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Revision as of 08:10, 6 April 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit		Latest revision as of 03:43, 22 May 2024 edit undo0dorkmann (talk | contribs)244 edits infobox img do-it-yourself
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	{{chembox		{{chembox
			| verifiedrevid = 422659402
⚫	| ImageFile = 3,3'-Dichlorobenzidine.svg
			| ImageFile_Ref = {{chemboximage|correct|??}}
		⚫	| ImageFile = 3,3'-Dichlorobenzidine-2D.svg
			| ImageFile2 = 3,3'-Dichlorobenzidine-3D.png
	| ImageSize = 250px		| ImageSize = 250px
			| PIN = 3,3′-Dichloro-4,4′-diamine
	| IUPACName = 4-(4-amino-3-chlorophenyl)-2-chloroaniline
	| Reference = <ref name="pubchem">, ].</ref>		| Reference = <ref name="pubchem">, ].</ref>
			| OtherNames = 4-(4-Amino-3-chlorophenyl)-2-chloroaniline<br />4,4′-Diamino-3,3′-dichlorobiphenyl<br />''o'',''o'''-Dichlorobenzidine<br />3,3′-Dichlorobiphenyl-4,4′-diamine<br />3,3′-Dichloro-4,4′-biphenyldiamine<br/>3,3′-Dichloro-4,4′-diaminobiphenyl
	| OtherNames = (1,1-Biphenyl)-4,4-Diamine,3,3-dichloro; 3,3-dichloro-4,4-biphenyldiamine
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6803		| ChemSpiderID = 6803
	| InChI = 1/C12H10Cl2N2/c13-9-5-7(1-3-11(9)15)8-2-4-12(16)10(14)6-8/h1-6H,15-16H2		| InChI = 1/C12H10Cl2N2/c13-9-5-7(1-3-11(9)15)8-2-4-12(16)10(14)6-8/h1-6H,15-16H2
	| InChIKey = HUWXDEQWWKGHRV-UHFFFAOYAF		| InChIKey = HUWXDEQWWKGHRV-UHFFFAOYAF
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 314470		| ChEMBL = 314470
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C12H10Cl2N2/c13-9-5-7(1-3-11(9)15)8-2-4-12(16)10(14)6-8/h1-6H,15-16H2		| StdInChI = 1S/C12H10Cl2N2/c13-9-5-7(1-3-11(9)15)8-2-4-12(16)10(14)6-8/h1-6H,15-16H2
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = HUWXDEQWWKGHRV-UHFFFAOYSA-N		| StdInChIKey = HUWXDEQWWKGHRV-UHFFFAOYSA-N
	| CASNo = 91-94-1		| CASNo = 91-94-1
			| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 1SDI2328UX
	| PubChem = 7070		| PubChem = 7070
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C19225
	| SMILES = Clc2cc(c1ccc(N)c(Cl)c1)ccc2N		| SMILES = Clc2cc(c1ccc(N)c(Cl)c1)ccc2N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>12</sub>H<sub>10</sub>Cl<sub>2</sub>N<sub>2</sub>		| Formula = C<sub>12</sub>H<sub>10</sub>Cl<sub>2</sub>N<sub>2</sub>
	| MolarMass = 253.13 g/mol		| MolarMass = 253.13 g/mol
	| Appearance = Gray or purple crystalline solid		| Appearance = Gray or purple crystalline solid
			| MeltingPtC = 132 to 133
	| Density =
	| MeltingPt = 132-133 °C
	| BoilingPtC = 402		| BoilingPtC = 402
	| Solubility = }}		| Solubility = 0.07% (15°C)<ref name=PGCH/>}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards = Potential carcinogen<ref name=PGCH>{{PGCH|0191}}</ref>
			| PEL = carcinogen<ref name=PGCH/>
	| FlashPt =
			| IDLH = Ca <ref name=PGCH/>
	| Autoignition = }}
			| REL = Ca<ref name=PGCH/>
			}}
	}}		}}
			'''3,3'-Dichlorobenzidine''' is an ] with the formula (C<sub>6</sub>H<sub>3</sub>Cl(NH<sub>2</sub>))<sub>2</sub>. The pure compound is pale yellow, but commercial samples are often colored. It is barely soluble in water and is often supplied as a wet paste. It is widely used in the production of ] pigments used in the production of printing inks.<ref name=Ullmann1>{{cite encyclopedia|author=K. Hunger|author2=W. Herbst |title=Pigments, Organic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2012|doi=10.1002/14356007.a20_371|isbn=9783527303854 }}</ref> Its use in the production of dyes has been largely discontinued because of concerns about carcinogenicity.
	'''3,3'-Dichlorobenzidine''' is used in the production of ]s and is considered a ].<ref name="pubchem"/> It contains two ]s.
			==Preparation and reactions==
			3,3'-Dichlorobenzidine is prepared in two steps from ]. The first step involves reduction with zinc in base to afford 2,2'-dichlorodi]. This intermediate undergoes the ] to afford 3,3'-dichlorobenzidine.<ref name=Ullmann>{{cite encyclopedia | author = Schwenecke, H. | author2 = Mayer, D. | title = Benzidine and Benzidine Derivatives | encyclopedia = Ullmann’s Encyclopedia of Industrial Chemistry | year = 2005 | publisher = Wiley-VCH | place = Weinheim | doi = 10.1002/14356007.a03_539| isbn = 9783527303854 }}</ref>
			Aqueous solutions of 3,3'-dichlorobenzidine degrade in light to monochloro derivative. It undergoes chlorination (for example in water treatment plants) to give the tetrachloro derivative.
			The most widely practiced reaction of 3,3'-dichlorobenzidine is its double ]. This bis(diazo) intermediate is then coupled to derivatives of acetoacetylaminobenzene (CH<sub>3</sub>C(O)CH<sub>2</sub>C(O)NHAr). In this way, the following commercial yellow pigments are produced: ], ], ], ] and pigment ]<ref name=Ullmann1/>
			], an industrially significant ], is produced via the diazonium derivative of 3,3'-dichlorobenzidine.]]
			==Safety==
			3,3'-Dichlorobenzidine is considered a ].<ref name="pubchem"/> This compound has been shown to increase the incidence of tumors in animals.<ref name=EPA>"". ], Integrated Risk Information System. 7 March 2011. Accessed 3 May 2011.</ref> Because it is structurally similar to ], a known carcinogen, it is believed that it may share a similar mechanism in causing ] in humans.<ref name=EPA/>
	==References==		==References==
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	==External links==		==External links==
	*		*
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	{{DEFAULTSORT:Dichlorobenzidine, 3,3'-}}		{{DEFAULTSORT:Dichlorobenzidine, 3,3'-}}
	]		]
	]		]
	]		]
	]		]
	{{aromatic-stub}}
	]
	]