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922-67-8,MFCD00008572
Catalog No.:AA0035G6

922-67-8 | Methyl propiolate

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1g
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5g
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$20.00   $14.00
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10g
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  • Technical Information
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA0035G6
Chemical Name:
Methyl propiolate
CAS Number:
922-67-8
Molecular Formula:
C4H4O2
Molecular Weight:
84.0734
MDL Number:
MFCD00008572
SMILES:
COC(=O)C#C
NSC Number:
154164
Properties
Properties
 
BP:
104.0°C  
Form:
Liquid  
Refractive Index:
n20/D 1.408(lit.)  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
95.4  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
6  
Hydrogen Bond Acceptor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
0.6  

Literature

Title: Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes.

Journal: Organic & biomolecular chemistry 20121114

Title: Reactivity of 16-electron half-sandwich cobalt compounds containing a chelating 1,2-dicarba-closo-dodecaborane-1,2-dithiolate ligand towards methyl propiolate and dithio ligands.

Journal: Dalton transactions (Cambridge, England : 2003) 20121021

Title: High-pressure-promoted Diels-Alder approach to biaryls: application to the synthesis of the cannabinols family.

Journal: The Journal of organic chemistry 20120921

Title: Cobalt-promoted B-H and C-H activation: facile B-C coupling of carboranedithiolate and cyclopentadienyl.

Journal: Journal of the American Chemical Society 20120627

Title: Synthesis of ferrocene-labeled steroids via copper-catalyzed azide-alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes.

Journal: Steroids 20120601

Title: Synthesis of polyfunctionalized acrylates via one-pot reactions of arylamines, methyl propiolate, aromatic aldehydes, and active methylene compounds.

Journal: Molecular diversity 20120201

Title: Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D.

Journal: Journal of the American Chemical Society 20120125

Title: Highly regio- and stereoselective Diels-Alder cycloadditions via two-step and multicomponent reactions promoted by infrared irradiation under solvent-free conditions.

Journal: International journal of molecular sciences 20120101

Title: Synthesis of functionalized 2-aminohydropyridines and 2-pyridinones via domino reactions of arylamines, methyl propiolate, aromatic aldehydes, and substituted acetonitriles.

Journal: ACS combinatorial science 20110711

Title: Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate and N-{5-benzoyl-2-[(Z)-2-methoxyethenyl]-4-methylphenyl}benzamide.

Journal: Acta crystallographica. Section C, Crystal structure communications 20110601

Title: Methyl 1-(2,6-difluoro-benz-yl)-1H-1,2,3-triazole-4-carboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20110401

Title: Methyl (Z)-3-({5-[(E)-(tert-butyl-amino)-methyl-idene]-4-oxo-4,5-dihydro-1,3-thia-zol-2-yl}sulfan-yl)prop-2-enoate.

Journal: Acta crystallographica. Section E, Structure reports online 20100901

Title: Methyl 1-benzyl-1H-1,2,3-triazole-4-carboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20100701

Title: Reactions of alkynes with phosphido niobocenes: a combined experimental and theoretical study.

Journal: Dalton transactions (Cambridge, England : 2003) 20100227

Title: 4-(9,10-Dihydroacridin-9-ylidene)thiosemicarbazide and its five-membered thiazole and six-membered thiazine derivatives.

Journal: Acta crystallographica. Section C, Crystal structure communications 20100201

Title: Synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives from amino acids.

Journal: Molecules (Basel, Switzerland) 20091209

Title: Total synthesis and stereochemical assignment of (-)-ushikulide A.

Journal: Journal of the American Chemical Society 20091021

Title: Vinylidene rutheniums with an electrostructurally-flexible NO ligand and their ruthenacyclobutene formation.

Journal: Chemical communications (Cambridge, England) 20090528

Title: Operationally simple copper-promoted coupling of terminal alkynes with benzyl halides.

Journal: The Journal of organic chemistry 20090515

Title: N-Benzyl-2-propynamide.

Journal: Acta crystallographica. Section E, Structure reports online 20090501

Title: A short entry to alpha-substituted gamma-alkylidene pentenolides. Synthesis and preliminary biological evaluation of novel gelastatin analogues.

Journal: The Journal of organic chemistry 20090116

Title: Highly enantioselective zinc/amino alcohol-catalyzed alkynylation of aldehydes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20090101

Title: Base-catalyzed highly stereoselective conversion of gamma-hydroxy-alpha,beta-acetylenic esters to gamma-acetoxy dienoates.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20090101

Title: Dimethyl 7a-carbonyl-2-meth-oxy-7a,7a-bis-(triphenyl-phosphino)-7a-ruthena-1-benzofuran-4,7-dicarboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20090101

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

Journal: Langmuir : the ACS journal of surfaces and colloids 20081007

Title: Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions.

Journal: Organic letters 20081002

Title: Reactions of 16e CpCo half-sandwich complexes containing a chelating 1,2-dicarba-closo-dodecaborane-1,2-dichalcogenolate ligand with ethynylferrocene and dimethyl acetylenedicarboxylate.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20080101

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

Journal: Acta crystallographica. Section E, Structure reports online 20080101

Title: Highly enantioselective synthesis of gamma-hydroxy-alpha,beta-acetylenic esters catalyzed by a beta-sulfonamide alcohol.

Journal: Organic letters 20070607

Title: A substrate-based folding process incorporating chemodifferentiating ABB' three-component reactions of terminal alkynoates and 1,2-dicarbonyl compounds: a skeletal-diversity-oriented synthetic manifold.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: Investigations on the coupling of ethylene and alkynes in [IrTp Me2] compounds: water as an effective trapping agent.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: Pd(OAc)2-catalyzed coupling/cyclization of 2,3-allenoic acids and methyl propiolate: observation of double 1,7-hydrogen shifts.

Journal: Angewandte Chemie (International ed. in English) 20060911

Title: 1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products.

Journal: Organic & biomolecular chemistry 20060621

Title: Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids.

Journal: Organic letters 20060511

Title: 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).

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20060412

Title: DFT-HSAB prediction of regioselectivity in 1,3-dipolar cycloadditions: behavior of (4-substituted)benzonitrile oxides towards methyl propiolate.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20060123

Title: Efficient synthesis of N-methoxyindoles via alkylative cycloaddition of nitrosoarenes with alkynes.

Journal: The Journal of organic chemistry 20060120

Title: Aza-Baylis-Hillman reactions of N-tosylated aldimines with activated allenes and alkynes in the presence of various Lewis base promoters.

Journal: The Journal of organic chemistry 20051125

Title: [Benzo[h][1 ,6]naphthyridines from dimethyl 1,2-dihydro-2-(2-nitrophenyl)-pyridine-3,5-dicarboxylate].

Journal: Die Pharmazie 20050301

Title: Activation of a 1,10-phenanthroline ligand on a rhenium tricarbonyl complex.

Journal: Chemical communications (Cambridge, England) 20050107

Title: New synthetic method for indole-2-carboxylate and its application to the total synthesis of duocarmycin SA.

Journal: Organic letters 20040819

Title: Insertion of alkynes into the Pt-Si bond of silylplatinum complexes leading to the formation of 4-sila-3-platinacyclobutenes and 5-sila-2-platina-1,4-cyclohexadienes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20040123

Title: [Benzo[c][2,7]naphthyridines from 2,6-dinor-nifedipine and its dimethyl 2,5-dicarboxylate isomer].

Journal: Die Pharmazie 20040101

Title: Ruthenacarboranes from the reaction of nido-1,2-(Cp*RuH)2B3H7 with HC [triple bond] CCO2Me, Cp* = eta5-C5Me5. Hydrometalation, alkyne incorporation, and functional group modification via cooperative metal-boron interactions within a metallaborane cluster framework.

Journal: Journal of the American Chemical Society 20031231

Title: Arylazide cycloaddition to methyl propiolate: DFT-based quantitative prediction of regioselectivity.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20030616

Title: Fluorous catalysis under homogeneous conditions without fluorous solvents: a 'greener' catalyst recycling protocol based upon temperature-dependent solubilities and liquid/solid phase separation.

Journal: Journal of the American Chemical Society 20030514

Title: Regiochemical switching in Diels-Alder cycloadditions by change in oxidation state of removable diene sulfur substituents. Synthesis of carbazoles by sequential heteroannulation and Diels-Alder cycloaddition.

Journal: The Journal of organic chemistry 20030418

Title: alpha-Keto amides as precursors to heterocycles--generation and cycloaddition reactions of piperazin-5-one nitrones.

Journal: Organic & biomolecular chemistry 20030407

Title: Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20030404

Title: Reactions of 5-mercaptoazoles and pyridine-2-thiones with acetylenic esters. Selectivity of the formation of novel fused thiazin-4-ones and thiazolidin-4-ones.

Journal: Organic & biomolecular chemistry 20030107

Title: Diphosphanylketenimines: new reagents for the synthesis of unique phosphorus heterocycles.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20020902

Title: An expedient synthesis of highly functionalized naphthyridones and quinolines from a common N-aryl pyridinone template.

Journal: Organic letters 20020613

Title: Preparation of vinylogous 2-sulfonylindolines by the palladium-catalyzed heteroannulation of o-iodoanilines with dienyl sulfones and their further transformation to indoles and carbazoles.

Journal: The Journal of organic chemistry 20011214

Title: DFT-based quantitative prediction of regioselectivity: cycloaddition of nitrilimines to methyl propiolate.

Journal: The Journal of organic chemistry 20010727

Title: Bocdene and mocdene derivatives of catechols and catecholamines.

Journal: Organic letters 20010503

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Tags:922-67-8 Molecular Formula|922-67-8 MDL|922-67-8 SMILES|922-67-8 Methyl propiolate |Organic_Building_Blocks