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762-21-0,MFCD00009186
Catalog No.:AA0034NA

762-21-0 | Diethyl acetylenedicarboxylate

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5g
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10g
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25g
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100g
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500g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0034NA
Chemical Name:
Diethyl acetylenedicarboxylate
CAS Number:
762-21-0
Molecular Formula:
C8H10O4
Molecular Weight:
170.1626
MDL Number:
MFCD00009186
SMILES:
CCOC(=O)C#CC(=O)OCC
Properties
Properties
 
BP:
107-110°C at 760 mmHg  
Form:
Liquid  
MP:
1-3 °C  
Refractive Index:
n20/D 1.443(lit.)  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
208  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
4  
Rotatable Bond Count:
4  
XLogP3:
1.5  

Literature

Title: rac-Diethyl 5-oxo-2-[(2,4,4-trimethyl-pentan-2-yl)amino]-4,5-dihydro-pyrano[3,2-c]chromene-3,4-dicarboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20120101

Title: Effects of 5-chloro-2-methyl-4-isothiazolin-3-one and other candidate biodiesel biocides on rat alveolar macrophages and NR8383 cells.

Journal: Archives of toxicology 20111101

Title: Enhanced toxicity of the protein cross-linkers divinyl sulfone and diethyl acetylenedicarboxylate in comparison to related monofunctional electrophiles.

Journal: Chemical research in toxicology 20110919

Title: 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.

Journal: ACS combinatorial science 20110711

Title: Diethyl 4,5-diphenyl-3,6-bis-(trimethyl-sil-yl)benzene-1,2-dicarboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20110701

Title: Unprecedented noncatalyzed anti-carbozincation of diethyl acetylenedicarboxylate through alkylzinc group radical transfer.

Journal: Organic letters 20110401

Title: Structure-activity comparison of the cytotoxic properties of diethyl maleate and related molecules: identification of diethyl acetylenedicarboxylate as a thiol cross-linking agent.

Journal: Chemical research in toxicology 20110114

Title: Multicomponent reaction of imidazo[1,5-a]pyridine carbenes with aldehydes and dimethyl acetylenedicarboxylate or allenoates: a straightforward approach to fully substituted furans.

Journal: The Journal of organic chemistry 20101001

Title: Multicomponent reactions of dimethyl methoxymalonate and dialkyl acetylenedicarboxylate in the presence of N-nucleophiles: one-pot synthesis of 2H-pyridinyl-2-butenedioates in water.

Journal: Molecular diversity 20100801

Title: Novel cellulose-based polyelectrolytes synthesized via the click reaction.

Journal: Carbohydrate research 20100527

Title: Probing substituent effects in aryl-aryl interactions using stereoselective Diels-Alder cycloadditions.

Journal: Journal of the American Chemical Society 20100317

Title: Diels-Alder reactivity of polycyclic aromatic hydrocarbon bay regions: implications for metal-free growth of single-chirality carbon nanotubes.

Journal: Journal of the American Chemical Society 20091111

Title: The [3 + 2] cycloaddition reaction of thiazole carbene-derived C-C-Se 1,3-dipoles: a concise and highly efficient strategy for the construction of multifunctional dihydroselenophenes and selenopheno[2,3-b]pyrazines.

Journal: Organic & biomolecular chemistry 20090821

Title: An efficient synthesis of substituted 2-iminothiazolidin-4-one and thiadiazoloquinazolinone derivatives.

Journal: Molecular diversity 20090801

Title: Synthesis and antinociceptive activity of pyrazolyl isoxazolines and pyrazolyl isoxazoles.

Journal: Bioorganic & medicinal chemistry letters 20090701

Title: Synthesis of the anti-virus compound shuangkangsu's analogs.

Journal: Journal of Asian natural products research 20090701

Title: Copper-catalyzed domino rearrangement/dehydrogenation oxidation/carbene oxidation for one-pot regiospecific synthesis of highly functionalized polysubstituted furans.

Journal: Organic letters 20090507

Title: Diethyl 3H-naphtho[2,1-b]pyran-2,3-dicarboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20090401

Title: Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoxime, DMAD, and Br2.

Journal: The Journal of organic chemistry 20090116

Title: Intermolecular sequential [4 + 2]-cycloaddition-aromatization reaction of aryl-substituted allenes with DMAD affording phenanthrene and naphthalene derivatives.

Journal: Organic & biomolecular chemistry 20081007

Title: Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. Synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones.

Journal: The Journal of organic chemistry 20080905

Title: Mechanistic twist of the [8+2] cycloadditions of dienylisobenzofurans and dimethyl acetylenedicarboxylate: stepwise [8+2] versus [4+2]/[1,5]-vinyl shift mechanisms revealed through a theoretical and experimental study.

Journal: Journal of the American Chemical Society 20070905

Title: Microwave assisted condensation reactions of 2-aryl hydrazonopropanals with nucleophilic reagents and dimethyl acetylenedicarboxylate.

Journal: Molecules (Basel, Switzerland) 20070824

Title: A highly efficient cycloaddition of vinylarenes with electron-deficient alkynes affording 1,2-disubstituted-3,4-dihydronaphthalenes catalysed by N,N-dimethylformamide dimethyl acetal.

Journal: Organic & biomolecular chemistry 20070621

Title: Novel multicomponent reaction of [60]fullerene: the first example of 1,4-dipolar cycloaddition reaction in fullerene chemistry.

Journal: Organic & biomolecular chemistry 20061121

Title: A one-pot entry to a novel 3-H-benzo[d]pyrazolo[1,5-b]isothiazole ring system.

Journal: Molecular diversity 20060501

Title: Reaction of dimethoxycarbene-DMAD zwitterion with 1,2-diones and anhydrides: a novel synthesis of highly substituted dihydrofurans and spirodihydrofurans.

Journal: The Journal of organic chemistry 20060317

Title: Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and urea or N-methylurea.

Journal: Molecular diversity 20060201

Title: Facile synthesis of highly substituted 3-aminofurans from thiazolium salts, aldehydes, and dimethyl acetylenedicarboxylate.

Journal: The Journal of organic chemistry 20051028

Title: Engaging the pyridine-DMAD zwitterion in a novel strategy for the selective synthesis of highly substituted benzene and cyclopentenedione derivatives.

Journal: Organic letters 20051013

Title: Addition products of a P(III)-isothiocyanate to dialkyl acetylenedicarboxylates: a spirocyclic phosphinimine and a triphosphorus heterocycle with tetra- and penta-coordinate phosphorus.

Journal: Dalton transactions (Cambridge, England : 2003) 20050521

Title: Synthesis and biological evaluation of himanimide C and unnatural analogues.

Journal: Organic letters 20050217

Title: Metal-metal bonded homo- and heterobimetallic compounds of Pt(I) and Pd(I) supported by a bridging-N,P:N',P' moiety of a potentially hexadentate ligand.

Journal: Inorganic chemistry 20040628

Title: Highly chemo- and regioselective intermolecular cyclotrimerization of alkynes catalyzed by cationic rhodium(I)/modified BINAP complexes.

Journal: Organic letters 20031127

Title: The surprising nucleophilic addition of aminochlorocarbenes to diethyl acetylenedicarboxylate and to oxalyl chloride: quinolines and benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in the presence of Hünig's base.

Journal: Organic & biomolecular chemistry 20031021

Title: Unusual coupling reactions of aldehydes and alkynes: a novel preparation of substituted phthalic acid derivatives by automated synthesis.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20030523

Title: Synthesis, chemistry, and dynamic NMR study of new atropisomeric 4-dialkylamino-5-chloro-1,2-dithiole-3-thiones.

Journal: Organic letters 20030320

Title: The importance of chromatographic separation in LC/MS/MS quantitation of drugs in biological fluids: detection, characterization, and synthesis of a previously unknown low-level nitrone metabolite of a substance P antagonist.

Journal: Analytical chemistry 20030201

Title: The unique nucleophilic reactivity of arylaminochlorocarbenes.

Journal: Chemical communications (Cambridge, England) 20030107

Title: Synthesis and biological activities of (Z) and (E) alpha-ethenyl acyclonucleosides.

Journal: Nucleosides, nucleotides & nucleic acids 20010801

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