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Dimethyl acetylenedicarboxylate: Difference between revisions

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Revision as of 22:22, 25 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - updated 'UNII_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemica← Previous edit Latest revision as of 08:33, 13 August 2023 edit undoAnomieBOT (talk | contribs)Bots6,584,511 editsm Dating maintenance tags: {{Fact}} 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 396342961
| Name = Dimethyl acetylenedicarboxylate | verifiedrevid = 430919861
| Name = Dimethyl acetylenedicarboxylate
| ImageFile = DMAD.png | ImageFile = DMAD.png
| ImageName = Chemical structure of DMAD | ImageName = Chemical structure of DMADuak
| ImageFile1 = Dimethyl-acetylenedicarboxylate-3D-balls.png | ImageFile1 = Dimethyl-acetylenedicarboxylate-3D-balls.png
| ImageSize1 = 220px | ImageSize1 = 220px
| ImageName1 = Ball-and-stick model | ImageName1 = Ball-and-stick model
| IUPACName = Dimethyl<br /> acetylenedicarboxylate | PIN = Dimethyl but-2-ynedioate
| OtherNames = DMAD<br />Acetylenedicarboxylic<br />acid, dimethyl ester | OtherNames = DMAD<br />Acetylenedicarboxylic<br />acid dimethyl ester
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| SMILES = COC(=O)C#CC(=O)OC | SMILES = COC(=O)C#CC(=O)OC
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12440 | ChemSpiderID = 12440
| InChI = 1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3 | InChI = 1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
Line 21: Line 22:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 762-42-5 | CASNo = 762-42-5
| RTECS = ES0175000 | RTECS = ES0175000
| PubChem = 12980
| EC_number = 212-098-4
| UNII = 7HZA2PL15F
| ChEMBL = 3248452
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>4</sub> | Formula = C<sub>6</sub>H<sub>6</sub>O<sub>4</sub>
| MolarMass = 142.11 g/mol | MolarMass = 142.11 g/mol
| Appearance = Colorless liquid | Appearance = Colorless liquid
| Density = 1.1564 g/cm³ | Density = 1.1564 g/cm<sup>3</sup>
| Solubility = Insoluble | Solubility = Insoluble
| Solvent = other solvents | Solvent = other solvents
| SolubleOther = Soluble in most<br />organic solvents | SolubleOther = Soluble in most<br />organic solvents
| MeltingPt =c | MeltingPtC =-18
| BoilingPtC = 195 to 198
| BoilingPt = 195–198 °C<br />96–98° at 8 mm Hg | BoilingPt_notes = (96–98° at 8 mm Hg)
| RefractIndex = 1.447 | RefractIndex = 1.447
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| Dipole = 0 ] | Dipole = 0 ]
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = Toxic gas | MainHazards = Toxic
| FlashPt = 187 °F | FlashPtC = 187
| RPhrases = {{R34}} | GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| SPhrases = {{S23}} {{S26}} {{S27}}<br />{{S36/37/39}} {{S45}}
| HPhrases = {{H-phrases|302|314}}
| PPhrases = {{P-phrases|260|264|270|280|301+312|301+330+331|303+361+353|304+340|305+351+338|310|321|330|363|405|501}}
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherCpds = Methyl ],<br />],<br />] | OtherCompounds = ],<br />],<br />]
}} }}
}} }}


'''Dimethyl acetylenedicarboxylate''' (DMAD) is the ] with the formula CH<sub>3</sub>O<sub>2</sub>CC<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub>. This ], which exists as a liquid at room temperature, is highly ]. As such, DMAD, as it is commonly called in the laboratory, is widely employed as a ] in cycloaddition reactions, such as the ]. It is also a potent ].<ref>Stelmach, J. E.; Winkler, J. D. “Dimethyl Acetylenedicarboxylate”in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.</ref><ref>{{cite journal | last1 = Sahoo | first1 = Manoj | title = Dimethyl Acetylene Dicarboxylate | journal = Synlett | volume = 2007 | pages = 2142 | year = 2007 | doi = 10.1055/s-2007-984894}}</ref> '''Dimethyl acetylenedicarboxylate''' (DMAD) is an ] with the formula CH<sub>3</sub>O<sub>2</sub>CC<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub>. It is a di-] in which the ester groups are conjugated with a C-C triple bond. As such, the molecule is highly ], and is widely employed as a ] in cycloaddition reactions, such as the ]. It is also a potent ].<ref>Stelmach, J. E.; Winkler, J. D. "Dimethyl Acetylenedicarboxylate"in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi|10.1002/047084289X}}.</ref><ref>{{cite journal | last1 = Sahoo | first1 = Manoj | title = Dimethyl Acetylene Dicarboxylate | journal = Synlett | volume = 2007 | issue = 13 | pages = 2142–2143 | year = 2007 | doi = 10.1055/s-2007-984894| doi-access = free }}</ref> This compound exists as a colorless liquid at room temperature. This compound was used in the preparation of ].


==Preparation== ==Preparation==
Although inexpensively available, DMAD is prepared today as it was originally. ] is ] and the resulting dibromo] is ] with ] yielding ].<ref>{{cite journal | last1 = Bandrowski | first1 = E. | title = Ueber Acetylendicarbonsäure | journal = Berichte der deutschen chemischen Gesellschaft | volume = 10 | pages = 838 | year = 1877 | doi = 10.1002/cber.187701001231}}</ref><ref>{{OrgSynth | author = Abbott, T. W.; Arnold, R. T.; Thompson, R. B. | title = Acetylenedicarboxylic acid | collvol = 2 | collvolpages = 10 | prep = cv2p0010}}</ref> The acid is then ] with ] and ] as a catalyst:<ref>{{OrgSynth | author = Huntress, E. H. Lesslie, T. E.; Bornstein, J. | title = Dimethyl Acetylenedicarboxylate | collvol = 4 | collvolpages = 329 | prep = cv4p0329}}</ref> Although inexpensively available, DMAD is prepared today as it was originally. ] is ] and the resulting dibromo] is ] with ] yielding ].<ref>{{cite journal | last1 = Bandrowski | first1 = E. | title = Ueber Acetylendicarbonsäure | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 10 | pages = 838–842 | year = 1877 | doi = 10.1002/cber.187701001231| url = https://zenodo.org/record/1425134 }}</ref><ref>{{OrgSynth | author = Abbott, T. W. | author2 = Arnold, R. T. | author3 = Thompson, R. B. | title = Acetylenedicarboxylic acid | journal = Organic Syntheses | year = 1938 | volume = 18 | page = 3 | collvol = 2 | collvolpages = 10 |prep=cv2p0010 |doi=10.15227/orgsyn.018.0003 }}</ref> The acid is then ] with ] and ] as a catalyst:<ref>{{OrgSynth | author = Huntress, E. H. | author2 = Lesslie, T. E. | author3 = Bornstein, J. | title = Dimethyl Acetylenedicarboxylate | journal = Organic Syntheses | year = 1952 | volume = 32 | page = 55 | collvol = 4 | collvolpages = 329 |prep= cv4p0329 |doi=10.15227/orgsyn.032.0055 }}</ref>


:] :]


==Safety== ==Safety==
DMAD is a ] and a ]. DMAD is a ] and a ].{{fact|date=August 2023}}


==References== ==References==
{{Reflist}}
<references/>


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