Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Primuline: Difference between pages

{{Other uses|Primulin (disambiguation)}}

| Verifiedfields = changed

| verifiedrevid = 464214351

| ImageFile = Primuline.svg

| ImageSize =

| PIN = Sodium 2′-(4-aminophenyl)-6-methyl[2,6′-bi-1,3-benzothiazole]-7-sulfonate

| OtherNames = Direct yellow 59

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 90399

| EC_number = 233-781-3

| InChI = 1/C21H15N3O3S3.Na/c1-11-2-8-16-18(19(11)30(25,26)27)29-21(24-16)13-5-9-15-17(10-13)28-20(23-15)12-3-6-14(22)7-4-12;/h2-10H,22H2,1H3,(H,25,26,27);/q;+1/p-1

| InChIKey = RSRNHSYYBLEMOI-REWHXWOFAP

| StdInChI = 1S/C21H15N3O3S3.Na/c1-11-2-8-16-18(19(11)30(25,26)27)29-21(24-16)13-5-9-15-17(10-13)28-20(23-15)12-3-6-14(22)7-4-12;/h2-10H,22H2,1H3,(H,25,26,27);/q;+1/p-1

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 8064-60-6

| PubChem = 3769888

| SMILES = [Na+].[O-]S(=O)(=O)c1c(ccc2nc(sc12)c4ccc3nc(sc3c4)c5ccc(N)cc5)C

|Section2={{Chembox Properties

| Formula = C₂₁H₁₅N₃O₃S₃ (free acid)

| MolarMass = 453.557 g/mol (free acid)

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

'''Primuline''' is a [[dye]] containing the [[benzothiazole]] ring system. Primuline itself is also known as '''Direct yellow 7''', '''Carnotine''', or '''C.I. 49010'''.

The primulines are considered derivatives of [[dehydrothiotoluidine]] (aminobenzenyltoluylmercaptan), which is obtained when [[toluidine|para-toluidine]] is heated with [[sulfur]] for eighteen hours at 180–190 °C and then for a further six hours at 200–220 °C<ref>{{cite journal| title=N/A| author=P. Jacobson| journal=[[Chemische Berichte|Ber.]]| date=1889 |volume = 22| pages =333}}<br/>[[L. Gatterrnann]], ibid. p. 1084</ref>

Dehydrothiotoluidine is not itself a dye-stuff, but if the heating is carried out at a higher temperature in the presence of more sulfur, then a base is formed, which gives '''primuline yellow''' upon sulfonation.<ref>{{cite journal| title=N/A| author=[[Arthur George Green|A. G. Green]]| journal=J. Soc. Chem. Ind.| year= 1888| volume= 1| pages=194}}</ref>

Primuline yellow is a mixture of sodium salts and probably contains at least three thiazole rings in combination. It is a substantive [[cotton]] dye of rather fugitive shade, but can be [[diazo]]tized on the fibre and then developed with other components, yielding a series of ingrain colors.<ref name=EB1911>{{cite EB1911 |wstitle=Primuline |volume=22 |page=342}}</ref>

Primuline is usually available as a sodium salt. Primuline is [[fluorescent]].

[[Thioflavin T]] is obtained by the [[methylation]] of dehydrothiotoluidine with [[methanol]] in the presence of [[hydrochloric acid]]. [[Thioflavin S]] results from the methylation of dehydrothiotoluidine with [[sulfonic acid]]. This sulfonic acid on [[oxidation]] with bleaching powder or with [[lead peroxide]], in alkaline solution yields '''chloramine yellow''', which dyes [[cotton]] a beautiful yellow.<ref name=EB1911/>

==References==

<references/>

[[Category:Anilines]]

[[Category:Benzothiazoles]]

[[Category:Sulfonic acids]]

[[Category:Thiazole dyes]]