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)

| Solubility = 0.002% (20°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

}}

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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

References