2-NAPHTHYLAMINE

2-Naphthylamine is used to make azo dyes.
Currently, 2-Naphthylamine is only used in laboratory research.
2-Naphthylamine is used to make dyes and agricultural chemicals.

CAS Number: 91-59-8 
EC Number: 202-080-4
Chemical formula: C10H9N
Molar mass: 143.189 g·mol−1

SYNONYMS:
Naphthalen-2-amine, 2-Naphthaleneamine, 2-Aminonaphthalene, β-Naphthylamine, β-Aminonaphthalene, 2-NAPHTHYLAMINE, 2-Aminonaphthalene, 91-59-8, naphthalen-2-amine, 2-Naphthalenamine, beta-Naphthylamine, 6-Naphthylamine, beta-Naftilamina, 2-Naphthalamine, 2-Naphthylamin, Fast Scarlet Base B, 2-Aminonaftalen, 2-Naftylamine, beta-Naphthylamin, 2-Naftylamin, beta-Naftalamin, beta-Naftylamin, Naphthalen-2-ylamine, 2-naftilamina, beta-naftyloamina, RCRA waste number U168, USAF CB-22, 2-Naphthylamine mustard, C.I. 37270, DTXSID2020921, CKR7XL41N4, CI 37270, CHEBI:27878, DTXCID60921, 2 Naphthylamine, beta Naphthylamine, 2 Aminonaphthalene, RefChem:88656, 202-080-4, 2-Naphtylamine, .beta.-Naphthylamine, MFCD00004112, BNA, naphthalene, 2-amino-, 2-Naftylamin [Czech], 2-Naftylamine [Dutch], beta-Naftalamin [Czech], beta-Naftylamin [Czech], 2-Aminonaftalen [Czech], 2-Naphthylamin [German], |A-Naphthylamine, beta-Naftilamina [Italian], beta-Naftyloamina [Polish], beta-Naphthylamin [German], CAS-91-59-8, CCRIS 424, HSDB 1131, 612-52-2, EINECS 202-080-4, UN1650, RCRA waste no. U168, UNII-CKR7XL41N4, napthylamine, 2-napthylamine, AI3-02912, 2-aminonapthalene, 2-naphthyl amine, 2-naphthaleneamine, .beta.-Naftalamin, .beta.-Naftylamin, .beta.-Naftilamina, C10-H9-N, .beta.-naftyloamina, 2-aminonaphthylamine, .beta.-Naphthylamin, 2-Amino-naphthalene, beta-amino-naphthalene, B-naphthylamine isopac, Dapoxetine Impurity 24, 2-Naphthylamine, powder, SCHEMBL74680, SCHEMBL75079, SCHEMBL76713, MLS002302990, 2-NAPHTHYLAMINE [MI], SCHEMBL130318, SCHEMBL408287, SCHEMBL729534, .BETA.-AMINONAPHTHALENE, CHEMBL278164, SCHEMBL2252105, SCHEMBL2252898, SCHEMBL2257839, SCHEMBL2945485, SCHEMBL2945487, 2-NAPHTHYLAMINE [HSDB], 2-NAPHTHYLAMINE [IARC], 2-Naphthylamine, Purity >97%, SCHEMBL29394720, MSK1204, HMS3091M06, 2-Aminonaphthalene, b-Naphthylamine, CS-M0912, 2-Naphthylamine, analytical standard, Tox21_202091, Tox21_300048, BDBM50520351, MSK1204-100M, SBB057506, STL163340, AKOS000119160, MSK1204-1000M, FN26154, GS-3283, UN 1650, NCGC00091131-01, NCGC00091131-02, NCGC00091131-03, NCGC00254076-01, NCGC00259640-01, beta-Naphthylamine [UN1650] [Poison], SMR001252278, DB-005971, NS00020126, ST45255280, EN300-21274, C02227, 2-Aminonaphthalene 10 microg/mL in Acetonitrile, 2-Naphthylamine Solution in Methanol, 100ug/mL, 004A112, 2-Naphthylamine Solution in Methanol, 1000ug/mL, Q209450, 2-Aminonaphthalene, ?-Naphthylamine, 2-Naphthalenamine, 2-Aminonaphthalene 1000 microg/mL in Dichloromethane, Z104494980, InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H, β-Naphthylamine, 2-Aminonaphthalene, 2-Naphthylamine, β-Naphthylamine, C.I. 37270, Fast Scarlet Base B, 2-Aminonaphthalene, 2-Aminonaftalen, β-naftyloamina, β-Naftalamin, β-Naftilamina, 2-Naftylamin, 2-Naftylamine, 2-Naphthalamine, β-Naftylamin, β-Naphthylamin, 2-Naphthylamin, 6-Naphthylamine, RCRA waste number U168, UN 1650, USAF CB-22, 2-Naphthalenamine, 2-Naphthylamine, C.I. 37270, 2-Aminonaphthalene, Fast Scarlet Base B, β-Naphthylamine, Naphthalen-2-ylamine, β-Aminonaphthalene, o-Aminonaphthalene, 2-AMINONAPHTHALENE, 2-Aminonaftalen, 2-Naftylamin, 2-Naftylamine, 2-Naphthalamine, 2-Naphthylamin, 2-Naphthylamine, 6-Naphthylamine, BETA-NAPHTHYLAMINE, C.I. 37270, Fast Scarlet Base B, RCRA waste number U168, UN 1650, USAF CB-22, «beta»-Naftalamin, «beta»-Naftilamina, «beta»-Naftylamin, «beta»-Naphthylamin, «beta»-Naphthylamine, «beta»-naftyloamina, «beta»-Naftalamin, «beta»-Naftilamina, «beta»-Naftylamin, «beta»-Naphthylamin, «beta»-Naphthylamine, «beta»-naftyloamina, 2-Aminonaphthalene, C.I. 37270, Fast Scarlet Base B, Naphthalen-2-ylamine, o-Aminonaphthalene, β-Aminonaphthalene, β-Naphthylamine, 2-Naphthylamine (8CI), 2-Aminonaphthalene, β-Naphthylamine, β-Aminonaphthalene, Naphthalen-2-amine, 2-Naphthalenamine, Fast Scarlet Base B, BNA, C.I. 37270, β-Naftyloamina, β-Naftilamina

2-Naphthylamine was previously used as a dye precursor and rubber antioxidant in the 1930s, 40s and 50s.
Dupont stopped using 2-Naphthylamine in the 1970s.
2-Naphthylamine is activated in the liver but quickly deactivated by conjugation to glucuronic acid.

In the bladder, glucuronidase re-activates 2-Naphthylamine by deconjugation, which leads to the development of bladder cancer.
2-Naphthylamine is an amine compound used for research purposes.
2-Naphthylamine appears as a white to reddish colored solid in the form of flakes.

2-Naphthylamine is slightly soluble in hot water and denser than water.
2-naphthylamine is a naphthylamine carrying the amino group at position 2.
2-Naphthylamine is a synthetic, air-sensitive, colorless crystalline solid that is soluble in hot water, alcohol, ether and many organic solvents.

2-Naphthylamine is an aromatic amine.
2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200–210 °C; or in the form of its acetyl derivative by heating 2-naphthol with ammonium acetate to 270–280 °C.

2-Naphthylamine forms odorless, colorless plates which melt at 111–112 °C.
2-Naphthylamine gives no color with ferric chloride.
When reduced by sodium in boiling amyl alcohol solution 2-Naphthylamine forms alicyclic tetrahydro-3-naphthylamine, which has most of the properties of the aliphatic amines; it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized.

On oxidation 2-Naphthylamine yields ortho-carboxy-hydrocinnamic acid, HO2CC6H4CH2CH2CO2H.
Numerous sulfonic acids derived from 2-Naphthylamine are known.
Numerous sulfonic acid derivatives of 2-naphthylamine are used in commerce, such as precursors to dyes.

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

2-Naphthylamine is an aromatic amine used to make azo dyes.
Studies indicate that 2-Naphthylamine decreases the enzymatic functions of monoamine oxidase A and B.
2-Naphthylamine is known that the main source of this compound is obtained from cigarette smoke.

2-Naphthylamine, also known as 2-Aminonaphthalene or beta-naphthylamine, has been recognized since 1980.
2-Naphthylamine is a yellowish crystalline solid that can turn purplish-red when exposed to air and has a distinct ammoniacal odor.
2-Naphthylamine is also known as β-Naphthylamine, it is white to pink shiny flaky crystal, it is volatile with water vapor.

The relative density of 2-Naphthylamine is 1.0614 (98/4℃), m.p. is 111~113℃, boiling point is 306℃.
2-Naphthylamine is insoluble in water, but soluble in hot water, ethanol, ether and benzene etc.
2-Naphthylamine appears as a white to reddish colored solid in the form of flakes.

2-Naphthylamine is slightly soluble in hot water and denser than water.
2-Naphthylamine is odorless, white to red crystals with a faint, aromatic odor.
2-Naphthylamine darkens in air to a reddish-purple color.

2-Naphthylamine appears as a white to reddish colored solid in the form of flakes.
2-Naphthylamine is slightly soluble in hot water and denser than water.
2-naphthylamine is a naphthylamine carrying the amino group at position 2.

2-Naphthylamine has a role as a carcinogenic agent.
2-Naphthylamine is a synthetic, air-sensitive, colorless crystalline solid that is soluble in hot water, alcohol, ether and many organic solvents.
2-Naphthylamine is an aromatic amine that is considered the archetype of carcinogens.

USES and APPLICATIONS of 2-NAPHTHYLAMINE:
2-Naphthylamine is used to make azo dyes.
Currently, 2-Naphthylamine is only used in laboratory research.
2-Naphthylamine is used to make dyes and agricultural chemicals.
2-Naphthylamine is an amine compound used for research purposes.

Current Uses of 2-Naphthylamine: Very limited — primarily research chemical only.
2-Naphthylamine has been used mainly as an intermediate in the chemical industry, especially in the development of synthetic dyes and pigments.
2-Naphthylamine played an important role in the early growth of the textile, leather, and paper dyeing industries, where it was used to produce a variety of colorants with strong color intensity and durability.

2-Naphthylamine has also been utilized as a chemical intermediate in organic synthesis for the preparation of other aromatic compounds, particularly naphthalene-based derivatives.
These intermediates were important in the advancement of industrial organic chemistry and fine chemical manufacturing.

In scientific and industrial research, 2-Naphthylamine has been used as a reference compound in studies related to aromatic amines.
2-Naphthylamine has contributed to a better understanding of reaction mechanisms, substitution patterns on naphthalene rings, and structure–property relationships in organic chemistry.

Historically, 2-Naphthylamine was investigated in pharmaceutical and chemical research as a starting material for the synthesis of more complex molecules.
Although it is no longer widely applied in product development, 2-Naphthylamine remains relevant in academic literature and chemical history.
Today, 2-Naphthylamine is mainly encountered in educational, analytical, and reference contexts, where it is discussed for its role in the development of dye chemistry and aromatic amine research rather than for active commercial applications.

-Dye and Pigment Industry (Historical) uses of 2-Naphthylamine:
2-Naphthylamine is formerly used as a key intermediate in azo dyes.
Enabled production of bright, colorfast dyes for textiles, leather, and paper.

-Chemical Intermediate (Restricted) uses of 2-Naphthylamine:
*2-Naphthylamine is used in the past for synthesizing:
Azo compounds
Naphthalene-based aromatic amines
Today, such use is limited to closed systems under strict regulatory control, if allowed at all.

-Analytical and Research Applications of 2-Naphthylamine:
2-Naphthylamine is occasionally used in research laboratories:
2-Naphthylamine is used as a reference compound in toxicology and carcinogenicity studies.
In studies related to aromatic amine metabolism and occupational exposure.
Handled only in licensed facilities with full protective measures.

-Pharmaceutical Research (Historical / Experimental) uses of 2-Naphthylamine:
Investigated historically as a starting material for certain drug-related compounds.
No modern pharmaceutical use due to toxicity concerns.

-2-Naphthylamine is used as a model substance in:
Industrial hygiene studies
Cancer risk assessment research
Development of workplace exposure limits

-Historical / Former Uses of 2-Naphthylamine:
Intermediate in the manufacture of azo dyes and dyestuffs.
Antioxidant in rubber industry (older use).
Intermediate for synthesis of organic chemicals.

BENEFITS/CHARACTERISTICS of 2-NAPHTHYLAMINE:
Unlike many industrial chemicals, 2-naphthylamine has no significant current beneficial industrial uses because of its high toxicity and carcinogenicity.
Historically, 2-Naphthylamine served mainly as a chemical intermediate in dye manufacture.

OCCURRENCE/USE of 2-NAPHTHYLAMINE:
2-Naphthylamine is research chemical; component of cigarette smoke.
2-Naphthylamine is formerly used as a chemical intermediate for dyes, as a rubber antioxidant, and in the production of 2-chloronaphthylamine.

PREPARATION of 2-NAPHTHYLAMINE:
2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200–210 °C, the Bucherer reaction.
2-Naphthylamine's acetyl derivative can be obtained by heating 2-naphthol with ammonium acetate to 270–280 °C.

REACTIONS of 2-NAPHTHYLAMINE:
2-Naphthylamine gives no color with iron(III) chloride.
When reduced by sodium in boiling amyl alcohol solution, 2-Naphthylamine 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, 2-Naphthylamine yields ortho-carboxy-hydrocinnamic acid, HO2CC6H4CH2CH2CO2H.

PHYSICAL and CHEMICAL PROPERTIES of 2-NAPHTHYLAMINE:
Chemical formula: C10H9N
Molar mass: 143.189 g·mol−1
Appearance: White to red crystals
Odor: odorless
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
Vapor pressure: 1 mmHg (107°C)

Acidity (pKa): 3.92
Magnetic susceptibility (χ): −98.00·10−6 cm3/mol
CAS Number: 91-59-8
EC Number: 202-080-4
Molecular Weight: 143.18 g/mol
XLogP3: 2.3
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0

Exact Mass: 143.073499291 Da
Monoisotopic Mass: 143.073499291 Da
Topological Polar Surface Area: 26 Ų
Heavy Atom Count: 11
Formal Charge: 0
Complexity: 133
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0

Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Linear Formula: C10H7NH2
CAS Number: 91-59-8
Molecular Weight: 143.19
UNSPSC Code: 12352103
NACRES: NA.25
PubChem Substance ID: 24897863

EC Number: 202-080-4
Beilstein/REAXYS Number: 3939429
MDL number: MFCD00004112
Physical state: solid
Form: powder
Color: white, to, light red
Odor: No data available
Melting point/range: 111 - 113 °C

Method: lit.
Boiling point/boiling range: 306 °C
Method: lit.
Flammability: No data available
Upper explosion limit / Upper flammability limit: No data available
Lower explosion limit / Lower flammability limit: No data available
Flash point: No data available
Autoignition temperature: No data available
Decomposition temperature: No data available
pH: No data available

Viscosity, dynamic: No data available
Viscosity, kinematic: No data available
Flow time: No data available
Water solubility: soluble in hot water
Partition coefficient: noctanol/water No data available
Vapor pressure: No data available
Relative density: No data available
Density: 1,061 g/cm3 (25 °C)
Method: lit.

Relative vapour density: No data available
Explosives: Not classified as explosive
Oxidizing properties: none
Burning rate: No data available
Evaporation rate: No data available
Molecular weight: 143,19 g/mol
Physical State: Solid
Solubility: Soluble in Ethyl Acetate and Methanol
Storage: Store at 4° C

Melting Point: 111-113° C
Boiling Point: 306° C
Density: 1.06 g/cm3 at 25° C
Molecular Weight: 143.19
Exact Mass: 143.19
EC Number: 202-080-4
UNII: CKR7XL41N4
ICSC Number: 0610
UN Number: 1650

DSSTox ID: DTXSID2020921
NCI Thesaurus Code: C44311
Color/Form: White to red crystals
PSA: 26
XLogP3: 2.28
Appearance: White to reddish crystals
Density: 1.061 g/cm3
Melting Point: 111-113 °C
Boiling Point: 306 °C
Flash Point: 315°F

Refractive Index: 1.694
Water Solubility: Soluble in hot water, ethanol, ether
Storage Conditions: -20°C Freezer
Vapor Pressure: 2.56 x 10 -4 mmHg at 20–30 °C
Vapor Density: 4.95
Explosive limit: Nonexplosive
Odor: Faint aromatic odor
PH: WEAK BASE
Henrys Law Constant: 8.10e-08 atm-m3/mole

Dissociation Constants: pKa = 4.16
Experimental Properties: Reduces warm ammoniacal silver nitrate
Air and Water Reactions: Darkens in air to a reddish-purple color; slightly soluble in hot water
Reactive Group: Amines, Aromatic
Reactivity Profile: Weak base; incompatible with strong oxidizing agents, strong acids, and nitrous acid; reduces warm ammoniacal silver nitrate
Ionization Potential: 9.71 eV

Physical Dangers: Dust explosion possible if in powder or granular form, mixed with air
Corrosivity: NOT CORROSIVE
InChI: InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
InChI Key: JBIJLHTVPXGSAM-UHFFFAOYSA-N
Formula: C10H9N
SMILES: Nc1ccc2ccccc2c1
Molecular Weight: 143.19
CAS: 91-59-8
Common Name: 2-Naphthylamine
IUPAC Name: Naphthalen-2-amine

Molecular Formula: C10H9N
Molecular Weight: 143.19 g/mol
Appearance: White to reddish crystals that darken on exposure to air
Odor: Faint or aromatic odor
EC / EINECS Number: 202-080-4
CAS Number: 91-59-8
UN Number: UN 1650
RTECS Number: QM2100000
State at 20 °C: Solid
Density: ~1.06 g/cm³
Melting Point: ≈111–113 °C
Boiling Point: ≈306 °C

Solubility in Water: Poor overall; miscible in hot water
Solubility in Organic Solvents: Soluble in ethanol, ether, many organic solvents
Vapor Pressure: 1 mmHg around ~107 °C
Flash Point: ~315 °F
Relative Vapor Density: ~4.9
Chemical Type: Aromatic amine
Reactivity: Incompatible with strong oxidizing agents, strong acids, and nitrous acid; oxidizes in air
SMILES: c12ccccc1ccc(N)c2
InChIKey: JBIJLHTVPXGSAM-UHFFFAOYSA-N

FIRST AID MEASURES of 2-NAPHTHYLAMINE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of 2-NAPHTHYLAMINE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of 2-NAPHTHYLAMINE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of 2-NAPHTHYLAMINE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of 2-NAPHTHYLAMINE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of 2-NAPHTHYLAMINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available