1-Naphthylamine
{{chembox
| Verifiedimages = changed
| Watchedfields = changed
| verifiedrevid = 477208220
| Name = 1-Naphthylamine
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = 1-Naphthylamine.png
| ImageSize = 150
| ImageName = Skeletal formula
| ImageFile1 = 1-Naphthylamine-3D-balls.png
| ImageSize1 = 180
| ImageName1 = Ball-and-stick model
| PIN = Naphthalen-1-amine
| OtherNames = (Naphthalen-1-yl)amine
1-Naphthylamine
α-Naphthylamine
1-Aminonaphthalene
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50450
| ChemSpiderID = 8319
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14790
| InChI = 1/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2
| InChIKey = RUFPHBVGCFYCNW-UHFFFAOYAD
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 57394
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RUFPHBVGCFYCNW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 134-32-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9753I242R5
| PubChem = 8640
| SMILES = Nc1c2ccccc2ccc1
}}
|Section2={{Chembox Properties
| Formula = C10H9N
| Appearance = Colorless crystals (reddish-purple in air)
| Odor = ammonia-like
| MolarMass = 143.19 g/mol
| Density = 1.114 g/cm3
| MeltingPtC = 47 to 50
| MeltingPt_notes =
| BoilingPtC = 301
| BoilingPt_notes =
| VaporPressure = 1 mmHg (104°C)
| MagSus = {{Plainlist|
- −98.8·10−6 cm3/mol
- −127.6·10−6 cm3/mol (HCl salt)
}}
}}
|Section3={{Chembox Hazards
| ExternalSDS = [http://www.hazard.com/msds/f2/bqv/bqvsx.html] [http://www.einstein.yu.edu/docs/administration/environmental-health-safety/A-naphthylamine.pdf]
| FlashPtF = 315
| FlashPt_ref = {{PGCH|0441}}
}}
|Section4={{Chembox Related
| OtherCompounds = 2-Naphthylamine
1-Naphthol
Naphthalene
Aniline
1,8-Bis(dimethylamino)naphthalene
}}
}}
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.{{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 }}.
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.[http://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STANDARDS&p_id=10007 OSHA Standard 1910.1003]
See also
- Used in preparation of aptiganel.