686V
BCBC9689V

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Synthesis and multi-photon absorption properties of symmetric bisarylacetylene chromophores using functionalized isomeric pyrazinoindenocarbazole units as the rigid aryl substituents.
Lin TC, et al.
Dyes and Pigments, 132, 347-359 (2016)
Two-and three-photon absorption properties of fan-shaped dendrons derived from 2, 3, 8-trifunctionalized indenoquinoxaline units: synthesis and characterization.
Lin TC, et al.
Journal of Material Chemistry C, 5(32), 8219-8232 (2017)
Copper (I)-Catalyzed Radical Addition of Acetophenones to Alkynes in Furan Synthesis.
Manna S and Antonchick AP.
Organic Letters, 17(17), 4300-4303 (2015)
Room temperature synthesis of metal-organic frameworks: MOF-5, MOF-74, MOF-177, MOF-199, and IRMOF-0.
Tranchemontagne DJ, et al.
Tetrahedron, 64(36), 8553-8557 (2008)
Monolayer Field?Effect Transistors of Nonplanar Organic Semiconductors with Brickwork Arrangement.
Shan L, et al.
Advanced Materials, 27(22), 3418-3423 (2015)
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