| Revision as of 16:39, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 457305363 of page 1-Fluoro-2,4-dinitrobenzene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 10:39, 11 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers30,881 edits Add: bibcode, issue. |
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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 = 457304099 |
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| verifiedrevid = 477207705 |
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|ImageFile=1-Fluoro-2,4-dinitrobenzene.svg |
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| ImageFile =1-Fluoro-2,4-dinitrobenzene.svg |
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|ImageSize=130px |
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| ImageSize = 130px |
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|IUPACName=1-fluoro-2,4-dinitrobenzene |
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| ImageFile1 = 1-Fluoro-2,4-dinitrobenzene-3D-spacefill.png |
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| ImageSize1 = 160 |
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|OtherNames=Dinitrofluorobenzene |
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| ImageAlt1 = DNFB molecule |
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| PIN = 1-Fluoro-2,4-dinitrobenzene |
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| OtherNames = Dinitrofluorobenzene<br />Sanger's reagent |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = DNFB |
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| Abbreviations = DNFB, FDNB |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 53049 |
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| ChEBI = 53049 |
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| ChemSpiderID = 21106037 |
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| ChemSpiderID = 21106037 |
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| InChI = 1/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H |
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| InChI = 1/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H |
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| InChIKey = LOTKRQAVGJMPNV-UHFFFAOYAZ |
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| InChIKey = LOTKRQAVGJMPNV-UHFFFAOYAZ |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 167423 |
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| ChEMBL = 167423 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H |
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| StdInChI = 1S/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LOTKRQAVGJMPNV-UHFFFAOYSA-N |
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| StdInChIKey = LOTKRQAVGJMPNV-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=70-34-8 |
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| CASNo =70-34-8 |
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| PubChem=6264 |
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| PubChem =6264 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = D241E059U6 |
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| UNII = D241E059U6 |
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| SMILES = O=()c1cc(ccc1F)()=O |
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| SMILES = O=()c1cc(ccc1F)()=O |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 6 | H = 3 | F = 1 |N = 2 | O = 4 |
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| C=6 | H=3 | F=1 | N=2 | O=4 |
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| Appearance= yellow crystals<ref name="Oxford MSDS"/> |
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| Appearance = yellow crystals<ref name="Oxford MSDS"/> |
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| Density= 1.4718 g·cm<sup>−3</sup> (54 °C)<ref name="CRC"/> |
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| Density = 1.4718 g·cm<sup>−3</sup> (54 °C)<ref name="CRC"/> |
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| MeltingPtC = 25.8 |
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| MeltingPt= 25.8 °C<ref name="CRC">'']'', 90. edition, CRC Press, Boca Raton, Florida, 2009, ISBN 978-1-4200-9084-0, Section 3, ''Physical Constants of Organic Compounds'', p. 3-260.</ref> |
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| MeltingPt_ref = <ref name="CRC">'']'', 90. edition, CRC Press, Boca Raton, Florida, 2009, {{ISBN|978-1-4200-9084-0}}, Section 3, ''Physical Constants of Organic Compounds'', p. 3-260.</ref> |
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| BoilingPt= 296 °C<ref name="CRC"/> |
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| BoilingPtC = 296 |
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| BoilingPt_ref = <ref name="CRC"/> |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| HPhrases = {{H-phrases|301|311|331|340|350}} |
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| EUClass = {{Hazchem T}} |
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| PPhrases = {{P-phrases|260|280|282|315}} |
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| ExternalMSDS = <ref name="Oxford MSDS"></ref> |
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| GHSPictograms = {{GHS06}} |
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| FlashPt= |
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}} |
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| LD50 = 50 mg/kg-1 |
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| LDLo = 100 mg/kg-1 |
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| ExternalSDS = <ref name="Oxford MSDS"></ref> |
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| FlashPt = |
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'''1-Fluoro-2,4-dinitrobenzene''' (commonly called '''Sanger's reagent''', '''dinitrofluorobenzene''', '''DNFB''' or '''FDNB''') is a chemical that reacts with the ] of ]. This can be helpful for ]. |
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== Preparation == |
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In 1936, Gottlieb presented a synthesis in which ] reacted with ] (KF) in ]:<ref>{{cite journal | last1 = Billroth Gottlieb | first1 = Hans | year = 1936 | title = The Replacement of Chlorine by Fluorine in Organic Compounds | journal = ] | volume = 58 | issue = 3| pages = 532–533 | doi = 10.1021/ja01294a502 }}</ref> |
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:] |
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== Uses == |
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] |
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In 1945, ] described its use for determining the ] ] in polypeptide chains, in particular ].<ref>{{cite journal | last1 = Sanger | first1 = F | title = The free amino groups of insulin | journal = The Biochemical Journal | volume = 39 | issue = 5 | pages = 507–15 | year = 1945 | pmid = 16747948 | pmc = 1258275 | doi=10.1042/bj0390507}}</ref> Sanger's initial results suggested that insulin was a smaller molecule than previously estimated (molecular weight 12,000), and that it consisted of four chains (two ending in ] and two ending in ]), with the chains cross-linked by ]s. Sanger continued work on insulin, using dinitrofluorobenzene in combination with other techniques, eventually resulted in the complete sequence of insulin (consisting of only two chains, with a molecular weight of 6,000).<ref name="Fruton">], ''Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology''. New Haven: Yale University Press, 1999. p. 216.</ref> |
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Following Sanger's initial report of the reagent, the dinitrofluorobenzene method was widely adopted for studying proteins, until it was superseded by other reagents for terminal analysis (e.g., ] and later ]s and ]s) and other general methods for sequence determination (e.g., ]).<ref name="Fruton"/> |
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Dinitrofluorobenzene reacts with the amine group in amino acids to produce ]-amino acids. These DNP-amino acids are moderately stable under ] conditions that break ]s. The DNP-amino acids can then be recovered, and the identity of those amino acids can be discovered through ]. More recently, Sanger's reagent has also been used for the rather difficult analysis of distinguishing between the reduced and oxidized forms of glutathione and cysteine in biological systems in conjunction with HPLC. This method is robust enough that it can be performed in such complex matrices as blood or cell lysate.<ref>{{cite journal | doi =10.1016/S0378-4347(01)00298-5 | pmid =11585123 | title =A new and versatile method for determination of thiolamines of biological importance | journal =Journal of Chromatography B: Biomedical Sciences and Applications | volume =761 | issue =1 | pages =1–12 | year =2001 | last1 =Dominick | first1 =Pamela K. | last2 =Cassidy | first2 =Pamela B. | last3 =Roberts | first3 =Jeanette C. }}</ref><ref>{{cite journal | doi = 10.1016/j.jchromb.2011.05.026 | pmid = 21665555 | title = RP-HPLC method for quantitative determination of cystathionine, cysteine and glutathione: An application for the study of the metabolism of cysteine in human brain | journal = Journal of Chromatography B | volume = 879 | issue = 21 | pages = 2005–2009 | year = 2011 | last1 = Bronowicka-Adamska | first1 = Patrycja | last2 = Zagajewski | first2 = Jacek | last3 = Czubak | first3 = Jerzy | last4 = Wróbel | first4 = Maria }}</ref> |
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==See also== |
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*] |
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== References == |
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{{reflist}} |
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== Literature == |
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* {{cite journal | doi =10.1139/v62-068| title =The Proton Magnetic Resonance Spectrum of 1-Fluoro-2,4-Dinitrobenzene| journal =Canadian Journal of Chemistry| volume =40| issue =3| pages =431–433| year =1962| last1 =Schaefer| first1 =T.| doi-access =free}} |
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* {{cite journal | doi =10.1080/00268976300101071| title =The1H and19F resonance spectra of 1-fluoro-2,4-dinitrobenzene| journal =Molecular Physics| volume =7| issue =4| pages =307–310| year =1964| last1 =Nageswara Rao| first1 =B.D.| bibcode =1964MolPh...7..307N}} |
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* {{cite journal | doi =10.1107/S0108270190007326| title =Structure of 1-fluoro-2,4-dinitrobenzene| journal =Acta Crystallographica Section C| volume =47| pages =220–221| year =1991| last1 =Wilkins| first1 =A.| last2 =Small| first2 =R. W. H.| issue =1| bibcode =1991AcCrC..47..220W}} |
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== External links == |
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{{DEFAULTSORT:Fluorodinitrobenzene 1 2 4}} |
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] |
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] |