1,8-Diaminonaphthalene: Difference between revisions

1,8-Diaminonaphthalene
Names
	IUPAC name naphthalene-1,8-diamine
	Other names deltamin, 1,8-naphthalenediamine
Identifiers
CAS Number	479-27-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL595537 ;
ChemSpider	61381 ;
ECHA InfoCard	100.006.846
PubChem CID	68067;
UNII	IKA7029YH9 ;
CompTox Dashboard (EPA)	DTXSID6044432 ;
	InChI InChI=1S/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2 Key: YFOOEYJGMMJJLS-UHFFFAOYSA-N ; InChI=1/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2 Key: YFOOEYJGMMJJLS-UHFFFAOYAU;
	SMILES C1=CC2=C(C(=C1)N)C(=CC=C2)N; c1(cccc2cccc(N)c12)N;
Properties
Chemical formula	C10H10N2
Molar mass	158.1998
Related compounds
Related Aromatic amines	1-Naphthylamine; 1,8-bis(dimethylamino)naphthalene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 16:53, 9 July 2020

1,8-Diaminonaphthalene is an organic compound with the formula C₁₀H₆(NH₂)₂. It is one of several isomeric naphthalenediamines. It is a colorless solid that darkens in air due to oxidation. It is a precursor to commercial pigments.^[1]

Synthesis and reactions

Chemical structure of 12-phthaloperinone, a derivative of 1,8-diaminonaphthalene

It is prepared by reduction of 1,8-dinitronaphthalene, which in turn is obtained as a mixture of isomers by nitration of 1-nitronaphthalene.

Upon treatment with phthalic anhydride derivatives, the diamine converts to phthaloperinones.^[2] The derivative from phthalic anhydride itself, Solvent Orange 60, is a useful orange pigment. It is a precursor to 1,8-bis(dimethylamino)naphthalene.

References

^ Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3527306732..
^ Mamada, Masashi; PéRez-BolíVar, César; Anzenbacher, Pavel (2011). "Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors". Organic Letters. 13 (18): 4882–4885. doi:10.1021/ol201973w. PMID 21863817.

[Ullmann-1] Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3527306732..

[2] Mamada, Masashi; PéRez-BolíVar, César; Anzenbacher, Pavel (2011). "Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors". Organic Letters. 13 (18): 4882–4885. doi:10.1021/ol201973w. PMID 21863817.

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[2]

@@ Line 3: / Line 3: @@
 | verifiedrevid = 477206675
 | ImageFile=1,8-Diaminonaphthalene.png
-| ImageSize= 108px
+| ImageSize= 100px
 | IUPACName=naphthalene-1,8-diamine
 | OtherNames= deltamin, 1,8-naphthalenediamine
@@ Line 28: / Line 28: @@
 | Formula=C{{sub|10}}H{{sub|10}}N{{sub|2}}
 | MolarMass=158.1998
+ }}
-| Appearance=
-| Density=
-| MeltingPt=
-| BoilingPt=
-| Solubility=
-  }}
-|Section3={{Chembox Hazards
-| MainHazards=
-| FlashPt=
-| AutoignitionPt =
-  }}
 |Section8={{Chembox Related
 | OtherFunction_label = [[Aromatic amine]]s
 | OtherFunction = [[1-Naphthylamine]]<br />[[1,8-bis(dimethylamino)naphthalene]]
-  }}
+ }}
 }}
@@ Line 48: / Line 38: @@
 ==Synthesis and reactions==
-[[File:Phthaloperinone.png|thumb|left|144 px|Chemical structure of 12-phthaloperinone, a derivative of 1,8-diaminonaphthalene.]]
+[[File:Phthaloperinone.png|thumb|left|144px|Chemical structure of 12-phthaloperinone, a derivative of 1,8-diaminonaphthalene]]
 It is prepared by reduction of 1,8-dinitronaphthalene, which in turn is obtained as a mixture of isomers by nitration of 1-nitronaphthalene.
-Upon treatment with [[phthalic anhydride]] derivatives, the diamine converts to phthaloperinones.<ref>{{cite journal |doi=10.1021/ol201973w|title=Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors|year=2011|last1=Mamada|first1=Masashi|last2=PéRez-BolíVar|first2=César|last3=Anzenbacher|first3=Pavel|journal=Organic Letters|volume=13|issue=18|pages=4882–4885|pmid=21863817}}</ref>  The derivative from phthalic anhydride itself, Solvent Orange 60, is a useful orange pigment.  It is a precursor to [[1,8-bis(dimethylamino)naphthalene]].
+Upon treatment with [[phthalic anhydride]] derivatives, the diamine converts to phthaloperinones.<ref>{{cite journal |doi=10.1021/ol201973w|title=Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors|year=2011|last1=Mamada|first1=Masashi|last2=PéRez-BolíVar|first2=César|last3=Anzenbacher|first3=Pavel|journal=Organic Letters|volume=13|issue=18|pages=4882–4885|pmid=21863817}}</ref> The derivative from phthalic anhydride itself, Solvent Orange 60, is a useful orange pigment. It is a precursor to [[1,8-bis(dimethylamino)naphthalene]].
 ==See also==