| Revision as of 12:03, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456124326 of page Pyridazine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 12:05, 15 October 2024 edit M97uzivatel (talk | contribs)Extended confirmed users6,573 edits multispace |
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{{short description|Heterocyclic organic compound (C4H4N2)}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 408973982 |
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| verifiedrevid = 464376879 |
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| ImageFile = Pyridazine 2D numbers.svg |
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| ImageSize = 135 |
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| ImageAlt = Skeletal formula with numbering convention |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1=Pyridazine numbering.png |
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| ImageFileL1=Pyridazine-3D-balls.png |
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| ImageNameL1 = C=black, H=white, N=blue |
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|ImageSizeL1=75px |
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| ImageAltL1 = Pyridazine molecule |
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|ImageFileR1=Pyridazine3d.png |
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| ImageFileR1=Pyridazine-3D-spacefill.png |
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|ImageSizeR1=100px |
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| ImageNameR1 = C=black, H=white, N=blue |
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|IUPACName=Pyridazine |
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| ImageAltR1 = Pyridazine molecule |
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|OtherNames=1,2-diazine, orthodiazine, oizine |
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| PIN = Pyridazine<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 141 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
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|Section1= {{Chembox Identifiers |
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| SystematicName = 1,2-Diazabenzene |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames = 1,2-Diazine<br />Orthodiazine<br />Oizine |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=289-80-5 |
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| Beilstein = 103906 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8902 |
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| ChemSpiderID = 8902 |
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| InChI = 1/C4H4N2/c1-2-4-6-5-3-1/h1-4H |
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| InChI = 1/C4H4N2/c1-2-4-6-5-3-1/h1-4H |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 15719 |
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| ChEMBL = 15719 |
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| EINECS = 206-025-5 |
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| Gmelin = 49310 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 449GLA0653 |
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| PubChem = 9259 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30954 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H4N2/c1-2-4-6-5-3-1/h1-4H |
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| StdInChI = 1S/C4H4N2/c1-2-4-6-5-3-1/h1-4H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PBMFSQRYOILNGV-UHFFFAOYSA-N |
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| StdInChIKey = PBMFSQRYOILNGV-UHFFFAOYSA-N |
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| SMILES = n1ncccc1 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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}} |
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| CASNo=289-80-5 |
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|Section2={{Chembox Properties |
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| PubChem = 9259 |
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| C=4|H=4|N=2 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| Appearance=Colorless liquid |
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| ChEBI = 30954 |
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| Density=1.107 g/cm<sup>3</sup> |
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| SMILES = c1ccnnc1 |
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| MeltingPtC=-8 |
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| RTECS=GY2390000 |
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| BoilingPtC=208 |
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| Solubility= miscible |
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|Section2= {{Chembox Properties |
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| SolubleOther = miscible in ], ] <br> soluble in ], ] <br> negligible in ], ] |
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| Formula=| C=4 | H=4 | N=2 |
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| pKa = |
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| MolarMass=80.09 g/mol |
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| pKb = |
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| Appearance=colorless liquid |
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| RefractIndex = 1.52311 (23.5 °C) |
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| Density=1.107 g/cm<sup>3</sup> |
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}} |
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| MeltingPtC=-8 |
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|Section3={{Chembox Thermochemistry |
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| BoilingPtC=208 |
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| DeltaHf = 224.9 kJ/mol |
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| Solubility= |
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}} |
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| pKa = 2.10<ref>Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.</ref> |
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|Section7={{Chembox Hazards |
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| pKb = |
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| GHS_ref=<ref>{{cite web |title=Pyridazine |url=https://pubchem.ncbi.nlm.nih.gov/compound/9259#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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| GHSPictograms = {{GHS07}} |
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|Section3= {{Chembox Hazards |
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| GHSSignalWord = Warning |
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| MainHazards= |
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| HPhrases = {{H-phrases|302|315|319|335}} |
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| FlashPt= |
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| PPhrases = {{P-phrases|261|264|264+265|270|271|280|301+317|302+352|304+340|305+351+338|319|321|330|332+317|337+317|362+364|403+233|405|501}} |
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| Autoignition= |
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| MainHazards= |
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| FlashPtC= 85 |
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| Section8 = {{Chembox Related |
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| AutoignitionPt = |
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| OtherCpds = ], ], ] |
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|Section8={{Chembox Related |
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| OtherCompounds = {{unbulleted list|]|]|]}} |
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'''Pyridazine''' is an ], ], ] with the molecular formula {{chem2|C4H4N2}}. It contains a six-membered ] with two adjacent ] atoms.<ref>{{cite journal | last1 = Gumus | first1 = S. | year = 2011 | title = A computational study on substituted diazabenzenes | url = http://journals.tubitak.gov.tr/chem/issues/kim-11-35-5/kim-35-5-11-1012-875.pdf | journal = Turk J Chem | volume = 35 | pages = 803–808 | access-date = 2014-04-10 | archive-url = https://web.archive.org/web/20160303181258/http://journals.tubitak.gov.tr/chem/issues/kim-11-35-5/kim-35-5-11-1012-875.pdf | archive-date = 2016-03-03 | url-status = dead }}</ref> It is a colorless liquid with a ] of 208 °C. It is ] with two other ] ({{chem2|C4H4N2}}) rings, ] and ]. |
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==Occurrence== |
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Pyridazines are rare in nature, possibly reflecting the scarcity of naturally occurring ], common building blocks for the synthesis of these heterocycles. The pyridazine structure is a popular ] which is found within a number of herbicides such as ], ] and ]. It is also found within the structure of several drugs such as ], ], ], ], and ]. |
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==Synthesis== |
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In the course of his classic investigation on the ], Emil Fischer prepared the first pyridazine via the condensation of ] and ].<ref>{{cite journal | last1 = Fischer | first1 = E. | year = 1886 | title = Indole aus Phenylhydrazin | url = https://zenodo.org/record/1427407| journal = Justus Liebigs Annalen der Chemie | volume = 236 | issue = 1–2| pages = 126–151 | doi = 10.1002/jlac.18862360107 }}</ref> The parent heterocycle was first prepared by oxidation of ] to the pyridazinetetracarboxylic acid followed by ]. A better route to this otherwise esoteric compound starts with the ]. These heterocycles are often prepared via condensation of 1,4-]s or 4-ketoacids with ]s.<ref>{{cite book | last1 = Tišler | first1 = M. | last2 = Stanovnik | first2 = B. | title = Advances in Heterocyclic Chemistry Volume 9 | chapter = Pyridazines | year = 1968 | volume = 9 | pages = 211–320 | doi = 10.1016/S0065-2725(08)60374-8 | isbn = 9780120206094}}</ref> |
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==References== |
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<references/> |
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{{Simple aromatic rings}} |
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{{Authority control}} |
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