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| verifiedrevid = 408212873 |
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|Reference=<ref>'']'', 11th Edition, '''7344'''.</ref> |
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| verifiedrevid = 440002476 |
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|ImageFile=Phthalazin - Phthalazine.svg |
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| Reference =<ref>'']'', 11th Edition, '''7344'''.</ref> |
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|ImageSize=180px |
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|IUPACName=Phthalazine |
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| ImageFile = Phthalazin - Phthalazine.svg |
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| ImageSize = 180 |
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|OtherNames=Benzo-orthodiazine<br>2,3-Benzodiazine<br>Benzopyridazine |
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| ImageAlt = Skeletal formula of phthalazine |
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| ImageFile1 = Phthalazine-3D-balls.png |
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| ImageSize1 = 180 |
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| ImageAlt1 = Ball-and-stick model of the phthalazine molecule |
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| PIN = Phthalazine<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 212 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| OtherNames = Benzo-orthodiazine<br />2,3-Benzodiazine<br />Benzopyridazine |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=253-52-1 |
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| CASNo=253-52-1 |
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| PubChem=9207 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=C1=CC=C2C=NN=CC2=C1 |
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| UNII = 91Y28DM24N |
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| PubChem = 9207 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8852 |
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| SMILES = C1=CC=C2C=NN=CC2=C1 |
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| InChI = 1/C8H6N2/c1-2-4-8-6-10-9-5-7(8)3-1/h1-6H |
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| InChIKey = LFSXCDWNBUNEEM-UHFFFAOYAE |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C8H6N2/c1-2-4-8-6-10-9-5-7(8)3-1/h1-6H |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = LFSXCDWNBUNEEM-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8|H=6|N=2 |
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| Formula=C<sub>8</sub>H<sub>6</sub>N<sub>2</sub> |
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| Appearance = Pale yellow needles |
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| MolarMass=130.15 g/mol |
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| Density= |
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| Appearance=Pale yellow needles |
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| MeltingPtC = 90 to 91 |
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| Density= |
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| BoilingPtC = 315 to 317 |
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| MeltingPt=90-91 °C |
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| BoilingPt=315-317 °C (decomposition) |
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| BoilingPt_notes= (decomposition) |
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| Solubility=Miscible |
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| Solubility = Miscible |
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| pKa=3.39<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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| pKa=3.39<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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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| AutoignitionPt = |
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'''Phthalazine''', also called benzo-orthodiazine or benzopyridazine, is a ] ] with the molecular formula C<sub>8</sub>H<sub>6</sub>N<sub>2</sub>. It is ]ic with ], ] and ]. |
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'''Phthalazine''', also called benzo-orthodiazine or benzopyridazine, is a ] ] with the molecular formula C<sub>8</sub>H<sub>6</sub>N<sub>2</sub>. It is ]ic with other ]s including ], ] and ]. |
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==Synthesis== |
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==Synthesis== |
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Phthalazine can be obtained by the ] of w-tetrabromorthoxylene with ], or by the ] of chlorphthalazine with ] and ]. |
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Phthalazine can be obtained by the ] of w-tetrabromorthoxylene with ], or by the ] of chlorphthalazine with ] and ].<ref name=EB1911>{{EB1911 |wstitle=Phthalazines |volume=21 |page=545 |inline=1}}</ref> |
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==Properties== |
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==Properties== |
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It possesses ] properties and forms addition products with ]s. |
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It possesses ] properties and forms addition products with ]s.<ref name=EB1911/> |
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==Reactions== |
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==Reactions== |
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Upon oxidation with ] ] it yields ]. ] and ] decompose it with formation of orthoxylylene diamine. The keto-hydro derivative ] (C<sub>8</sub>H<sub>6</sub>ON<sub>2</sub>), is obtained by condensing hydrazine with orthophthalaldehydoacid{{Citation needed|date=July 2011}}. On treatment with ], it yields a chlorphthalazine, which with ] and ] gives isoindole (C<sub>8</sub>H<sub>7</sub>N), and with ] and hydrochloric acid, phthalimidine (C<sub>8</sub>H<sub>7</sub>ON), the second ] ] being eliminated as ]. |
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Upon oxidation with ] ] it yields ]. ] and ] decompose it with formation of orthoxylylene diamine. The keto-hydro derivative ] (C<sub>8</sub>H<sub>6</sub>ON<sub>2</sub>), is obtained by condensing hydrazine with orthophthalaldehydoacid{{Citation needed|date=July 2011}}. On treatment with ], it yields a chlorphthalazine, which with ] and ] gives isoindole (C<sub>8</sub>H<sub>7</sub>N), and with ] and hydrochloric acid, phthalimidine (C<sub>8</sub>H<sub>7</sub>ON), the second ] ] being eliminated as ].<ref name=EB1911/> |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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* {{1911}} |
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