A15207

Acetylenedicarboxylic acid

95%

• Synonym(s): 2-Butynedioic acid
• Linear Formula: HOOCC≡CCOOH
• CAS Number: 142-45-0
• Molecular Weight: 114.06
• Beilstein/REAXYS Number: 878357
• EC Number: 205-536-0
• MDL number: MFCD00004362
• UNSPSC Code: 12352100
• PubChem Substance ID: 24890553
• NACRES: NA.22

Properties

• assay: 95%
• form: crystals
• mp: 180-187 °C (dec.) (lit.)
• storage temp.: 2-8°C
• SMILES string: OC(=O)C#CC(O)=O
• InChI: 1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)
• InChI key: YTIVTFGABIZHHX-UHFFFAOYSA-N

Description

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301,H315,H319,H335
• pcodes: P261 - P264 - P271 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• 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_germany: WGK 3
• flash_point_f: 267.8 °F
• flash_point_c: 131 °C
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges