Home Other Building Blocks Methyl propiolate

Methyl propiolate

CAS No.:
922-67-8
Catalog Number:
AG0035IY
Molecular Formula:
C4H4O2
Molecular Weight:
84.0734
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
25g
98%
In Stock USA
United States
$107
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Product Description
Catalog Number:
AG0035IY
Chemical Name:
Methyl propiolate
CAS Number:
922-67-8
Molecular Formula:
C4H4O2
Molecular Weight:
84.0734
MDL Number:
MFCD00008572
IUPAC Name:
methyl prop-2-ynoate
InChI:
InChI=1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3
InChI Key:
IMAKHNTVDGLIRY-UHFFFAOYSA-N
SMILES:
COC(=O)C#C
EC Number:
213-083-5
UNII:
T88NXO102K
NSC Number:
154164
Properties
Complexity:
95.4  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
84.021g/mol
Formal Charge:
0
Heavy Atom Count:
6  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
84.074g/mol
Monoisotopic Mass:
84.021g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
26.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.6  
Literature
Title Journal
Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes. Organic & biomolecular chemistry 20121114
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. Dalton transactions (Cambridge, England : 2003) 20121021
High-pressure-promoted Diels-Alder approach to biaryls: application to the synthesis of the cannabinols family. The Journal of organic chemistry 20120921
Cobalt-promoted B-H and C-H activation: facile B-C coupling of carboranedithiolate and cyclopentadienyl. Journal of the American Chemical Society 20120627
Synthesis of ferrocene-labeled steroids via copper-catalyzed azide-alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes. Steroids 20120601
Synthesis of polyfunctionalized acrylates via one-pot reactions of arylamines, methyl propiolate, aromatic aldehydes, and active methylene compounds. Molecular diversity 20120201
Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D. Journal of the American Chemical Society 20120125
Highly regio- and stereoselective Diels-Alder cycloadditions via two-step and multicomponent reactions promoted by infrared irradiation under solvent-free conditions. International journal of molecular sciences 20120101
Synthesis of functionalized 2-aminohydropyridines and 2-pyridinones via domino reactions of arylamines, methyl propiolate, aromatic aldehydes, and substituted acetonitriles. ACS combinatorial science 20110711
Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate and N-{5-benzoyl-2-[(Z)-2-methoxyethenyl]-4-methylphenyl}benzamide. Acta crystallographica. Section C, Crystal structure communications 20110601
Methyl 1-(2,6-difluoro-benz-yl)-1H-1,2,3-triazole-4-carboxyl-ate. Acta crystallographica. Section E, Structure reports online 20110401
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. Acta crystallographica. Section E, Structure reports online 20100901
Methyl 1-benzyl-1H-1,2,3-triazole-4-carboxyl-ate. Acta crystallographica. Section E, Structure reports online 20100701
Reactions of alkynes with phosphido niobocenes: a combined experimental and theoretical study. Dalton transactions (Cambridge, England : 2003) 20100227
4-(9,10-Dihydroacridin-9-ylidene)thiosemicarbazide and its five-membered thiazole and six-membered thiazine derivatives. Acta crystallographica. Section C, Crystal structure communications 20100201
Synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives from amino acids. Molecules (Basel, Switzerland) 20091209
Total synthesis and stereochemical assignment of (-)-ushikulide A. Journal of the American Chemical Society 20091021
Vinylidene rutheniums with an electrostructurally-flexible NO ligand and their ruthenacyclobutene formation. Chemical communications (Cambridge, England) 20090528
Operationally simple copper-promoted coupling of terminal alkynes with benzyl halides. The Journal of organic chemistry 20090515
N-Benzyl-2-propynamide. Acta crystallographica. Section E, Structure reports online 20090501
A short entry to alpha-substituted gamma-alkylidene pentenolides. Synthesis and preliminary biological evaluation of novel gelastatin analogues. The Journal of organic chemistry 20090116
Highly enantioselective zinc/amino alcohol-catalyzed alkynylation of aldehydes. Chemistry (Weinheim an der Bergstrasse, Germany) 20090101
Base-catalyzed highly stereoselective conversion of gamma-hydroxy-alpha,beta-acetylenic esters to gamma-acetoxy dienoates. Chemistry (Weinheim an der Bergstrasse, Germany) 20090101
Dimethyl 7a-carbonyl-2-meth-oxy-7a,7a-bis-(triphenyl-phosphino)-7a-ruthena-1-benzofuran-4,7-dicarboxyl-ate. Acta crystallographica. Section E, Structure reports online 20090101
Si(111) surface modified with alpha,beta-unsaturated carboxyl groups studied by MIR-FTIR. Langmuir : the ACS journal of surfaces and colloids 20081007
Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions. Organic letters 20081002
Reactions of 16e CpCo half-sandwich complexes containing a chelating 1,2-dicarba-closo-dodecaborane-1,2-dichalcogenolate ligand with ethynylferrocene and dimethyl acetylenedicarboxylate. Chemistry (Weinheim an der Bergstrasse, Germany) 20080101
Methyl 2-(1,3-dioxoisoindolin-2-yl)acrylate. Acta crystallographica. Section E, Structure reports online 20080101
Highly enantioselective synthesis of gamma-hydroxy-alpha,beta-acetylenic esters catalyzed by a beta-sulfonamide alcohol. Organic letters 20070607
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. Chemistry (Weinheim an der Bergstrasse, Germany) 20070101
Investigations on the coupling of ethylene and alkynes in [IrTp Me2] compounds: water as an effective trapping agent. Chemistry (Weinheim an der Bergstrasse, Germany) 20070101
Pd(OAc)2-catalyzed coupling/cyclization of 2,3-allenoic acids and methyl propiolate: observation of double 1,7-hydrogen shifts. Angewandte Chemie (International ed. in English) 20060911
1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products. Organic & biomolecular chemistry 20060621
Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids. Organic letters 20060511
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
DFT-HSAB prediction of regioselectivity in 1,3-dipolar cycloadditions: behavior of (4-substituted)benzonitrile oxides towards methyl propiolate. Chemistry (Weinheim an der Bergstrasse, Germany) 20060123
Efficient synthesis of N-methoxyindoles via alkylative cycloaddition of nitrosoarenes with alkynes. The Journal of organic chemistry 20060120
Aza-Baylis-Hillman reactions of N-tosylated aldimines with activated allenes and alkynes in the presence of various Lewis base promoters. The Journal of organic chemistry 20051125
[Benzo[h][1 ,6]naphthyridines from dimethyl 1,2-dihydro-2-(2-nitrophenyl)-pyridine-3,5-dicarboxylate]. Die Pharmazie 20050301
Activation of a 1,10-phenanthroline ligand on a rhenium tricarbonyl complex. Chemical communications (Cambridge, England) 20050107
New synthetic method for indole-2-carboxylate and its application to the total synthesis of duocarmycin SA. Organic letters 20040819
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. Chemistry (Weinheim an der Bergstrasse, Germany) 20040123
[Benzo[c][2,7]naphthyridines from 2,6-dinor-nifedipine and its dimethyl 2,5-dicarboxylate isomer]. Die Pharmazie 20040101
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 of the American Chemical Society 20031231
Arylazide cycloaddition to methyl propiolate: DFT-based quantitative prediction of regioselectivity. Chemistry (Weinheim an der Bergstrasse, Germany) 20030616
Fluorous catalysis under homogeneous conditions without fluorous solvents: a 'greener' catalyst recycling protocol based upon temperature-dependent solubilities and liquid/solid phase separation. Journal of the American Chemical Society 20030514
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. The Journal of organic chemistry 20030418
alpha-Keto amides as precursors to heterocycles--generation and cycloaddition reactions of piperazin-5-one nitrones. Organic & biomolecular chemistry 20030407
Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes. Chemistry (Weinheim an der Bergstrasse, Germany) 20030404
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. Organic & biomolecular chemistry 20030107
Diphosphanylketenimines: new reagents for the synthesis of unique phosphorus heterocycles. Chemistry (Weinheim an der Bergstrasse, Germany) 20020902
An expedient synthesis of highly functionalized naphthyridones and quinolines from a common N-aryl pyridinone template. Organic letters 20020613
Preparation of vinylogous 2-sulfonylindolines by the palladium-catalyzed heteroannulation of o-iodoanilines with dienyl sulfones and their further transformation to indoles and carbazoles. The Journal of organic chemistry 20011214
DFT-based quantitative prediction of regioselectivity: cycloaddition of nitrilimines to methyl propiolate. The Journal of organic chemistry 20010727
Bocdene and mocdene derivatives of catechols and catecholamines. Organic letters 20010503
Properties