Acetylenedicarboxylic acid
Product Information
Molecular Formula
C4H2O4
Molecular Weight
114.06
Description
Acetylenedicarboxylic acid (CAS# 142-45-0) is used as an electrolyte in the fabrication of anodic nanoporous alumina. It is also used as a reagent in the synthesis of several organic compounds including that of derivatives of metronodazole (antibiotic and antiprotozoal medication) which display increased antimicrobial and antiparasitic properties.
Synonyms
but-2-ynedioic acid
IUPAC Name
but-2-ynedioic acid
SMILES
C(#CC(=O)O)C(=O)O
InChI
InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)
InChI Key
YTIVTFGABIZHHX-UHFFFAOYSA-N
Boiling Point
362.4 °C at 760 mmHg
Melting Point
180-187 °C
Flash Point
131 °C
Density
1.699 g/cm3
Appearance
Cream coloured to beige crystalline powder or
Storage
2-8 °C
Refractive Index
1.5260 (estimate)
LogP
-0.84100
Safety Information
Hazards
H301:
Toxic if swallowed.
H314:
Causes severe skin burns and eye damage.
Toxic if swallowed.
H314:
Causes severe skin burns and eye damage.
Precautionary Statement
P260, P261, P264, P270, P271, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501
Signal Word
Danger
Computed Properties
XLogP3
0.1
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Exact Mass
113.99530854 g/mol
Monoisotopic Mass
113.99530854 g/mol
Topological Polar Surface Area
74.6Ų
Heavy Atom Count
8
Formal Charge
0
Complexity
161
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-113980204-A | Slump-retaining type polycarboxylate superplasticizer and preparation method thereof | 2021-11-29 |
| JP-2022009369-A | Deodorant for daily life odor | 2021-10-21 |
| CN-113880757-A | Method for synthesizing 4-pyridone and derivatives thereof by continuous flow | 2021-10-13 |
| CN-113681010-A | Wear-resistant corrosion-resistant hard alloy milling cutter and preparation method thereof | 2021-08-26 |
| CN-215827337-U | High stability type storage jar | 2021-08-26 |
| CN-113651684-A | Preparation method of 4-hydroxy-2-butynoic acid | 2021-08-16 |
| CN-113583012-A | Synthesis method of pyrano [4,3-b ] pyridine-2, 7-dione compound | 2021-08-05 |
| CN-113499860-A | Efficient flotation method for smelting slag recycled by copper regeneration | 2021-07-08 |
| CN-113292414-A | Preparation method of butynedioic acid | 2021-06-17 |
| CN-113372219-A | Method for preparing ethynylnaphthalene derivative by [4+2] cyclization reaction with water as solvent | 2021-05-17 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 23050691 | 2012-10-19 | Facile synthesis of dispirooxindole-fused heterocycles via domino 1,4-dipolar addition and Diels-Alder reaction of in situ generated Huisgen 1,4-dipoles | Organic letters |
| 22473421 | 2012-05-07 | Chiral cyclopalladated complex promoted asymmetric synthesis of diester-substituted P,N-ligands via stepwise hydrophosphination and hydroamination reactions | Dalton transactions (Cambridge, England : 2003) |
| 22590276 | 2012-05-01 | Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate | Acta crystallographica. Section E, Structure reports online |
| 22173695 | 2012-02-01 | Three-component reactions of isocyanides, dialkyl acetylenedicarboxylates, and trans-cinnamoyl chlorides for the synthesis of highly functionalized 2-vinyl furans | Molecular diversity |
| 22267194 | 2012-01-20 | Diversity oriented syntheses of conventional heterocycles by smart multi component reactions (MCRs) of the last decade | Molecules (Basel, Switzerland) |
| 22061642 | 2011-12-15 | Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis | Bioorganic & medicinal chemistry letters |
| 21568339 | 2011-07-11 | 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 | ACS combinatorial science |
| 20845925 | 2010-10-18 | Optimized synthesis of tetrafluoroterephthalic acid: a versatile linking ligand for the construction of new coordination polymers and metal-organic frameworks | Inorganic chemistry |
| 21588989 | 2010-10-09 | Trimethyl-3-meth-oxy-4-oxo-5-triphenyl-phospho-ranyl-idene-cyclo-pent-1-ene-1,2,3-tricarboxyl-ate | Acta crystallographica. Section E, Structure reports online |
| 20795634 | 2010-09-17 | Synthesis of symmetrical and unsymmetrical diarylalkynes from propiolic acid using palladium-catalyzed decarboxylative coupling | The Journal of organic chemistry |
