Para red

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 476994415

| ImageFile = Para Red Formula V.1.svg

| ImageSize = 250px

| PIN = 1-[(E)-(4-Nitrophenyl)diazenyl]naphthalen-2-ol

| OtherNames = 1-[(4-Nitrophenyl)azo]-2-naphthalenol, 1-((4-nitrophenyl)azo)-2-naphthol, 1-[(p-nitrophenyl)azo]-2-naphthalenol, 1-[(p-nitrophenyl)azo]-2-naphthol, 1-[(E)-(4-Nitrophenyl)diazenyl]-2-naphthol, paranitraniline red, Pigment Red 1, C.I. 12070, Recolite Para Red B, Carnelio Para Red BS

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 13544963

| InChI = 1/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+

| InChIKey = WOTPFVNWMLFMFW-ISLYRVAYBR

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

| StdInChI = 1S/C16H11N3O3/c20-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)19(21)22/h1-10,20H/b18-17+

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

| StdInChIKey = WOTPFVNWMLFMFW-ISLYRVAYSA-N

| CASNo_Ref = {{cascite|correct|PubChem}}

| CASNo = 6410-10-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = D54Q24K2EI

| EINECS = 229-093-8

| PubChem = 22917

| ChEMBL = 1967257

| SMILES = O=N(=O)c1ccc(cc1)/N=N/c2c3ccccc3ccc2O

}}

|Section2={{Chembox Properties

| C=16

| H=11

| N=3

| O=3

| Appearance = Red solid

| Density =

| MeltingPtC = 248 to 252

| MeltingPt_notes =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}

}}

}}

Para red (paranitraniline red, Pigment Red 1, C.I. 12070) is a dye. Chemically, it is similar to Sudan I. It was discovered in 1880 by von Gallois and Ullrich. It dyes cellulose fabrics a brilliant red color, but is not very fast. The dye can be washed away easily from cellulose fabrics if not dyed correctly. Acidic and basic stages both occur during the standard formation of Para Red, and acidic or basic byproducts may be present in the final product.

Synthesis

Para red is prepared by diazotization of para-nitroaniline at ice-cold temperatures, followed by coupling with β-naphthol:{{cite book

| last = Williamson

| first = Kenneth L.

| title = Macroscale and Microscale Organic Experiments, Fourth Edition

| publisher = Houghton-Mifflin

| year = 2002

| isbn = 0-618-19702-8

| url-access = registration

| url = https://archive.org/details/macroscalemicros00will_0

}}

:Image:Synthesis_Para_Red.svg{{clear-left}}

Regulation

Para red is not approved for use in food in any jurisdiction. In 2005, Old El Paso dinner kits were found to be contaminated with the dye and removed from supermarket shelves.{{cite news | url = http://www.food.gov.uk/news/newsarchive/2005/apr/oldelpaso | title = Old El Paso Dinner Kits for enchiladas and burritos found with illegal dye | publisher = Food Standards Agency | format = press release | date = 21 April 2005}}{{cite news | url = http://news.bbc.co.uk/1/hi/health/4518139.stm | title = Banned dye found in more products | publisher = BBC News | date = 5 May 2005}}

References