1,8-Diaminonaphthalene: Difference between revisions

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{{chembox
{{chembox
| Verifiedfields = changed
| verifiedrevid = 413090959
| verifiedrevid = 477206675
|ImageFile=1,8-Diaminonaphthalene.png
| ImageFile=Chemical structural formula of 1,8-diaminonaphthalene.svg
|ImageSize=
| ImageSize= 150px
|IUPACName=naphthalene-1,8-diamine
| PIN=Naphthalene-1,8-diamine
|OtherNames=
| OtherNames= Deltamin, 1,8-Naphthalenediamine
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 61381
| ChemSpiderID = 61381
| InChI = 1/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2
| InChI = 1/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YFOOEYJGMMJJLS-UHFFFAOYSA-N
| StdInChIKey = YFOOEYJGMMJJLS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=479-27-6
| CASNo=479-27-6
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem=68067
| UNII = IKA7029YH9
⚫
| SMILES=C1=CC2=C(C(=C1)N)C(=CC=C2)N
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| PubChem=68067
⚫
| SMILES=C1=CC2=C(C(=C1)N)C(=CC=C2)N
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>10</sub>H<sub>10</sub>N<sub>2</sub>
| Formula=C{{sub|10}}H{{sub|10}}N{{sub|2}}
| MolarMass=158.1998
| MolarMass=158.1998
⚫
}}
| Appearance=
⚫
|Section8={{Chembox Related
| Density=
⚫
| OtherFunction_label = [[Aromatic amine]]s
| MeltingPt=
⚫
| OtherFunction = [[1-Naphthylamine]]<br />[[1,8-bis(dimethylamino)naphthalene]]
| BoilingPt=
⚫
}}
| Solubility=
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}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
⚫
}}
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| Section8 = {{Chembox Related
⚫
| Function = [[Aromatic amine]]s
⚫
| OtherFunctn = [[1-Naphthylamine]]<br />[[1,8-bis(dimethylamino)naphthalene]]
}}
}}
}}


'''1,8-Diaminonaphthalene''' is an [[organic compound]] with the formula C{{sub|10}}H{{sub|6}}(NH{{sub|2}}){{sub|2}}. It is one of several [[isomer]]ic [[naphthalenediamine]]s. It is a colorless solid that darkens in air due to oxidation. It is a precursor to commercial pigments.<ref name=Ullmann>{{Ullmann|first1=Gerald|last1=Booth|title=Naphthalene Derivatives|year=2005|doi10.1002/14356007.a17_009}}.</ref>
'''1,8-Diaminonaphthalene''' is an aromatic [[amine]]. It is a precursor to [[1,8-bis(dimethylamino)naphthalene]].


==Synthesis and reactions==
⚫
{{DEFAULTSORT:Diaminonaphthalene, 1,8-}}
[[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|s2cid=32185653 |url=https://scholarworks.bgsu.edu/chem_pub/145}}</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]]. This compound used to produce perimidines by various aldehydes.<ref>{{cite journal|last=F.K. Behbahani, F.M.Golchin|doi=10.1016/j.jtusci.2015.10.004|title=A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4|journal=Journal of Taibah University for Science|year=2017|volume=11|issue=1 |pages=85–89|s2cid=98648448|doi-access=free|bibcode=2017JTUS...11...85B |url=https://zenodo.org/records/3593823/files/A%20new%20catalyst%20for%20the%20synthesis%20of%202%20substituted%20perimidines%20catalysed%20by%20FePO4(1).pdf}}</ref>
⚫
[[Category:Naphthylamines]]


==See also==
{{amine-stub}}
* [[C10H10N2|C<sub>10</sub>H<sub>10</sub>N<sub>2</sub>]]


==References==
[[fa:۱،۸-دی‌آمینونفتالن]]
{{Reflist}}
[[ja:1,8-ジアミノナフタレン]]

[[pt:1,8-Diaminonaftaleno]]
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{{DEFAULTSORT:Diaminonaphthalene, 1, 8-}}
⚫
[[Category:Naphthylamines]]
[[Category:Diamines]]

Latest revision as of 20:51, 22 February 2024

1,8-Diaminonaphthalene
Names
Preferred IUPAC name
Naphthalene-1,8-diamine
Other names
Deltamin, 1,8-Naphthalenediamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.846 Edit this at Wikidata
UNII
  • InChI=1S/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2 checkY
    Key: YFOOEYJGMMJJLS-UHFFFAOYSA-N checkY
  • InChI=1/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2
    Key: YFOOEYJGMMJJLS-UHFFFAOYAU
  • C1=CC2=C(C(=C1)N)C(=CC=C2)N
  • c1(cccc2cccc(N)c12)N
Properties
C10H10N2
Molar mass 158.1998
Related compounds
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).
☒N verify (what is checkY☒N ?)

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[edit]

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. This compound used to produce perimidines by various aldehydes.[3]

See also[edit]

References[edit]

  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. S2CID 32185653.
  3. ^ F.K. Behbahani, F.M.Golchin (2017). "A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4" (PDF). Journal of Taibah University for Science. 11 (1): 85–89. Bibcode:2017JTUS...11...85B. doi:10.1016/j.jtusci.2015.10.004. S2CID 98648448.
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