A15207
Acetylenedicarboxylic acid
95%
Synonym(s):
2-Butynedioic acid
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About This Item
Linear Formula:
HOOCC≡CCOOH
CAS Number:
Molecular Weight:
114.06
Beilstein:
878357
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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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:
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
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
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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