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			{{Redirect|TMPD|the Japanese police department in Tokyo|Tokyo Metropolitan Police Department}}
			{{Use dmy dates|date=May 2022}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 358154372		| verifiedrevid = 431217472
	| ImageFile = Tetramethylphenylendiamine.png		| ImageFile = Tetramethylphenylendiamine.svg
	| ImageSize = 120px		| ImageSize = 120px
			| PIN = ''N''<sup>1</sup>,''N''<sup>1</sup>,''N''<sup>4</sup>,''N''<sup>4</sup>-Tetramethylbenzene-1,4-diamine
	| IUPACName =
	| OtherNames = ''N'',''N'',''N<nowiki>'</nowiki>'',''N<nowiki>'</nowiki>''-Tetramethyl-1,4-phenylendiamin		| OtherNames = {{ubl|''N'',''N'',''N''′,''N''′-Tetramethyl-1,4-phenylenediamine|TMPD|Wurster's reagent |TL-85}}
	TMPD
	| Reference =		| Reference =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| Abbreviations =		| Abbreviations =
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 100-22-1		| CASNo = 100-22-1
			| UNII_Ref = {{fdacite|changed|FDA}}
			| UNII = P4P3AC32ZB
	| EINECS =		| EINECS =
	| PubChem = 7490		| PubChem = 7490
	| SMILES =		| SMILES =
⚫	| InChI =
	| RTECS =		| RTECS =
	| MeSHName =		| MeSHName =
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	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG =		| KEGG =
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫	| ATCCode_prefix =
			| ChemSpiderID = 21106585
⚫	| ATCCode_suffix =
			| SMILES2 = CN(C)c1ccc(cc1)N(C)C
⚫	| ATC_Supplemental =}}
			| InChI = 1/C10H16N2/c1-11(2)9-5-7-10(8-6-9)12(3)4/h5-8H,1-4H3
⚫	| Section2 = {{Chembox Properties
			| InChIKey = CJAOGUFAAWZWNI-UHFFFAOYAJ
	| Formula = C<sub>10</sub>H<sub>16</sub>N<sub>2</sub>
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
	| MolarMass = 164.25 g/mol
			| StdInChI = 1S/C10H16N2/c1-11(2)9-5-7-10(8-6-9)12(3)4/h5-8H,1-4H3
⚫	| Appearance = Colourless crystalline solid
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫	| Density = 0.992g/cm3
			| StdInChIKey = CJAOGUFAAWZWNI-UHFFFAOYSA-N
	| MeltingPtCL = 51
			}}
	| MeltingPtCH =
		⚫	|Section2={{Chembox Properties
	| Melting_notes =
			| C=10 | H=16 | N=2
		⚫	| Appearance = Colorless crystalline solid
		⚫	| Density = 0.992 g/cm<sup>3</sup>
			| MeltingPtC = 51
			| MeltingPt_notes =
	| BoilingPtC = 260		| BoilingPtC = 260
	| Boiling_notes =		| BoilingPt_notes =
	| Solubility = slightly in cold water more so in hot water		| Solubility = Slightly in cold water more so in hot water
	| SolubleOther = alcohol		| SolubleOther = Soluble in alcohol, chloroform
	| Solvent =		| Solvent = other solvents
	| pKa = 6.35		| pKa = 6.35
	| pKb = }}		| pKb = }}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| CrystalStruct =		| CrystalStruct =
	| Coordination =		| Coordination =
	| MolShape = }}		| MolShape = }}
	| Section4 = {{Chembox Thermochemistry		|Section5={{Chembox Thermochemistry
	| DeltaHf =		| DeltaHf =
	| DeltaHc =		| DeltaHc =
	| Entropy =		| Entropy =
	| HeatCapacity = }}		| HeatCapacity = }}
	| Section5 = {{Chembox Pharmacology		|Section6={{Chembox Pharmacology
		⚫	| ATCCode_prefix =
		⚫	| ATCCode_suffix =
		⚫	| ATC_Supplemental =
	| AdminRoutes =		| AdminRoutes =
	| Bioavail =		| Bioavail =
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	| Legal_AU =		| Legal_AU =
	| Legal_CA =		| Legal_CA =
	| PregCat =		| Pregnancy_category =
	| PregCat_AU =		| Pregnancy_AU =
	| PregCat_US = }}		| Pregnancy_US = }}
	| Section6 = {{Chembox Explosive		|Section4={{Chembox Explosive
	| ShockSens =		| ShockSens =
	| FrictionSens =		| FrictionSens =
	| ExplosiveV =		| DetonationV =
	| REFactor = }}		| REFactor = }}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| EUClass =
	| EUIndex =
	| MainHazards =		| MainHazards =
	| NFPA-H =		| NFPA-H =
	| NFPA-F =		| NFPA-F =
	| NFPA-R =		| NFPA-R =
	| NFPA-O =		| NFPA-S =
	| RPhrases =		| HPhrases =
	| SPhrases =		| PPhrases =
	| RSPhrases =		| GHS_ref =
	| FlashPt = 110°C		| FlashPtC = 110
	| Autoignition =		| AutoignitionPtC =
	| ExploLimits =		| ExploLimits =
	| PEL = }}		| PEL = }}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherAnions =		| OtherAnions =
	| OtherCations =		| OtherCations =
	| OtherFunctn =		| OtherFunction =
	| Function =		| OtherFunction_label =
	| OtherCpds = }}		| OtherCompounds =
			}}
	}}		}}
	'''Wurster's blue''' is the trivial name given to the chemical ''N,N,N′,N′''-tetramethyl-''p''-phenylenediamine, also known as '''TMPD'''. It is an easily oxidised ], which loses two ]s in one-electron ] steps; the ] is a characteristic blue-violet colour, which gives the compound part of its name. The remaining part of its name comes from its discoverer, the German ] Casimir Wurster (August 7, 1854 - 29 November 1913).		'''Wurster's blue''' is the radical cation of the colorless chemical ''N'',''N'',''N''′,''N''′-tetramethyl-''p''-phenylenediamine, also known as '''TMPD'''.<ref>{{Cite journal | doi = 10.1002/cber.187901202156 | title = Ueber die Einwirkung oxydirender Agentien auf Tetramethylparaphenylendiamin | date = 1879 | last1 = Wurster | first1 = C. | last2 = Schobig | first2 = E. | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 12 | issue = 2 | pages = 1807–1813 }}</ref> This is an easily oxidized ], which loses two ]s in one-electron ] steps; the ] is a characteristic blue-violet color, which gives the compound part of its name. The remaining part of its name comes from its discoverer, the German ] Casimir Wurster (7 August 1854 – 29 November 1913).
			]
	It finds use as a ] indicator in the ] and is also used in electron transport chain analysis; it is capable of donating electrons to cytochrome C.
		⚫	The hydrochloride salt of TMPD finds use as a ] indicator in the ] and is also used in electron transport chain analysis as it is capable of donating electrons to ]. The midpoint potential for titration of the first electron is given as 0.276 V vs ], and this transition is useful in ] as both a redox mediator and indicator. The two electron-oxidized colorless ]-diiminium cation is unstable in aqueous solutions;<ref>{{cite journal
	the hydrochloride form finds use in analytical chemistry as a reagent
		⚫	|author1=L. Michaelis |author2=M. P. Schubert |author3=S. Granick | title = The Free Radicals of the Type of Wurster's Salts
			| year = 1939
⚫	The term "Wurster's blue" is often reserved for the radical cation, the colorless diamine being called tetramethylphenylenediamine (TMPD). The midpoint potential for titration of the first electron is given as 0.276 V vs NHE, and this transition is useful in potentiometric titrations as both a redox mediator and indicator. The two electron-oxidized form (di-iminium) is unstable in aqueous solutions <ref>{{cite journal
		⚫	| volume = 61
	| author = L. Michaelis, M. P. Schubert, S. Granick
		⚫	| issue = 8
⚫	| title = The Free Radicals of the Type of Wurster's Salts
	| year = 1939		| pages = 1981–1992
		⚫	| doi = 10.1021/ja01877a013
⚫	| volume = 61
		⚫	| journal = J. Am. Chem. Soc.}}</ref> therefore, highly oxidizing conditions should be avoided in titrations relying on TMPD, or reached only during the final stage of the titration. The second oxidation step is not well separated from the first on the redox scale, so some instability will be encountered on the oxidizing side of 0.276, and it is impossible to prepare pure aqueous solutions of Wurster's blue due to its ] to the unstable di-iminium ion and TMPD.
	| issue = 8
	| pages = 1981–1992
⚫	| doi = 10.1021/ja01877a013
⚫	| journal = J. Am. Chem. Soc.}}</ref>, therefore highly oxidizing conditions should be avoided in titrations relying on TMPD, or reached only during the final stage of the titration. The second oxidation step is not well separated from the first on the redox scale, so some instability will be encountered on the oxidizing side of 0.276, and it is impossible to prepare pure aqueous solutions of Wurster's Blue due to its dismutation to the unstable diaminium and TMPD.
		⚫	==References==
	{{Reflist}}		{{Reflist}}
	==External links==
	*
⚫	==References==
	*
	]		]
			]
			]
	]
	]