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Revision as of 13:31, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 453603667 of page Safranin for the Chem/Drugbox validation project (updated: '').  Latest revision as of 17:04, 15 September 2024 edit InternetArchiveBot (talk | contribs)Bots, Pending changes reviewers5,382,321 edits Rescuing 1 sources and tagging 0 as dead.) #IABot (v2.0.9.5) (Whoop whoop pull up - 21247 
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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.}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 422462567
| Watchedfields = changed
⚫ | verifiedrevid = 464386081
| Name = Safranin | Name = Safranin
| ImageFile = Safranin Cl.svg | ImageFile = Safranin Cl.svg
<!-- | ImageSize = 200px --> | ImageSize = 200px
| ImageName = Safranin | ImageName = Safranin
| ImageFile1 = Safranin-3D-balls.png | ImageFile1 = Safranin-3D-balls.png
| ImageSize1 = 200px | ImageSize1 = 200px
| ImageName1 = Safranin | ImageName1 = Safranin
| IUPACName = Safranin | ImageFileL2 = Sample of Safranin O.jpg
| ImageSizeL2 = 130
| ImageCaptionL2 = Solid safranin
| ImageFileR2 = Safranin O in aqueous solution.jpg
| ImageSizeR2 = 130
| ImageCaptionR2 = Safranin in aqueous solution
| PIN = 3,7-Diamino-2,8-dimethyl-5-phenylphenazin-5-ium chloride
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2005991 | ChemSpiderID = 2005991
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 197447
| PubChem = 2723800 | PubChem = 2723800
| InChI = 1/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H | InChI = 1/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H
| InChIKey = OARRHUQTFTUEOS-UHFFFAOYAR | InChIKey = OARRHUQTFTUEOS-UHFFFAOYAR
| InChI2 = 1/C20H18N4/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17/h3-11H,1-2H3,(H3,21,22)/p+1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H | StdInChI = 1S/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OARRHUQTFTUEOS-UHFFFAOYSA-N | StdInChIKey = OARRHUQTFTUEOS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 477-73-6 | CASNo = 477-73-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = XTX0YXU2HV
| SMILES = .n1c4c((c2c1cc(c(N)c2)C)c3ccccc3)cc(c(c4)C)N | SMILES = .n1c4c((c2c1cc(c(N)c2)C)c3ccccc3)cc(c(c4)C)N
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=20|H=19|N=4|Cl=1
| Formula = C<sub>20</sub>H<sub>19</sub>N<sub>4</sub><sup>+</sup>, Cl<sup>-</sup>
| Appearance =
| MolarMass = 350,84 g/mol
| Density = | Density =
| MeltingPt = | MeltingPtC =
| BoilingPt = | MeltingPt_notes =

⚫ }}
| BoilingPtC =
| BoilingPt_notes =

| Solubility = Soluble
| Solvent1 = water
⚫ }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS corrosion}} {{GHS exclamation mark}}<ref name=labchem>{{cite web|title=Safety Data Sheet: Safranin O|url=http://www.labchem.com/tools/msds/msds/75583.pdf|website=LabChem|access-date=10 March 2016|archive-date=10 March 2016|archive-url=https://web.archive.org/web/20160310191854/http://www.labchem.com/tools/msds/msds/75583.pdf|url-status=dead}}</ref>
| GHSSignalWord = '''Danger'''<ref name=labchem />
| HPhrases = {{H-phrases|315|318}}<ref name=labchem />
| PPhrases = {{P-phrases|264|280|302+352|305+351+338|310|332+313|362}}<ref name=labchem />
| MainHazards =
| FlashPt =
| AutoignitionPt =
| NFPA-H = 2
| NFPA-F = 0
| NFPA-R = 0
| NFPA-S =
}}
}} }}

'''Safranin''' ('''Safranin O''' or '''basic red 2''') is a ] used in ] and ]. Safranin is used as a counterstain in some staining protocols, colouring ] red. This is the classic ] in both ]s and ]. It can also be used for the detection of ],<ref>{{cite journal | author = Rosenberg L | title = Chemical Basis for the Histological Use of Safranin O in the Study of Articular Cartilage | journal = J Bone Joint Surg Am | volume = 53 | issue = 1 | pages = 69–82 | year = 1971 | pmid = 4250366 | doi = 10.2106/00004623-197153010-00007| url = http://www.ejbjs.org/cgi/content/abstract/53/1/69 | format = abstract | url-status = dead | archive-url = https://web.archive.org/web/20080417005221/http://www.ejbjs.org/cgi/content/abstract/53/1/69 | archive-date = 2008-04-17 }}</ref> ] and ] granules.

Safranin typically has the chemical structure shown at right (sometimes described as '''dimethyl safranin'''). There is also '''trimethyl safranin''', which has an added ] in the ''ortho-'' position (see ]) of the lower ring. Both compounds behave essentially identically in biological staining applications, and most manufacturers of safranin do not distinguish between the two. Commercial safranin preparations often contain a blend of both types.

Safranin is also used as ] in ].

==Safranines==
'''Safranines''' are the azonium ]s of ] 2,8-dimethyl-3,7-diaminophenazine. They are obtained by the joint ] of one ] of a ''para''-diamine with two molecules of a ]; by the condensation of ''para''-aminoazo compounds with primary amines, and by the action of ''para''-nitrosodialkylanilines with secondary ] such as diphenylmetaphenylenediamine. They are ] solids showing a characteristic green metallic ]; they are readily soluble in water and ] red or violet. They are strong bases and form stable monacid ]s. Their ]ic solution shows a yellow-red ].<ref name=EB1911>{{EB1911|wstitle =Safranine|volume=23 |page=1000 |inline=y}}</ref>

Phenosafranine is not very stable in the free state{{citation needed|date=February 2023}}; its ] forms green plates{{clarification needed|date=February 2023}}. It can be readily diazotized, and the diazonium salt when boiled with alcohol yields aposafranine or benzene induline, C<sub>18</sub>H<sub>12</sub>N<sub>3</sub>. Friedrich Kehrmann showed that aposafranine could be diazotized in the presence of cold concentrated ], and the diazonium salt on boiling with alcohol yielded phenylphenazonium salts. Aposafranone, C<sub>18</sub>H<sub>12</sub>N<sub>2</sub>O, is formed by heating aposafranine with concentrated ]. These three compounds are perhaps to be represented as ''ortho''- or as ''para''-]s. The "safranine" of commerce is an ''ortho''-tolusafranine. The first ] dye-stuff to be prepared on a manufacturing scale was ], which was obtained by ] by heating crude aniline with ] and sulfuric acid.<ref name="EB1911" />

Mauveine was converted to ''parasafranine'' (1,8-dimethylsafranine) by Perkin in 1878 by ]/] loss of the 7''N''-''para''-tolyl group.<ref>{{cite journal | journal = ] | year = 1879 | volume = 35 | pages = 717–732 | doi = 10.1039/CT8793500717 | title = LXXIV.—On mauveine and allied colouring matters | author = W. H. Perkin F.R.S.| author-link = Sir William Henry Perkin | url = https://zenodo.org/record/2010519 }}</ref>
Another well known safranin is phenosafranine (C.I. 50200, 3,7-diamino-5-phenylphenazinium chloride) widely used as a histological dye, photosensitizer and redox probe.<ref>{{cite journal|last1=Zucca|first1=Paolo|last2=Vinci|first2=Carla|last3=Rescigno|first3=Antonio|last4=Dumitriu|first4=Emil|last5=Sanjust|first5=Enrico|title=Is the bleaching of phenosafranine by hydrogen peroxide oxidation catalyzed by silica-supported 5,10,15,20-tetrakis-(sulfonatophenyl)porphine-Mn(III) really biomimetic?|journal=Journal of Molecular Catalysis A: Chemical|date=14 April 2010|volume=321|issue=1–2|pages=27–33|doi=10.1016/j.molcata.2010.01.015}}</ref>

==References==
{{Reflist}}

{{Stains}}

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