1,5-Naphthalenediamine Chemical Properties

Melting point:

185-187 °C(lit.)

Boiling point:

200-210°C 5mm

Density 

1.4

vapor pressure 

0Pa at 20℃

refractive index 

1.6441 (estimate)

Flash point:

200-210°C/5mm

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

0.04g/l

pka

4.59±0.10(Predicted)

form 

Powder

color 

Gray to dark brown

Water Solubility 

<0.1 g/100 mL at 20.5 ºC

BRN 

907947

LogP

0.91

Dissociation constant

4.21 at 25℃

CAS DataBase Reference

2243-62-1(CAS DataBase Reference)

NIST Chemistry Reference

1,5-Naphthalenediamine(2243-62-1)

IARC

3 (Vol. 27, Sup 7) 1987

EPA Substance Registry System

1,5-Naphthalenediamine (2243-62-1)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

40-50/53

Safety Statements 

36/37-60-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

RTECS 

QJ3400000

HazardClass 

9

PackingGroup 

III

HS Code 

29215990

Hazardous Substances Data

2243-62-1(Hazardous Substances Data)

MSDS

• Language:English Provider:1,5-Diaminonaphthalene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,5-Naphthalenediamine Usage And Synthesis

Chemical Properties

GREY TO DARK BROWN POWDER. 1,5-Naphthalenediamine [2243-62-1]. 1,5-diaminonaphthalene, Alphamin, C10H10N2, Mr 158.2: oxidation of 97 with iron (III) chloride in water produces a blue-violet color. Treatment with boiling aqueous sodium bisulfite followed by addition of alkali gives a mixture of 1-amino-5-hydroxynaphthalene and 1,5-dihydroxynaphthalene. Sulfonation (5 % oleum, 100℃) gives 1,5-diaminonaphthalene2-sulfonic acid, and nitration in acetic acid produces 2,4,6,8-tetranitro-1,5-diaminonaphthalene. Coupling with diazo compounds takes place in the 2-position; reduction of the resulting azo compound with SnCl2– HCl produces 1,2,5- triaminonaphthalene.

Uses

1,5-Naphthalenediamineis an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. The reducing properties of 1,5-diaminonaphthalene (1,5-DAN) as a MALDI matrix ( matrix-assisted laser desorption ionization) to amino acid sequencing and disulfide bond mapping of human urotensin II possessing one disulfide bond, and human guanylin possessing two disulfide bonds.

Uses

Aromatic amines likely to have high carcinogenic potency. QSARs of aromatic amines.

Uses

1,5-naphthalenediamine be used as intermediates for the synthesis of materials.

Definition

ChEBI: A naphthalenediamine compound having amino substituents in the 1- and 5-positions.

Production Methods

1-Nitronaphthalene can be nitrated further to give a 40 : 60 mixture of 1,5- and 1,8-dinitronaphthalenes. Similar results are obtained by direct nitration of naphthalene with H2SO4– HNO3 under careful control of temperature over the range 40 – 80℃. Although separation of the isomers by fractional crystallization or solvent extraction is usually carried out at this stage, the mixed isomers can also be reduced and the resulting diamines separated. Reduction of the dinitronaphthalenes is achieved by treatment of a nonaqueous solution with iron or hydrogen in the presence of a catalyst. An alternative process for 1,5-naphthalenediamine involves amination of 1,5-dihydroxynaphthalene with ammonia and ammonium bisulfite. Although less efficient on a stage basis it offers an economical alternative to nitration and reduction if the 1,8-naphthalenediamine is not also required.

General Description

Colorless to pale purple crystals or lavender powder.

Air & Water Reactions

1,5-Naphthalenediamine is sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

1,5-Naphthalenediamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Hazard

Questionable carcinogen.

Fire Hazard

Flash point data for 1,5-Naphthalenediamine are not available. 1,5-Naphthalenediamine is probably combustible.

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic data. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Recrystallise the amino-naphthalene from boiling H2O, but this is wasteful due to poor solubility. Boil it in chlorobenzene (charcoal), filter hot and cool the filtrate (preferably under N2). This gives colourless crystals. Dry it in a vacuum till free from chlorobenzene (odour), and store it in sealed ampoules under N2 away from light. [Beilstein 13 IV 340.]

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