471-25-0 | Propiolic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$42.00	$30.00
5g	95%	in stock	$74.00	$52.00
25g	95%	in stock	$197.00	$138.00

Description

• Catalog Number: AB78621
• Chemical Name: Propiolic acid
• CAS Number: 471-25-0
• Molecular Formula: C3H2O2
• Molecular Weight: 70.0468
• MDL Number: MFCD00004360
• SMILES: OC(=O)C#C
• NSC Number: 16152

Computed Properties

• Complexity: 84.3
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 5
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• XLogP3: 0.3

Literature

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  Dalton transactions (Cambridge, England : 2003) 20120907

• Kinetic studies on the formation of sulfonyl radicals and their addition to carbon-carbon multiple bonds.

  The journal of physical chemistry. A 20120726

• Synthesis of symmetric 1,4-diamino-2-butynes via a Cu(I)-catalyzed one-pot A3-coupling/decarboxylative coupling of a propiolic acid, an aldehyde, and an amine.

  The Journal of organic chemistry 20120601

• Carboxyethynyl anchoring ligands: a means to improving the efficiency of phthalocyanine-sensitized solar cells.

  Angewandte Chemie (International ed. in English) 20120427

• Synthesis of heterocyclic N-(β-D-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase.

  Carbohydrate research 20120401

• CuI-promoted one-pot synthesis of N-Boc protected β-ketotriazole amino acids: application in the synthesis of new class of dipeptidomimetics.

  Protein and peptide letters 20120301

• N-[2-(N-Cyclo-hexyl-carbamo-yl)propan-2-yl]-N-(2-iodo-phen-yl)prop-2-ynamide.

  Acta crystallographica. Section E, Structure reports online 20120201

• Gold-catalyzed intermolecular reactions of propiolic acids with alkenes: [4 + 2] annulation and enyne cross metathesis.

  Journal of the American Chemical Society 20120111

• A modular strategy to prepare multivalent inhibitors of prostate-specific membrane antigen (PSMA).

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• (Phen-yl)(3-phenyl-sulfonyl-1,2-dihydro-pyrrolo-[1,2-a]quinoxalin-1-yl)methanone.

  Acta crystallographica. Section E, Structure reports online 20111101

• Microwave measurements of proton tunneling and structural parameters for the propiolic acid-formic acid dimer.

  The Journal of chemical physics 20111021

• Synthesis of variously coupled conjugates of D-glucose, 1,3,4-oxadiazole, and 1,2,3-triazole for inhibition of glycogen phosphorylase.

  Carbohydrate research 20110906

• Asymmetric alkynylation of aldehydes with propiolates without high reagent loading and any additives.

  Organic & biomolecular chemistry 20110621

• Syntheses of α-pyrones using gold-catalyzed coupling reactions.

  Organic letters 20110603

• Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols.

  The Journal of organic chemistry 20110603

• Microwave irradiated click reactions on silicon surfaces via derivertization of covalently grafted poly(PEGMA) brushes.

  Journal of colloid and interface science 20110601

• Electrophilic chemistry of propargylic alcohols in imidazolium ionic liquids: propargylation of arenes and synthesis of propargylic ethers catalyzed by metallic triflates [Bi(OTf)3, Sc(OTf)3, Yb(OTf)3], TfOH, or B(C6F5)3.

  Organic & biomolecular chemistry 20110407

• Pd-catalyzed decarboxylative coupling of propiolic acids: one-pot synthesis of 1,4-disubstituted 1,3-diynes via Sonogashira-homocoupling sequence.

  The Journal of organic chemistry 20110401

• Selective orthosteric free fatty acid receptor 2 (FFA2) agonists: identification of the structural and chemical requirements for selective activation of FFA2 versus FFA3.

  The Journal of biological chemistry 20110325

• Synthesis of symmetrical and unsymmetrical diarylalkynes from propiolic acid using palladium-catalyzed decarboxylative coupling.

  The Journal of organic chemistry 20100917

• Regiodivergent ligand-controlled rhodium-catalyzed [(2+2)+2] carbocyclization reactions with alkyl substituted methyl propiolates.

  Angewandte Chemie (International ed. in English) 20100802

• Temporal effects on spectroscopic line shapes, resolution, and sensitivity of the broad-band sum frequency generation.

  The Journal of chemical physics 20100621

• Cu-catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling.

  Organic letters 20100507

• Click chemistry aided synthesis of 1,4-substituted 1,2,3-triazole based N-Fmoc protected epsilon-amino acids: isolation, characterization and synthesis of novel triazole based unnatural amino acids.

  Protein and peptide letters 20100401

• PPh3-catalyzed reactions of alkyl propiolates with N-tosylimines: a facile synthesis of alkyl 2-[aryl(tosylimino)methyl]acrylate and an insight into the reaction mechanism.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20100208

• One-pot synthesis of 2-pyridones via chemo- and regioselective tandem Blaise reaction of nitriles with propiolates.

  The Journal of organic chemistry 20091002

• Structural analysis of glycosphingolipid analogues obtained by the saccharide primer method using CE-ESI-MS.

  Electrophoresis 20091001

• Highly regioselective Au(I)-catalyzed hydroamination of ynamides and propiolic acid derivatives with anilines.

  Organic letters 20090917

• Study of 1,4-dihydropyridine structural scaffold: discovery of novel sirtuin activators and inhibitors.

  Journal of medicinal chemistry 20090910

• Identification of the toxic trigger in mushroom poisoning.

  Nature chemical biology 20090701

• Highly enantioselective catalytic alkyl propiolate addition to aliphatic aldehydes.

  Organic letters 20090604

• N-Benzyl-2-propynamide.

  Acta crystallographica. Section E, Structure reports online 20090501

• Gold(I)-catalyzed coupling reactions for the synthesis of diverse small molecules using the build/couple/pair strategy.

  Journal of the American Chemical Society 20090422

• Kinetic glutathione chemoassay to quantify thiol reactivity of organic electrophiles--application to alpha,beta-unsaturated ketones, acrylates, and propiolates.

  Chemical research in toxicology 20090401

• Direct measurement of charge transport through helical poly(ethyl propiolate) nanorods wired into gaps in single walled carbon nanotubes.

  Nanotechnology 20090311

• Acetylides from alkyl propiolates as building blocks for C3 homologation.

  Angewandte Chemie (International ed. in English) 20090101

• Si(111) surface modified with alpha,beta-unsaturated carboxyl groups studied by MIR-FTIR.

  Langmuir : the ACS journal of surfaces and colloids 20081007

• Ring expansion of lactones and lactams via propiolate 1-carbon intercalation.

  Organic letters 20080918

• Thiol detection, derivatization and tagging at micromole to nanomole levels using propiolates.

  Bioorganic chemistry 20080601

• Catalytic addition of alkyne C-H, amine N-H, and phosphine P-H bonds to carbodiimides: an efficient route to propiolamidines, guanidines, and phosphaguanidines.

  Organic & biomolecular chemistry 20080521

• Three-component coupling reaction and cyclization of N-tosylimines and TMS-substituted propiolate mediated by DABCO.

  The Journal of organic chemistry 20080307

• One-pot synthesis of diarylalkynes using palladium-catalyzed sonogashira reaction and decarboxylative coupling of sp carbon and sp2 carbon.

  Organic letters 20080306

• Synthesis and characterization of polyacetylene with side-chain thiophene functionality.

  International journal of molecular sciences 20080301

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• Methyl 2-(1,3-dioxoisoindolin-2-yl)acrylate.

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• Matrix isolation and ab initio study of the HXeCCH...CO2 complex.

  The Journal of chemical physics 20071021

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  Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20070801

• Increases in microbial nitrogen production and efficiency in vitro with three inhibitors of ruminal methanogenesis.

  Canadian journal of microbiology 20070401

• Synthesis of modified nucleosides for incorporation of formyletheno and carboxyetheno adducts of adenine nucleosides into oligonucleotides.

  Nucleosides, nucleotides & nucleic acids 20070101

• UV photolysis products of propiolic acid in noble-gas solids.

  The journal of physical chemistry. A 20061012

• Reaction of thioketones with propiolic acids.

  Organic & biomolecular chemistry 20060721

• Chemo-differentiating MCRs based on alpha-ketoesters and terminal alkynoates. A homoaldol-based ABB' system.

  Chemical communications (Cambridge, England) 20060705

• Novel potent and selective alphavbeta3/alphavbeta5 integrin dual antagonists with reduced binding affinity for human serum albumin.

  European journal of medicinal chemistry 20060701

• Effects of butyrate precursors on electron relocation when methanogenesis is inhibited in ruminal mixed cultures.

  Letters in applied microbiology 20060601

• Trisoxazoline/Cu(II)-promoted Kinugasa reaction. Enantioselective synthesis of beta-lactams.

  The Journal of organic chemistry 20060428

• Synthesis of substituted chromenes through the DABCO-catalyzed reaction of but-3-yn-2-one and methyl propiolate with salicyl N-tosylimines (DABCO = 1,4-diazabicyclo[2.2.2]octane).

  Chemistry (Weinheim an der Bergstrasse, Germany) 20060412

• Monitoring Lactobacillus plantarum in grass silages with the aid of 16S rDNA-based quantitative real-time PCR assays.

  Systematic and applied microbiology 20060101

• A new protocol for the consecutive alpha- and beta-activation of propiolates towards electrophiles, involving conjugate addition of tertiary amines and intramolecular silyl migration.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20050905

• Inactivation of malonate semialdehyde decarboxylase by 3-halopropiolates: evidence for hydratase activity.

  Biochemistry 20050705

• A practical catalytic method for preparing highly substituted cyclobutanes and cyclobutenes.

  Journal of the American Chemical Society 20050323

• A modular, one-pot, four-component synthesis of polysubstituted 1,3-oxazolidines.

  The Journal of organic chemistry 20050204

• Reactions of 4-oxalocrotonate tautomerase and YwhB with 3-halopropiolates: analysis and implications.

  Biochemistry 20040127

• Effects of several inhibitors on pure cultures of ruminal methanogens.

  Journal of applied microbiology 20040101

• High-throughput synthesis and optimization of thrombin inhibitors via urazole alpha-addition and Michael addition.

  Bioorganic & medicinal chemistry letters 20030417

• In situ proton NMR analysis of alpha-alkynoate biotransformations. From 'invisible' substrates to detectable metabolites.

  European journal of biochemistry 20030401

• A novel modified baylis-hillman reaction of propiolate.

  Journal of the American Chemical Society 20030122

• Use of some novel alternative electron sinks to inhibit ruminal methanogenesis.

  Reproduction, nutrition, development 20030101

• Synthesis of seven-membered lactones via nickel- and zinc-catalyzed highly regio- and stereoselective cyclization of 2-iodobenzyl alcohols with propiolates.

  Journal of the American Chemical Society 20020522

• Regiochemistry in 1,3-dipolar cycloadditions of the azomethine ylide formed from diethyl aminomalonate and paraformaldehyde.

  The Journal of organic chemistry 20020111

• Palladium-catalyzed sulfinylzincation: 1-alkynyl sulfoxides as a sulfinyl anion equivalent.

  Organic letters 20011115