Misplaced Pages

Imidazolidinyl urea: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 13:25, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit Latest revision as of 18:27, 14 May 2023 edit undo86.153.213.93 (talk)No edit summary 
(20 intermediate revisions by 18 users not shown)
Line 1: Line 1:
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 415661782 | verifiedrevid = 443869604
| ImageFile=Imidazolidinyl urea correct formula.png | ImageFile=Imidazolidinyl urea correct formula.png
| ImageFile1=Imidazolidinyl urea erroneous formula.png | ImageFile1=Imidazolidinyl urea erroneous formula.png
| ImageSize= | ImageSize=
|IUPACName=<small><u>Correct</u> new structure (upper pic.):<br /> 1,1<nowiki>'</nowiki>-methylenebis{3-urea}<br /><u>Erroneous</u> old structure (lower pic.):<br /> 1,1'-methylenebis{3-urea}</small> {{Citation needed|date=February 2010}} | IUPACName=<small><u>Correct</u> new structure (upper pic.):<br /> 1,1′-methylenebis{3-urea}<br /><u>Erroneous</u> old structure (lower pic.):<br /> 1,1′-methylenebis{3-urea}</small>
| OtherNames=Imidurea, Germall 115; | OtherNames=Imidurea, Germall 115;
''N<nowiki>'</nowiki>'',''N<nowiki>''</nowiki>''-methylenebisurea]; <!--Note: Other forms of numbering of this exist, but are mostly more differing from IUPAC than this, thus more confusing. Cf. http://www.acdlabs.com/iupac/nomenclature/79/r79_661.htm for numbering of urea, and http://www.acdlabs.com/iupac/nomenclature/93/r93_171.htm for numbering of the complete name.--> ''N′'',''N″''-methylenebisurea]; <!--Note: Other forms of numbering of this exist, but are mostly more differing from IUPAC than this, thus more confusing. Cf. http://www.acdlabs.com/iupac/nomenclature/79/r79_661.htm for numbering of urea, and http://www.acdlabs.com/iupac/nomenclature/93/r93_171.htm for numbering of the complete name.-->


1-- 3-<nowiki> carbamoylamino]methyl]urea <!--Source: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=38258--> 1-- 3-<nowiki> carbamoylamino]methyl]urea <!--Source: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=38258-->
| Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 35067 | ChemSpiderID = 35067
| InChI = 1/C11H16N8O8/c20-2-18-4(6(22)16-10(18)26)14-8(24)12-1-13-9(25)15-5-7(23)17-11(27)19(5)3-21/h4-5,20-21H,1-3H2,(H2,12,14,24)(H2,13,15,25)(H,16,22,26)(H,17,23,27) | InChI = 1/C11H16N8O8/c20-2-18-4(6(22)16-10(18)26)14-8(24)12-1-13-9(25)15-5-7(23)17-11(27)19(5)3-21/h4-5,20-21H,1-3H2,(H2,12,14,24)(H2,13,15,25)(H,16,22,26)(H,17,23,27)
Line 22: Line 23:
| CASNo_Ref = {{cascite|correct|CAS}}= {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}= {{cascite|correct|CAS}}
| CASNo = 39236-46-9 | CASNo = 39236-46-9
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 38258
| UNII = M629807ATL
⚫ | EINECS=254-372-6
| ChEBI = 51805 | PubChem = 38258
⚫ | EINECS=254-372-6
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51805
| SMILES = O=C2N(CO)C(NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO)C(=O)N2 | SMILES = O=C2N(CO)C(NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO)C(=O)N2
| SMILES1 = C(NC(=O)NC1C(=O)NC(=O)N1CO)NC(=O)NC2C(=O)NC(=O)N2CO | SMILES1 = C(NC(=O)NC1C(=O)NC(=O)N1CO)NC(=O)NC2C(=O)NC(=O)N2CO
}} }}
| Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>11</sub>H<sub>16</sub>N<sub>8</sub>O<sub>8</sub> | Formula=C<sub>11</sub>H<sub>16</sub>N<sub>8</sub>O<sub>8</sub>
| MolarMass=388.29 g/mol | MolarMass=388.29 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
| Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
Line 48: Line 52:
== Safety == == Safety ==


Some people have a contact ] to imidazolidinyl urea causing ].<ref name="NIEHS"> (NTP NIEHS)</ref> Such people are often also allergic to ]. Some people have a contact ] to imidazolidinyl urea causing ].<ref name="NIEHS"> (NTP NIEHS)</ref> Such people are often also allergic to ].


== Chemistry == == Chemistry ==


Imidazolidinyl urea was poorly characterized until recently and still has a wrong ] structure assigned to it. New data show that the ] ] of the ] ring is attached to the ], not the ] atom <ref name="structure"> Imidazolidinyl urea was poorly characterized until recently and the single ] structure assigned to it is probably not the major one in the commercial material. Instead, new data indicate that the ] ] of each ] ring is attached to the ], rather than on the ] atom:<ref name="structure">{{cite journal
| author1 = Lehmann SV
{{cite journal
| author2 = Hoeck U
| author = Lehmann SV, Hoeck U, Breinholdt J, Olsen CE, Kreilgaard B.
| author3 = Breinholdt J
| author4 = Olsen CE
| author5 = Kreilgaard B.
| year = 2006 | year = 2006
| title = Characterization and chemistry of imidazolidinyl urea and diazolidinyl urea | title = Characterization and chemistry of imidazolidinyl urea and diazolidinyl urea
Line 61: Line 68:
| issue = 1 | issue = 1
| pages = 50–58 | pages = 50–58
⚫ | pmid = 16426294
| location =
⚫ | pmid =16426294
| doi = 10.1111/j.0105-1873.2006.00735.x | doi = 10.1111/j.0105-1873.2006.00735.x
| s2cid = 25897828
| url = http://www.blackwell-synergy.com/doi/abs/10.1111/j.0105-1873.2006.00735.x
}} }}</ref>
</ref>:


{| :{|
|- align="center" valign="middle" |- align="center" valign="middle"
| ] | ]
| ] | ]
|- align="center" |- align="center"
| Correct new structure | Originally reported structure
| Erroneous old structure | Hoeck's revised structure
|} |}


=== Synthesis === === Synthesis ===


Imidazolidinyl urea is produced by the ] of ] and ] in the presence of ] solution and heat. The reaction mixture is then ] with ] and ]: Imidazolidinyl urea is produced by the ] of ] and ] in the presence of ] solution and heat. The reaction mixture is then ] with ] and ]:


2 ] + 3 H<sub>2</sub>C=O → ] :2 ] + 3 H<sub>2</sub>C=O → ]


Commercial imidazolidinyl urea is a mixture of different formaldehyde addition products including polymers.<ref name="structure" /> Commercial imidazolidinyl urea is a mixture of different formaldehyde addition products including polymers.<ref name="structure" />