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Revision as of 12:20, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 421119818 of page Methyl_yellow for the Chem/Drugbox validation project (updated: 'ChEMBL').  Latest revision as of 19:33, 24 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,127 edits added Category:Dimethylamino compounds using HotCat 
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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
| Watchedfields = changed
| verifiedrevid = 402497095 | verifiedrevid = 462250782
| ImageFile = Methyl yellow.png | ImageFile = Methyl yellow.svg
| ImageSize = | ImageSize =
| PIN = ''N'',''N''-Dimethyl-4-(phenyldiazenyl)aniline
| IUPACName = p-Dimethylaminoazobenzene
| OtherNames = 4-Dimethylaminoazobenzene, N,N-Dimethyl-4-phenylazoaniline, N,N-Dimethyl-4-aminoazobenzene, Butter Yellow, Solvent Yellow 2, C.I. 11020 | OtherNames = 4-Dimethylaminoazobenzene<br />''p''-Dimethylaminoazobenzene<br />DAB<br />''N'',''N''-Dimethyl-4-phenylazoaniline<br />''N'',''N''-Dimethyl-4-aminoazobenzene<br />Butter Yellow<br />Solvent Yellow 2<br />C.I. 11020
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5829 | ChemSpiderID = 5829
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
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| StdInChIKey = JCYPECIVGRXBMO-FOCLMDBBSA-N | StdInChIKey = JCYPECIVGRXBMO-FOCLMDBBSA-N
| CASNo = 60-11-7 | CASNo = 60-11-7
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 200-455-7 | EINECS = 200-455-7
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 263116 | ChEMBL = 263116
| PubChem = 6053 | PubChem = 6053
| SMILES = N(=N/c1ccccc1)\c2ccc(N(C)C)cc2 | SMILES = N(=N/c1ccccc1)\c2ccc(N(C)C)cc2
| RTECS = BX7350000 | RTECS = BX7350000
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=14 | H=15 | N=3
| Formula = C<sub>14</sub>H<sub>15</sub>N<sub>3</sub>
⚫ | Appearance = Yellow crystals
| MolarMass = 225.289 g.mol<sup>-1</sup>
| Density =
⚫ | Appearance = Yellow crystals
| Density = | MeltingPtC = 111-116
| MeltingPt_notes = <br> decomposes<ref name="sigma"></ref>
| MeltingPt = 116 °C (decomp.)
| BoilingPt = | BoilingPt =
| LogP = 4.58 | LogP = 4.58
| Solubility = 13.6 mg.l<sup>-1</sup> | Solubility = 13.6 mg/l
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| GHSPictograms = {{GHS06}}{{GHS08}}<ref name="sigma" />
| MainHazards = Toxic ('''T''')
| GHSSignalWord = Danger
| RPhrases = {{R25}}, {{R40}}
| HPhrases = {{H-phrases|301|351}}<ref name="sigma" />
| SPhrases = {{S36/37}}, {{S45}}
| PPhrases = {{P-phrases|281|301+310}}<ref name="sigma" />
| NFPA-H = 2
| NFPA-F = 1 | NFPA-H = 2
| NFPA-R = 0 | NFPA-F = 1
| NFPA-O = | NFPA-R = 0
| FlashPt = | NFPA-S =
| Autoignition = | FlashPt =
| AutoignitionPt =
| MainHazards = Carcinogen<ref name=PGCH>{{PGCH|0220}}</ref>
| PEL = OSHA-regulated carcinogen<ref name=PGCH/>
| IDLH = Ca <ref name=PGCH/>
| REL = Ca<ref name=PGCH/>
}} }}
}} }}

'''Methyl yellow''', or '''C.I. 11020''', is an ] with the formula C<sub>6</sub>H<sub>5</sub>N<sub>2</sub>C<sub>6</sub>H<sub>4</sub>N(CH<sub>3</sub>)<sub>2</sub>. It is an ] derived from ]. It is a yellow solid. According to ], the C<sub>14</sub>N<sub>3</sub> core of the molecule is planar.<ref>{{cite journal|title=Crystal and molecular structure of C.I. Solvent Yellow 2, 1-Phenylazo-4 (N,N-dimethylamine)-phenyl |journal=Journal of Crystallographic and Spectroscopic Research |year=1992 |volume=22 |pages= 151–155| vauthors = Whitaker A |issue=2 |doi= 10.1007/BF01186250 |s2cid=93052691 }}</ref>

It is used as a dye for plastics and may be used as a ]. {{pH_indicator_template|indicator_name=Methyl yellow|low_pH=2.9|high_pH=4.0|low_pH_color=red|low_pH_text=white|high_pH_color=yellow}} In aqueous solution at low pH, methyl yellow appears red. Between pH 2.9 and 4.0, methyl yellow undergoes a transition, to become yellow above pH 4.0.

==Safety==
It is a possible ].<ref name=PGCH/> As "butter yellow", the agent had been used as a food additive in butter and margarine before its toxicity was recognized.<ref>{{cite journal | vauthors = Opie EL | title = The Pathogenesis of Tumors of the Liver Produced by Butter Yellow | journal = The Journal of Experimental Medicine | volume = 80 | issue = 3 | pages = 231–46 | date = September 1944 | pmid = 19871411 | pmc = 2135460 | doi = 10.1084/jem.80.3.231 }}</ref>

== History ==
Butter yellow was synthesized by ] in the 1860s at the ] in London.<ref name=":0">{{Cite book |url=https://books.google.com/books?id=snUGDAAAQBAJ |title=Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives |last1=Ortiz-Gómez|first1=Teresa|last2=Santesmases|first2=María Jesús | name-list-style = vanc |date=2016-04-22|publisher=Routledge |isbn=978-1-317-12981-3 }}</ref> The dye was used to dye butter in ]<ref name=":0" /><ref name=":1">{{Cite book|url=https://archive.org/details/naziwaroncancer00proc/page/165|title=The Nazi War on Cancer|last=Robert|first=Proctor|name-list-style=vanc|publisher=Princeton University Press|year=1999|isbn=978-0-691-00196-8|location=Princeton, N.J|pages=|url-access=registration}}</ref> and other parts of the world{{Citation needed|reason=This is implied, but can't find a direct source say so.|date=November 2018}} during the latter half of the 19th century and the beginning of the 20th before being phased out in the 1930s and 40s. It was in the 1930s that research led by ] showed the link between several ] and cancer, linking butter yellow to ] in rats after two to three months exposure.<ref>{{cite journal | vauthors = Kinosita R | title = Studies on the Cancerogenic Azo and Related Compounds | journal = The Yale Journal of Biology and Medicine | volume = 12 | issue = 3 | pages = 287–300 | date = January 1940 | pmid = 21433884 | pmc = 2602186 }}</ref> In 1939, the ] issued a recommendation for the banning of cancer-causing food dyes (including butter yellow) from food production.<ref name=":0" /><ref name=":1" />

In 2014, dried tofu products (a.k.a. '']'' 豆乾) from Taiwan were found to have been adulterated with methyl yellow, used as a coloring agent.<ref>{{cite web | url=http://www.channelnewsasia.com/news/asiapacific/taiwan-recalls-tainted/1535406.html | title=Taiwan recalls tainted dried tofu in fresh food scare | work=Channel NewsAsia | date=17 December 2014 | access-date=13 July 2016 | archive-url=https://web.archive.org/web/20141219111820/http://www.channelnewsasia.com/news/asiapacific/taiwan-recalls-tainted/1535406.html | archive-date=19 December 2014 | url-status=dead}}</ref>

== See also ==
Structurally similar compounds:
* ]
* ]
* ]

== References ==
{{reflist}}

== Further reading ==
{{refbegin}}
* {{cite journal | vauthors = Chung KT, Fulk GE, Andrews AW | title = Mutagenicity testing of some commonly used dyes | journal = Applied and Environmental Microbiology | volume = 42 | issue = 4 | pages = 641–8 | date = October 1981 | doi = 10.1128/AEM.42.4.641-648.1981 | pmid = 7039509 | pmc = 244076 | bibcode = 1981ApEnM..42..641C }}
{{refend}}

== External links ==
* {{ICSC|1498|14}}
* {{ cite web | url = http://www.inchem.org/documents/iarc/vol08/p-dimethylaminobenzene.html | title = para-dimethylaminoazobenzene | publisher = Inchem }}
*

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