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1-Naphthylamine: Difference between revisions

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Revision as of 22:29, 13 December 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - updated 'DrugBank_Ref', 'UNII_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Latest revision as of 01:49, 13 November 2024 edit undoMdewman6 (talk | contribs)Extended confirmed users, Page movers, New page reviewers, Pending changes reviewers, Rollbackers21,986 edits no such thing as 1-naphthoquinone; the correction is at least analogous to aniline 
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| Verifiedimages = changed | Verifiedimages = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443257246 | verifiedrevid = 477208220
| Name = 1-Naphthylamine | Name = 1-Naphthylamine
| ImageFile_Ref = {{chemboximage|changed|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = 1-Naphthylamine.png | ImageFile = 1-Naphthylamine.png
| ImageSize = 150 | ImageSize = 150
| ImageName = Skeletal formula | ImageName = Skeletal formula
| ImageFile1 = 1-Naphthylamine-3D-balls.png | ImageFile1 = 1-Naphthylamine-3D-balls.png
| ImageSize1 = 180 | ImageSize1 = 180
| ImageName1 = Ball-and-stick model | ImageName1 = Ball-and-stick model
| PIN = Naphthalen-1-amine
| IUPACName = 1-Aminonaphthalene
| OtherNames = 1-Naphthylamine<br />α-Naphthylamine | OtherNames = (Naphthalen-1-yl)amine<br />1-Naphthylamine<br />α-Naphthylamine<br />1-Aminonaphthalene
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50450 | ChEBI = 50450
Line 30: Line 30:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 134-32-7 | CASNo = 134-32-7
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 8640
| UNII = 9753I242R5
| SMILES = c1cccc2cccc(N)c12
⚫ | PubChem = 8640
| SMILES = Nc1c2ccccc2ccc1
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>9</sub>N | Formula = C<sub>10</sub>H<sub>9</sub>N
| Appearance = Colorless crystals (reddish-purple in air)<ref name=PGCH/>
⚫ | MolarMass = 143.19 g/mol
| Odor = ]-like<ref name=PGCH/>
⚫ | Density = 1.114 g/cm³
⚫ | MolarMass = 143.19 g/mol
| MeltingPt = 47–50&nbsp;°C
⚫ | Density = 1.114 g/cm<sup>3</sup>
| BoilingPt = 301&nbsp;°C
| MeltingPtC = 47 to 50
| MeltingPt_notes =
| BoilingPtC = 301
| BoilingPt_notes =
| VaporPressure = 1 mmHg (104°C)<ref name=PGCH/>
| Solubility = 0.002% (20°C)<ref name=PGCH/>
| MagSus = {{Plainlist|
* -98.8·10<sup>−6</sup> cm<sup>3</sup>/mol
* -127.6·10<sup>−6</sup> cm<sup>3</sup>/mol (HCl salt)
}}
}}
|Section3={{Chembox Hazards
| ExternalSDS =
| FlashPtF = 315
| FlashPt_ref = <ref name=PGCH>{{PGCH|0441}}</ref>
}} }}
| Section2 = {{Chembox Related |Section4={{Chembox Related
| OtherCpds = ]<br>]<br>]<br>]<br>] | OtherCompounds = ]<br>]<br>]<br>]<br>]
}} }}
}} }}


'''1-Naphthylamine''' is an ] ]. It can be prepared by ] 1-nitronaphthalene with ] and ] at about 70&nbsp;°C, the reaction mixture being neutralized with ], and the naphthylamine ]-]ed. It may also be prepared, in the form of its ] derivative, by heating ] with ], ] and ]; by heating 1-naphthol with ]-] to 270&nbsp;°C; and by heating ], ], ] and ] to 300&nbsp;°C. It ]s in colorless needles which melt at 50&nbsp;°C. It possesses a disagreeable odor, ]s readily, and turns brown on exposure to air. ]s, such as ], give a blue ] with solutions of its ]s. ] converts it into ]. ] in boiling ] '''1-Naphthylamine''' is an ] ] derived from ]. It can cause bladder cancer (transitional cell carcinoma). It ]s in colorless needles which melt at 50&nbsp;°C. It possesses a disagreeable odor, ]s readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.<ref name=Ullmann>{{cite encyclopedia|author=Gerald Booth|title=Naphthalene Derivatives|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_009|isbn=9783527303854 }}.</ref>
reduces it to ] tetrahydro-1-naphthylamine, a substance having the properties of an ], for it can be ]tized and does not possess an ] smell. Since it does not form an addition product with ], reduction must have taken place in one of the nuclei only, and on account of the aromatic character of the compound it must be in that nucleus which does not contain the ] group. This tetrahydro compound yields ], (C<sub>6</sub>O<sub>4</sub>H<sub>10</sub>), when ]d by ]. The 1-naphthylamine ]s are used for the preparation of azo ]s, these dyes possessing the important property of dyeing unmordanted ]. The most important is naphthionic acid, 1-amino-4-sulfonic acid, produced by heating 1-naphthylamine and ] to 170–180&nbsp;°C with about 3% of crystallized ]. It forms small needles, very sparingly soluble in water. With diazotized benzidine it
gives ].


==Preparation and reactions==
It can be prepared by ] 1-nitronaphthalene with ] and ] followed by ].<ref name=Ullmann/>

]s, such as ], give a blue ] with solutions of its ]s. ] converts it into ]. ] in boiling ]
reduces the unsubstituted ring, giving tetrahydro-1-naphthylamine. This tetrahydro compound yields ] when ]d by ].

At 200 °C in sulfuric acid, it converts to ].

==Use in dyes==
The ] are used for the preparation of ]. These compounds possess the important property of dyeing unmordanted ].

An important derivative is ] (1-aminonaphthalene-4-sulfonic acid), which is produced by heating 1-naphthylamine and ] to 170–180&nbsp;°C in the presence of crystallized ]. It forms small needles, very sparingly soluble in water. Upon treatment with the bis(diazonium) derivative of benzidine, 1-aminonaphthalene-4-sulfonic acid gives ].

==Safety==
It is listed as one of the 13 carcinogens covered by the OSHA General Industry Standards.<ref></ref>
==See also==
*Used in preparation of ].
==References== ==References==
{{reflist}}
{{Unreferenced|date=September 2007}}
<references/>


{{DEFAULTSORT:Naphthylamine, 1-}} {{DEFAULTSORT:Naphthylamine, 1-}}
] ]
]

] ]
]
]
]
]

Latest revision as of 01:49, 13 November 2024

1-Naphthylamine
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name Naphthalen-1-amine
Other names (Naphthalen-1-yl)amine
1-Naphthylamine
α-Naphthylamine
1-Aminonaphthalene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.672 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2Key: RUFPHBVGCFYCNW-UHFFFAOYSA-N
  • InChI=1/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2Key: RUFPHBVGCFYCNW-UHFFFAOYAD
SMILES
  • Nc1c2ccccc2ccc1
Properties
Chemical formula C10H9N
Molar mass 143.19 g/mol
Appearance Colorless crystals (reddish-purple in air)
Odor ammonia-like
Density 1.114 g/cm
Melting point 47 to 50 °C (117 to 122 °F; 320 to 323 K)
Boiling point 301 °C (574 °F; 574 K)
Solubility in water 0.002% (20°C)
Vapor pressure 1 mmHg (104°C)
Magnetic susceptibility (χ)
  • -98.8·10 cm/mol
  • -127.6·10 cm/mol (HCl salt)
Hazards
Flash point 157 °C; 315 °F; 430 K
Safety data sheet (SDS)
Related compounds
Related compounds 2-Naphthylamine
1-Naphthol
Naphthalene
Aniline
1,8-Bis(dimethylamino)naphthalene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer (transitional cell carcinoma). It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.

Preparation and reactions

It can be prepared by reducing 1-nitronaphthalene with iron and hydrochloric acid followed by steam distillation.

Oxidizing agents, such as ferric chloride, give a blue precipitate with solutions of its salts. Chromic acid converts it into 1,4-naphthoquinone. Sodium in boiling amyl alcohol reduces the unsubstituted ring, giving tetrahydro-1-naphthylamine. This tetrahydro compound yields adipic acid when oxidized by potassium permanganate.

At 200 °C in sulfuric acid, it converts to 1-naphthol.

Use in dyes

The sulfonic acid derivatives of 1-naphthylamine are used for the preparation of azo dye. These compounds possess the important property of dyeing unmordanted cotton.

An important derivative is naphthionic acid (1-aminonaphthalene-4-sulfonic acid), which is produced by heating 1-naphthylamine and sulfuric acid to 170–180 °C in the presence of crystallized oxalic acid. It forms small needles, very sparingly soluble in water. Upon treatment with the bis(diazonium) derivative of benzidine, 1-aminonaphthalene-4-sulfonic acid gives Congo red.

Safety

It is listed as one of the 13 carcinogens covered by the OSHA General Industry Standards.

See also

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0441". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Gerald Booth (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN 9783527303854..
  3. OSHA Standard 1910.1003
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