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2-Naphthylamine
Names
Preferred IUPAC name
Other names
(Naphthalen-2-yl)amine
Identifiers
CAS Number
3D model (JSmol )
Beilstein Reference
606264
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.892
EC Number
Gmelin Reference
165176
KEGG
PubChem CID
RTECS number
UNII
UN number
1650
CompTox Dashboard (EPA )
InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8 )7-10/h1-7H,11H2 Y
Key: JBIJLHTVPXGSAM-UHFFFAOYSA-N Y
InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8 )7-10/h1-7H,11H2
Key: JBIJLHTVPXGSAM-UHFFFAOYAA
Properties
Chemical formula
C 10 H 9 N
Molar mass
−1
Appearance
White to red crystals[1]
Odor
odorless[1]
Density
1.061 g/cm3
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[1]
Vapor pressure
1 mmHg (107°C)[1]
Acidity (p K a 3.92
Magnetic susceptibility (χ)
-98.00·10−6 cm 3
Hazards
GHS labelling
Pictograms
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 [77 °F], 100 kPa).
Infobox references
Chemical compound
2-Naphthylamine is one of two isomeric aminonaphthalenes, compounds with the formula C10 H 7 NH 2 azo dyes , but it is a known carcinogen and has largely been replaced by less toxic compounds.[2]
Preparation [ edit ]
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 [ edit ]
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, HO2 CC 6 H 4 CH 2 CH 2 CO 2
Numerous sulfonic acid derivatives of 2-naphthylamine are used in commerce, such as precursors to dyes .[2] 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.[3]
Role in disease [ edit ]
2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer .[4]
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 [ edit ]
References [ edit ]
^ a b Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi :10.1002/14356007.a17_009 .
^ Castleman, Barry (1979), Dupont's Record In Business Ethics: Another View, Washington Post, July 15th 1979
^ CDC - NIOSH Pocket Guide to Chemical Hazards
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● T h i s p a g e w a s l a s t e d i t e d o n 2 8 D e c e m b e r 2 0 2 2 , a t 0 3 : 0 1 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
