1-Naphthylamine

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.[2]

1-Naphthylamine
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Naphthalen-1-amine
Other names
(Naphthalen-1-yl)amine
1-Naphthylamine
α-Naphthylamine
1-Aminonaphthalene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.672
KEGG
UNII
  • InChI=1S/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2 checkY
    Key: RUFPHBVGCFYCNW-UHFFFAOYSA-N checkY
  • InChI=1/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2
    Key: RUFPHBVGCFYCNW-UHFFFAOYAD
  • Nc1c2ccccc2ccc1
Properties
C10H9N
Molar mass 143.19 g/mol
Appearance Colorless crystals (reddish-purple in air)[1]
Odor ammonia-like[1]
Density 1.114 g/cm3
Melting point 47 to 50 °C (117 to 122 °F; 320 to 323 K)
Boiling point 301 °C (574 °F; 574 K)
0.002% (20°C)[1]
Vapor pressure 1 mmHg (104°C)[1]
  • -98.8·10−6 cm3/mol
  • -127.6·10−6 cm3/mol (HCl salt)
Hazards
Flash point 157 °C; 315 °F; 430 K[1]
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 [77 °F], 100 kPa).
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Infobox references

Preparation and reactions

It can be prepared by reducing 1-nitronaphthalene with iron and hydrochloric acid followed by steam distillation.[2]

Oxidizing agents, such as ferric chloride, give a blue precipitate with solutions of its salts. Chromic acid converts it into 1-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.[3]

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..
  3. OSHA Standard 1910.1003
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