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2-Naphthylamine

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2-Naphthylamine
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name Naphthalen-2-ylamine
Other names 2-Naphthaleneamine
2-Aminonaphthalene
β-Naphthylamine
β-Aminonaphthalene
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 606264
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.892 Edit this at Wikidata
EC Number
  • 202-080-4
Gmelin Reference 165176
KEGG
PubChem CID
RTECS number
  • QM2100000
UNII
UN number 1650
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2Key: JBIJLHTVPXGSAM-UHFFFAOYSA-N
  • InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2Key: JBIJLHTVPXGSAM-UHFFFAOYAA
SMILES
  • c12ccccc1ccc(N)c2
Properties
Chemical formula C10H9N
Molar mass 143.189 g·mol
Appearance White to red crystals
Odor odorless
Density 1.061 g/cm
Melting point 111 to 113 °C (232 to 235 °F; 384 to 386 K)
Boiling point 306 °C (583 °F; 579 K)
Solubility in water miscible in hot water
Vapor pressure 1 mmHg (107°C)
Acidity (pKa) 3.92
Magnetic susceptibility (χ) -98.00·10 cm/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H302, H350, H411
Precautionary statements P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, P501
Flash point 157 °C; 315 °F; 430 K
Related compounds
Related compounds 2-Naphthol
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

2-Naphthylamine or 2-aminonaphthalene is one of two isomeric aminonaphthalenes, compounds with the formula C10H7NH2. It is a colorless solid, but samples take on a reddish color in air because of oxidation. It was formerly used to make azo dyes, but it is a known carcinogen and has largely been replaced by less toxic compounds.

Preparation

2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C, the Bucherer reaction. Its acetyl derivative can be obtained by heating 2-naphthol with ammonium acetate to 270-280 °C.

Reactions

It gives no color with iron(III) chloride. When reduced by sodium in boiling amyl alcohol solution, it forms tetrahydro-3-naphthylamine, which exhibits the properties of the aliphatic amines in that it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized.

On oxidation, it yields ortho-carboxy-hydrocinnamic acid, HO2CC6H4CH2CH2CO2H.

Numerous sulfonic acid derivatives of 2-naphthylamine are used in commerce, such as precursors to dyes. Owing to the carcinogenicity of the amine, these derivatives are mainly prepared by amination of the corresponding naphthols. Of them, the δ-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.

2-Naphthylamine was previously used as a dye precursor and rubber antioxidant in the 1930s, 40s and 50s. Dupont stopped using it in the 1970s.

Role in disease

2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer.

It is activated in the liver but quickly deactivated by conjugation to glucuronic acid. In the bladder, glucuronidase re-activates it by deconjugation, which leads to the development of bladder cancer.

See also

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0442". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.
  3. Castleman, Barry (1979), Dupont's Record In Business Ethics: Another View, Washington Post, July 15th 1979
  4. CDC - NIOSH Pocket Guide to Chemical Hazards
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