Alizarine Yellow R

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477314571

| Name = Alizarine Yellow R

| ImageFile1 = Alizarin-yellow-R-1718-34-9-sodium-salt-2D-skeletal.png

| ImageSize1 = 220px

| ImageName1 = Alizarin Yellow R (sodium salt)

| ImageFile2 = Alizarine-Yellow-R-sodium-3D-spacefill.png

| ImageAlt2 = Space-filling model of Alizarine Yellow R as a sodium salt

| ImageFile3 = Alizarin-yellow-R-2243-76-7-acid-2D-skeletal.png

| ImageSize3 = 200px

| ImageName3 = Alizarin Yellow R (acid)

| IUPACName = Sodium 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoate

| OtherNames = 5-[(p-Nitrophenyl)azo]salicylic acid sodium salt
Chrome orange
Mordant orange 1
C.I. 14030

| Section1 = {{Chembox Identifiers

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

| ChemSpiderID = 17215762

| InChI = 1/C13H9N3O5.Na/c17-12-6-3-9(7-11(12)13(18)19)15-14-8-1-4-10(5-2-8)16(20)21;/h1-7,17H,(H,18,19);/q;+1/p-1/b15-14+;

| InChIKey = HXKKTXMJSVFQSL-QUIZLSBABP

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C13H9N3O5.Na/c17-12-6-3-9(7-11(12)13(18)19)15-14-8-1-4-10(5-2-8)16(20)21;/h1-7,17H,(H,18,19);/q;+1/p-1/b15-14+;

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HXKKTXMJSVFQSL-WPDLWGESSA-M

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 1718-34-9

| CASNo_Comment =(Na salt)

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 2243-76-7

| CASNo2_Comment = (acid){{cite book|title=CRC Handbook of Chemistry and Physics, 88th Edition|url=https://books.google.com/books?id=SdW_QgAACAAJ|url-access =limited|last=Lide|first=David R.|date=25 June 2007|publisher=CRC Press|oclc=1024315229|isbn=9780849304880|pages=[https://archive.org/details/handbookchemistr00lide_885/page/n884 3]–10}}

| PubChem = 6504724

| PubChem_Comment =(Na salt)

| EC_number = 209-536-1

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = R1T3O0G585

| UNII1_Comment = (Na salt)

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = OBF2VZO457

| UNII2_Comment = (acid)

| SMILES = [Na+].O=C([O-])c1cc(ccc1O)/N=N/c2ccc(cc2)[N+]([O-])=O

}}

| Section2 = {{Chembox Properties

| Formula = C13H8N3NaO5 (Na salt)
C13H9N3O5 (acid)

| MolarMass = 309.21 g mol−1 (Na salt)
287.23 g mol−1 (acid)

| Density =

| MeltingPt =

| BoilingPt =

}}

| Section3 = {{Chembox Hazards

| FlashPt =

| AutoignitionPt =

| GHSPictograms = {{GHS exclamation mark}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|H302|H319}}

| PPhrases = {{P-phrases|P264|P270|P280|P301+P312|P305+P351+P338|P330|P337+P313|P501}}

| Hazards_ref = {{Sigma-Aldrich|id=R320897|name=ALIZARINE YELLOW R|accessdate=09 April 2023}}

}}

}}

{{pH indicator template|indicator_name=Alizarine Yellow R|low_pH=10.1|high_pH=12.0|low_pH_color=yellow|high_pH_color=red|high_pH_text=white}}

Alizarine Yellow R is a yellow colored azo dye made by the diazo coupling reaction. It is usually commercially available as a sodium salt. In its pure form, it is a rust-colored solid.{{cite web|url=http://msds.chem.ox.ac.uk/AL/alizarin_yellow_R.html|url-status=dead|title=Safety Datasheet (MSDS) for alizarin yellow R|archive-url=https://web.archive.org/web/20110319233005/http://msds.chem.ox.ac.uk/AL/alizarin_yellow_R.html|date=2005|access-date=11 October 2008|archive-date=19 March 2011|publisher=Department of Chemistry, University of Oxford}} It is mainly used as a pH indicator.

Preparation

Alizarine Yellow R is produced by azo coupling of salicylic acid and diazonium derivative of 4-Nitroaniline

File:Synthese von Alizaringelb R.svg

References

{{Reflist}}